Updated on 2021/06/22

写真b

 
MORIMOTO Masakazu
 
*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 Field of Study: Chemistry
Graduate School of Science Field of Study: Chemistry
Title*
Professor
Degree
修士(工学) ( 九州大学 ) / 博士(工学) ( 九州大学 ) / 学士(工学) ( 九州大学 ) / Bachelor of Engineering ( Kyushu University ) / Doctor of Engineering ( Kyushu University ) / Master of Engineering ( Kyushu University )
Contact information
Mail Address
Research Theme*
  • 有機光化学。光の照射により異性化反応を起こして色を変化させるフォトクロミック分子などの光応答分子に関する研究を行っている。光応答分子およびその集積体を合成し、それらの構造や光応答挙動を観測・解析することにより、光機能の発現のための物質設計の指針を確立するとともに、新しい光応答分子デバイスを創出することをめざしている。

  • Research Interests
  • Organic photochemistry

  • Campus Career*
    • 4 2017 - Present 
      College of Science   Department of Chemistry   Professor
    • 4 2017 - Present 
      Graduate School of Science   Field of Study: Chemistry   Professor
    • 4 2017 - Present 
      Graduate School of Science   Field of Study: Chemistry   Professor
    • 4 2010 - 3 2017 
      College of Science   Department of Chemistry   Associate Professor
    • 4 2007 - 3 2010 
      College of Science   Department of Chemistry   Assistant Professor
     

    Research Areas

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

    • Nanotechnology/Materials / Functional solid state chemistry  / Organic photochemistry

    Research History

    • 4 2017 - Present 
      RIKKYO UNIVERSITY   Graduate School of Science Field of Study: Chemistry   Professor

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    • 4 2017 - Present 
      RIKKYO UNIVERSITY   Graduate School of Science Field of Study: Chemistry   Professor

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    • 4 2017 - Present 
      RIKKYO UNIVERSITY   College of Science Department of Chemistry   Professor

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    • 4 2010 - 3 2017 
      RIKKYO UNIVERSITY   College of Science Department of Chemistry   Associate Professor

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    • 10 2007 - 3 2011 
      PRESTO, Japan Science and Technology Agency

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    • 4 2007 - 3 2010 
      RIKKYO UNIVERSITY   College of Science Department of Chemistry   Assistant Professor

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    • 9 2006 - 3 2007 
      Tohoku University   Graduate School of Science

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    • 4 2006 - 8 2006 
      Tohoku University   Graduate School of Science

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    • 4 2004 - 3 2006 
      Japan Society for the Promotion of Science   Special researcher of the Japan Society for the Promotion of Science

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    Education

    • 4 2003 - 3 2006 
      Kyushu University   Department of Chemistry and Biochemistry

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      Country: Japan

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    • 4 2001 - 3 2003 
      Kyushu University   Department of Chemistry and Biochemistry

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      Country: Japan

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    • 4 1997 - 3 2001 
      Kyushu University   Faculty of Engineering   Department of Materials Science and Engineering

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      Country: Japan

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    Awards

    • 9 2017  
      The Japanese Photochemistry Association  The Japanese Photochemistry Association Award for Young Scientist 2017  Development of novel photofunctional molecular crystals based on crystal-engineering strategy
       
      Masakazu Morimoto

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      Award type:Award from Japanese society, conference, symposium, etc.  Country:Japan

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    Papers

    • Cyclization from higher excited states of diarylethenes having a substituted azulene ring Peer-reviewed

      Yohei Hattori, Tatsuya Maejima, Yumi Sawae, Jun‐ichiro Kitai, Masakazu Morimoto, Ryojun Toyoda, Hiroshi Nishihara, Satoshi Yokojima, Shinichiro Nakamura, Kingo Uchida

      Chemistry-A European Journal26 ( 50 ) 11441 - 11450   4 9 2020

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

      DOI: 10.1002/chem.202001671

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    • Optical microresonator arrays of fluorescence-switchable diarylethenes with unreplicable spectral fingerprints Peer-reviewed

      Daichi Okada, Zhan-Hong Lin, Jer-Shing Huang, Osamu Oki, Masakazu Morimoto, Xuying Liu, Takeo Minari, Satoshi Ishii, Tadaaki Nagao, Masahiro Irie, Yohei Yamamoto

      Materials Horizons7 ( 7 ) 1801 - 1808   1 7 2020

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

      DOI: 10.1039/D0MH00566E

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    • Turn-on mode fluorescent diarylethenes: Effect of electron-donating and electron-withdrawing substituents on photoswitching performance Peer-reviewed

      Ryota Iwai, Masakazu Morimoto, Masahiro Irie

      Photochemical & Photobiological Sciences19 ( 6 ) 783 - 789   1 6 2020

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      DOI: 10.1039/D0PP00064G

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    • A cytosolically localized far-red to near-infrared rhodamine-based fluorescent probe for calcium ions Peer-reviewed

      Koji Numasawa, Kenjiro Hanaoka, Takayuki Ikeno, Honami Echizen, Tomoe Ishikawa, Masakazu Morimoto, Toru Komatsu, Tasuku Ueno, Yuji Ikegaya, Tetsuo Nagano, Yasuteru Urano

      Analyst   2020

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

      DOI: 10.1039/D0AN01739F

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    • Photoinduced swing of a diarylethene thin broad sword shaped crystal: a study on the detailed mechanism Peer-reviewed

      Ayako Fujimoto, Noriko Fujinaga, Ryo Nishimura, Eri Hatano, Luna Kono, Akira Nagai, Akiko Sekine, Yohei Hattori, Yuko Kojima, Nobuhiro Yasuda, Masakazu Morimoto, Satoshi Yokojima, Shinichiro Nakamura, Ben L. Feringa, Kingo Uchida

      Chemical Science   2020

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

      DOI: 10.1039/D0SC05388K

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    • Stepwise assembly of ultrathin poly(vinyl alcohol) films on photoresponsive diarylethene crystals Peer-reviewed

      Hiroka Chiba, Masakazu Morimoto, Masahiro Irie

      Chemistry Letters   2020

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

      DOI: 10.1246/cl.200693

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    • An all-photonic full color RGB system based on molecular photoswitches Peer-reviewed

      Gaowa Naren, Chien-Wei Hsu, Shiming Li, Masakazu Morimoto, Sicheng Tang, Jordi Hernando, Gonzalo Guirado, Masahiro Irie, Françisco M. Raymo, Henrik Sundén, Joakim Andréasson

      Nature Communications10   3996   5 9 2019

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

      DOI: 10.1038/s41467-019-11885-4

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    • Thermally reversible photochromism of dipyrrolylethenes Peer-reviewed

