Updated on 2024/02/03

写真b

 
MINOURA Mao
 
*Items subject to periodic update by Rikkyo University (The rest are reprinted from information registered on researchmap.)
Affiliation*
College of Science Department of Chemistry
Graduate School of Science Doctoral Program in Chemistry
Graduate School of Science Master's Program in Chemistry
Title*
Professor
Degree
Ph. D. ( The University of Tokyo )
Contact information
Mail Address
Research Theme*
  • 有機元素化学・物理有機化学。周期表上の様々な元素の特性を引き出すことを目的とし、新規有機元素化合物の合成と構造・反応・物性に関する実験的および理論的研究に取り組む。これまでに未知である化学結合の性質解明による学術的再生産や元素の性質を活かした機能性分子創製、新反応の開発をめざしている。

  • Research Interests
  • Organoelement Chemstry

  • Environmental Chemistry

  • Organometallic Chemistry

  • Organic Chemistry

  • 結晶学

  • Crystallography

  • Campus Career*
    • 4 2013 - Present 
      College of Science   Department of Chemistry   Professor
    • 4 2013 - Present 
      Graduate School of Science   Master's Program in Chemistry   Professor
    • 4 2013 - Present 
      Graduate School of Science   Doctoral Program in Chemistry   Professor
     

    Research Areas

    • Nanotechnology/Materials / Green sustainable chemistry and environmental chemistry  / Environmental Chemistry

    • Life Science / Bioorganic chemistry  / Organoelement Chemistry

    • Nanotechnology/Materials / Structural organic chemistry and physical organic chemistry  / Organoelement Chemistry

    Research History

    • 4 2021 - Present 
      Vice President, Rikkyo University

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    • 4 2013 - Present 
      RIKKYO UNIVERSITY   Graduate School of Science Field of Study: Chemistry   Professor

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    • 4 2013 - Present 
      RIKKYO UNIVERSITY   Graduate School of Science Field of Study: Chemistry   Professor

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    • 4 2013 - Present 
      RIKKYO UNIVERSITY   College of Science Department of Chemistry   Professor

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    • 4 2008 - 3 2013 
      Kitasato University   School of Science

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    • 4 2008 - 3 2009 
      Kyoto University   Institute for Chemical Research

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    • 9 1999 - 3 2008 
      Kitasato University   School of Science

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    • 9 2003 - 8 2004 
      Columbia University   Visiting Scientist

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    • 4 1995 - 8 1999 
      Hiroshima University   Faculty of Science

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    Education

    • - 3 1995 
      The University of Tokyo   Graduate School, Division of Science

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      Country: Japan

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    • - 9 1990 
      Saitama University   Graduate School, Division of Natural Science

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      Country: Japan

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    • 4 1984 - 3 1988 
      Saitama University   Faculty of Science

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      Country: Japan

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    Papers

    • Zn-based Metal-Organic Frameworks Using Triptycene Hexacarboxylate Ligands: Synthesis, Structure, and Gas-Sorption Properties. Peer-reviewed International journal

      Koh Sugamata, Shoko Yamada, Daichi Yanagisawa, Natsuki Amanokura, Akihiro Shirai, Mao Minoura

      Chemistry (Weinheim an der Bergstrasse, Germany)   e202302080   17 8 2023

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      Language:English   Publishing type:Research paper (scientific journal)  

      A series of metal-organic frameworks (MOFs) based on zinc ions and two triptycene ligands of different size were synthesized under solvothermal conditions. The structural analyses revealed that these are isostructural three-dimensional-network MOFs. The high porosity and thermal stability of these MOFs can be attributed to the highly rigid triptycene-based ligands. Their BET specific surface areas depend on the size of the triptycene ligands. In contrast to these surface-area data, the H2 and CO2 adsorption of these MOFs is larger for MOFs with small pores. Consequently, we introduced functional groups to the bridge-head position of the triptycene ligands and investigated their effect on the gas-sorption properties. The corresponding results unveiled the role of the functional groups in the specific CO2 binding via an induced interaction between adsorbates and the functional groups. Excellent H2 and CO-2 properties in these MOFs were achieved in the absence of open metal sites.

      DOI: 10.1002/chem.202302080

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    • Synthesis, Structure, and Redox and Optical Properties of 5,10,15,20-Tetraaryl-5-azaporphyrinium Salts. Peer-reviewed International journal

      Yuta Kudoh, Emi Suzuki, Hikari Ochiai, Kakeru Ise, Yoshifumi Kimura, Mao Minoura, Haruyuki Nakano, Yoshihiro Matano

      Chemistry (Weinheim an der Bergstrasse, Germany)   e202302148   9 8 2023

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      Language:English   Publishing type:Research paper (scientific journal)  

      The fundamental properties of azaporphyrins can be modulated over a wide range by changing the number of meso-nitrogen atoms. Reported herein are the first examples of 5,10,15,20-tetraaryl-5-azaporphyrinium (MTAMAP) salts, which were prepared via metal-templated cyclization of the corresponding zinc(II) and copper(II) complexes of 10-aryl-1-chloro-19-benzoyl-5,15-dimesityl-10-azabiladiene-ac. The inclusion of one meso-nitrogen atom in the 5,10,15,20-tetraarylporphyrin skeleton considerably changes the redox and optical properties as well as the degree of aromaticity of the porphyrin ring. The present findings suggest that MTAMAP salts would be promising scaffolds for the development of new azaporphyrin-based ionic fluorophores and photosensitizers.

      DOI: 10.1002/chem.202302148

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    • Synthesis and Structural Analysis of Organic Cyclic Polyselenides Obtained from the Reaction of a Bissilylcarbenoid with Selenium Peer-reviewed

      Koh Sugamata, Teppei Asakawa, Mao Minoura

      European Journal of Inorganic Chemistry26 ( 11 )   11 4 2023

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:WILEY-V C H VERLAG GMBH  

      The synthesis and isolation of the first examples of a tetraselenolane and a hexaselenepane, obtained from the reaction of a bissilylcarbenoid ((R2CBrLi)-C-Si; R-Si=SiMePh2) with elemental selenium, is reported. The molecular structures of these cyclic polyselenides were determined using single-crystal X-ray diffraction analysis. The selective synthesis of these polyselenides was achieved by controlling the reaction temperature. Stoichiometric deselenation of the hexaselenepane with triphenylphosphine afforded the corresponding tetraselenolane in quantitative yield. Further deselenation of the tetraselenolane with excess triphenylphosphine did not furnish the expected selenoketone but the diselenirane, as confirmed by spectroscopic analysis.

      DOI: 10.1002/ejic.202200780

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    • A Linear C=Ge=C Heteroallene with a Di-coordinated Germanium Atom. Peer-reviewed International journal

      Koh Sugamata, Teppei Asakawa, Daisuke Hashizume, Mao Minoura

      Angewandte Chemie (International ed. in English)62 ( 24 ) e202302836   11 4 2023

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      Allenes (>C=C=C<) are classified as cumulated dienes with a linear structure and an sp-hybridized central carbon atom. We have synthesized and isolated a stable 2-germapropadiene with bulky silyl substituents. The 2-germapropadiene allene moiety adopts a linear structure both in the solid state and in solution. An X-ray diffraction electron-density-distribution (EDD) analysis of this 2-germapropadiene confirmed the linear C=Ge=C geometry with a formally sp-hybridized germanium atom that bears two orthogonal C=Ge π-bonds. Based on detailed structural and computational studies, we concluded that the linear geometry of the isolated 2-germapropadiene most likely arises from the negative hyperconjugation of the silyl substituents at the terminal carbon atoms. The 2-germapropadiene reacts rapidly with nucleophiles, indicating that the linearly oriented germanium atom is highly electrophilic.

      DOI: 10.1002/anie.202302836

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    • Controlling the Flexibility of Carbazole-Based Metal-Organic Frameworks by Substituent Effects. Peer-reviewed International journal

      Koh Sugamata, Akihiro Shirai, Mao Minoura

      Chemistry (Weinheim an der Bergstrasse, Germany)29 ( 25 ) e202203442   19 2 2023

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      Language:English   Publishing type:Research paper (scientific journal)  

      We have developed highly porous Cu-based metal-organic frameworks (MOFs) using carbazole-type linkers. The novel topological structure of these MOFs was revealed by single-crystal X-ray diffraction analysis. Molecular adsorption/desorption experiments indicated that these MOFs are flexible and change their structure upon adsorption/desorption of organic solvents and gas molecules. These MOFs exhibit unprecedented properties that allow controlling their flexibility by adding a functional group onto the central benzene ring of the organic ligand. For example, the introduction of electron-donating substituents increases the robustness of the resulting MOFs. These MOFs also exhibit flexibility-dependent differences in gas-adsorption and -separation performance. Thus, this study represents the first example of controlling the flexibility of MOFs with the same topological structure via the substituent effect of functional groups introduced into the organic ligand.

      DOI: 10.1002/chem.202203442

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    • Development of Porous Coordination Polymers for Gas Storage and Separation Materials Peer-reviewed

      Sugamata Koh, Shirai Akihiro, Minoura Mao

      Journal of Synthetic Organic Chemistry, Japan81 ( 1 ) 46 - 52   1 1 2023

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      Language:Japanese   Publisher:The Society of Synthetic Organic Chemistry, Japan  

      Gas storage and separation are closely related to various aspects of human society, such as the alleviation of greenhouse effect, promoting clean energy, and controlling harmful gases. In particular, hydrogen has been enthusiastically researched as a clean energy source that emits no greenhouse gases. Therefore, there are requirements for safe methods to manufacture, store, and transport hydrogen. Conventionally, hydrogen storage materials are metal hydrides and metal amides that react violently with moisture, and their usage environments are limited by the extreme conditions required for hydrogen gas generation. Metal-organic frameworks (PCP/MOFs) are porous coordination materials that are composed of organic ligands and metal ions. Because of their ability to efficiently adsorb small molecules, PCP/MOFs have potential applications in e.g., gas adsorption, catalysis, as well as energy storage and conversion. Functionalization and modification of the organic ligands to construct new MOFs are fascinating and significant areas in crystal engineering owing to the potential applications of the resulting materials. We describe the synthesis and gas-adsorption properties of novel MOFs using the functionalized organic ligands.

      DOI: 10.5059/yukigoseikyokaishi.81.46

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    • Two-Step Substitution Reaction of Phosphonates Carrying a Binaphthyl Group with Grignard Reagents Leading to the Formation of P-Chirogenic Phosphine Oxides Peer-reviewed

      Toshiaki Murai, Shunya Ono, Aya Sugiyama, Nao Sakamoto, Kazuma Kuwabara, Mao Minoura

      Synlett   15 11 2022

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      Publishing type:Research paper (scientific journal)   Publisher:Georg Thieme Verlag KG  

      Abstract

      The reaction of phosphonates carrying a binaphthyl group with a range of Grignard reagents was complete within two hours at 0 °C to give phosphinates carrying a hydroxybinaphthyl group with high ­efficiency and diastereoselectivity. The resulting phosphinates were further subjected to a substitution reaction with MeMgBr. The reaction at reflux temperature in THF or toluene permitted the formation of P-chirogenic tertiary phosphine oxides with a high enantiomeric ratio. Rare examples of P-chirogenic alkynyl phosphine oxides were also obtained. The sequential one-pot substitution reaction of phosphonates bearing a binaphthyl group with two different Grignard reagents successfully gave the corresponding P-chirogenic phosphine oxides with enantiomeric ratios nearly equal to those of oxides derived from two-step reactions.

      DOI: 10.1055/a-1979-6245

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    • Tellurium-Centered Bent Allenes: Synthesis, Characterization, and Reactivity. Peer-reviewed International journal

      Koh Sugamata, Teppei Asakawa, Yukiko Urao, Mao Minoura

      Inorganic chemistry61 ( 44 ) 17641 - 17645   7 11 2022

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      Language:English   Publishing type:Research paper (scientific journal)  

      Compounds with multiple bonds between elements of the second and fifth periods are extremely unstable, and systematic investigations into their properties remain elusive. Herein, we report a tellurium-centered heteroallene that contains multiple bonds between carbon and tellurium. This compound is the first example of bis(methylene)-λ4-tellane, which was synthesized and fully characterized using multinuclear NMR spectroscopy and X-ray crystallography. In the solid state, this λ4-tellane exhibits a bent allene structure for the C═Te═C moiety and unsaturated Te-C bonds. Interestingly, the allene-type structure is retained in the solution, which is reflected in an absorption band due to the π-π* transition at 610 nm. This λ4-tellane also exhibits unique reactivity toward dihalogermylenes, which yielded rare cyclic telluragermetanes.

      DOI: 10.1021/acs.inorgchem.2c02697

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    • Two-Step Transesterification of Phosphates, Phosphorothioates, and Phosphonates with a Binaphthyl Group for the Synthesis of P-Chirogenic Phosphates and Phosphonates Peer-reviewed

      Toshiaki Murai, Chikako Endo, Yurika Inoue, Toshifumi Maruyama, Mao Minoura

      Synthesis   21 9 2022

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      Publishing type:Research paper (scientific journal)   Publisher:Georg Thieme Verlag KG  

      Abstract

      Two-step transesterification of four-coordinate pentavalent organophosphorus compounds with a binaphthyl group has been studied in detail. The first step involves transfer of the axial chirality of a ­hydroxybinaphthyl group to the central chirality of the phosphorus atom. The second step is the substitution reaction of P-chirogenic compounds with a hydroxybinaphthyl group with lithium alkoxides, leading to the formation of P-chirogenic phosphates and phosphonates with primary and secondary alkoxy groups.

      DOI: 10.1055/a-1948-3003

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    • Synthesis and Optical Properties of 1,2,5,10-Tetraphenylanthra[2,3-b]phosphole Derivatives Peer-reviewed International journal

      Yuta Kudoh, Kaori Fujii, Yoshifumi Kimura, Mao Minoura, Yoshihiro Matano

      The Journal of Organic Chemistry87 ( 15 ) 10493 - 10500   5 8 2022

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society ({ACS})  

      1,2,5,10-Tetraphenylanthra[2,3-b]phosphole oxides and 1-methyl-1,2,5,10-tetraphenylanthra[2,3-b]phospholium salts were prepared, and their optical properties were investigated. The substituent at the para position and the fused anthracene moiety were found to exert significant impacts on the fluorescence properties of the P-bridged 2-styrylanthracene skeleton.

      DOI: 10.1021/acs.joc.2c01107

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    • 9‐(Diphenylphosphoryl)‐10‐(phenylethynyl)anthracene Derivatives: Synthesis and Implications for the Substituent and Solvent Effects on the Light‐Emitting Properties Peer-reviewed

      Nina Murayama, Joel Hao Jorolan, Mao Minoura, Haruyuki Nakano, Tadaaki Ikoma, Yoshihiro Matano

      ChemPhotoChem   13 6 2022

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      Herein, we report a series of 9-(diphenylphosphoryl)-10-(phenylethynyl)anthracenes (DPPPEAs) as novel fluorescent 9,10-disubstituted anthracene derivatives. The DPPPEAs were prepared by Sonogashira coupling of (10-bromoanthracen-9-yl)diphenylphosphine oxide with terminal arylacetylenes, and their structures were fully characterized. UV/Vis fluorescence spectroscopy and theoretical calculations were used to evaluate substituent effects on fluorescence properties of DPPPEAs. The nature of emissive excited state of DPPPEAs was found to vary greatly depending on the substituent, solvent, and temperature. Unsubstituted DPPPEA emitted intense fluorescence from locally excited (LE) state, whereas donor-acceptor (D-A) type DPPPEAs substituted with diphenylamino groups showed strong solvatofluorochromism derived from the charge-transfer (CT) state. Notably, carbazolyl derivatives exhibited fluorescence from LE hybridized with CT state. The disappearance of CT emission in rigid media suggests that solvent reorganization plays a crucial role in producing large Stokes shifts of D-A type derivatives. The DPPPEAs have also been found to function as annihilators in porphyrin-sensitized triplet–triplet annihilation processes.

      DOI: 10.1002/cptc.202200100

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    • Stereoselective Transesterification of P ‐Chirogenic Hydroxybinaphthyl Phosphinates Peer-reviewed International journal

      Akari Kawajiri, Taro Udagawa, Mao Minoura, Toshiaki Murai

      ChemistryOpen11 ( 11 ) e202100294   8 3 2022

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:Wiley  

      The substitution reaction of phosphinates with a binaphthyloxy group at the phosphorus atom with lithium alkoxides proceeded with good to high efficiencies to give P-chirogenic phosphinates with a high enantiomeric ratio. As alcohols, primary, secondary, and tertiary alcohols could be used, and the use of tert-butyl alcohol yielded the products with a higher enantiomeric ratio. A substrate with two different alkyl groups on the phosphorus atom could also participate in the substitution reaction to give the corresponding products in good yields with excellent selectivity. The molecular structures of one of the substrates and the corresponding products, determined by X-ray analyses, proved that the substitution reaction at the phosphorus atom proceeded with inversion of the absolute configuration. The usefulness of the reaction was demonstrated by using it to prepare a drug candidate for Duchenne muscular dystrophy. Finally, thionation of the resulting phosphinates was carried out to form P-chirogenic phosphinothioates.

      DOI: 10.1002/open.202100294

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    • Copper(II) Complexes of 10,20-Diaryl-5,15-diazaporphyrin: Alternative Synthesis, Excited State Dynamics, and Substituent Effect on the <sup>1</sup>O<inf>2</inf>-Generation Efficiency Peer-reviewed

      Hikari Ochiai, Tomoaki Miura, Tadaaki Ikoma, Mao Minoura, Haruyuki Nakano, Yoshihiro Matano

      Bulletin of the Chemical Society of Japan95 ( 3 ) 427 - 432   2022

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      The synthesis, excited state dynamics, and substituent effect on the 1O2-generation efficiency of several copper(II) complexes of 5,15-diazaporphyrin (CuDAPs) bearing peripheral substituents are reported. 10,20-Diaryl-CuDAPs were prepared via a new method consisting of metal-templated cyclization and N-dealkylation as key steps. The effect of the β-substituents on the optical and redox properties of CuDAP was stronger than that of the meso-aryl groups, which can be explained by considering the characteristics of the HOMO and LUMO of the DAP ring. The excited state dynamics and 1O2-generation efficiency of CuDAPs were studied using time-resolved spectroscopic techniques; the electronic effect of the meso-aryl groups on the triplet lifetime and 1O2-generation quantum yield was relatively weak, whereas that of the β-(1-pyrazolyl) groups was appreciable. The analysis of the temperature dependence of phosphorescence spectra of 10,20-bis(2,4,6-trimethylphenyl)-CuDAP allowed the energy gap between the excited trip-quartet and trip-doublet states to be determined. The relatively long triplet lifetimes of CuDAPs show their potential for future application as photosensitizers.

      DOI: 10.1246/bcsj.20220002

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    • Primary Phosphines and Phosphine Oxides with a Stereogenic Carbon Center Adjacent to the Phosphorus Atom: Synthesis and Anti-Markovnikov Radical Addition to Alkenes Peer-reviewed

      Toshiaki Murai, Ryota Wada, Kouji Iwata, Yuuki Maekawa, Kazuma Kuwabara, Mao Minoura

      Organics   11 2021

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      DOI: 10.3390/org2040023

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    • Synthesis, Optical Properties, and Electrochemical Behavior of 5,10,15,20-Tetraaryl-5,15-diazaporphyrin-Amine Hybrids Peer-reviewed International journal

      Yuna Satoh, Yutaro Fujita, Naoya Muramatsu, Ko Furukawa, Tadaaki Ikoma, Mao Minoura, Haruyuki Nakano, Yoshihiro Matano

      ChemPlusChem86 ( 10 ) 1476 - 1486   10 2021

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:Wiley  

      This work reports a series of covalently linked hybrids comprising 5,10,15,20-tetraaryl-5,15-diazaporphyrinoids (M-TADAP; M = Ni, Zn, Cu) and amines. M-TADAP-amine hybrids were prepared via the metal-templated cyclization of the corresponding metal(II)-dipyrrin complexes and redox reactions on the DAP unit. In the UV/vis/near-IR absorption spectra of the hybrids containing an 18π-electron DAP ring, broad charge-transfer bands were observed, reflecting the electron-donating property of the para-aminophenyl groups and the electron-accepting property of the 18π TADAP dication. The electrochemical behavior of the M-TADAP-amine hybrids was strongly dependent on the structure of the peripheral amine units. Further electrochemical oxidation of the hybrids bearing N-Ph groups conceivably generated amine-centered radicals, which sequentially underwent irreversible coupling to form benzidine-linked M-TADAP polymer films. The Ni-TADAP-benzidine polymer exhibited the electric conductivity of 2×10−3 S m−1.

      DOI: 10.1002/cplu.202100429

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    • Gas Adsorption in R 2 ‐MOF‐5 Difunctionalized with Alkyl Groups Peer-reviewed

      Koh Sugamata, Sho Kobayashi, Teruyuki Iihama, Mao Minoura

      European Journal of Inorganic Chemistry2021 ( 31 ) 3185 - 3190   20 8 2021

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      Publishing type:Research paper (scientific journal)   Publisher:Wiley  

      Zinc terephthalate metal−organic framework (MOF) MOF-5 and some of its dialkylated derivatives (R2-MOF-5; R=Me, Et, Pr, Bu) were obtained from a solvothermal synthesis using 2,5-dialkyl-1,4-benzenedicarboxylic acids with zinc nitrite. The effect of the solvent on the solvothermal synthesis of R2-MOF-5 was investigated. For R=H and Me, interpenetrating or non-interpenetrating MOFs obtained depending on the choice of reaction solvent, while for R=Et, Pr, and Bu, no such solvent effect was observed, and only jungle-gym-type MOFs were generated. All compounds were fully characterized using powder X-ray diffraction analysis (PXRD), Fourier-transform infrared (FT-IR) spectroscopy, and thermogravimetric analysis (TGA). After activation, all these compounds exhibit significant porosity, as confirmed by N2-, H2-, and CO2-sorption experiments. The N2-adsorption capacity of these compounds depends on the size of the attached alkyl groups, while the H2-uptake values tend to increase for the alkyl-functionalized MOFs relative to the unfunctionalized parent MOFs and exhibit a maximum value for Pr2-MOF-5.

      DOI: 10.1002/ejic.202100466

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    • Synthesis of Dialkyl-Diphosphenes and -Distibenes that Bear Extended Triptycyl Groups Peer-reviewed

      Ryohei Nishino, Mao Minoura

      Bulletin of the Chemical Society of Japan94 ( 12 ) 2919 - 2921   2021

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      Dialkyl-diphosphenes and -distibenes of the type RTrp*2E2 (E = P, Sb; R = H, n-Pr) were synthesized and isolated using the steric protection of extended triptycyl groups (Trp*). The solubility of these diphosphenes and distibenes can be increased by installing a propyl group onto the bridgehead position of the triptycyl core (n-PrTrp*).

      DOI: 10.1246/bcsj.20210350

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    • Broadened bioactivity and enhanced durability of two structurally distinct metal–organic frameworks containing Zn2+ ions and thiabendazole Peer-reviewed International journal

      Daiya Kobayashi, Akira Hamakawa, Yuki Yamaguchi, Toshiaki Takahashi, Mitsuhiro Yanagita, Shigebumi Arai, Mao Minoura

      Dalton Transactions50 ( 21 ) 7176 - 7180   2021

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:Royal Society of Chemistry ({RSC})  

      Novel metal-organic frameworks (MOFs) based on thiabendazole (TBZ) were developed. The two structurally distinct TBZ-MOFs synthesized in this study exhibited enhanced durability and a broader biocidal spectrum than either individual bioactive species (i.e., Zn2+ and TBZ). The characteristics of each TBZ-MOF are related to the coordination modes among the Zn2+ ions and ligand donors. The difference in water solubility between the two TBZ-MOFs due to the structural design allows for the controlled release of the desired bioactive component.

      DOI: 10.1039/D1DT00733E

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    • Chemoselective and Stereoselective Alcoholysis of Binaphthyl Phosphonothioates: Straightforward Access to Both Stereoisomers of Biologically Relevant P-Stereogenic Phosphonothioates Peer-reviewed International journal

      Kazuma Kuwabara, Yuuki Maekawa, Mao Minoura, Toshifumi Maruyama, Toshiaki Murai

      The Journal of Organic Chemistry85 ( 22 ) 14446 - 14455   20 11 2020

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

      P-Stereogenic phosphonothioates have attracted great attention due to their potent biological activities as analogues of phosphoric acids and phosphorothioates. We demonstrate here straightforward access to P-stereogenic phosphonothioates through the use of binaphthyl phosphonothioates as a chiral template. The first-step alcoholysis of binaphthyl phosphonothioates proceeded via a transfer of the axial chirality of a binaphthyl group to the central chirality of a phosphorus atom to give only monoalcohol adducts with moderate to excellent diastereoselectivities. Further alcoholysis of the obtained products in the presence of a small excess of alcohol and base proceeded with complete elimination of a binaphthyl group to give the corresponding P-stereogenic phosphonothioates with high enantiomeric excess. A DFT study of the reaction mechanisms in first-step alcoholysis indicated that the coordination of a sulfur atom to a sodium cation is the key factor in controlling the diastereoselectivities. This method can be applied to prepare both stereoisomers of a G6P analogue with high diastereomeric purity.

      DOI: 10.1021/acs.joc.0c00687

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    • Structural analysis of interpenetrated methyl-modified MOF-5 and its gas-adsorption properties. Peer-reviewed International journal

      Koh Sugamata, Daichi Yanagisawa, Keiko Awano, Teruyuki Iihama, Mao Minoura

      Acta crystallographica. Section C, Structural chemistry76 ( Pt 9 ) 845 - 849   1 9 2020

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      The first example of an interpenetrated methyl-modified MOF-5 with the formula Zn4O(DMBDC)3(DMF)2, where DMBDC2- is 2,5-dimethylbenzene-1,4-dicarboxylate and DMF is N,N-dimethylformamide (henceforth denoted as Me2MOF-5-int), namely, poly[tris(μ4-2,5-dimethylbenzene-1,4-dicarboxylato)bis(N,N-dimethylformamide)-μ4-oxido-tetrazinc(II)], [Zn4(C10H8O4)3O(C3H7NO)2]n, has been obtained from a solvothermal synthesis of 2,5-dimethylbenzene-1,4-dicarboxylic acid and Zn(NO3)2·6H2O in DMF. A systematic study revealed that the choice of solvent is of critical importance for the synthesis of phase-pure Me2MOF-5-int, which was thoroughly characterized by single-crystal and powder X-ray diffraction (PXRD), as well as by gas-adsorption analyses. The Brunauer-Emmett-Teller surface area of Me2MOF-5-int (660 m2 g-1), determined by N2 adsorption, is much lower than that of nonpenetrated Me2MOF-5 (2420 m2 g-1). However, Me2MOF-5-int displays an H2 uptake capacity of 1.26 wt% at 77 K and 1.0 bar, which is comparable to that of non-interpenetrated Me2MOF-5 (1.51 wt%).

      DOI: 10.1107/S2053229620010177

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    • Structural analysis of and selective CO<inf>2</inf>adsorption in mixed-ligand hydroxamate-based metal-organic frameworks Peer-reviewed International journal

      Koh Sugamata, Chikaze Takagi, Keiko Awano, Teruyuki Iihama, Mao Minoura

      Dalton Transactions49 ( 29 ) 9948 - 9952   7 8 2020

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:Royal Society of Chemistry ({RSC})  

      Two mixed-ligand metal-organic frameworks, [Zn2(BDHA)0.5(INA)3] (MOF-1: H2BDHA = benzene-1,4-dihydroxamic acid; HINA = isonicotinic acid) and [Co2(BDHA)0.5(INA)3(DMF)] (MOF-2), were solvothermally synthesized and fully characterized by single-crystal X-ray crystallography as well as N2, H2, and CO2 gas-sorption measurements. The results constitute the first detailed analysis of the bonding environment around the hydroxamates in such MOFs, which are simultaneously decorated with Lewis-basic sites from the hydroxamate moieties and metal sites predisposed for coordinative unsaturation. MOF-2 shows a desirably selective adsorption of CO2 relative to N2.

      DOI: 10.1039/d0dt01105c

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    • N,N-Diarylthiazol-5-amines: Structure-Specific Mechanofluorochromism and White Light Emission in the Solid State Peer-reviewed

      Yuki Tsuchiya, Kirara Yamaguchi, Yohei Miwa, Shoichi Kutsumizu, Mao Minoura, Toshiaki Murai

      Bulletin of the Chemical Society of Japan93 ( 7 ) 927 - 935   15 7 2020

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      A range of N,N-diarylthiazol-5-amines having a 4-pyridyl group on a thiazole ring were developed, and their photophysical properties were elucidated. Their synthesis was achieved by applying our methods to the combination of N-arylmethyl secondary thioamides and N,N-diarylthioformamides. This enabled us to obtain amines with different types of aromatic groups on the nitrogen atom. Their absorption and emission spectra in solution were examined. The 4-pyridyl group gives higher polarity to the amines. The solid-state emissions of the amines were also evaluated. Several amines showed mechanofluorochromism (MFC). A 4-pyridyl group on a thiazole ring was a requisite for the expression of MFC properties. Although N-(5thiazolyl) N,N-di(2-naphthyl)amines did not exhibit MFC by grinding of the pristine powder, white-light emission was observed when the ground powder was fumed with acetone vapor.

      DOI: 10.1246/bcsj.20200083

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    • (Thio)(silyl)carbene and (seleno)(silyl)carbene gold(i) complexes from the reaction of bis(methylene)-λ<sup>4</sup>-sulfane and bis(methylene)-λ<sup>4</sup>-selane with chloro(dimethylsulfide)gold(i) Peer-reviewed International journal

      Koh Sugamata, Yukiko Urao, Mao Minoura

      Dalton Transactions49 ( 23 ) 7688 - 7691   21 6 2020

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      The dinuclear (thio)(silyl)carbene and (seleno)(silyl)carbene gold(i) complexes1and2were obtained from the reaction of two equivalents of AuCl(SMe2) with the stable bis(methylene)-λ4-chalcogenanes3and4, respectively. The reaction proceeds under elimination of the chlorosilane moiety of3and4. Complexes1and2were characterized by spectroscopic and X-ray diffraction (XRD) analyses. The13C NMR signals for the carbene centers of 1 (309 ppm) and 2 (345 ppm) are by more than 150 ppm downfield shifted relative to those for other known (NHC)AuCl complexes. These results indicate that (chalcogeno)(silyl)carbenes, like (amino)(silyl)carbenes, belong to the push-spectator family of carbenes.

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    • Synthesis, structure, and reactivity of a thermally stable dialkylgermylene Peer-reviewed

      Fumiaki Suzuki, Ryohei Nishino, Mariko Yukimoto, Koh Sugamata, Mao Minoura

      Bulletin of the Chemical Society of Japan93 ( 2 ) 249 - 251   1 2 2020

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      The dialkylgermylene Trp*2Ge: (Trp*: peripherally extended sterically demanding alkyl groups based on the triptycyl (Trp) framework), was obtained from the reaction of Trp*Li with GeCl2¢ dioxane. The structure of Trp*2Ge: was unequivocally determined by NMR and UV-vis spectroscopy, mass spectrometry, and a single-crystal X-ray diffraction analysis. Moreover, the reactivity of Trp*2Ge: was examined.

      DOI: 10.1246/BCSJ.20190338

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    • Naphthalene diimide-incorporated helical thienoacene: a helical molecule with high electron mobility, good solubility, and thermally stable solid phase Peer-reviewed International journal

      Nobuhiko Ohtsuka, Masahiro Nakano, Sae Nakagawa, Md. Shahiduzzaman, Makoto Karakawa, Tetsuya Taima, Mao Minoura

      Chemical Communications56 ( 82 ) 12343 - 12346   2020

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      A Naphthalene diimide (NDI)-incorporated helical thienoacene was developed. The compound has high electron mobility (1.4 cm2 V-1 s-1) thanks to its two-dimensional π-π interaction assisted by the intermolecular C-HO hydrogen bonding of the NDI moieties. Moreover, its bow-shaped π-skeleton reduces molecular fluctuation and gives the compound a thermally stable solid phase, which enables us to fabricate thermally stable organic devices.

      DOI: 10.1039/D0CC04634E

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    • 2‐(2‐Hydroxyphenyl)‐5‐aminothiazoles: Synthesis and Properties Involving Dual Emissions Peer-reviewed

      Toshiaki Murai, Mari Yoshihara, Kirara Yamaguchi, Mao Minoura

      Asian Journal of Organic Chemistry8 ( 7 ) 1102 - 1106   7 2019

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      2-(2-Hydroxyphenyl)-5-aminothiazoles were prepared by two different methods to elucidate their photophysical properties. The first synthetic method involved the addition of thioamide dianions derived from secondary thioamides and nBuLi to thioforamides. Alternatively, Pd-catalyzed sequential addition of aromatic groups and diarylamines to commercially available thiazoles led to the precursors of the desired thiazoles. The molecular structures of the resulting thiazoles were determined by X-ray analyses. The thiazoles showed dual-emission in cyclohexane and in the solid state.

      DOI: 10.1002/ajoc.201900194

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      Other Link: https://onlinelibrary.wiley.com/doi/full-xml/10.1002/ajoc.201900194

    • Synthesis of Redox-Switchable 5,15-Dialkyl-10,20-diaryl-5,15-diazaporphyrins and Diversification of Their N-Alkyl Groups Peer-reviewed

      Mai Mutoh, Keisuke Sudoh, Ko Furukawa, Mao Minoura, Haruyuki Nakano, Yoshihiro Matano

      Asian J. Org. Chem8 ( 3 ) 352 - 355   3 2019

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      Nickel(II) and copper(II) complexes of redox-switchable 20π, 19π, and 18π 5,15-dialkyl-10,20-diaryl-5,15-diazaporphyrins were prepared through a metal-templated cyclization method. Furthermore, the terminal silyloxy groups in the peripheral N-alkyl chains were transformed into hydroxy groups by deprotection. It is worth noting that redox reactions between the 19π and 18π systems bearing hydroxy groups caused a change in the water solubility of the diazaporphyrin chromophore.