      Kohei Inaba, Ryota Iwai, Masakazu Morimoto, Masahiro Irie

      Photochemical & Photobiological Sciences18 ( 9 ) 2136 - 2141   1 9 2019

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

      DOI: 10.1039/C8PP00557E

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    • Object Transportation System Mimicking the Cilia of Paramecium aurelia Making Use of the Light‐Controllable Crystal Bending Behavior of a Photochromic Diarylethene Peer-reviewed

      Ryo Nishimura, Ayako Fujimoto, Nobuhiro Yasuda, Masakazu Morimoto, Tatsuhiro Nagasaka, Hikaru Sotome, Syoji Ito, Hiroshi Miyasaka, Satoshi Yokojima, Shinichiro Nakamura, Ben. L. Feringa, Kingo Uchida

      Angewandte Chemie International Edition58   13308 - 13312   7 2019

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    • Photosalient Effect of Diarylethene Crystals of Thiazoyl and Thienyl Derivatives Peer-reviewed

      NAKAGAWA Yuma, MORIMOTO Masakazu, YASUDA Nobuhiro, HYODO Kengo, YOKOJIMA Satoshi, NAKAMURA Shinichiro, UCHIDA Kingo

      Chemistry - A European Journal25 ( 33 ) 7874 - 7880   6 2019

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

      DOI: 10.1002/chem.201900811

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    • Synthesis, structures, and magnetic properties of two coordination assemblies of Mn(III) single molecule magnets bridged via photochromic diarylethene ligands Peer-reviewed

      Ahmed Fetoh, Goulven Cosquer, Masakazu Morimoto, Masahiro Irie, Ola El-Gammal, Gaber M. Abu El-Reash, Brian K. Breedlove, Masahiro Yamashita

      Inorganic Chemistry58 ( 4 ) 2307 - 2314   18 2 2019

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

      DOI: 10.1021/acs.inorgchem.8b02578

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    • The photoregulation of a mechanochemical polymer scission Peer-reviewed

      Jumpei Kida, Keiichi Imato, Raita Goseki, Daisuke Aoki, Masakazu Morimoto, Hideyuki Otsuka

      Nature Communications9   3504   29 8 2018

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

      DOI: 10.1038/s41467-018-05996-7

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    • A turn-on mode fluorescent diarylethene: Solvatochromism of fluorescence Peer-reviewed

      Masakazu Morimoto, Yuta Takagi, Karina Hioki, Tatsuhiro Nagasaka, Hikaru Sotome, Syoji Ito, Hiroshi Miyasaka, Masahiro Irie

      Dyes and Pigments153   144 - 149   6 2018

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      © 2018 Elsevier Ltd Environment-sensitive fluorophores have been used as molecular probes to acquire physical and chemical information in microstructures. Here, we report on solvatochromism of a fluorescent diarylethene, which is switched by photoirradiation. A turn-on mode photoswitchable fluorescent diarylethene derivative, 1,2-bis(2-ethyl-6-(5-methylthiophen-2-yl)-1-benzothiophen-1,1-dioxide-3-yl)perfluorocyclopentene (1a), underwent a cyclization reaction upon irradiation with ultraviolet (UV) light to form fluorescent closed-ring isomer 1b. 1b dramatically changed the fluorescent color in response to solvent polarity, such as green in n-hexane, yellow in tetrachloromethane (CCl4), orange in dichloromethane (CH2Cl2), and red in dimethyl sulfoxide (DMSO), and showed high fluorescence quantum yields of 0.6–0.8 in these solvents. The fluorescent solvatochromism is ascribed to the intramolecular charge-transfer (ICT) character of 1b, which consists of electron-donating thiophene rings at both ends and central electron-accepting benzothiophene 1,1-dioxide groups. The analysis based on the Mataga-Lippert plot revealed that the difference in the dipole moments between the excited and ground states of 1b is as large as 12 D. Such a solvatochromic fluorophore with photoswitching ability can find potential applications in super-resolution fluorescence imaging of microscopic polarity in biological cells and materials.

      DOI: 10.1016/j.dyepig.2018.02.016

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    • Mesoscopic Motion of Optically Trapped Particle Synchronized with Photochromic Reactions of Diarylethene Derivatives Peer-reviewed

      Syoji Ito, Morio Mitsuishi, Kenji Setoura, Mamoru Tamura, Takuya Iida, Masakazu Morimoto, Masahiro Irie, Hiroshi Miyasaka

      Journal of Physical Chemistry Letters9 ( 10 ) 2659 - 2664   17 5 2018

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      © 2018 American Chemical Society. Not only the energy but also the momentum of photons transfers to material via photoabsorption; this momentum transfer, known as radiation pressure, can induce motions of small particles. It can therefore be expected to induce mechanical motions of mesoscopic materials synchronized with the reversible change of their absorption coefficient by external stimuli. We demonstrated quantitative photomechanical motions in mesoscopic regions by combining optical tweezer and photochromic reactions of diarylethene (DAE). A microparticle including DAE was optically trapped with 532 nm laser and the absorption band of the DAE was photoswitched with UV laser, resulting in the modulation of the radiation force through the change in the complex dielectric constant of the particle. In this process, mesoscopic mechanical motions were successfully induced by the photochromic reaction. The present approach is potentially applicable in a wide variety of nano/micromechanical devices and also paves the way for monitoring the absorption of photons by molecules via photomechanical response.

      DOI: 10.1021/acs.jpclett.8b00890

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    • Multiphoton-gated cycloreversion reaction of a fluorescent diarylethene derivative as revealed by transient absorption spectroscopy Peer-reviewed

      Tatsuhiro Nagasaka, Tomohiro Kunishi, Hikaru Sotome, Masafumi Koga, Masakazu Morimoto, Masahiro Irie, Hiroshi Miyasaka

      Physical Chemistry Chemical Physics20 ( 30 ) 19776 - 19783   2018

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      © the Owner Societies 2018. The one- and two-photon cycloreversion reactions of a fluorescent diarylethene derivative with oxidized benzothiophene moieties were investigated by means of ultrafast laser spectroscopy. Femtosecond transient absorption spectroscopy under the one-photon excitation condition revealed that the excited closed-ring isomer is simply deactivated into the initial ground state with a time constant of 2.6 ns without remarkable cycloreversion, the results of which are consistent with the very low cycloreversion reaction yield (<10-5) under steady-state light irradiation. On the other hand, an efficient cycloreversion reaction was observed under irradiation with a picosecond laser pulse at 532 nm. The excitation intensity dependence of the cycloreversion reaction indicates that a highly excited state attained by the stepwise two-photon absorption is responsible for the marked increase of the cycloreversion reaction, and the quantum yield at the highly excited state was estimated to be 0.018 from quantitative analysis, indicating that the reaction is enhanced by a factor of >1800.