      DOI: 10.1002/ajoc.201900085

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    • Systematic synthesis and crystal structures of tetraaryltellurium compounds Ar<inf>4</inf>Te<sup>IV</sup> Peer-reviewed

      Sho Kobayashi, Koh Sugamata, Mao Minoura

      Bulletin of the Chemical Society of Japan92 ( 3 ) 661 - 663   2019

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      Hypervalent tetraaryltellurium(IV) compounds of the type Ar4TeIV(1: Ar = C6H5; 2: Ar = p-H3CC6H4; 3: Ar = p-t-BuC6H4; 4: Ar = p-F3CC6H4) were prepared via a convenient one-pot reaction between the isolated corresponding ArLi reagent and TeCl4. X-ray crystallographic analyses of 14 revealed distorted pseudo-trigonal-bipyramidal (TBP) structures for Ar4Te and the TBP character was analyzed by the dihedral angle method.

      DOI: 10.1246/bcsj.20180380

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    • A stable bis(methylene)-λ<sup>4</sup>-selane with a &gt;cSeC&lt; bond containing Se(IV) Peer-reviewed

      K. Sugamata, Y. Urao, M. Minoura

      Chemical Communications55 ( 57 ) 8254 - 8257   2019

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      Bis(methylene)-λ4-selane 1, which represents a new class of heteroallenes, was synthesized and isolated as a stable purple crystalline solid. X-ray crystallographic analysis revealed a bent allene-type structure with pseudo C2v symmetry and a bent CSeC moiety that contains a 3-center-4-electron π-bond. The NMR spectrum of 1 shows compelling evidence for a slow rotation of the SeC moieties at room temperature. The 77Se NMR spectrum of 1 contains one signal in the region characteristic for Se(iv) compounds.

      DOI: 10.1039/c9cc04121d

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    • Nature of the E⋯E′ interactions (E, E′ = O, S, Se, and Te) at naphthalene 1,8-positions with fine details of the structures: Experimental and theoretical investigations Peer-reviewed

      Satoko Hayashi, Manabu Uegaito, Taro Nishide, Eiichiro Tanaka, Waro Nakanishi, Takahiro Sasamori, Norihiro Tokitoh, Mao Minoura

      New Journal of Chemistry43 ( 36 ) 14224 - 14237   2019

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      The intrinsic dynamic and static natures of the E⋯E′ interactions at the 1,8-positions of 1-(MeE)-8-(MeE′)C10H6 [1a-1f (E ≠ E′) and 1g-1j (E = E′)] were elucidated with QTAIM-DFA, after structural determination of 1-(PhE)-8-(PhE′)C10H6 (3a-3f), where (E, E′: x) = (O, S: A), (O, Se: b), (O, Te: c), (S, Se: d), (S, Te: e), (Se, Te: f), (O, O: g), (S, S: h), (Se, Se: i) and (Te, Te: j) (χE ≥ χE′). While the AB structures are confirmed for 3a, 3b and 3d-3f, which consist of the np(E)⋯σ∗(E′-CPh) interactions, the structure was BB for 3c, where the E-CR/E′-CR (R = Ph) bond is perpendicular to the naphthyl plane in A and it is placed on the plane in B. While the AB structures are determined by the p(E)-π(Ph) conjugations, the BB structure is by the crystal packing effect. The BA structure with np(E′)⋯σ∗(E-CPh) was not detected. While the nature of a typical hydrogen bond with covalency was predicted for BB, AA and BA, with the CT-MC (molecular complex formation through charge transfer) nature for AB in 1e and 1f (R = Me for E-CR/E′-CR), the CT-MC nature was predicted for all conformers of 1j, for example. NBO analysis for 1a-1f revealed that the acceptor orbitals contribute much more than the donor orbitals and the order is σ∗(O-CMe: <0.5 kcal mol-1) ≪ σ∗(S-CMe: ≈5 kcal mol-1) ≪ σ∗(Se-CMe: ≈10 kcal mol-1) ≪ σ∗(Te-CMe: ≈16 kcal mol-1) for np(S), np(Se) and np(Te). The E(2) values proportionally correlate to Cii-1 for AB and/or BA of 1a-1j, if analyzed separately for σ∗(S-C), σ∗(Se-C) and σ∗(Te-C).

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    • Double aromaticity arising from σ- and π-rings Peer-reviewed

      Shunsuke Furukawa, Masahiro Fujita, Yoshihiko Kanatomi, Mao Minoura, Miho Hatanaka, Keiji Morokuma, Kazuya Ishimura, Masaichi Saito

      Communications Chemistry1 ( 1 )   1 12 2018

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      Aromaticity has been a central concept in chemistry since the discovery of benzene in the 19th century and has impacted the science of delocalized π-electron systems. The aromaticity of conventional aromatic compounds usually originates from electron delocalization through a single ring that consists of π-symmetric orbitals. Although double aromaticity, i.e. aromaticity composed of two circularly delocalized orbitals, has been theoretically predicted for over 20 years, the double aromaticity of a bench-stable compound is not well explored by experiment. Here we report the synthesis and isolation of the dication of hexakis(phenylselenyl)benzene, as well as its double aromaticity based on structural, energetic, and magnetic criteria. In this dication, cyclic σ-symmetric and π-symmetric delocalized orbitals are formally occupied by ten and six electrons, respectively, and the aromaticity thus follows the 4n + 2 (n = 1, 2,…) electron Hückel rule, regardless of the σ-orbital or π-orbital symmetry.

      DOI: 10.1038/s42004-018-0057-4

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    • Hydrolysis of Phosphonothioates with a Binaphthyl Group: P-Stereogenic O-Binaphthyl Phosphonothioic Acids and Their Use as Optically Active Ligands and Chiral Discriminating Agents Peer-reviewed International journal

      Kuwabara Kazuma, Maekawa Yuuki, Minoura Mao, Murai Toshiaki

      ORGANIC LETTERS20 ( 5 ) 1375 - 1379   2 3 2018

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      The hydrolysis of phosphonothioates with a binaphthyl group afforded the first example of O-(2′-hydroxy)binaphthyl phosphonothioic acids in good to high yields and >95:5 diastereoselectivity. The reaction proceeds via an axis-to-center chirality-transfer reaction. The ability of these acids to act as chiral molecular auxiliaries was demonstrated by using them as optically active ligands for the asymmetric ethylation of benzaldehyde and as a chiral discriminating agent for chiral aliphatic amines.

      DOI: 10.1021/acs.orglett.8b00147

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    • Direct and Regioselective Amination of β-Unsubstituted 5,15-Diazaporphyrins with Amines: A Convenient Route to Near-Infrared-Responsive Diazaporphyrin Sensitizers Peer-reviewed

      Satoshi Omomo, Takuma Sugai, Mao Minoura, Haruyuki Nakano, Yoshihiro Matano

      Angewandte Chemie130 ( 14 ) 3859   3 2018

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      DOI: 10.1002/ange.201800471

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    • Synthesis of a peripherally extended triptycyl group as an aliphatic steric protection group and its application to the kinetic stabilization of an aliphatic sulfenic acid<sup>#</sup> Peer-reviewed

      Mariko Yukimoto, Ryohei Nishino, Fumiaki Suzuki, Michihiro Ishihara, Koh Sugamata, Mao Minoura

      Chemistry Letters47 ( 4 ) 425 - 428   2018

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      Trp*, a novel triptycene (Trp)-based aliphatic steric protection group was synthesized, and its potential to offer kinetic stabilization by steric protection was evaluated in the context of synthesizing a sulfenic acid (RSOH), i.e., a highly reactive sulfur-containing species. The isolated sulfenic acid Trp*SOH is thermally very stable, which clearly demonstrates the steric protection provided by Trp*.

      DOI: 10.1246/cl.171230

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    • The synthesis of a novel bulky primary alkyl group and its application toward the kinetic stabilization of a tetraalkyldisilene Peer-reviewed

      Mariko Yukimoto, Mao Minoura

      Bulletin of the Chemical Society of Japan91 ( 4 ) 585 - 587   2018

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      A novel, peripherally extended sterically demanding primary alkyl group based on the triptycene (Trp) framework, Trp∗CH2, was designed and synthesized via a convenient one-pot reaction using the Friedel-Crafts alkylation of the corresponding TrpCH2 precursor. The introduction of the Trp∗CH2 groups onto a Si=Si double bond allowed isolating the first stable tetraalkyldisilene that contains primary alkyl groups.

      DOI: 10.1246/bcsj.20170422

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    • Heterobimetallic triple-decker complexes derived from a dianionic aromatic stannole ligand Peer-reviewed International journal

      Masaichi Saito, Naoki Matsunaga, Jumpei Hamada, Shunsuke Furukawa, Mao Minoura, Susann Wegner, Juri Barthel, Christoph Janiak

      Dalton Transactions47 ( 27 ) 8892 - 8896   2018

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      A neutral heterobimetallic triple-decker stannole complex was prepared by the reaction of an anionic ruthenocene bearing a stannole dianionic ligand with [Rh(cod)Cl]2 (cod = 1,5-cyclooctadiene), and the resulting Ru-Rh complex exhibits an electronic property different from those of the corresponding Ru-Ru and Rh-Rh complexes. The Ru-Rh complex can be decomposed in ionic liquids to metal nanoparticles.

      DOI: 10.1039/C8DT01455H

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    • Group 2 metal bis(arenecarbochalcogenoate)(crown ether) complexes: Isolation and structural analysis Peer-reviewed International journal

      Yoshiharu Tatematsu, Shinzi Kato, Norio Nakata, Masahiro Ebihara, Osamu Niyomura, Koh Sugamata, Mariko Yukimoto, Mao Minoura

      Dalton Transactions47 ( 29 ) 9787 - 9794   2018

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      A series of Group 2 metal bis(arenecarbochalcogenoato)(crown ether) complexes M(EE′CAr)2(L)(L′)x (M = Mg, Ca, Sr, Ba; Ar = aryl; E = S, Se; E′ = O, S; L = H2O or THF; L′ = 15-crown-5, 18-crown-6) were synthesized and their structures were revealed by X-ray analyses. The two carbothioato ligands in Mg, Ca and Sr 15-crown-5 complexes are located on the same side of the crown ether plane, while those in Mg, Ca, Sr, and Ba 18-crown-6 compounds are on both sides of the 18-crown-6 plane (trans relative to the plane). For the Ca 15-crown-5 complex, both carbothioato ligands are connected to the central Ca ion through an oxygen atom in a monodentate manner, and the two hydrogen atoms of the coordinated water molecule are intramolecularly hydrogen-bonded with thiocarbonyl sulfur atoms. One of the two carbothioate groups in the Ca 18-crown-6 complex is connected in a bidentate manner to the central metal, while the other is connected in a monodentate manner through an oxygen atom. The two thiocarboxylato ligands in the Sr 15-crown-5 congener are connected in a bidentate fashion to the same side of the crown ether plane. The Ca and Sr compounds are the first examples of alkali earth metal carbochalcogenoate complexes in which carbochalcogenolato ligands are connected in a monodentate manner through an oxygen atom. Both chalcogenoato ligands in Ba(SOCC6H4Me-4)2(18-crown-6) and Sr(SeOCC6H4Me-4)2(18-crown-6) are coordinated in a bidentate manner to the central metal ion.

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    • β-Functionalization of 5,15-Diazaporphyrins with Phosphorus, Oxygen, and Sulfur-Containing Substituents Peer-reviewed

      Takuma Sugai, Mao Minoura, Haruyuki Nakano, Yoshihiro Matano

      Bulletin of the Chemical Society of Japan91 ( 8 ) 1264 - 1266   2018

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      The β-functionalization of 5, 15-diazaporphyrins (DAPs) with phosphoryl, phenoxy, sulfanyl, and sulfonyl groups was achieved by either cross-coupling or aromatic nucleophilic substitution reactions of β-bromo- and β, β′-dibromo-DAPs. The heteroatom-containing functional groups at the β- positions strongly affected the redox properties of the DAP π-systems.

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    • Regioselective Functionalization at the 7-Position of 1,2,3-Triphenyl[b]benzophosphole Oxide via P=O-Directed Lithiation Peer-reviewed International journal

      Ayana Wakatsuki, Mariko Yukimoto, Mao Minoura, Kaori Fujii, Yoshifumi Kimura, Yoshihiro Matano

      Dalton Transactions47 ( 21 ) 7123 - 7127   2018

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      Various 7-substituted benzo[b]phosphole derivatives were prepared by PO-directed lithiation of 1,2,3-triphenylbenzo[b]phosphole P-oxide and subsequent iodination and cross-coupling reactions. The electron-donating groups introduced at the 7-position produced dramatic solvatofluorochromism owing to the strong charge-transfer character of the excited state of the entire π-system.

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    • Direct and Regioselective Amination of β-Unsubstituted 5,15-Diazaporphyrins with Amines: A Convenient Route to Near-Infrared-Responsive Diazaporphyrin Sensitizers Peer-reviewed International journal

      Satoshi Omomo, Takuma Sugai, Mao Minoura, Haruyuki Nakano, Yoshihiro Matano

      Angewandte Chemie International Edition57 ( 14 ) 3797 - 3800   2018

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      We have established a convenient method for the base-promoted direct amination of β-unsubstituted 5,15-diazaporphyrins (DAPs) with secondary and primary amines to produce 3,7,13,17-tetraamino- and 3-amino-DAPs, respectively, regioselectively. The amino groups attached at the periphery cause significant red shifts of the absorption bands as a result of their perturbation of the HOMO and/or LUMO in the DAP π-system. The palladium complex of a 3,7,13,17-tetrakis(diphenylamino)-DAP generated singlet oxygen in high yield under irradiation with near-infrared light.

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    • Syntheses, Properties, and Catalytic Activities of Metal(II) Complexes and Free Bases of Redox-Switchable 20 pi, 19 pi, and 18 pi 5,10,15,20-Tetraaryl-5,15-diazaporphyrinoids Peer-reviewed International journal

      Keisuke Sudoh, Takaharu Satoh, Toru Amaya, Ko Furukawa, Mao Minoura, Haruyuki Nakano, Yoshihiro Matano

      CHEMISTRY-A EUROPEAN JOURNAL23 ( 64 ) 16364 - 16373   11 2017

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      In spite of significant advances in redox-active porphyrin-based materials and catalysts, little attention has been paid to 20 pi and 19 pi porphyrins because of their instability in air. Here we report the meso-modification of 5,10,15,20-tetraarylporphyrin with two nitrogen atoms, which led to redox-switchable 20 pi, 19 pi, and 18 pi 5,10,15,20-tetraaryl-5,15-diazaporphyrinoids (TADAPs). Three kinds of metal(II) complexes and free bases of TADAP were prepared by the metal-templated annulation of the corresponding metal-bis(dipyrrin) complexes. The inductive and resonance effects of the meso-nitrogen atoms on the aromatic, optical, electrochemical, and magnetic properties of the entire TADAP pi-systems were assessed by using various spectroscopic measurements and density functional theory calculations. The aromaticity and pi-pi* electronic transition energies of the TADAPs varied considerably, and were shown to be dependent on the oxidation states of the pi-systems. In contrast to the isoelectronic 5,10,15,20-tetraarylporphyrin derivatives, the 20 pi and 19 pi TADAPs were chemically stable under air. In particular, the 19 pi TADAP radical cations were extremely stable towards dioxygen, moisture, and silica gel. This reflected the low-lying singly occupied molecular orbitals of their pi-systems and the efficient delocalization of their unshared electron spin. The capability of MgTADAP to catalyze aerobic biaryl formation from aryl Grignard reagents was demonstrated, which presumably involved a 19 pi/20 pi redox cycle.

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    • Anisotropic Crystals Based on a Main-Group Coordination Polymer with Alignment of Rigid π Skeletons Peer-reviewed

      Masaichi Saito, Tomoki Akiba, Shunsuke Furukawa, Mao Minoura, Masahiko Hada, Hiroshi Y. Yoshikawa

      Organometallics36 ( 14 ) 2487 - 2490   24 7 2017

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      We succeeded in the alignment of π skeletons, resulting in the formation of anisotropic crystals. The combination of plumbacyclopentadienylidene, which has a divalent lead atom incorporated into the π skeleton, and 1,4-dioxane afforded a coordination polymer, where the π skeletons are completely aligned in the same direction. The resulting plumbylene chains are also aligned in the same direction in the solid state, and therefore the crystals are noncentrosymmetric, showing second-harmonic generation (SHG) properties. Using pyrazine instead of 1,4-dioxane afforded an adduct composed of three plumbole units and two pyrazine molecules, and the crystals are symmetric and exhibit no SHG properties. The solid-state structures and optical properties are highly dependent on the Lewis base utilized. The present findings spotlight the use of group 14 divalent species incorporated into a π skeleton as a novel, useful method for the creation of a π-aligned coordination polymer with NLO properties.

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    • Nitrogen-Bridged Metallodiazaporphyrin Dimers: Synergistic Effects of Nitrogen Bridges and meso-Nitrogen Atoms on Structure and Properties Peer-reviewed International journal

      Masahiro Kawamata, Takuma Sugai, Mao Minoura, Yasuhisa Maruyama, Ko Furukawa, Cole Holstrom, Victor N. Nemykin, Haruyuki Nakano, Yoshihiro Matano

      CHEMISTRY-AN ASIAN JOURNAL12 ( 7 ) 816 - 821   4 2017

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      NH-bridged and pyrazine-fused metallodiazaporphyrin dimers have been prepared from nickel(II) and copper(II) complexes of 3-amino-5,15-diazaporphyrin by Pd-catalyzed C-N cross-coupling and oxidative dimerization reactions, respectively. The synergistic effects of the nitrogen bridges and meso-nitrogen atoms play major roles in enhancing the light-harvesting properties and delocalization of an electron spin over the entire pi-skeletons of the metallodiazaporphyrin dimers.