      DOI: 10.1039/c8cp01467a

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    • Photoswitchable Turn-on Mode Fluorescent Diarylethenes: Strategies for Controlling the Switching Response Invited Peer-reviewed

      Masahiro Irie, Masakazu Morimoto

      Bulletin of the Chemical Society of Japan91 ( 2 ) 237 - 250   2018

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:Chemical Society of Japan  

      A new type of photoswitchable fluorescent diarylethenes, which have no fluorophore unit but emit strong fluorescence (¯f 3 0.9) in the closed-ring isomers, has been developed. They are sulfone derivatives of 1,2-bis(2-alkyl-4-methyl-5-phenyl-3-thienyl)perfluorocyclopentenes and 1,2-bis(2-alkyl-1-benzothiophen-3-yl)perfluorocyclopentenes. By chemical modifications of the structures their switching response was tuned to meet the requirements for super-resolution fluorescence microscopies. The water-soluble derivatives have been successfully applied to acquire super-resolution bioimages using a single-wavelength visible beam.

      DOI: 10.1246/bcsj.20170365

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    • Fluorescence Photoswitching of a Diarylethene by Irradiation with Single-Wavelength Visible Light Peer-reviewed

      Ryota Kashihara, Masakazu Morimoto, Syoji Ito, Hiroshi Miyasaka, Masahiro Irie

      JOURNAL OF THE AMERICAN CHEMICAL SOCIETY139 ( 46 ) 16498 - 16501   11 2017

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:AMER CHEMICAL SOC  

      Photoswitchable turn-on mode fluorescent molecules have been so far successfully used in super resolution fluorescence microscopies. Here, we report on fluorescence photoswitching of 1,2-bis(2-ethyl-6-phenyl-1b enz othiophene- 1,1- dioxide-3-y1) perfluoro cyclopentene (1) by irradiation with single-wavelength visible (420 nm &lt; 2 &lt; 470 nm) light, the wavelength of which is longer than the 0-0 transition of open-ring isomer la, without UV light excitation. By absorbing very weak hot bands or Urbach tails la underwent a cyclization reaction to produce fluorescent closed-ring isomer lb. Both cyclization and cycloreversion reactions of 1 took place with the visible light in the far off-resonance region of the absorption edge. Based on numerical simulations of the formation process of lb from la by irradiation with 450 nm light, weak absorption coefficients at 450 nm in n-hexane and CCl4 were estimated to be 0.084 and 0.19 M-1 cm(-1), respectively. The reversible fluorescence photoswitching with the single visible light is advantageously applicable to super-resolution fluorescence imaging in biological systems.

      DOI: 10.1021/jacs.7b10697

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    • Thermal decomposition product of 1,2-bis(2-methyl-1-benzofuran-3-yl) perfluorocyclopentene Peer-reviewed

      Tadatsugu Yamaguchi, Tsuyoshi Nakagawa, Toru Ozeki, Mitsuhiro Fukuda, Masakazu Morimoto, Shizuka Takami

      TETRAHEDRON LETTERS58 ( 47 ) 4447 - 4449   11 2017

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:PERGAMON-ELSEVIER SCIENCE LTD  

      1,2-Bis(2-methyl-l-benzofuran-3-yl)perfluorocyclopentene shows photochromism in n-hexane at room temperature. We have identified a new compound produced by the thermal decomposition in a mixture of cis- and trans-decahydronaphthalene above 100 degrees C in the absence of light. (C) 2017 Elsevier Ltd. All rights reserved.

      DOI: 10.1016/j.tetlet.2017.10.017

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    • Photosalient Phenomena that Mimic Impatiens Are Observed in Hollow Crystals of Diarylethene with a Perfluorocyclohexene Ring Peer-reviewed

      Eri Hatano, Masakazu Morimoto, Takahito Imai, Kengo Hyodo, Ayako Fujimoto, Ryo Nishimura, Akiko Sekine, Nobuhiro Yasuda, Satoshi Yokojima, Shinichiro Nakamura, Kingo Uchida

      ANGEWANDTE CHEMIE-INTERNATIONAL EDITION56 ( 41 ) 12576 - 12580   10 2017

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

      A diarylethene with a perfluorocyclohexene ring formed hollow crystals by sublimation under normal pressure. Upon UV irradiation of the crystals, they showed remarkable photosalient phenomena and scattered into small pieces. The speed of the flying debris released from the crystal by UV irradiation exceeded several meters per second. To clearly show a photosalient effect resembling the scattering behavior of Impatiens on a smaller scale, small fluorescent beads (1-mu m diameter) were inserted into the hollow crystal. Consequently, scattering of the beads was observed as UV irradiation caused deformation and bursting of the hollow structure. This phenomenon is unique to hollow crystals, and the ability to effectively induce remarkable photosalient phenomena is similar to the behavior of hollow-structured Impatiens in nature.

      DOI: 10.1002/anie.201706684

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    • Photoswitchable Fluorescent Diarylethene Derivatives with Thiophene 1,1-Dioxide Groups: Effect of Alkyl Substituents at the Reactive Carbons Peer-reviewed

      Masakazu Morimoto, Takaki Sumi, Masahiro Irie

      MATERIALS10 ( 9 ) 1021   9 2017

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

      Photoswitching and fluorescent properties of sulfone derivatives of 1,2-bis(2-alkyl-4-methyl-5-phenyl-3-thienyl)perfluorocyclopentene, 1-5, having methyl, ethyl, n-propyl, i-propyl, and i-butyl substituents at the reactive carbons (2- and 2'-positions) of the thiophene 1,1-dioxide rings were studied. Diarylethenes 1-5 underwent isomerization reactions between open-ring and closed-ring forms upon alternate irradiation with ultraviolet (UV) and visible light and showed fluorescence in the closed-ring forms. The alkyl substitution at the reactive carbons affects the fluorescent property of the closed-ring isomers. The closed-ring isomers 2b-5b with ethyl, n-propyl, i-propyl, and i-butyl substituents show higher fluorescence quantum yields than 1b with methyl substituents. In polar solvents, the fluorescence quantum yield of 1b markedly decreases, while 2b-5b maintain the relatively high fluorescence quantum yields. Although the cycloreversion quantum yields of the derivatives with methyl, ethyl, n-propyl, and i-propyl substituents are quite low and in the order of 10(-5), introduction of i-butyl substituents was found to increase the yield up to the order of 10(-3). These results indicate that appropriate alkyl substitution at the reactive carbons is indispensable for properly controlling the photoswitching and fluorescent properties of the photoswitchable fluorescent diarylethenes, which are potentially applicable to super-resolution fluorescence microscopies.

      DOI: 10.3390/ma10091021

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    • Turn-on mode fluorescent diarylethenes: Control of the cycloreversion quantum yield Peer-reviewed

      Yuta Takagi, Masakazu Morimoto, Ryota Kashihara, Sae Fujinami, Syoji Ito, Hiroshi Miyasaka, Masahiro Irie

      TETRAHEDRON73 ( 33 ) 4918 - 4924   8 2017

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:PERGAMON-ELSEVIER SCIENCE LTD  

      Turn-on mode fluorescence switching molecules are applicable to super-resolution fluorescence microscopy, such as PALM (photoactivation localization microscopy), STORM (stochastic optical reconstruction microscopy) or RESOLFT (reversible saturable (switchable) optical linear fluorescence transitions) microscopy. Here we report on a molecular design strategy to control the cycloreversion quantum yield of the turn-on mode fluorescent diarylethenes, 1,2-bis(2-ethyl-6-aryl-1-benzothiophene-1,1-dioxide-3-yl)perfluorocyclopentenes. Diarylethene derivatives having ortho-substituted phenyl rings at 6- and 6'-positions of 1,2-bis(2-ethyl-1-benzothiophene-1,1-dioxide-3-yl)perfluorocyclopentene were synthesized and their photophysical and photochemical properties were evaluated. The ortho-substitution of the phenyl rings with fluorine or methyl groups decreases the extension of pi-conjugation length, resulting in a small blue shift of the absorption spectrum and a substantial increase in the cycloreversion quantum yield from 10(-4) to 10(-2) without significant influence on the fluorescence quantum yield. Water-soluble derivatives having sodium sulfonate groups were also synthesized. These derivatives fulfill requirements necessary for the application to RESOLFT super-resolution fluorescence microscopy. (C) 2017 Elsevier Ltd. All rights reserved.

      DOI: 10.1016/j.tet.2017.03.040

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    • Photoregulation of Retro-Diels-Alder Reaction at the Center of Polymer Chains Peer-reviewed

      Jumpei Kida, Keiichi Imato, Raita Goseki, Masakazu Morimoto, Hideyuki Otsuka

      CHEMISTRY LETTERS46 ( 7 ) 992 - 994   7 2017

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:CHEMICAL SOC JAPAN  

      Photoregulation of polymer chain scission based on a Diels-Alder (DA) adduct containing diarylethene (DAE) was investigated. Poly(epsilon-caprolactone) with a DA adduct conjugated with DAE skeleton (DAE/DA) at the center of the chain was synthesized by ring-opening living cationic polymerization of epsilon-caprolactone, initiating from diol-type DAE/DA, and its chain scission via thermally induced retro-DA reaction was successfully controlled by photoisomerization of DAE.

      DOI: 10.1246/cl.170251

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    • One-colour control of activation, excitation and deactivation of a fluorescent diarylethene derivative in super-resolution microscopy Peer-reviewed

      Yuhei Arai, Syoji Ito, Hajime Fujita, Yusuke Yoneda, Takahiro Kaji, Satoshi Takei, Ryota Kashihara, Masakazu Morimoto, Masahiro Irie, Hiroshi Miyasaka

      CHEMICAL COMMUNICATIONS53 ( 29 ) 4066 - 4069   4 2017

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:ROYAL SOC CHEMISTRY  

      We demonstrated one-colour control of activation, excitation and deactivation of a fluorescent diarylethene derivative by using a 532 nm CW laser at a weak output power. This one-colour control method was applied to single-molecule tracking in polymer films over a total duration of a few hours at room temperature and PALM for the nanostructures of polymer systems.

      DOI: 10.1039/c6cc10073b

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    • Diastereoselective photocyclization of a photochromic diarylethene having a benzo[b]phosphole P-oxide group Peer-reviewed

      Tomohiro Ichikawa, Masakazu Morimoto, Masahiro Irie

      DYES AND PIGMENTS137   214 - 220   2 2017

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:ELSEVIER SCI LTD  

      A photochromic diarylethene derivative 1 having a chiral benzo[b]phosphole P-oxide at the aryl moiety underwent a diastereoselective photocyclization reaction in acetonitrile upon irradiation with ultraviolet (UV) light. It was found that the diastereomeric excess (d.e.) value changes depending on the conversion ratio from the open- to closed-ring isomer as well as the irradiation wavelength. This is attributed to the difference in the photocycloreversion quantum yields of diastereomers of the closed-ring isomer. The diarylethene showed a high photocyclization quantum yield owing to a high population of photoreactive conformers of the open-ring isomer by the steric effect of the benzo[b]phosphole P-oxide group. (C) 2016 Elsevier Ltd. All rights reserved.

      DOI: 10.1016/j.dyepig.2016.10.010

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    • 光駆動分子結晶アクチュエーター:分子マシンをめざす1つの試み Invited Peer-reviewed

      森本 正和, 入江 正浩

      有機合成化学協会誌74 ( 12 ) 1217 - 1224   12 2016

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

      DOI: 10.5059/yukigoseikyokaishi.74.1217

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    • Photosalient Effect of a Diarylethene with a Perfluorocyclohexene Ring Peer-reviewed

      Eri Hatano, Masakazu Morimoto, Kengo Hyodo, Nobuhiro Yasuda, Satoshi Yokojima, Shinichiro Nakamura, Kingo Uchida

      CHEMISTRY-A EUROPEAN JOURNAL22 ( 36 ) 12680 - 12683   8 2016

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

      Crystals of a diarylethene with a perfluorocyclohexene ring exhibit a remarkable photosalient effect upon UV light irradiation that is attributed to the structural changes that occur when going from open-to closed-ring isomers in the crystalline state, together with the existence of two conformers with different photoconversions compared with those of a perfluorocyclopentene derivative. Our current results give a design principle for molecular structures so as to achieve the photosalient effect for photochromic crystals.