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    • Synthesis and reactivity of a ruthenocene-type complex bearing an aromatic π-ligand with the heaviest group 14 element Peer-reviewed International journal

      Marisa Nakada, Takuya Kuwabara, Shunsuke Furukawa, Masahiko Hada, Mao Minoura, Masaichi Saito

      Chemical Science8 ( 4 ) 3092 - 3097   2017

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      An anionic ruthenocene derived from a dilithioplumbole complex was prepared. In the complex, the plumbole ligand coordinates a ruthenium atom in an η5-fashion, similar to the cyclopentadienyl ligand in ferrocene. The ruthenocene that has the aromatic π-ligand with the heaviest group 14 element reacted with electrophiles to afford the plumbole complexes wherein the plumbole ligands show deviation from planarity, in contrast to the planar plumbole ring in the anionic ruthenocene. The bent angles of the plumbole ligands are dependent on the substituents on the lead atoms. Cyclic voltammetry measurements revealed that the plumbole complexes are oxidized more easily than the corresponding stannole complexes.

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    • Nitrogen-Bridged Metallodiazaporphyrin Dimers: Synergistic Effects of Nitrogen Bridges and meso-Nitrogen Atoms on Structure and Properties Peer-reviewed International journal

      Masahiro Kawamata, Takuma Sugai, Mao Minoura, Yasuhisa Maruyama, Ko Furukawa, Cole Holstrom, Victor N. Nemykin, Haruyuki Nakano, Yoshihiro Matano

      Chemistry-An Asian Journal12 ( 7 ) 816 - 821   2017

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      NH-bridged and pyrazine-fused metallodiazaporphyrin dimers have been prepared from nickel(II) and copper(II) complexes of 3-amino-5,15-diazaporphyrin by Pd-catalyzed C-N cross-coupling and oxidative dimerization reactions, respectively. The synergistic effects of the nitrogen bridges and meso-nitrogen atoms play major roles in enhancing the light-harvesting properties and delocalization of an electron spin over the entire π-skeletons of the metallodiazaporphyrin dimers.

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    • Syntheses, Properties, and Catalytic Activities of Metal(II) Complexes and Free Bases of Redox-Switchable 20π, 19π, and 18π 5,10,15,20-Tetraaryl-5,15-diazaporphyrinoids Peer-reviewed International journal

      Keisuke Sudoh, Takaharu Satoh, Toru Amaya, Ko Furukawa, Mao Minoura, Haruyuki Nakano, Yoshihiro Matano

      Chemistry-A European Journal23 ( 64 ) 16364 - 16373   2017

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      In spite of significant advances in redox-active porphyrin-based materials and catalysts, little attention has been paid to 20π and 19π porphyrins because of their instability in air. Here we report the meso-modification of 5,10,15,20-tetraarylporphyrin with two nitrogen atoms, which led to redox-switchable 20π, 19π, and 18π 5,10,15,20-tetraaryl-5,15-diazaporphyrinoids (TADAPs). Three kinds of metal(II) complexes and free bases of TADAP were prepared by the metal-templated annulation of the corresponding metal-bis(dipyrrin) complexes. The inductive and resonance effects of the meso-nitrogen atoms on the aromatic, optical, electrochemical, and magnetic properties of the entire TADAP π-systems were assessed by using various spectroscopic measurements and density functional theory calculations. The aromaticity and π-π* electronic transition energies of the TADAPs varied considerably, and were shown to be dependent on the oxidation states of the π-systems. In contrast to the isoelectronic 5,10,15,20-tetraarylporphyrin derivatives, the 20π and 19π TADAPs were chemically stable under air. In particular, the 19π TADAP radical cations were extremely stable towards dioxygen, moisture, and silica gel. This reflected the low-lying singly occupied molecular orbitals of their π-systems and the efficient delocalization of their unshared electron spin. The capability of MgTADAP to catalyze aerobic biaryl formation from aryl Grignard reagents was demonstrated, which presumably involved a 19π/20π redox cycle.

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    • A Self-Assembled Rectangular Host with Terpyridine-Platinum(II) Moieties That Binds Unsubstituted Pentacene in Solution Peer-reviewed

      Yusuke Yamaki, Takashi Nakamura, Sayuri Suzuki, Masaki Yamamura, Mao Minoura, Tatsuya Nabeshima

      European Journal of Organic Chemistry2016 ( 9 ) 1678 - 1683   1 3 2016

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      Pentacene has attracted much attention as an organic electric material, but it often suffers from its very low solubility. We now report self-assembled rectangular host 18+ that has two pairs of terpyridine-PtII moieties aligned parallel to each other and connected by diyne linkers. The host encapsulated unsubstituted pentacene (2) with a remarkably strong binding constant of Ka ≈ 107 M-1 and solubilized it in acetonitrile up to the millimolar level. For smaller acenes (i.e., naphthalene to tetracene), a planar arrangement of two molecules inside the cavity was achieved. These results made it possible to analyze the acenes in the solution phase and provided a way to align the guests by a solution-processing method as a possible application, and thus, they contribute to fundamental physical organic chemistry as well as organic electronics.

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    • Redox-Switchable 20π-, 19π-, and 18π-Electron 5,10,15,20-Tetraaryl-5,15-diazaporphyrin -oid Nickel(II) Complexe Peer-reviewed International journal

      Satoh T, Minoura M, Nakano H, Furukawa K, Matano Y

      Angewandte Chemie International Edition55 ( 6 ) 2235 - 2238   5 2 2016

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      The first examples of air-stable 20π-electron 5,10,15,20-tetraaryl-5,15-diaza-5,15-dihydroporphyrins, their 18π-electron dications, and the 19π-electron radical cation were prepared through metal-templated annulation of nickel(II) bis(5-arylamino-3-chloro-8-mesityldipyrrin) complexes followed by oxidation. The neutral 20π-electron derivatives are antiaromatic and the cationic 18π-electron derivatives are aromatic in terms of the magnetic criterion of aromaticity. The meso N atoms in these diazaporphyrinoids give rise to characteristic redox and optical properties for the compounds that are not typical of isoelectronic 5,10,15,20-tetraarylporphyrins.

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    • Redox-Switchable 20-, 19-, and 18-Electron 5,10,15,20-Tetraaryl-5,15-diazaporphyrinoid Nickel(II) Complexes Peer-reviewed

      Takaharu Satoh, Mao Minoura, Haruyuki Nakano, Ko Furukawa, Yoshihiro Matano

      ANGEWANDTE CHEMIE-INTERNATIONAL EDITION55 ( 6 ) 2235 - 2238   2 2016

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      The first examples of air-stable 20-electron 5,10,15,20-tetraaryl-5,15-diaza-5,15-dihydroporphyrins, their 18-electron dications, and the 19-electron radical cation were prepared through metal-templated annulation of nickel(II) bis(5-arylamino-3-chloro-8-mesityldipyrrin) complexes followed by oxidation. The neutral 20-electron derivatives are antiaromatic and the cationic 18-electron derivatives are aromatic in terms of the magnetic criterion of aromaticity. The meso Natoms in these diazaporphyrinoids give rise to characteristic redox and optical properties for the compounds that are not typical of isoelectronic 5,10,15,20-tetraarylporphyrins.

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    • Phosphonoselenoic acid esters from the reaction between phosphoroselenoyl chlorides and Grignard reagents: synthetic and stereochemical aspects Peer-reviewed

      Toshiaki Murai, Yuuki Maekawa, Yuuki Hirai, Kazuma Kuwabara, Mao Minoura

      RSC ADVANCES6 ( 18 ) 15180 - 15183   2016

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      Substitution reactions between a phosphoroselenoyl chloride and Grignard reagents proceeded smoothly at the phosphorus atom to furnish phosphonoselenoic acid esters. The resulting mixture of diastereoisomers could be readily distinguished on the basis of P-31 NMR, and separated by recrystallization or column chromatography to afford diastereoisomerically enriched products. For one of these diastereoisomers, the absolute configuration was determined by carrying out a single-crystal X-ray diffraction analysis.

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    • A reversible two-electron redox system involving a divalent lead species International journal

      Masaichi Saito, Marisa Nakada, Takuya Kuwabara, Mao Minoura

      Chemical Communications51 ( 22 ) 4674 - 4676   18 3 2015

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      Reduction of THF-stabilized plumbacyclopentadienylidene with lithium afforded dilithioplumbole. On the other hand, oxidation of the dilithioplumbole provided the starting plumbacyclopentadienylidene. This is the unprecedented example of a reversible interconversion between group 14 M(ii) and its dianionic species bearing organic substituents. This journal is

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    • Unexpected dehalogenation reactions of dichloroborane bearing a NCN-pincer ligand: Formation of a borenium salt

      Masaichi Saito, Kaori Matsumoto, Masahiro Fujita, Mao Minoura

      Heteroatom Chemistry25 ( 5 ) 354 - 360   1 11 2014

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      2,6-Bis[(diisopropylamino)methyl]phenyllithium 1 reacted with trichloroborane etherate to afford dichloroarylborane 4. The treatment of 4 with Ag triflate provided bistriflate 5. The reaction of 4 with AgBF<inf>4</inf>, however, afforded an unexpected product, borenium salt 6.

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    • Synthesis, structure, and thermolysis of tetracoordinated 1λ<sup>4</sup>,2-selenazetidines bearing two chiral centers at the 3-and 4-positions

      Yuya Daicho, Naokazu Kano, Mariko Yukimoto, Mao Minoura, Takayuki Kawashima

      Heteroatom Chemistry25 ( 5 ) 492 - 499   1 11 2014

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      The title trans and cis isomers (trans-3 and cis-3) were successfully synthesized as stable compounds by taking advantage of the Martin ligand. The X-ray crystallographic analysis of trans-3 showed that it has a distorted pseudotrigonal bipyramidal structure, and that the two phenyl groups at the 3-and 4-positions are cis to each other. The thermolysis of trans-3 in the presence of excess dimethyl acetylenedicarboxylate (DMAD) gave a mixture of the corresponding aziridines (trans-7 and cis-7) and cycloadducts (11a and 11b) of the azomethine ylides formed by ring opening of the aziridines with DMAD. Heating of cis-7 and excess DMAD under the same conditions gave diastereomeric mixtures of both the aziridines and the cycloadducts, which means that the stereochemistry of the aziridine formation from the 1,2-selenazetidine cannot be determined in this system.

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    • Enhancement of stannylene character in stannole dianion equivalents evidenced by NMR and Mössbauer spectroscopy and theoretical studies of newly synthesized silyl-substituted dilithiostannoles

      Takuya Kuwabara, Jing Dong Guo, Shigeru Nagase, Mao Minoura, Rolfe H. Herber, Masaichi Saito

      Organometallics33 ( 11 ) 2910 - 2913   9 6 2014

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      Dilithiostannoles, which are aromatic tin-containing ring compounds, were proposed to have stannylene character, as judged from their NMR analysis. We herein report on the synthesis of silyl-substituted dilithiostannoles, which were characterized by NMR spectroscopy and X-ray diffraction analysis. The silyl-substituted derivatives also exhibit features characteristic of aromatic dilithiostannoles such as 7Li NMR signals at high-field area and no C-C bond alternation in the stannole rings. Theoretical calculations and the 119Sn NMR chemical shifts revealed that the stannylene character in the silyl-substituted dilithiostannoles is enhanced due to greater interaction between 5p (Sn) and LUMO (butadiene) in comparison to those in alkyl and aryl derivatives. The 119Sn Mössbauer spectra of dilithiostannoles were measured for the first time, indicating that each of the tin atoms in dilithiostannoles can be characterized as having Sn(II) character. © 2014 American Chemical Society.

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    • Synthesis and structures of monomeric group 14 triols and their reactivity

      Lucian Cristian Pop, Nobuaki Kurokawa, Hiroaki Ebata, Katsuya Tomizawa, Tomoyuki Tajima, Masatoshi Ikeda, Michikazu Yoshioka, Monique Biesemans, Rudolph Willem, Mao Minoura, Masaichi Saito

      Canadian Journal of Chemistry92 ( 6 ) 542 - 548   6 2014

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      The first stable stannanetriol and germanetriol bearing sterically congested aryl groups were synthesized by hydrolysis of the corresponding trichloro-stannane and-germane.The stannanetriol is monomeric in solution as well as in the crystalline state, as evidenced by X-ray diffraction analysis and CP-MAS NMR spectroscopy.The stannanetriol reacted with silicone grease to afford a cagelike compound having three Sn-O-Si-O-Sn linkages in the molecule.All the group 14 triols can be converted to the corresponding trihalo compounds in good yields.© 2014 Published by NRC Research Press.

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    • Aziridine formation with retention of configuration from a pentacoord inated 1, 2-thiazetidine bearing two chiral centers at the 3- And 4-positions

      Yuya Daicho, Yuki Watanabe, Naokazu Kano, Mariko Yukimoto, Mao Minoura, Takayuki Kawashima

      Bulletin of the Chemical Society of Japan87 ( 9 ) 1005 - 1012   2014

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      Tetracoordinated and pentacoordinated 1,2-thiazetidines bearing the Martin ligand, trans-5 and trans-6, were synthesized as stable compounds. The X-ray crystallographic analyses showed that trans-5 and trans-6 have distorted pseudotrigonal bipyramidal (pseudo-TBP) and TBP structures, respectively, and that the two phenyl groups at the 3- and 4-positions of both compounds are cis to each other. Thermal isomerization of the aziridine cis-11, which is considered a thermolysis product of trans-6, occurred even at relatively low temperature (100°C) in solution and made it difficult to determine the stereochemistry of the aziridine formation from trans-6 in solution. Flash vacuum pyrolysis, which potentially prevents the isomerization of the product, was applied to trans-6 to give eventually the stereochemistry-retained aziridine cis-11. This result indicates a ligand coupling pathway in the aziridine formation process from trans-6.

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    • Fluorinative hydrolysis of phosphorothioic acid esters with a binaphthyl group through axis-to-center chirality transfer leading to the formation of P-chiral phosphorothioic monofluoridic acid salts Peer-reviewed International journal

      Murai Toshiaki, Hayashi Takae, Yamada Kyohei, Maekawa Yuuki, Minoura Mao

      CHEMICAL COMMUNICATIONS50 ( 83 ) 12473 - 12475   2014

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      Asymmetric synthesis of P-chiral phosphorothioic monofluoridic acid ammonium salts was achieved via axis-to-center chirality transfer reactions by using phosphorothioic acid O-esters with a binaphthyl group, and the absolute stereochemistry of the salts was determined by X-ray analyses and by comparison of their CD spectra.

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    • Synthesis, structure, and reactivity of lewis base stabilized plumbacyclopentadienylidenes International journal

      Masaichi Saito, Tomoki Akiba, Misumi Kaneko, Toshiaki Kawamura, Minori Abe, Masahiko Hada, Mao Minoura

      Chemistry - A European Journal19 ( 50 ) 16946 - 16953   9 12 2013

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      Plumbacyclopentadienylidenes, in which the lead atoms have divalent states and are coordinated by THF, pyridine and N-heterocyclic carbene, were synthesized and characterized. The THF-and pyridine-stabilized compounds can be regarded as rare examples of hypervalent 10-X-4 species. The equilibrium between the THF adduct and the free plumbacyclopentadienylidene was evidenced by spectroscopic analysis and theoretical calculations. The THF adduct in benzene converted into a plumbylene dimer, where one of the lead centers is coordinated by THF and the other lead atom is coordinated by a divalent lead atom, the dimer gradually decomposing into spiroplumbole. The THF adduct unexpectedly reacted with trifluoroborane and trichlorogallane to afford fluoroborole and chlorogallole, which are the first examples of non-annulated fluoroborole and gallole, respectively. Plumbacyclopentadienylidenes, in which the lead atoms have divalent states and are coordinated by THF, pyridine, and an N-heterocyclic carbene, were synthesized and characterized. The THF-stabilized compound can be regarded as a rare example of hypervalent 10-X-4 species, which converts into a plumbylene dimer and reacts with trifluoroborane and trichlorogallane to afford the corresponding fluoroborole and chlorogallole, respectively (see scheme; R=Me2tBuSi). © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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    • Synthesis of new dipyrido-annulated N-heterocyclic carbenes with ortho substituents International journal

      Shin Ichi Fuku-En, Junki Yamamoto, Mao Minoura, Satoshi Kojima, Yohsuke Yamamoto

      Inorganic Chemistry52 ( 20 ) 11700 - 11702   21 10 2013

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      A method for the introduction of various substituents at the 4 and 8 positions of 2,10-di-tert-butyldipyrido[1,2-c;2′,1′-e]imidazolium salts, is described. The new imidazolium salts bearing substituents (R′ = Cl, SPh) at the 4 and 8 positions are synthesized in three-step procedures, and carbenes generated from the imidazolium salts can be used to give the corresponding rhodium complexes. The role of the 4,8-substituents can be either bystanders or coordinating ligands according to the nature of the metal moiety. © 2013 American Chemical Society.