      DOI: 10.1002/chem.201603020

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    • 1D chains of lanthanoid ions and a dithienylethene ligand showing slow relaxation of the magnetization

      M. A. Yatoo, G. Cosquer, M. Morimoto, M. Irie, B. K. Breedlove, M. Yamashita

      Magnetochemistry2 ( 2 ) 21   3 2016

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

      DOI: 10.3390/magnetochemistry2020021

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    • Photo-activation of Single Molecule Magnet Behavior in a Manganese-based Complex Peer-reviewed

      Ahmed Fetoh, Goulven Cosquer, Masakazu Morimoto, Masahiro Irie, Ola El-Gammal, Gaber Abu El-Reash, Brian K. Breedlove, Masahiro Yamashita

      SCIENTIFIC REPORTS6   23785   3 2016

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:NATURE PUBLISHING GROUP  

      A major roadblock to fully realizing molecular electronic devices is the ability to control the properties of each molecule in the device. Herein we report the control of the magnetic properties of single-molecule magnets (SMMs), which can be used in memory devices, by using a photo-isomerizable diarthylenthene ligand. Photo-isomerization of the diarylethene ligand bridging two manganese salen complexes with visible light caused a significant change in the SMM behavior due to opening of the six-membered ring of diarylethene ligand, accompanied by reorganization of the entire molecule. The ring-opening activated the frequency-dependent magnetization of the complex. Our results are a major step towards the realization of molecular memory devices composed of SMMs because the SMM behaviour can be turned on and off simply by irradiating the molecule.

      DOI: 10.1038/srep23785

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    • Photochromism of diarylethene derivatives having benzophosphole and benzothiophene groups Peer-reviewed

      Tomohiro Ichikawa, Masakazu Morimoto, Hikaru Sotome, Syoji Ito, Hiroshi Miyasaka, Masahiro Irie

      DYES AND PIGMENTS126   186 - 193   3 2016

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:ELSEVIER SCI LTD  

      Asymmetric diarylethene derivatives having benzophosphole and benzothiophene groups at the aryl moieties were synthesized and their photochromic properties were examined. Three diarylethene derivatives, 1 having benzophosphole and benzothiophene groups, 2 having benzophosphole P-oxide and benzothiophene groups, and 3 having benzophosphole P-oxide and benzothiophene S,S-dioxide groups, were synthesized by appropriately controlled oxidation of benzophosphole and benzothiophene groups. Diarylethenes 1-3 underwent photochromic reactions in acetonitrile as well as in the powder solid state upon alternate irradiation with ultraviolet (UV) and visible light. The closed-ring isomer of diarylethene 3 emitted fluorescence with a quantum yield of 0.05 in acetonitrile solution. The fluorescence quantum yield dramatically increased up to 0.55 in the solid state. (C) 2015 Elsevier Ltd. All rights reserved.

      DOI: 10.1016/j.dyepig.2015.11.023

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    • Emission color tuning and white-light generation based on photochromic control of energy transfer reactions in polymer micelles Peer-reviewed

      Magnus Balter, Shiming Li, Masakazu Morimoto, Sicheng Tang, Jordi Hernando, Gonzalo Guirado, Masahiro Irie, Francisco M. Raymo, Joakim Andreasson

      CHEMICAL SCIENCE7 ( 9 ) 5867 - 5871   2016

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      We encapsulate a fluorescent donor molecule and a photochromic acceptor unit (photoswitch) in polymer micelles and show that the color of the emitted fluorescence is continuously changed from blue to yellow upon light-induced isomerization of the acceptor. Interestingly, white-light generation is achieved in between. With the photoswitch in the colorless form, intense blue emission from the donor is observed, while UV-induced isomerization to the colored form induces an energy transfer reaction that quenches the donor emission and sensitizes the yellow emission from the colored photoswitch. The process is reversed by exposure to visible light, triggering isomerization to the colorless form.

      DOI: 10.1039/c6sc01623e

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    • Photoinduced reversible formation of a superhydrophilic surface by crystal growth of diarylethene Peer-reviewed

      Kazuki Takase, Kengo Hyodo, Masakazu Morimoto, Yuko Kojima, Hiroyuki Mayama, Satoshi Yokojima, Shinichiro Nakamura, Kingo Uchida

      CHEMICAL COMMUNICATIONS52 ( 42 ) 6885 - 6887   2016

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      When visible light is irradiated onto the melted microcrystalline-surface of a diarylethene having ionic structures by UV irradiation, it induces crystal-growth of the open-ring isomer of the diarylethene; consequently, the surface covered with lumpy crystals shows super-hydrophilicity that can be reversibly controlled by alternating irradiation with UV and visible light.

      DOI: 10.1039/c6cc01638c

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    • Photoinduced topographical changes on microcrystalline surfaces of diarylethenes Peer-reviewed

      Noriko Fujinaga, Naoki Nishikawa, Ryo Nishimura, Kengo Hyodo, Seiji Yamazoe, Yuko Kojima, Kazuki Yamamoto, Tsuyoshi Tsujioka, Masakazu Morimoto, Satoshi Yokojima, Shinichiro Nakamura, Kingo Uchida

      CRYSTENGCOMM18 ( 38 ) 7229 - 7235   2016

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      By alternate irradiation with UV and visible light, reversible topographical changes were observed on the microcrystalline surfaces of diarylethene derivatives above the glass transition temperatures (T-g) of their open-ring isomers. For the photogenerated closed-ring isomers, the crystal growth proceeded at the surface softened by molecular movement. This is the self-aggregation of the closed-ring isomers. The photogenerated surface topographies appear depending on the crystal habits of the closed-ring isomers. Reflecting the properties (crystal habits) of diarylethene derivatives, we obtained cubic, needle, and plate-shaped crystals of the closed-ring isomers on the microcrystalline surfaces of the open-ring isomers by irradiation with UV light. Even a derivative having one isopropyl group at a reactive carbon atom, whose closed-ring isomer is thermally unstable, showed photoinduced topographical changes, because the Tg of the open-ring isomer is around ambient temperature.

      DOI: 10.1039/c6ce00718j

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    • Turn-on mode fluorescence photoswitching of diarylethene single crystals Peer-reviewed

      Masakazu Morimoto, Ryota Kashihara, Katsuya Mutoh, Yoichi Kobayashi, Jiro Abe, Hikaru Sotome, Syoji Ito, Hiroshi Miyasaka, Masahiro Irie

      CRYSTENGCOMM18 ( 38 ) 7241 - 7248   2016

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      The photochromic and fluorescence properties of two diarylethene derivatives having benzo[b] thiophene S, S-dioxide groups were studied in the single-crystalline phase. The derivatives showed reversible photochromic reactions and turn-on mode photoswitching of fluorescence in solution as well as in the single-crystalline phase. Upon irradiation with UV light, the open-ring isomers in the crystals underwent cyclization reactions to produce fluorescent closed-ring isomers. The UV-irradiated crystals emitted green or yellow-green fluorescence and exhibited dichroism of their absorption and fluorescence spectra under linearly polarized light. Upon irradiation with visible light, the closed-ring isomers reverted to the open-ring isomers and the fluorescence of the crystals disappeared. The switching cycles could be repeated more than 50 times without detectable deterioration. Area-selective switching of the fluorescence in the single crystal was demonstrated by patterned light irradiation, suggesting potential applications of the photo-switchable fluorescent molecular crystals in optical memory and display devices.

      DOI: 10.1039/c6ce00725b

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    • Fluorescent Photochromic Diarylethene That Turns on with Visible Light Peer-reviewed

      Takaki Sumi, Tomohiro Kaburagi, Masakazu Morimoto, Kanako Une, Hikaru Sotome, Syoji Ito, Hiroshi Miyasaka, Masahiro Irie

      ORGANIC LETTERS17 ( 19 ) 4802 - 4805   10 2015

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      A new fluorescent photochromic diarylethene that can be activated by irradiation with 405 nm light was synthesized. The turn-on mode switching of fluorescence with visible light is favorable for application to biological systems. The fluorescence quantum yield of the photogenerated closed-ring isomer was as high as 0.8 in less or medium polar solvents, and even in polar acetonitrile the yield was higher than 0.6.

      DOI: 10.1021/acs.orglett.5b02361

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    • A diarylethene as the SO2 gas generator upon UV irradiation Peer-reviewed

      Ryuhei Kodama, Kimio Sumaru, Kana Morishita, Toshiyuki Kanamori, Kengo Hyodo, Takashi Kamitanaka, Masakazu Morimoto, Satoshi Yokojima, Shinichiro Nakamura, Kingo Uchida

      CHEMICAL COMMUNICATIONS51 ( 9 ) 1736 - 1738   2015

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      A closed-ring isomer of a diarylethene having a sulfone group works as the reagent for SO2 gas generation with thermal stability even at 70 degrees C, and it rapidly reverts to the open-ring isomer and generates the SO2 gas to induce cell death upon UV irradiation.

      DOI: 10.1039/c4cc07790c

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    • Light-driven bending of diarylethene mixed crystals Peer-reviewed

      Satoko Ohshima, Masakazu Morimoto, Masahiro Irie

      CHEMICAL SCIENCE6 ( 10 ) 5746 - 5752   2015

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      Mixed crystals composed of 1,2-bis(2-methyl-5-(p-methoxyphenyl)-3-thienyl)perfluorocyclopentene (1a) and 1,2-bis(5-methyl-2-(p-methoxyphenyl)-4-thiazolyl)perfluorocyclopentene (2a) were prepared, and their photochromic as well as light-driven bending performance was studied to reveal how shape changes of individual molecules cause the bending response. 1a and 2a molecules, having similar geometrical structures, randomly mix with each other in a single crystal. The absorption spectra of the closed-ring isomers 1b and 2b were, however, distinctly different. The difference of the spectra made it possible to discriminate the cycloreversion reactions of 1b and 2b in the mixed crystals by irradiation with 750 nm light. The bending response of the mixed crystals by the selective photoisomerization revealed that the local shape change of each molecule is additively linked to the macroscopic deformation of the crystals.

      DOI: 10.1039/c5sc01994j

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    • Photo-control of the magnetic properties of Dy(III) and Ho(III) homometal coordination polymers bridged by a diarylethene ligand Peer-reviewed

      Goulven Cosquer, Masakazu Morimoto, Masahiro Irie, Ahmed Fetoh, Brian K. Breedlove, Masahiro Yamashita

      DALTON TRANSACTIONS44 ( 13 ) 5996 - 6002   2015

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      Two-dimensional Dy(III) and Ho(III) homometal coordination polymers containing the photochromic ligand 1,2-bis(5-carboxyl-2-methyl-3-thienyl) perfluorocyclopentene (DTE) with the general formula [Ln(2)(DTE)(3)(bipyridine)(2)(H2O)(2)](n) (Ln = Dy and Ho) were obtained, and the magnetic properties of their open (Dy-o and Ho-o) and closed forms (Dy-c and Ho-c) were investigated. The Dy complexes exhibited slow magnetic relaxation without an external dc field. The magnetic properties of the Dy complexes were irreversibly affected by the conformation of the ligand.

      DOI: 10.1039/c4dt03093a

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    • Two-colour fluorescent imaging in organisms using self-assembled nano-systems of upconverting nanoparticles and molecular switches Peer-reviewed

      Tuoqi Wu, Bob Johnsen, Zhaozhao Qin, Masakazu Morimoto, David Baillie, Masahiro Irie, Neil R. Branda

      NANOSCALE7 ( 26 ) 11263 - 11266   2015

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      The water-insolubility of a potentially versatile photoresponsive 'turn-on' fluorescence probe was overcome by incorporating it into a nano-assembly containing an upconverting nanoparticle wrapped in an amphiphilic polymer. The appeal of the nano-system is not only in the ability to turn "on" and "off" the fluorescence from the organic chromophore using UV and visible light, it is in the fact that the nanoparticle acts as a static probe because it emits red and green light when excited by near infrared light, which is not effected by UV and visible light. This dual-functioning emission behaviour was demonstrated in live organisms.

      DOI: 10.1039/c5nr03058g

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    • A photo- and halochromic multicolor switching system consisting of diarylethene and malachite green moieties Peer-reviewed

      Yuto Tatsumi, Noriko Fujinaga, Megumi Kasuno, Masakazu Morimoto, Satoshi Yokojima, Shinichiro Nakamura, Kingo Uchida

      NEW JOURNAL OF CHEMISTRY38 ( 12 ) 5706 - 5714   12 2014

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      A diarylethene with an attached malachite green moiety was synthesized. The diarylethene moiety undergoes reversible cyclization and cycloreversion reactions upon alternate irradiation with UV (313 nm) and visible (435 nm) light, while the malachite green moiety reversibly changes between neutral, monocationic, and dicationic states up to the proton concentration. The photochromic and halochromic reactions could be controlled, and this provided a multi-reversible system with six states. The cyclization and cycloreversion quantum yields of the diarylethene moiety were dependent on the states of the malachite green moiety.