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    • Studies on chalcogen-containing heterocycles. Part 38: Regio- and stereoselective tandem addition-iodocyclization of 2-ethynylphenyl isothiocyanates with N- and O-nucleophiles affording 4-(iodoalkylidene)benzo[d] [1,3]thiazines

      Haruki Sashida, Mamoru Kaname, Mao Minoura

      Tetrahedron69 ( 31 ) 6478 - 6487   5 8 2013

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      The treatment of the o-ethynylphenyl isothiocyanates with primary and secondary amines in 1,2-DCE, followed by the addition of I2 and then heating resulted in the regio- and stereoselective tandem addition- iodocyclization to give the (4E)-2-amino-4-(1-iodomethylidene)benzo[d][1,3] thiazine derivatives as the sole product in high yields via the 6-exo-dig mode cyclization. The 2-alkoxy-1,3-benzothiazines were similarly produced from the o-ethynylphenyl isothiocyanates and the corresponding sodium alkoxides. © 2013 Elsevier Ltd. All rights reserved.

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    • Studies on chalcogen-containing heterocycles. Part 37: M-CPBA oxidation of isotellurochromenes and isoselenochromenes

      Haruki Sashida, Mamoru Kaname, Kazuo Ohyanagi, Mao Minoura

      Tetrahedron68 ( 51 ) 10502 - 10509   23 12 2012

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      The oxidation of the 1-unsubstituted isotellurochromenes and isoselenochromenes with m-CPBA resulted in a novel ring-opening reaction to give the o-formyl distyryl ditellurides and diselenides as the sole products in good yields, respectively. The o-benzoyl distyryl ditelluride and diselenide were also produced from the corresponding 1-phenylisochromenes. In contrast, the 1-benzyl and 1-n-butylisochromenes were oxidized to afford the (Z)-1-benzylideneisochromenes and (Z)-1-butylideneisochromenes under similar conditions; no distyryl compounds were obtained. The distyryl compounds were also obtained by the hydrolysis of the corresponding 2-benzochalcogenopyrylium salts, which were easily converted from the 2-benzoisochromenes by treatment with triphenylcarbenium tetrafluoroborate (Ph 3C+BF 4-). © 2012 Elsevier Ltd. All rights reserved.

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    • Synthesis, structures, and optical properties of heterasumanenes containing group 14 elements and their related compounds

      Tomoharu Tanikawa, Masaichi Saito, Jing Dong Guo, Shigeru Nagase, Mao Minoura

      European Journal of Organic Chemistry ( 36 ) 7135 - 7142   12 2012

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      Triphenylenogermole, triphenylenodigermole, and trigermasumanene were prepared by repetitive lithiation of triphenylene followed by introduction of germanium functionalities. This is the first example of a trigermasumanene. Tin congeners were also synthesized and investigated. X-ray diffraction analysis of trisilasumanene 6, which does not have any substituents on the carbon atoms of the benzene rings, is also demonstrated. The optical properties of trigermasumanene and its derivatives were investigated by UV/Vis and fluorescence spectroscopy. Theoretical calculations were carried out to understand the properties of the thus-obtained triphenylenometallole derivatives. © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

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    • Molecular structure and electronic state of the dibenzo[a,e]pentalene anion radical International journal

      Masaichi Saito, Yoko Hashimoto, Tomoyuki Tajima, Kazuya Ishimura, Shigeru Nagase, Mao Minoura

      Chemistry - An Asian Journal7 ( 3 ) 480 - 483   5 3 2012

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      Undergoing a radical change! The reduction of dibenzo[a,e]pentalene by KC 8 afforded the corresponding anion radical, the structure of which was characterized for the first time by X-ray diffraction analysis. The electronic state of the anion radical is discussed with the aid of theoretical calculations. © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

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    • 2D s-d mixed-metal coordination polymer containing potassium, chromium(III) and dipicolinate ions: Preparation and crystal structure

      Mohammad Hakimi, Boris Marko Kukovec, Mao Minoura

      Journal of Chemical Crystallography42 ( 3 ) 290 - 294   3 2012

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      The reaction of pyridine-2,6-dicarboxylic acid (dipicolinic acid, dipicH2) with potassium tetraperoxochromate( V) in the mixture of water and ethanol led to the formation of a 2D s-d mixed-metal coordination polymer of {K[Cr(dipic)2]}n (1). The compound was characterized by spectroscopic methods (IR, Raman, UV/Vis). Single crystal X-ray diffraction analysis revealed that dipicolinate ligand is coordinated to the chromium(III) ion in an O,N,O0-tridentate fashion, while its uncoordinated and coordinated carboxylate O atoms (with respect to Cr(III) ion) are in turn bound to potassium ions. Therefore, each dipicolinate ligand bridges two potassium ions and a chromium(III) ion between them, giving rise to a 2D coordination network. The coordination of chromium(III) ions is octahedral, while the coordination number of potassium ions is 8. The coordination networks are in turn assembled only by π-π stacking interactions into a 3D structure. © The Author(s) 2011.

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    • Synthesis, characterization and crystal structure of a binuclear cadmium iodide complex with a multi-N-donor oxazolidine ligand

      Mohammad Hakimi, Zahra Mardani, Keyvan Moeini, Mao Minoura, Heidar Raissi

      Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences66 ( 11 ) 1122 - 1126   11 2011

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      The ligand, 2-(2-(pyridin-2-yl)oxazolidin-3-yl)-N-(pyridin-2-ylmethylene) ethanamine, POPME, was prepared via microwave-supported Schiff base and oxazolidination reactions. The cadmium iodide complex [Cd2(POPME) (μ-I)2I2] was prepared and identified by elemental analysis, IR, Raman and 1H and 13C NMR spectroscopy and single-crystal X-ray diffraction. In the crystal structure two Cd(II) ions with coordination numbers four and six are bridged by two iodide anions. Cd 1 and Cd2 have distorted octahedral CdI2N 4 and tetrahedral CdI4 geometries, respectively.Weak intermolecular hydrogen bonds H⋯I and H⋯O stabilize the supramolecular network. © 2011 Verlag der Zeitschrift für Naturforschung, Tübingen.

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    • One-pot copper-catalyzed tandem addition-cyclization of 2-iodoanilines with isoselenocyanates for the practical preparation of 2-aminobenzoselenazoles

      Mamoru Kaname, Mao Minoura, Haruki Sashida

      Tetrahedron Letters52 ( 4 ) 505 - 508   26 1 2011

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      A convenient and successful one-pot preparation of the 2- aminobenzoselenazoles via the phenylselenoureas has been accomplished by the copper-catalyzed ligand-free reaction of the 2-iodoanilines and isoselenocyanates; the intermediate, selenoureas, were isolated, and quantitatively transformed into the selenazaoles. © 2010 Elsevier Ltd. All rights reserved.

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    • Reaction of 2-(aminomethyl)pyridine with selenium dioxide: Synthesis and structure of selenium-bridged imidazo[1,5-a]pyridine derivatives

      Osamu Niyomura, Yoshimi Yamaguchi, Souhei Tamura, Mao Minoura, Yoshihisa Okamoto

      Chemistry Letters40 ( 5 ) 449 - 451   2011

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      Reaction of 2-(aminomethyl)pyridine with selenium dioxide leads to the formation of imidazo[1,5-a]pyridine (2-azaindolizin6) skeleton in a single step. The major products of the reactions are 3-(2-pyridyl)imidazo[1,5-a]pyridine, bis[3-(2-pyridyl) imidazo[1,5-a]pyridin-1-yl] selenide, or the corresponding diselenide depending upon the reaction conditions. The structures of these selenium-bridged imidazo[1,5-a]pyridine derivatives are disclosed by X-ray crystal structural analyses. For the diselenide, the unusual dihedral angle CSeSeC of 56.0° was observed indicating π-π intramolecular interaction between the fused six-membered rings. © 2011 The Chemical Society of Japan.

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    • Regioselective electrophilic cyclization of o-ethynylbenzyl phenyl selenides to (Z)-1-methylidene-2-phenyl-1,3-dihydro-1H-benzo[c]selenophenium salts

      Haruki Sashida, Shoko Nakabayashi, Hirokazu Suzuki, Mamoru Kaname, Mao Minoura

      Tetrahedron Letters51 ( 41 ) 5395 - 5398   13 10 2010

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      o-Ethynylbenzyl phenyl selenides regioselectively reacted with trifluoromethanesulfonic acid to afford the (Z)-1-methylidene-2-phenyl-1,3- dihydro-1H-benzo[c]selenophenium salts as the major products during the 5-exo-dig mode cyclization in good yields together with minor E isomers. The structure of the major (Z)-selenophenium salt was established by the single crystal X-ray crystallographic analysis using a tert-butyl derivative. © 2010 Elsevier Ltd. All rights reserved.

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    • A straightforward double intramolecular cyclization of dibenzyl dichalcogenols into a triple bond

      Haruki Sashida, Mamoru Kaname, Akemi Nakayama, Hirokazu Suzuki, Mao Minoura

      Tetrahedron66 ( 27-28 ) 5149 - 5157   3 7 2010

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      The intramolecular cyclizations of four types of dibenzyl chalcogenols, which contained one or two ethynyl groups, were carried out. Either the double 5-exo or 6-endo-dig mode ring closure reaction regio- and stereoselectively proceeded to give the corresponding symmetrical bis(benzoc1chalcogeno- phene) or bis(isochromene) derivatives from the dibenzyl chalcogenols having a diyne moiety. In contrast, the regioselective tandem 5-exo-dig mode intramolecular ring closure reactions of dibenzyl thiol and selenol having a mono-yne into a triple bond gave the trans-biisobenzothiophene and selenophene as the sole product. However, the similar cyclization of dibenzyl tellurol proceeded in both tandem 5-exo and 6 endo dig modes to afford the trans biisobenzotellurophene and ditellurachrysene in good yields with the ratio of 1:1. The X-ray structural analysis of these novel compounds is also presented. © 2010 Elsevier Ltd.

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    • Synthesis, structure, spirocyclization mechanism, and glutathione peroxidase-like antioxidant activity of stable spirodiazaselenurane and spirodiazatellurane International journal

      Bani Kanta Sarma, Debasish Manna, Mao Minoura, Govindasamy Mugesh

      Journal of the American Chemical Society132 ( 15 ) 5364 - 5374   4 2010

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      The first examples of stable spirodiazaselenurane and spirodiazatellurane were synthesized by oxidative spirocyclization of the corresponding diaryl selenide and telluride and were structurally characterized. X-ray crystal structures of the spirodiazaselenurane and spirodiazatellurane suggest that the structures are distorted trigonal bipyramidal (TBP) with the electronegative nitrogen atoms occupying the apical positions and two carbon atoms and the lone pair of Se/Te occupying the equatorial positions. Interestingly, the spirodiazatellurane underwent spontaneous chiral resolution during crystallization, and the absolute configurations of its enantiomers were confirmed by single-crystal X-ray analyses. A detailed mechanistic study indicates that the cyclization to spirodiazaselenurane and spirodiazatellurane occurs via selenoxide and telluroxide intermediates. The chalcogenoxides cyclize to the corresponding spiro compounds in a stepwise manner via the involvement of hydroxyl chalcogenurane intermediates, and the activation energy for the spirocyclization reaction decreases in the order S > Se > Te. In addition to the synthesis, characterization, and mechanism of cyclization, the glutathione peroxidase (GPx) mimetic activity of the newly synthesized compounds was evaluated. These studies suggest that the tellurium compounds are more effective as GPx mimics than their selenium counterparts due to the fast oxidation of the tellurium center in the presence of peroxide and the involvement of an efficient redox cycle between the telluride and telluroxide intermediate. © 2010 American Chemical Society.

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    • 2-Substituted isotellurochromenium salt derivatives: Preparations, structures, spectroscopic properties

      Haruki Sashida, Shoko Nakabayashi, Mamoru Kaname, Mao Minoura

      Heterocycles80 ( 2 ) 1339 - 1352   1 3 2010

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      Several types of novel isotellurochromenium salt derivatives (210) were prepared from the isotellurochromenes (1). The isotellurochromenium tetrafluoroborates (2), triflates (35), tosylates (6) and mesylates (7) are telluronium salts, and the dihalogenoisotellurochromenes (810) are telluranes. The molecular structures of the isotellurochromenium tosylate (6a) and the dichloroisotellurochromene (8a) were characterized by an X-ray crystallographic analysis using the 3-tert-butyl derivatives. © 2010 The Japan Institute of Heterocyclic Chemistry Received.

      DOI: 10.3987/COM-09-S(S)124

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    • A facile and practical solvent-free one-pot synthesis of (Z)-4-methylene-3-selenaquinoline derivatives from o-ethynylanilines and isoselenocyanates

      Haruki Sashida, Chao Pan, Mamoru Kaname, Mao Minoura

      Synthesis ( 18 ) 3091 - 3096   2010

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      Heating of o-ethynylanilines with isoselenocyanates directly resulted in the 6-exo-dig mode ring-closure reaction of the adducts to give the (Z)-2-imino-4-methylene-3-selenaquinolines in moderate to good yields. Based on this convenient, solvent-free, catalyst-free method, several 3-selenaquinoline derivatives (3,1-benzoselenazines) were easily obtained in one pot. Successful application of the microwave-assisted synthesis of these compounds was also investigated. © Georg Thieme Verlag Stuttgart - New York.

      DOI: 10.1055/s-0030-1258171

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    • Evidence for effective p(Z)-π(Ar) conjugations (Z = S, Se, and Te, as well as Z = O) in 9-(Arylchalcogenyl)triptycenes: Experimental and theoretical investigations International journal

      Satoko Hayashi, Takashi Nakamoto, Mao Minoura, Waro Nakanishi

      Journal of Organic Chemistry74 ( 13 ) 4763 - 4771   3 7 2009

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      (Chemical Equation Presented) The p(Z)-π(Ar) conjugations must operate fully in the ground states of 9-(arylchalcogenyl)triptycenes (p-YC 6H4ZTpc:1 (Z = O), 2 (Z = S), 3 (Z = Se), and 4 (Z = Te)), where the p-YC6H4 group is placed in the bisected area between two phenyl planes of the triptycyl group with the parallel orientation. The ground-state geometries, which we call (A: pl), are confirmed by X-ray analysis. However, the conjugations never operate in the transition states between (A: pl) and/or the topomeric structures (A′: pl′), where the Z-CTpc bond is perpendicular to the plane. The site-exchange processes correlate to the conjugations. Temperature-dependent 1H NMR spectra are analyzed for 2 and 3 to demonstrate the effective p(Z)-π(Ar) conjugations. The activation energies for the interconversion between (A: pl) and (A′: pl′) (GR: gear process) were obtained for 2 (ΔG ‡GR(2)) and 3 (ΔG‡GR(3)). ΔG‡GR(3) correlate well with ΔG‡GR(2), and ΔG ‡GR(2) are well analyzed by the Hammett-type dual parameters. ΔG‡GR(2) and ΔG ‡GR(3) are demonstrated to be controlled by the resonance interaction of the p(Z)-π(C6H4)-p(Y) conjugations. QC calculations are performed on the ground and exited states of 1-4, which clarify the effective p(Z)-π(C6H4)-p(Y) conjugations for Z of heavier atoms. © 2009 American Chemical Society.

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    • Chemistry of 1-Benzotelluropyrylium salts: Synthesis, structure and reactions

      Haruki Sashida, Mao Minoura

      Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry67 ( 7 ) 714 - 723   7 2009

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      The three main parts; i.e., the preparations, structures and reactions of the 1-benzotelluropyryli- um salts are described. The synthetic workup has been achieved by transformation from the tel-lurochromones, which were simply prepared by the reaction of the o-bromophenyl ethynyl ketones with sodium hydrogen telluride (NaHTe). The synthetic method for the preparation of the tellurochromones is based on the intramolecular ring closure of a tellurol moiety into a triple bond. The study shows that these salts, although being stable compounds, are highly reactive with various nucleophiles including OMē, diethylamine, CN̄, an active methylene compound and Grignard reagents, and also hydrogenation and hydrolysis to afford the successful corresponding 2- or 4-substituted tellurochromene derivatives. The chemistry of the 1-benzoselenopyrylium salts is also described. The thermolysis of the 2-azidoselenochromenes, which were easily obtained by the reaction of the selenopyrylium salts with sodium azide, resulted in a ring expansion to produce the novel stable 1,3-benzoselenazepines. X-ray structural analyses of the terf-butyltelluro- and selenopyrylium salts are also reported.

      DOI: 10.5059/yukigoseikyokaishi.67.714

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    • Structures and dynamic stereochemistry of 9-arylselanyltriptycenes: X-ray crystallographic, spectroscopic and theoretical investigations

      Takashi Nakamoto, Satoko Hayashi, Waro Nakanishi, Mao Minoura, Gaku Yamamoto

      New Journal of Chemistry33 ( 7 ) 1588 - 1595   2009

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      9-(Arylselanyl)triptycenes (1: p-YC6H4SeTpc) should supply the planar structure (pl) around the p-YC6H4Se (ArSe) group in the ground state, irrespective of the p-Y substituents. 1 with Y = H (a), NMe2 (b), OMe (c), Cl (d), CN (e) and NO2 (f) are prepared. Structures of 1a-d and 1f are determined by X-ray analysis and dynamic 1H NMR spectroscopy is applied to 1a, 1c, 1e and 1f. For convenience of discussion, the structure of 1 is defined as follows: a conformer around the triptycyl group in 1 is called A where the Se-CAr bond is placed in the bisected area between two phenyl planes of the triptycyl group and it is B where the bond is on a phenyl plane of the triptycyl group. A conformer for the Ar group is named pl where the Se-CTpc bond is on the Ar plane, while it is pd if the bond is perpendicular to the plane. The structure of 1 is confirmed to be (A: pl) in the ground state by X-ray analysis. 1 (A: pl) changes to the equivalent one via a transition state of 1 (B: pd) (the gear process). The activation energies are determined by dynamic 1H NMR spectroscopy: the values are 36.4, 41.6, 42.3 and <34 kJ mol-1 for 1a, 1e, 1f and 1c, respectively. The MP2 level of calculations reproduced the observed values: they are evaluated to be 34, 39, 40 and 29 kJ mol-1 for 1a, 1e, 1f and 1b′ (Y = NH2), respectively, where 1b′ is employed in place of 1c. Another process (the isolated rotation process) is also operating for the interconversion of 1 (A: pl), which proceeds via1 (A: pd). The activation energies for the process are predicted to be 25, 30, 30 and 20 kJ mol-1 for 1a, 1e, 1f and 1b′, respectively, at the MP2 level. The results demonstrate that (A: pl) is the global minimum in 1: the 1 (A: pl) structure is well established for all Y examined in the ground state. © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2009.

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    • One-pot synthesis of indolizine derivative and its application as multi-dentate ligand

      Osamu Niyomura, Yoshimi Yamaguchi, Ryo Sakao, Mao Minoura, Yoshihisa Okamoto

      Heterocycles75 ( 2 ) 297 - 304   1 2 2008

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      1-Cyano-3-(2-pyridinecarboxamido)-2-(2-pyridiyl)indolizine (2) was readily synthesized by the one-pot reaction of 2-(cyanomethyl)pyridine (1a) with selenium dioxide. The reaction of 3- or 4-(cyanomethyl)pyridines (1b,c) under the same reaction conditions gave 2,3-bi(3-pyridyl)-2-butenedinitrile (3b) and 2,3-bi(4-pyridyl)-2-butenedinitrile (3c), respectively. The indolizine 2 (L-H) reacted with Ni(NO3)2·6H2O in ethanol to produce the NiL2 complex (4). The structure was determined by X-ray crystallography. © 2008 The Japan Institute of Heterocyclic Chemistry.

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    • Synthesis and structural characterization of 1-mesityl-1,3-dihydro- imidazole-2-selone and bis(1-mesitylimidazol-2-yl)diselenide: Experimental evidence that the selone is more stable than the selenol tautomer International journal

      Victoria K. Landry, Mao Minoura, Keliang Pang, Daniela Buccella, Bryte V. Kelly, Gerard Parkin

      Journal of the American Chemical Society128 ( 38 ) 12490 - 12497   27 9 2006

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      1-Mesityl-1,3-dihydro-imidazole-2-selone, (seimMes)H, may be obtained from 1-mesitylimidazole via (i) deprotonation with BunLi, (ii) treatment with elemental selenium, and (iii) addition of HCl(aq). Structural characterization of (seimMes)H by X-ray diffraction demonstrates that the compound exists as the selone rather than selenol tautomer, a result that is in accord with DFT calculations. Solutions of (seimMes)H are oxidized by air to give bis(1-mesitylimidazol-2-yl) diselenide, (seimMes)2. A corresponding investigation of (seimMe)H demonstrates that, in contrast to a previous report, the selenium analogue of methimazole exists in the selone form with a structure analogous to that of methimazole. 1H and 77Se NMR studies demonstrate that the (seimR) groups of the selone (seimR)H and diselenide (seimR)2 undergo facile exchange on the NMR time scale. © 2006 American Chemical Society.

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    • Synthesis and structural characterization of tris(2-seleno-1- mesitylimidazolyl) hydroborato complexes: A new type of strongly electron donating tripodal selenium ligand International journal

      Mao Minoura, Victoria K. Landry, Jonathan G. Melnick, Keliang Pang, Luciano Marchiò, Gerard Parkin

      Chemical Communications ( 38 ) 3990 - 3992   2006

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      A new tripodal ligand that features three selenium donors, namely the tris(2-seleno-1-mesitylimidazolyl)hydroborato ligand, [TseMes], has been constructed via the reaction of KBH4 with 1-mesitylimidazole-2- selone; comparison of the IR spectroscopic data of [TseMes]Re(CO) 3 with those of a variety of related LRe(CO)3 complexes demonstrates that the [TseMes] ligand is more strongly electron donating than Cp, Cp*, [Tp], [TpMe2] and [Tm Mes] ligands. © The Royal Society of Chemistry 2006.

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    • Deamination of 1-alkyl-9-aminomethyltriptycenes. Participation of a neighboring 1-alkyl substituent

      Gaku Yamamoto, Ai Koseki, Jun Sugita, Hisashi Mochida, Mao Minoura

      Bulletin of the Chemical Society of Japan79 ( 10 ) 1585 - 1600   2006

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      Deamination reactions of 1-alkyl-9-aminomethyltriptycenes (alkyl = Me, Et, i-Pr, and t-Bu) and 9-(1-aminoethyl)-1-methyltriptycene were performed in CHCl 3 and in AcOH, and product distributions were studied. The results suggest that the loss of N 2 from a primary alkanediazonium ion predominantly takes place concomitantly with participation of a C-H bond of the neighboring 1-alkyl group to form a nonclassical cationic species with a three-center two-electron bonding, while the loss of N 2 from a secondary alkanediazonium ion occurs spontaneously to form a secondary carbocation. Solvent effects (CHCl 3 vs AcOH) are explained in terms of lower nucleophilicity/basicity of the AcO - in AcOH than in CHCl 3 due to solvation. © 2006 The Chemical Society of Japan.

      DOI: 10.1246/bcsj.79.1585

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    • Synthesis and structures of 9-triptycylallene derivatives

      Gaku Yamamoto, Yuriko Kobayashi, Kasumi Ono, Emiko Yano, Mao Minoura, Yasuhiro Mazaki

      Bulletin of the Chemical Society of Japan79 ( 8 ) 1293 - 1299   2006

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      9-Triptycylallene (1) was synthesized by LiAlH 4 reduction of 1-(9-triptycyl)-2-propynyl methanesulfonate (7), and three 3-substituted derivatives of 1 were also obtained by reacting compound 7 with appropriate metal reagents. LiAlH 4 reduction of 1,3-di(9-triptycyl)-2-propynyl methanesulfonate (10) gave 1,3-di(9-triptycyl)propyne (12). The molecular structures of some of the allenes and of the propyne were determined by X-ray crystallography. As well, the allenes and some of the related compounds were characterized by NMR spectroscopy. © 2006 The Chemical Society of Japan.

      DOI: 10.1246/bcsj.79.1293

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    • Static and dynamic stereochemistry of tris(9-triptycyl)stannane derivatives

      Gaku Yamamoto, Shozo Ohta, Megumi Kaneko, Kaoru Mouri, Miki Ohkuma, Ryo Mikami, Yosuke Uchiyama, Mao Minoura

      Bulletin of the Chemical Society of Japan78 ( 3 ) 487 - 497   15 3 2005

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      Static and dynamic stereochemistry of several tris(9-triptycyl)stannane derivatives Tp3SnX (X = H, halogens, and alkyl groups) were studied. X-ray crystallography of the bromo and methyl compounds showed that the Sn atom was fundamentally tetrahedral and that the three Tp groups meshed with each other like bevel gears and formed a near-C3 chiral conformation. The rate constants for enantiomerization of the chiral conformation in solution could be obtained by the lineshape analysis of the aromatic proton signals, even when a direct probe for enantiomerization such as a benzyl group was absent. The energy barrier to enantiomerization decreased as the substituent X became bulkier, suggesting that the ground state is more destabilized than the transition state upon introduction of a bulkier group. © 2005 The Chemical Society of Japan.

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    • Open-cage fullerene derivatives suitable for the encapsulation of a hydrogen molecule

      Shigeru Nagase, Iwamatsu S, Nagase S, Naomi Mizorogi, Kobayashi K, Yukihiro Andoh, Shizuaki Murata, Sho-ichi Iwamatsu, Mao Minoura

      The Journal of Organic Chemistry   2005

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    • Synthesis and characterization of stable hypervalent carbon compounds (10-C-5) bearing a 2,6-bis(p-substituted phenyloxymethyl)benzene ligand Peer-reviewed International journal

      Akiba KY, Moriyama Y, Mizozoe M, Inohara H, Nishii T, Yamamoto Y, Minoura M, Hashizume D, Iwasaki F, Takagi N, Ishimura K, Nagase S

      Journal of the American Chemical Society127 ( 16 ) 5893 - 5901   2005

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      X-ray analysis of bis(p-fluorophenyl)methyl cation bearing a 2,6-bis(p-tolyloxymethyl)benzene ligand showed a symmetrical structure (10-C-5) where the two C-O distances are identical, although the distance (2.690(4) Å) is longer than those (2.43(1) and 2.45(1) Å) of 1,8-dimethoxy-9-dimethoxymethyl-anthracene monocation, which was recently reported by us. However, X-ray analysis of the more stable aromatic xanthylium cation with the same benzene ligand showed the tetracoordinate carbon structure where only one of the two oxygen ligands is coordinated with the central carbon atom. These results clearly indicate that the carbocations (10-C-5) bearing the sterically flexible benzene ligand were quite sensitive to the electronic effect on the central carbon atom. The electron distribution analysis by accurate X-ray measurements and the density functional calculation on the initially mentioned bis(p-fluorophenyl)methyl cation clearly show that the central carbon atom and the two oxygen atoms are bonded even if the bond is weak and ionic based on the small value of the electron density (ρ(r)) and the small positive Laplacian value (∇2ρ(r)) at the bond critical points. © 2005 American Chemical Society.

      DOI: 10.1021/ja043802t

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    • Syntheses and reactions of hexavalent organotellurium compounds bearing five or six tellurium-carbon bonds International journal

      Masataka Miyasato, Takao Sagami, Mao Minoura, Yohsuke Yamamoto, Kin Ya Akiba

      Chemistry - A European Journal10 ( 10 ) 2590 - 2600   17 5 2004

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      A variety of hexaorganotellurium compounds, Ar6-n(CH 3)nTe [Ar = 4-CF3C6H4, n = 0 (1a), n = 1 (3a), n = 2 (trans-4a and cis-4a), n = 3 (mer-5a), n = 4 (trans-6a); Ph, n = 0 (1b), n = 1 (3b), n = 2 (trans-4b); 4-CH3C 6H4, n = 0 (1c), n = 1 (3c), n = 2 (trans-4c), n = 4 (trans-6c); 4-BrC6H4, n = 0 (1d)] and Ar5(R)Te [Ar = 4-CF3C6H4, R = 4-CH3OC 6H4 (8); Ar = 4-CF3C6H4, R = vinyl (9), Ar = Ph, R = vinyl (10), Ar = 4-CF3C6H 4, R = PhSCH2 (11), Ar = Ph, R = PhSCH2 (12), Ar = 4-CF3C6H4, R = nBu (13)] and pentaorganotellurium halides, Ar5TeX [Ar = 4-CF3C 6H4, X = Cl (2a-Cl), X = Br (2a-Br); Ar = Ph, X = Cl (2b-Cl), X = Br (Zb-Br); Ar = 4-CH3C6H4, X = Cl (2c-Cl), X = Br (2c-Br); Ar = 4-BrC6H4, X = Br (2d-Br)] and (4-CF3C6H4)4(CH3)TeX [X = Cl (trans-7a-Cl) and X = Br (trans-7a-Br)] were synthesized by the following methods: 1) one-pot synthesis of 1a, 2) the reaction of SO 2Cl2 or Br2 with Ar5Te Li + generated from TeCl4 or TeBr4 with five equivalents of ArLi, 3) reductive cleavage of Ar6-m(CH 3)mTe (m = 0 or 2) with KC8 followed by treatment with CH3I, 4) valence expansion reaction from low-valent tellurium compounds by treatment with KC8 followed by reaction with CH3I, 5) nucleophilic substitution of Ar6-y-z(CH 3)zTeXy-z (X=Cl, Br, OTf; z = 0, 1; y= 1, 2) with organolithium reagents. The scope and limitations and some details for each method are discussed and electrophilic halogenation of the hexaorganotellurium compounds is also described.

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    • Synthesis and stereochemistry of N-phenyl-N-9-triptycylhydroxylamine derivatives and related compounds

      Chiharu Agawa, Keiko Otsuka, Mao Minoura, Yasuhiro Mazaki, Gaku Yamamoto

      Bulletin of the Chemical Society of Japan77 ( 12 ) 2273 - 2281   2004

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      During the course of attempts at synthesis of N-phenyl-N-9- triptycylhydroxylamine (1), we found that the reaction of N-9- triptycylhydroxylamine (5) with benzenediazonium-2-carboxylate afforded 3-(2-carboxyphenyl)-1-(9-triptycyl)-triazene 1-oxide (6), the structure of which was confirmed by X-ray crystallography. Oxidation of N-(9-triptycyl)aniline (4) with mCPBA gave phenyl 9-triptycyl nitroxide (7) and N-(9-triptycyl)-1,4- benzoquinonimine (8) in small yields. Reduction of 7 with phenylhydrazine gave 1, and O-ethylation of 1 gave O-ethyl-N-phenyl-N-9-triptycylhydroxylamine (2). Results of X-ray crystallography for compounds 2, 4, 7, and 8 and results of dynamic NMR studies for 1, 2, and 8 are presented. In compound 8, Tp-N rotation and C=N topomerization took place on the NMR timescale at high temperatures above 60 °C, and the energy barriers to both processes were obtained. In compounds 1 and 2. dynamic NMR behavior was observed at very low temperatures below ca. -50 °C, and the energy barriers to the respective processes could not be determined except for those related to "Ph-passing".

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    • Dynamic Stereochemistry of Alkyltris(9-triptycyl)stannanes

      Gaku Yamamoto, Megumi Kaneko, Miki Ohkuma, Mao Minoura

      Chemistry Letters32 ( 10 ) 964 - 965   5 10 2003

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      1H dynamic NMR study of benzyltris(9-triptycyl)stannane (4) using two probes, the benzylic methylene and the aromatic peri-proton signals, revealed that the enantiomerization of the chiral conformers took place with ΔG‡ of 64.2 kJ mol-1 at 300 K.

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    • Static and dynamic stereochemistry of O-substituted N-9-triptycylhydroxylamines

      Gaku Yamamoto, Chiharu Agawa, Mao Minoura

      Bulletin of the Chemical Society of Japan76 ( 4 ) 825 - 829   4 2003

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      The static and dynamic stereochemistry of N-9-triptycylhydroxylamine derivatives (TpNHOR) with O-benzyl (3), O-ethyl (4), and O-phenyl (5) groups were studied. X-ray crystallographic analysis revealed that these compounds reside in a chiral conformation, with the Tp-N-O-R dihedral angle of 140-160°. Dynamic NMR studies of 3 and 4 show the presence of two separate stereomutation processes: chirality reversal (enantiomer interconversion) and rotation of the Tp-N bond with retaining the chirality, the latter having a lower energy barrier. Compound 5 gave solely information on the Tp-N rotation because of the lack of a probe for chirality reversal.

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    • Static and dynamic stereochemistry of N-(1,4-dimethyl-9-triptycyl)-hydroxylamine derivatives

      Gaku Yamamoto, Chiharu Agawa, Takahiro Ohno, Mao Minoura, Yasuhiro Mazaki

      Bulletin of the Chemical Society of Japan76 ( 9 ) 1801 - 1811   2003

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      Static and dynamic stereochemistry of N-alkyl, O-alkyl, and N,O-dialkyl derivatives of N-(1,4-dimethyl-9-triptycyl)hydroxylamine were studied. X-ray crystallographic analysis revealed that an N-alkyl derivative adopts R*-(-sc)* conformation while N,O-dialkyl derivatives adopt R*-ap conformation. In solufion, stereomutation was almost frozen on the NMR timescale at ca. -60 °C. The same conformer as found in the crystal was the major conformer in solution in each compound, and a small amount of a second conformer was found in equilibrium with the major one for the N-alkyl and N,O-dialkyl derivatives. The stereomutation was interpreted in terms of diastereomerization and enantiomerization, and the 1H NMR lineshape analysis afforded the activation parameters for these processes.

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    • Novel Valence Expansion Reactions Using KC_8 : A New Route to Hexavalent Organotellurium Compounds from Divalent Tellurium

      MIYASATO Masataka, MINOURA Mao, YAMAMOTO Yohsuke, AKIBA Kin-ya

      Chemistry Letters2002 ( 3 ) 288 - 289   5 3 2002

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      Hexavalent tellurium compounds, Ar&lt;SUB&gt;5&lt;/SUB&gt;(CH&lt;SUB&gt;3&lt;/SUB&gt;)Te, Ar&lt;SUB&gt;4&lt;/SUB&gt;(CH&lt;SUB&gt;3&lt;/SUB&gt;)&lt;SUB&gt;2&lt;/SUB&gt;Te, and Ar&lt;SUB&gt;2&lt;/SUB&gt;(CH&lt;SUB&gt;3&lt;/SUB&gt;)&lt;SUB&gt;4&lt;/SUB&gt;Te (Ar=4-CF&lt;SUB&gt;3&lt;/SUB&gt;C&lt;SUB&gt;6&lt;/SUB&gt;H&lt;SUB&gt;4&lt;/SUB&gt;, Ph, 4-CH&lt;SUB&gt;3&lt;/SUB&gt;C&lt;SUB&gt;6&lt;/SUB&gt;H&lt;SUB&gt;4&lt;/SUB&gt;), were synthesized by the reaction of Ar&lt;SUB&gt;2-n&lt;/SUB&gt;(CH&lt;SUB&gt;3&lt;/SUB&gt;)&lt;SUB&gt;n&lt;/SUB&gt;Te (n=0–1) or Ar&lt;SUB&gt;3-m&lt;/SUB&gt;(CH&lt;SUB&gt;3&lt;/SUB&gt;)&lt;SUB&gt;m&lt;/SUB&gt;Te&lt;SUP&gt;+&lt;/SUP&gt;X&lt;SUP&gt;-&lt;/SUP&gt; (m=0–2) with KC&lt;SUB&gt;8&lt;/SUB&gt; followed by the treatment with CH&lt;SUB&gt;3&lt;/SUB&gt;I.