      DOI: 10.1039/c4nj00434e

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    • Control of the Single-Molecule Magnet Behavior of Lanthanide-Diarylethene Photochromic Assemblies by Irradiation with Light Peer-reviewed

      Dawid Pinkowicz, Min Ren, Li-Min Zheng, Saki Sato, Miki Hasegawa, Masakazu Morimoto, Masahiro Irie, Brian K. Breedlove, Goulven Cosquer, Keiichi Katoh, Masahiro Yamashita

      CHEMISTRY-A EUROPEAN JOURNAL20 ( 39 ) 12502 - 12513   9 2014

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

      Lanthanide-based extended coordination frameworks showing photocontrolled single-molecule magnet (SMM) behavior were prepared by combining highly anisotropic Dy-III and Ho-III ions with the carboxylato-functionalized photochromic molecule 1,2-bis(5-carboxyl-2-methyl-3-thienyl)perfluorocyclopentene (H(2)dae), which acts as a bridging ligand. As a result, two new compounds of the general formula [{Ln(2)(III)(dae)(3)(DMSO)(3)(MeOH)}center dot 10MeOH](n) (M=Dy for 1a and Ho for 2) and two additional pseudo-polymorphs [{Dy-2(III)(dae)(3)(DMSO)(3)(H2O)}center dot xMeOH](n) (1b) and [{Dy-2(III)(dae)(3)(DMSO)(3)-DMSO)}center dot xMeOH](n) (1c) were obtained. All four compounds have 2D coordination-layer topologies, in which carboxylate-bridged Ln(2) units are linked together by dae(2-) anions into grid-like frameworks. All four compounds exhibited a strong reversible photochromic response to UV/Vis light. Moreover, both 1a and 2 show field-induced SMM behavior. The slow magnetic relaxation of 1a is influenced by the photoisomerization reaction leading to the observation of the cross-ffect: photocontrolled SMM behavior.

      DOI: 10.1002/chem.201402647

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    • Photochromism and fluorescence properties of 1,2-bis(2-alkyl-1-benzothiophene-3-yl)perhydrocyclopentenes Peer-reviewed

      Tadatsugu Yamaguchi, Manabu Hosaka, Keigo Shinohara, Toru Ozeki, Mitsuhiro Fukuda, Shizuka Takami, Yukihide Ishibashi, Tsuyoshi Asahi, Masakazu Morimoto

      JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY285   44 - 51   7 2014

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      Three 1,2-bis(2-alkyl-1-benzothiophene-3-yl)perhydrocyclopentenes with different alkyl chain lengths (methyl, ethyl, and propyl) at the reactive carbons were synthesized, and their photophysical properties were compared with those of 1,2-bis(2-alkyl-1-benzothiophene-3-yl)perfluorocyclopentenes. The structures of the perhydrocyclopentenes were analyzed by X-ray crystallography, and their cyclization/cycloreversion reaction and fluorescence quantum yields, and fluorescence lifetimes were measured by steady-state spectroscopy and the time-correlated single photon counting method, respectively. From these results, we found the following three differences between perhydrocyclopentenes and perfluorocyclopentenes. (1) For the closed-ring isomers, the absorption bands of the perhydrocyclopentenes (around 450 nm) shifted to a shorter wavelength than those of the perfluorocyclopentenes (around 530 nm) because of the acceptor nature of the perfluorocyclopentene moiety. (2) The cyclization/cycloreversion quantum yields of the perhydrocyclopentenes were slightly larger than those of the perfluorocyclopentenes in hexane. (3) Interestingly, the fluorescence of both the open- and closed-ring isomers was observed only for the perhydrocyclopentenes, and the lifetimes of the closed-ring isomers were estimated to be &lt;30 ps. The fluorescence of the closed-ring isomers of the perhydrocyclopentenes was mainly due to the suppression of nonradiative deactivation from the excited state directly to the ground state compared with the perfluorocyclopentenes. (C) 2014 Elsevier B.V. All rights reserved.

      DOI: 10.1016/j.jphotochem.2014.04.007

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    • Photochromic Reaction of Diarylethenes Having Phenol Moiety as an Aryl Ring Peer-reviewed

      Tadatsugu Yamaguchi, Yusuke Kamihashi, Toru Ozeki, Ayaka Uyama, Jun-ichiro Kitai, Megumi Kasuno, Kimio Sumaru, Yoshiro Kimura, Satoshi Yokojima, Shinichiro Nakamura, Masakazu Morimoto, Kingo Uchida

      BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN87 ( 4 ) 528 - 538   4 2014

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      Three types of diarylethenes having one phenol moiety as an aromatic unit were synthesized in order to control pH change upon irradiation with UV and visible light. Upon irradiation with 313 nm light, these open-ring isomers were transformed to thermally unstable colored isomers in methanol solution. During the storage of the photoirradiated diarylethene solutions in the dark for 10 min, the thermally unstable closed-ring isomers were converted to thermally stable keto isomers. The structures of these isomers were characterized by H-1-NMR and X-ray crystallography. The keto isomers were transformed to the initial phenol isomer upon irradiation with visible light. Additionally, we also found the formation of a novel photochromic diarylethene derivative having one keto group on the cyclopentane ring during UV irradiation. A pH change between the two isomers was observed in a mixture of ethanol and water.

      DOI: 10.1246/bcsj.20130252

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    • Photocontrol Over Self-Assembled Nanostructures of pi-pi Stacked Dyes Supported by the Parallel Conformer of Diarylethene Peer-reviewed

      Shiki Yagai, Kazunori Iwai, Mitsuaki Yamauchi, Takashi Karatsu, Akihide Kitamura, Shinobu Uemura, Masakazu Morimoto, Hao Wang, Frank Wuerthner

      ANGEWANDTE CHEMIE-INTERNATIONAL EDITION53 ( 10 ) 2602 - 2606   3 2014

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

      Diarylethenes (DAEs) have rarely been used in the design of photoresponsive supramolecular assemblies with a well-defined morphology transition owing to rather small structural changes upon photoisomerization. A supramolecular design based on the parallel conformation of DAEs enables the construction of photoresponsive dye assemblies that undergo remarkable nanomorphology transitions. The cooperative stacking of perylene bisimide (PBI) dyes was used to stabilize the parallel conformer of DAE through complementary hydrogen bonds. Atomic force microscopy, UV/Vis spectroscopy, and molecular modeling revealed that our DAE and PBI building blocks coassembled in nonpolar solvent to form well-defined helical nanofibers featuring J-type dimers of PBI dyes. Upon irradiating the coassembly solution with UV and visible light in turn, a reversible morphology change between nanofibers and nanoparticles was observed. This system involves the generation of a new self-assembly pathway by means of photocontrol.