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    • Studies on tellurium-containing heterocycles. Part 18. Preparation and structure of 2-benzotelluropyrylium salts and 2-benzoselenopyrylium salts

      Haruki Sashida, Kazuo Ohyanagi, Mao Minoura, Kin Ya Akiba

      Journal of the Chemical Society. Perkin Transactions 12 ( 5 ) 606 - 612   22 2 2002

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      The regioselective and stereospecific intramolecular ring closure reactions of o-ethynylbenzyl tellurols 5A and o-ethynylbenzyl selenols 5B, which were readily generated by the reaction of the o-ethynylbenzyl bromides 4 with sodium hydrogen telluride (NaHTe) or sodium hydrogen selenide (NaHSe), produced the isotellurochromenes 6A and isoselenochromenes 6B together with (Z)-1-methylidene-2-telluraindans 7A and (Z)-1-methylidene-2-selenaindans 7B, respectively. The obtained isochromenes 6A and 6B were transformed into the corresponding 2-benzotelluropyrylium tetrafluoroborates 9A and 2-benzoselenopyrylium tetrafluoroborates 9B by treatment with triphenylcarbenium tetrafluoroborate (Ph3C+BF4 −) in excellent yields, respectively. An X-ray structural analysis of the tert-butyl derivatives 9Ac and 9Bc is also described. © 2002 The Royal Society of Chemistry.

      DOI: 10.1039/b111045b

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    • Coordination of trimethylphosphine with pentaphenyltelluronium salts

      Masataka Miyasato, Takahiro Mukuda, Mao Minoura, Yohsuke Yamamoto, Kin Ya Akiba

      Phosphorus, Sulfur and Silicon and Related Elements177 ( 8-9 ) 2043 - 2044   2002

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      DOI: 10.1080/10426500213441

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    • Cleavage of tellurium - Carbon bonds of hexavalent organotellurium compounds by potassium graphite International journal

      Masataka Miyasato, Mao Minoura, Kin Ya Akiba

      Angewandte Chemie - International Edition40 ( 14 ) 2674 - 2676   16 7 2001

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      The potassium ion intercalated in graphite results in unique reactivity of Ar5Te-K+C8 (1), formed by cleavage of one of the Te-C(Ar) bonds of Ar6Te (see scheme) by KC8. Thus, 1 reacted quantitatively with CH3I to give Ar5TeCH3, which was not obtainable from Ar5Te-Li+. The Te-CH3 bond of Ar5TeCH3 is cleaved in preference to the Te-C(Ar) bonds, and formation of Ar4Te(CD3)2 suggests the intermediacy of the hypervalent dianion Ar4Te2-.

      DOI: 10.1002/1521-3773(20010716)40:14<2674::AID-ANIE2674>3.0.CO;2-H

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    • Convenient one-pot synthesis and structures of pentaphenyltellurium monohalides

      Mao Minoura, Takao Sagami, Kin Ya Akiba

      Organometallics20 ( 12 ) 2437 - 2439   11 6 2001

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      A novel family of organochalcogens, Ph5TeX (X = Cl, Br), was readily obtained by the halogenation of Ph5TeLi, which was prepared by reaction of 5 equiv of PhLi with 1 equiv of TeCl4 or TeBr4; Ph5TeF was obtained by treating the bromide with KF. The Te atom is in the highest oxidation state, Te(VI), and is covalently bonded to the halogen atom, in contrast to the ionic bonding in R3TeIVX.

      DOI: 10.1021/om001075e

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    • Synthesis and structure of pentaphenyl-telluronium salts of perchlorate and tetrakis{3,5-bis(trifluoromethyl)phenyl}borate: hypervalent onium compounds

      Mao Minoura, Takahiro Mukuda, Takao Sagami, Kin Ya Akiba

      Heteroatom Chemistry12 ( 5 ) 380 - 384   2001

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      Publishing type:Research paper (scientific journal)  

      The reaction of pentaphenyltellurium chloride 2 with silver perchlorate afforded the pentaphenyltelluronium salt, Ph5Te+ClO4-, (1b), and treatment of 2 with silver triflate and sodium tetrakis{3,5-bis(trifluoromethyl)phenyl}borate provided Ph5Te+[3,5-(CF3)2C6H 3]4B- (1c), which were isolated as stable yellow solids. X-ray crystallographic analysis of the hypervalent telluronium salts revealed square pyramidal geometry around the tellurium, which are rare examples for penta-substituted main group element compounds.

      DOI: 10.1002/hc.1057

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    • Synthesis and characterization of a hypervalent tellurium cation, Ph<inf>5</inf>Te<sup>+</sup>: A stable nonclassical onium compound [13]

      Mao Minoura, Takahiro Mukuda, Takao Sagami, Kin Ya Akiba

      Journal of the American Chemical Society121 ( 46 ) 10852 - 10853   24 11 1999

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      Publishing type:Research paper (scientific journal)  

      DOI: 10.1021/ja992828v

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    • Structure of azabismocines, hexacoordinate pentavalent organobismuth compounds

      Mao Minoura, Yuka Kanamori, Akira Miyake, Kin Ya Akiba

      Chemistry Letters ( 9 ) 861 - 862   1999

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      Publishing type:Research paper (scientific journal)  

      Azabisomocine derivatives having a pentavalent bismuth and a nitrogen at 1,5-position were synthesized. The X-ray structural analysis reveals that these compounds have hexacoordinate distorted octahedral geometry which is caused by transannular bond formation between the bismuth and the nitrogen.

      DOI: 10.1246/cl.1999.861

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    • Stable Telluroketones: Synthesis and Characterization Peer-reviewed

      Mao Minoura, Takayuki Kawashima, Norihiro Tokitoh, Renji Okazaki

      Phosphorus, Sulfur, and Silicon and the Related Elements136 ( 1 ) 549 - 552   1 1 1998

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      Publishing type:Research paper (scientific journal)   Publisher:Informa UK Limited  

      DOI: 10.1080/10426509808545993

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    • Synthesis and characterization of hexaaryltellurium (TeAr<inf>6</inf>); The first neutral hexaarylated element compound

      Mao Minoura, Takao Sagami, Masataka Miyasato, Kin Ya Akiba

      Tetrahedron53 ( 36 ) 12195 - 12202   8 9 1997

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      Publishing type:Research paper (scientific journal)  

      Te(C6H4-CF3)6 1a was obtained by the unique one-pot reaction of LiC6H4-4-CF3 with TeCl4. The Te atom resides in the highest oxidation state (Te(VI)) having six C-Te bonds in 1a. Compound la is extremely thermally stable and not light sensitive unlike tetraorganotellurium compounds. The X-ray crystallographic analysis of 1a revealed a rare example of approximately T(h) molecular symmetry.

      DOI: 10.1016/S0040-4020(97)00552-8

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    • Δ-1,3,4-Telluradiazolines, a novel tellurium containing heterocycle: One-pot synthesis, structure, and reactivity

      Mao Minoura, Takayuki Kawashima, Norihiro Tokitoh, Renji Okazaki

      Tetrahedron53 ( 24 ) 8137 - 8148   16 6 1997

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      Publishing type:Research paper (scientific journal)  

      The one-pot reaction of sterically hindered hydrazones with tellurium dichloride or tellurium tetrahalide in the presence of triethylamine in benzene afforded Δ3-1,3,4-telluradiazolines 1, a novel heterocycle, via 1,3-dipolar cycloaddition of telluroketones and diazo compounds, both generated in situ. The molecular structure of 1a was established by X-ray crystallographic analysis. The photolysis of In led to instant and quantitative formation of the corresponding azine 8a, whereas the thermolysis of in in the solid state afforded the corresponding retrocyclization products.

      DOI: 10.1016/S0040-4020(97)00498-5

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    • The first isolation of a telluroketone and its reversible dimerization

      Mao Minoura, Takayuki Kawashima, Renji Okazaki

      Tetrahedron Letters38 ( 14 ) 2501 - 2504   4 1997

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      Publishing type:Research paper (scientific journal)  

      The solid-state thermolysis of a sterically hindered Δ3-1,3,4-telluradiazoline 2 afforded products resulting from intermediary tellone 1 and diazo compound 8 formed by retrocyclization, whereas the flash vacuum thermolysis of 2 led to isolation of tellone 1 as green needles. The spontaneous dimerization of 1 thus obtained occurred in the solid state to give the corresponding 1,3-ditelluretane 10, which underwent the thermal cycloreversion in solution to regenerate pure tellone 1.

      DOI: 10.1016/S0040-4039(97)00377-8

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    • Weak coordination of a telluroketone in an η<sup>1</sup>-mode complex: Synthesis and characterization of pentacarbonyl(1,1,3,3-tetramethylindantellone)tungsten

      Mao Minoura, Takayuki Kawashima, Norihiro Tokitoh, Renji Okazaki

      Chemical Communications ( 2 ) 123 - 124   1996

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      Publishing type:Research paper (scientific journal)  

      Treatment of a stable telluroketone with W(CO)5·thf affords the title compound, the X-ray crystal structure of which shows η1,σ-complexation and the trans influence of the weakly coordinated telluroketone; the regeneration of a 'free' telluroketone by ligand exchange of the complex under mild conditions is also reported.

      DOI: 10.1039/CC9960000123

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    • Hexaaryltellurium

      Mao Minoura, Takao Sagami, Kin Ya Akiba, Claudia Modrakowski, Allexander Sudau, Konrad Seppelt, Stephan Wallenhauer

      Angewandte Chemie (International Edition in English)35 ( 22 ) 2660 - 2662   1996

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      Publishing type:Research paper (scientific journal)  

      DOI: 10.1002/anie.199626601

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    • Stable Telluroketones and Their Related Compounds: Synthesis, Structure, and Reactivity Peer-reviewed

      Mao MINOURA

          30 3 1995

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      Language:English   Publishing type:Doctoral thesis  

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    • Tropothione <i>S</i> -Sulfide. A New Class of Thiosulfine

      Mao Minoura, Shinichi Yamabe, Takahisa Machiguchi, Taketoshi Minato

      Chemistry Letters   1995

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      Publishing type:Research paper (scientific journal)  

      DOI: 10.1246/CL.1995.103

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    • Synthesis structure, and reactivity of 1,4,2-oxa-tellurazole: A novel tellurium-containing heterocycle

      Mao Minoura, T. Takayukikawashima, Renji Okazaki

      Phosphorus, Sulfur, and Silicon and the Related Elements93 ( 1-4 ) 403 - 404   1 8 1994

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      Publishing type:Research paper (scientific journal)  

      A novel tellurium containing heterocycle, 1,4,2-oxatellurazole, was characterized by X-ray crystallographic analysis which showed a remarkably small C-Te-C bond angle (79.4°), and its 1,3-dipolar cycloreversion is discussed. © 1994, Taylor & Francis Group, LLC. All rights reserved.

      DOI: 10.1080/10426509408021877

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    • STRUCTURE AND THERMOLYSIS OF A 1,4,2-OXATELLURAZOLE, A NOVEL TELLURIUM CONTAINING HETEROCYCLE

      Renji Okazaki, Takayuki Kawashima, Mao Minoura

      Chemistry Letters   1994

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      Publishing type:Research paper (scientific journal)  

      DOI: 10.1246/CL.1994.1691

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    • SYNTHESIS OF DELTA-3-1,3,4-TELLURADIAZOLINES, A NOVEL TELLURIUM-CONTAINING HETEROCYCLE

      Takayuki Kawashima, Renji Okazaki, Mao Minoura

      Chemistry Letters   1993

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      Publishing type:Research paper (scientific journal)  

      DOI: 10.1246/CL.1993.1047

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    • 1,1,3,3-Tetramethylindantellone, the first telluroketone stable in solution

      Mao Minoura, Takayuki Kawashima, Renji Okazaki

      Journal of the American Chemical Society115 ( 15 ) 7025 - 7026   1993

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      Publishing type:Research paper (scientific journal)  

      DOI: 10.1021/ja00068a088

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    Misc.

    Books and Other Publications

    • ラウドン有機化学

      Loudon, G. Marc, Parise, Jim, 後藤, 敬, 豊田, 真司, 箕浦, 真生, 村田, 滋, 山本, 学

      東京化学同人  2018  ( ISBN:9784807909438

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      Total pages:2冊   Language:Japanese

      CiNii Books

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    • 有機化学

      奥山 格, 石井昭彦, 箕浦真生( Role: Joint author)

      丸善出版  29 1 2016  ( ISBN:4621089773

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      Language:Japanese Book type:Textbook, survey, introduction

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    Professional Memberships

    •  
      The Society of Physical Organic Chemistry, Japan

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    •  
      The Society of Silicon Chemistry, Japan

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    •  
      日本結晶学会

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    •  
      American Chemical Society

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    •  
      Society of Synthetic Organic Chemistry

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    •  
      Chemical Society of Japan

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    Research Projects

    • ジシレンジアニオン種を鍵分子とする未踏典型元素共役系分子の創製

      日本学術振興会  科学研究費助成事業 基盤研究(C) 

      箕浦 真生

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      4 2022 - 3 2025

      Grant number:22K05085

      Grant amount:\4290000 ( Direct Cost: \3300000 、 Indirect Cost:\990000 )

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    • Creation of Unexplored Highly Reactive Chemical Species with pi-Electrons of Main Group Elements

      Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research 

      MINOURA Mao

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      4 2019 - 3 2022

      Grant number:19K05425

      Grant amount:\4290000 ( Direct Cost: \3300000 、 Indirect Cost:\990000 )

      In this research project, in order to understand the properties of π-electrons involving heavier main group elements, we utilized Trp* as a versatile alkyl stereoprotecting group based on a triptycyl skeleton, which was developed through a new molecular design, to provide sufficient kinetic stabilization to highly reactive π-bonds and elucidate the properties of fundamental π-bonds that are confined to 2nd period elements of the periodic table. The target molecules were dialkyl diphosphenes with group 15 inter-elemental π-bonds, dialkyl germylenes, a group 14 divalent chemical species, and disilene dianions with a negative charge on each silicon double bond (disilenes).

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    • Creation of Novel Main Group Compounds Containing Tautomerizable Double Bonds

      Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C) 

      MINOURA Mao

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      4 2015 - 3 2018

      Grant number:15K05439

      Authorship:Principal investigator  Grant type:Competitive

      The concept of keto-enol type tautomerization contains fundamental importance in organic chemistry. However, little is known about the chemistry of tautomerization of the heavier congener of chalcogen compounds, due to their instability. In order to investigate the properties of such reactive species, we used "kinetic stabilization".
      For the synthesis of tautomerizable heavier analogs of main group element compounds, a novel peripherally extended sterically demanding primary alkyl group based on the triptycene (Trp) framework, Trp*CH2, was designed and synthesized. The introduction of the Trp*CH2 and Trp groups onto a Si atom of Si=S allowed observation of a stable silanetion. The corresponding Si=Si double bond compound was also synthesized as the first stable tetraalkyldisilene that contains primary alkyl groups.
      The observed non-bonding meshing-gear system of Trp* and Trp groups should offer an effective means of protecting the reactive chemical bonds.

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    • 多様な酸化状態を有する高周期16族元素感応性化学種の創製と反応

      文部科学省  科学研究費助成事業 

      箕浦真生

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      4 2015 - 3 2017

      Grant number:15H00962

      Authorship:Principal investigator  Grant type:Competitive

      含高周期カルコゲン(Te, Se, S)有機化合物には、酸素がもたない種々の酸化状態の変化に伴う多様性があり、興味が持たれているにも関わらず、化合物の合成的困難さのため、基本的性質が不明であり、十分な研究が行われていない。
      本課題は、高反応(不安定)性のため、合成が避けられていたカルコゲン化合物群の創製を行うものであり、酸素がもたない種々の酸化状態の変化に伴う多様性と感応性を解明することを目的とする。
      「感応性超原子価4および6価カルコゲン化合物」:第五周期元素であるテルルを中心元素とする四価中性有機テルル(Ar4Te)の酸化的ハロゲン化とその脱ハロゲン化により六価有機テルルジカチオン(Ar4Te2+)の一般的合成法とその官能基化手法を確立した。ジカチオン種を用いることで多様な中性六価有機テルル化合物へ誘導可能となった。
      「感応性2価カルコゲン化合物」:剛直な骨格を有するトリプチシル基の周縁領域をアルキル基により拡張した新規立体保護基を開発・活用し、橋頭位に硫黄、セレン、テルルをそれぞれ導入し、対応するスルフェン酸、セレネン酸、テルレン酸の合成検討を行った。テルルの場合は分解反応を抑制できなかったが、硫黄・セレンの場合には熱的に安定な二価化学種を合成単離することが出来た。

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    • Creation of Heterocyclic Compounds Based on Generation of Heavier Group 14 Element Cations and Activation of Small Molecules

      Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C) 

      Kawashima Takayuki

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      4 2014 - 3 2017

      Grant number:26410035

      Grant type:Competitive

      Silacyclic compounds were synthesized by the generation of silyl cations from hydrosilanes bearing an aromatic ring and trityl cation, their reactions with alkynes, alkenes, and carbon dioxide, etc., and sequential reactions of formed carbocations with the aromatic ring. π-Extended siloles such as benzosiloles, naphthosiloles, and disiloles, etc. were synthesized by its application to aromatic compounds bearing 1 or 2 sets of alkynyl group and hydrosilyl group at the neighboring position. Furthermore, germa-Friedel-Crafts reaction was developed for the synthesis of dibenzogermoles.

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    • 種々の酸化状態を有する高周期カルコゲン感応性化学種の創製と反応

      日本学術振興会  科学研究費助成事業 新学術領域研究(研究領域提案型) 

      箕浦 真生

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      4 2013 - 3 2015

      Grant number:25109541

      Grant amount:\7280000 ( Direct Cost: \5600000 、 Indirect Cost:\1680000 )

      本課題は、高反応(不安定)性のため、合成が避けられていた感応性カルコゲン化合物群の創製を行うものであり、酸素がもたない種々の酸化状態の変化に伴う多様性を解明することを目的とし、とりわけ合成が困難とされている電子供与性置換基を有する4および6価の高酸化状態をもつ「感応性超原子価カルコゲン化合物」の創製と反応を行うことを中心課題として研究を行った。
      「感応性超原子価カルコゲン化合物」:ジメチルアミノフェニル(Ar)基を電子供与性置換基として選び、中性4価テトラアリールテルル(Ar4Te)の合成検討を行った。各種合成条件を検討し、純粋なアリールリチウムを単離し供することで、中性4価テトラアリールテルルの合成単離に成功した。酸素・水等により容易に分解し、また微量の不純物の混入が分解を促進することも明らかとなった。合成単離したAr4Teは熱的にも高反応性であり、加熱により還元的脱離反応をおこし、定量的にAr2TeとAr2を与える事が明らかとなった。
      対応する6価テトラアリールテルルジフルオリドへもXeF2による酸化的ハロゲン化により導くことが出来た。結晶構造解析により、固体中ではテルルを中心とするオクタヘドラル構造を有している。芳香族置換基のパラ位に各種置換基を導入したAr*4TeF2を合成・比較したところ、電子供与性効果が大きいほど長く弱いTe-F結合となることが認められた。
      等電子構造を有する超原子価アンチモン化合物であるAr**5Sbを合成し、Ar*4Teとの混合条件下では、配位子交換反応が速やかにおこり、続く還元的脱離が進行することを実験的に初めて証明することが出来た。この交換反応は超原子価感応性化学種が高反応性を示す要因の一つと見なすことが出来ると考えられる。

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    • Creation of Novel Group 16 Element Compounds having Weak Chemical Bonds

      Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C) 

      MINOURA Mao

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      4 2012 - 3 2015

      Grant number:24550063

      Grant amount:\5590000 ( Direct Cost: \4300000 、 Indirect Cost:\1290000 )

      The chemistry of heavier main group elements has been developed with respect to weak multiple-bond (pi-bonding) utilizing the kinetic stabilization method. However, organoelement compounds containing weak sigma-bonds were less explored due to their instability.
      In this project, we investigated on weak sigma bonds containing group 16 elements. 1) Bis-silyl/germyltellurides were prepared using pure and isolated reagents, 2) Imidazolium-selone/-tellone having weak polar bonding system were successfully synthesized, 3) an Enesulfenic acid which is regarded as a sulfur analogue of reactive peroxide was isolated.

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    • Preparation of chalcogen-containing heterocycles using isoselenocyanates and their relatives

      Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C) 

      SASHIDA Haruki, KANAME Mamoru, MINOURA Mao

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      2011 - 2013

      Grant number:23590023

      Grant amount:\5460000 ( Direct Cost: \4200000 、 Indirect Cost:\1260000 )

      (1) The cycloaddion of several nucleophiles having a triple bond or an appropriative leaving group with the isoselenocyanates and the relatives was examined. (2) The cycloaddion of the isoselenocyanates having a triple bond (or a leaving group) with some nucleophiles was also carried out. The novel heterocycles containing a chalcogen element (Se, S, Te) were effectively obtained by these two original methods. The application and functionalities (structure and reactivity) were studied. Furthermore, the iodocyclization of these substrates and the nucleophiles was focused to give more functionalized products. The novel iodocyclization of the dichalcogenides was also found to prepare the heterocycles containing a chalcogen element.

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    • Synthesis and Characterization of Novel Group 16 Element Compounds with Oxidation State IV or VI Having Carbon Ligands

      Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C) 

      MINOURA Mao

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      2008 - 2010

      Grant number:20550050

      Grant amount:\4940000 ( Direct Cost: \3800000 、 Indirect Cost:\1140000 )

      We report here, 1) the systematic synthesis hypervalent tetraaryltellurium(IV) compounds bearing substituents at the para position of the aryl rings, and the first SP structure of Te(IV) compound was found; 2) Newly prepared organotelluronium salts showed green-blue color in solution as the heavier main group element homologue and analogue instead of the central carbon atom of Crystal Violet; 3) Functionalization reactions of hexaorganotelluriums(VI) were investigated using (4-bromophenyl)pentaphenyltellurium(VI) which was prepared form the reaction of pentaphenyltellurium cation with 4-bromophenyl lithium. Functionalization reactions of the bromo-compound were proceeded to give useful cross-coupling products having octahedral structure around Te(VI).

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    • Synthesis and Characterization of Hypervalent OrganotelluriumAnion Species

      Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C) 

      MINOURA Mao

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      2006 - 2007

      Grant number:18550045

      Grant amount:\4190000 ( Direct Cost: \3800000 、 Indirect Cost:\390000 )

      Intensive efforts have been recently directed toward the hypervalent organochalcogen compounds because of the peculiarity of chalcogens to have two accessible higher oxidation states (IV and VI) which can form variety of compounds of potential. However, very little is known for those with valence VI chalcogen compounds and no hexaarylated chalcogen had been described until we recently reported the synthesis of hexaaryltellurium, Ar6Te, as neutral compound comprising Te^<VI>. Moreover, we also reported on the synthesis and characterization of pentaphenyltelluronium, Ph_5Te^+, as the hypervalent onium compound. Although corresponding anion species, Ph_5Te^-, has been reported as an unstable intermediate in the reaction of Ph_4Te with PhLi, isolated hypervalent tellurium ate compounds have been the missing class of compound. Here, we present the first isolation of hypervalent organotellurium anion species, Ph_5Te^-Li^+(DME)_3, and its structure.
      The synthesis of Ph_5Te^-Li^+(DME)_3 was achieved by the reaction of freshly prepared Ph_4Te with PhLi. After exchange of the solvent from THE to DME of the mixture, Ph_5Te^-Li^+(DME)_3 was obtained as yellow-orange solid. All manipulations were carried out at -78℃. The single crystals were grown from DME at low temperature and X-ray crystallographic analysis was performed at -160℃. The molecular structure indicates that the Ph_5Te^- has square-pyramidal (pseudo octahedral) structure around the tellurium and the Te-C (basal) bond lengths (2. 329-2. 342 A) are longer than the apical Te-C bond length (2. 153Å). The isolated hypervalent anion is relatively stable at -30℃ in the solid state. The reaction of the tellurium anion with CH_3I or SO_2Cl_2 gave corresponding neutral hexavalent organotellurium species, respectively.

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    • Synthesis and Development of Novel Main Group Element Compounds having Tin-based Steric Protection Group

      Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C) 

      MINOURA Mao

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      2004 - 2005

      Grant number:16550043

      Grant amount:\3700000 ( Direct Cost: \3700000 )

      In recent years there has been much interest in the reactive main group element compounds having an efficient steric protection group because of their unique chemical properties. Although many successes and developments of the steric protection groups have been reported, the central atom has been limited to carbon in many cases. In this research project, we have been investigating on the tin-based steric protection groups for the kinetic stabilization of reactive functional groups. For example, tris(9-triptycyl)stannyl group (Trp_3Sn-) has been shown as an effective steric protection group for-SOH function. Also, we synthesized and investigated on the related compounds bearing three 9,10-dihydro-9,10-ethenoanthracen-l-yl (Dbb) groups on a central tin atom (Dbb_3Sn-) as a novel tin-based steric protection group. Also, the synthesis and functionalization of methylbis(9-triptycyl)stannyl group (Trp_2MeSn-) has been studied.
      Moreover, static and dynamic stereochemistry of several Trp3Sn-compounds were studied. X-ray crystallography of the Trp3SnX (X= hologenes, alkyl groups) showed that the three Trp goups meshed with each other like bevel gears and formed near-C3 chiral conformation. In solution, the process of enantiomerization of those Trp3SnX compounds has been investigated by VT-NMR method.

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    • 非古典的オニウム種Ph_5Te^+を機軸とする新規超原子価典型元素化合物の合成

      日本学術振興会  科学研究費助成事業 奨励研究(A) 

      箕浦 真生

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      2000 - 2001

      Grant number:12740352

      Grant amount:\600000 ( Direct Cost: \600000 )

      スルホニウムに代表される16族元素オニウム化学種Ph_3Ch^+(Ch=S, Se, Te)は有機化学の発展の過程で古くから研究対象となり用いられてきた。しかしながら超原子価となる16族元素オニウム種Ph_5Ch^+は全く未知であった。本申請課題では中心元素としてテルルを選び、非古典的オニウム種として種々のPh_5Te^+Z^-の合成を行い、性質を明らかにすることを目的とした。
      オニウム種Ph_5Te^+Z^-の合成前駆体としてPh_5TeX(X=F, Cl, Br)の簡便合成法を開発し、テルルーハロゲン結合が共有結合であることを結晶構造解析により明らかにした。このPh_5TeXを用いてPh_5Te^+Z^-(Z=ClO_4, [(CF_3)_2C_6H_3]_4B)の合成をハロゲンの引き抜き反応と続くカウンターアニオン交換により行い、いずれも安定な結晶として単離した。X線結晶構造解析により固体中Ph_5Te^+カチオンのテルル周りではいずれも四角錐構造を有していることが明らかになった。通常の中性5配位典型元素化合物や遷移金属化合物が三方両錐構造を有していることとは対照的であり、これら非古典的オニウム種の特徴と言える。Ph_5Te^+Z^-と求核試剤との反応では対応する中性6価有機テルル化合物を高収率で与え、新しい6価有機テルル化合物の良い前駆体となることがわかった。さらに、容易に得られるようになった中性6価テルル化合物を出発物質として用い、対応する超原子価アニオン種R_5Te^-Y^+およびアニオン種R_4Te^<2->2Y^+(R=4-CF_3C_6H_4,4-CH_3C_6H_4;Y=KC_8)の合成にも初めて成功した。超原子価アニオン種と求電子試剤との反応により、非対称6価有機テルル化合物へ導くなど、反応性を明らかにできた。今後はここで得られた知見に基づき、新規超原子価化合物としの新しい特性の創出へ繋げたいと考えている。

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    • 酸化数の異なる5配位有機テルル種の創製とそれらを用いる超原子価化合物の合成と反応

      日本学術振興会  科学研究費助成事業 奨励研究(A) 

      箕浦 真生

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      1998 - 1999

      Grant number:10740296

      Grant amount:\2100000 ( Direct Cost: \2100000 )

      5つの芳香族置換基を有する15族元素(例えばEAr_5,E=P,As,Sb,Bi)や関連するAr_4E^±、Ar_3Te^±などは古くから研究されているものの、対応する超原子価16族元素化合物(Ar_5Te^+またはAr_5Te^-)は全く未知である。最近申請者らが合成した芳香族環を6つ有する元素の初めての例であるTeAr_6の新しい知見に基づき、炭素配位子から成る5配位有機テルル種Ar_5Te^±を合成し、新しい結合様式である超原子価テルルの性質を明らかにする目的で研究を行った。
      本申請課題のAr_5Te^+の合成は昨年度合成に成功した炭素配位子を5つ有するAr_5TeX(Ar=Ph-,p-CF_3C_6H_4-,X=F,Cl,Br)を用いてハロゲンを引き抜くことで合成した。この超原子価カチオン種Ar_5Te^+は驚くべきことに室温下安定に存在し、その構造はX線結晶構造解析により確定し四角錐型構造を有することを明らかにした。溶液中ではBerryの擬回転状態にあること見いだした。また古典的オニウム種Ar_3Te^+との対比から新しい反応性として還元的脱離反応、不均反応などを起こすことが明らかになった。対応するアニオン種Ar_5Te^-はAr_6Teの金属カリウムとの反応により溶液中低温下存在することを各種スペクトルデータおよび反応により確認した。この超原子価アニオン種は炭素官能基化が可能であり新しい6価有機テルル化合物へと導くことが出来た。

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    • 炭素配位子からなる6配位有機テルル化合物の合成とリガンドカップリング反応

      日本学術振興会  科学研究費助成事業 奨励研究(A) 

      箕浦 真生

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      1996 - 1996

      Grant number:08740497

      Grant amount:\1000000 ( Direct Cost: \1000000 )

      炭素配位子のみを有する安定な6配位化合物はこれまでに知られていなかった。本研究では超原子価有機16族元素化合物、特にテルルに注目し炭素配位子からなる安定な6配位有機テルル化合物の創製およびその反応性の解明を目的とし、中性で非共有電子対を持たない炭素配位子のみからなる安定な6配位有機テルル化合物の合成を行った。炭素配位子として芳香族置換基、特にパラ位にトリフルオロメチル基を有するp-CF3C6H4-=Arを用い、炭素配位子のみからなる安定な6配位有機テルル化合物としてTeAr6の合成に成功した。TeAr6は対応するArLiにTeCl4を反応させることでone-potで簡便に合成出来、安定な融点320℃の結晶として単離された。TeAr6はX線結晶構造解析により6つのC-Te結合はすべて等価な正八面体構造を有していることが明らかとなり、極めて希なThの対称性を有している。TeAr6は酸素、水および光に対して高い安定性を有しており、融点以下での加熱では全く分解しないものの、350℃の加熱によりラジカル分解生成物に相当する化合物が得られ、また高圧水銀灯による6時間以上の光照射によりTeAr6以外にTeAr2,Ar2等の分解生成物が得られた。これらの挙動はこれまでの2および4配位有機テルル化合物とは全く異なっている。またTeAr6のテルル原子上はハロゲン等にも不活性であり、この6配位状態を保ったまま芳香族環上の官能基化が可能である。今後、3次元的に広がる高い対称性と剛直性、安定性を合わせ持っているTeAr6を核とし、官能基修飾が可能なことを利点とする6配位構造を機軸とする、TeAr6の多修飾機能物質の合成へと展開させる予定である。

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    • アミノ基含有化合物及びその製造方法、反応型難燃剤、並びに、組成物

      猪原 英樹, 箕浦 真生, 竹下 空澄

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      Applicant:東ソー株式会社

      Application no:特願2021-134055  Date applied:19 8 2021

      Announcement no:特開2023-028383  Date announced:3 3 2023

      J-GLOBAL

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    • イソシアネート基含有化合物及びその製造方法、反応型難燃剤、並びに、組成物

      猪原 英樹, 箕浦 真生, 竹下 空澄

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      Applicant:東ソー株式会社

      Application no:特願2021-134092  Date applied:19 8 2021

      Announcement no:特開2023-028408  Date announced:3 3 2023

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    • チアベンダゾール含有配位高分子

      箕浦 真生, 小林 大哉, 濱川 陽, 柳田 光広

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      Applicant:日本曹達株式会社

      Application no:特願2020-134883  Date applied:7 8 2020

      Announcement no:特開2022-030705  Date announced:18 2 2022

      J-GLOBAL

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    • 芳香族酸ポリ無水物及びその製造方法

      猪原 英樹, 箕浦 真生

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      Applicant:東ソー株式会社

      Application no:特願2019-188795  Date applied:15 10 2019

      Announcement no:特開2020-063245  Date announced:23 4 2020

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    • 新規有機テルロニウムおよびセレノニウム化合物

      箕浦 真生, 石井 華, 山本 学, 真崎 康博

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      Applicant:学校法人北里研究所

      Application no:特願2009-210669  Date applied:11 9 2009

      Announcement no:特開2011-057637  Date announced:24 3 2011

      Patent/Registration no:特許第5515029号  Date registered:11 4 2014 

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    • 新規有機テルロニウムおよびセレノニウム化合物

      箕浦 真生, 石井 華, 山本 学, 真崎 康博

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      Applicant:学校法人北里研究所

      Application no:特願2009-210669  Date applied:11 9 2009

      Announcement no:特開2011-057637  Date announced:24 3 2011

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    • 新規超原子価テルル化合物

      箕浦 真生, 秋葉 欣哉, 石川 佳代, 小野沢 孝

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      Applicant:東京化成工業株式会社

      Application no:特願2000-074902  Date applied:14 2 2000

      Announcement no:特開2001-226348  Date announced:21 8 2001

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