      DOI: 10.1002/anie.201310773

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    • Asymmetric photoreaction of a diarylethene in hydrogen-bonded cocrystals with chiral molecules Peer-reviewed

      Tomohiro Ichikawa, Masakazu Morimoto, Masahiro Irie

      PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES13 ( 2 ) 199 - 204   2014

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      A photochromic diarylethene having 2-methyl-4-pyridyl groups formed chiral cocrystals with (R)- or (S)-1,1'-bi-2-naphthol (BINOL). X-ray crystal structure analysis revealed that the diarylethene forms O-H center dot center dot center dot N type hydrogen bonds with BINOL and the central hexatriene moiety is fixed in P-or M-helix conformation in the cocrystals. The diarylethene molecules underwent reversible cyclization reactions in the single-component crystal as well as in the cocrystals upon alternate irradiation with ultraviolet (UV) and visible light. In the chiral cocrystals, a highly enantioselective photocyclization reaction took place owing to the conformational confinement.

      DOI: 10.1039/c3pp50239b

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    • Photoirradiation wavelength dependence of cycloreversion quantum yields of diarylethenes Peer-reviewed

      Takaki Sumi, Yuta Takagi, Akira Yagi, Masakazu Morimoto, Masahiro Irie

      CHEMICAL COMMUNICATIONS50 ( 30 ) 3928 - 3930   2014

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      The cycloreversion quantum yields of compounds 1b and 2b increased upon irradiation with light at shorter wavelengths. The irradiation wavelength dependence is ascribed to the energy barrier on the 2A potential energy surface in the excited electronic state.

      DOI: 10.1039/c4cc00396a

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    • Photochromic Diarylethene Derivatives Bearing Hydrophilic Substituents Peer-reviewed

      Yuichiro Shoji, Akira Yagi, Masahiro Horiuchi, Masakazu Morimoto, Masahiro Irie

      ISRAEL JOURNAL OF CHEMISTRY53 ( 5 ) 303 - 311   5 2013

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      Photochromic diarylethene derivatives bearing hydrophilic N,N-bis(2-(2-(2-methoxyethoxy)ethoxy)ethyl)sulfonamide (SO2NTEG2) (13) or myo-inositol (46) substituents were synthesized. Although the solubility in aqueous solution of the derivatives containing the four tri(ethylene glycol) chains was relatively poor, the solubility was improved by introducing two myo-inositol residues. The derivatives could be dissolved even in pure water and underwent photochromism upon alternate irradiation with ultraviolet (UV) and visible light, in both organic and aqueous solutions. The absorption maxima of the open- and closed-ring isomers of these derivatives and the photostationary conversion ratios from the open- to the closed-ring isomers upon UV irradiation did not change much, even when the solvent polarity was changed. These results indicate that the diarylethene derivatives are mono-molecularly dissolved in aqueous solution and that intermolecular interactions between the derivatives are negligible when the concentration is less than 1x104molL1.

      DOI: 10.1002/ijch.201300018

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    • Crystal Structures and Dielectric Properties of 2-Imidazoline Derivatives Having Intermolecular Hydrogen-bonded Networks Peer-reviewed

      Masakazu Morimoto, Naoya Takashio, Masahiro Irie

      CHEMISTRY LETTERS41 ( 5 ) 525 - 527   5 2012

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      A 2-imidazoline derivative and its monoprotonated iodide salt construct different types of intermolecular N-H center dot center dot center dot N hydrogen bonds in the crystalline state. The two crystals give completely different dielectric responses, and the difference is correlated to their different hydrogen-bonded networks.

      DOI: 10.1246/cl.2012.525

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    • Photoinduced Reversible Heteroepitaxial Microcrystal Growth of a Photochromic Diarylethene on (110) Surface of SrTiO3 Peer-reviewed

      Shingo Sakiyama, Seiji Yamazoe, Ayaka Uyama, Masakazu Morimoto, Satoshi Yokojima, Yuko Kojima, Shinichiro Nakamura, Kingo Uchida

      CRYSTAL GROWTH & DESIGN12 ( 3 ) 1464 - 1468   3 2012

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:AMER CHEMICAL SOC  

      Diarylethene 1 shows reversible transformation between the open-ring isomer (1o) and the closed-ring isomer (1c) by alternate UV and visible light irradiation, accompanied with reversible melting and crystallization of the microcrystalline film of 1 at 67 degrees C, which is the eutectic temperature of 10 and 1c. The reversible epitaxial crystal growth of an 1o of a diarylethene derivative was observed on a 110 surface of a strontium titanate (SrTiO3) single crystal by maintaining a constant temperature and monitoring six reversible intensity changes (within 2 h of repeating cycles) of the reflection of 004 of 1o on XRD measurements.

      DOI: 10.1021/cg201560f

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    • Photoreversible Supramolecular Polymerisation and Hierarchical Organization of Hydrogen-Bonded Supramolecular Co-polymers Composed of Diarylethenes and Oligothiophenes Peer-reviewed

      Shiki Yagai, Keisuke Ohta, Marina Gushiken, Kazunori Iwai, Atsushi Asano, Shu Seki, Yoshihiro Kikkawa, Masakazu Morimoto, Akihide Kitamura, Takashi Karatsu

      CHEMISTRY-A EUROPEAN JOURNAL18 ( 8 ) 2244 - 2253   2 2012

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      Diarylethene 1 equipped with two monotopic melamine hydrogen-bonding sites and oligothiophene-functionalized ditopic cyanurate (OTCA) were mixed in a nonpolar solvent to form AA-BB-type supramolecular co-polymers (SCPs) bearing photoswitchable moieties in their main chains and extended p systems as side chains. UV/Vis, fluorescence, dynamic light scattering (DLS), TEM, and AFM studies revealed that the two functional co-monomers formed flexible quasi-one-dimensional SCPs in solution that hierarchically self-organized into helical nanofibers through H-aggregation of the oligothiophene side chains. Upon irradiating the SCPs with UV light, a transition occurred from the H-aggregated state to non-aggregated monomeric oligothiophene side chains, as shown by spectroscopic studies, which indicates the formation of small oligomeric species held together only by hydrogen-bonding interactions. TEM and AFM visualized unfolded fibrils corresponding to elongated single SCP chains formed upon removal of solvent. The helical nanofibers were regenerated upon irradiating the UV-irradiated solution with visible light. These results demonstrated that the supramolecular polymerisation followed by hierarchical organization can be effectively controlled by proper supramolecular designs using diarylethenes and pi-conjugated oligomers.

      DOI: 10.1002/chem.201103465

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    • Light-Driven Molecular-Crystal Actuators: Rapid and Reversible Bending of Rodlike Mixed Crystals of Diarylethene Derivatives Peer-reviewed

      Fumitaka Terao, Masakazu Morimoto, Masahiro Irie

      ANGEWANDTE CHEMIE-INTERNATIONAL EDITION51 ( 4 ) 901 - 904   2012

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      DOI: 10.1002/anie.201105585

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    • Photoswitchable fluorescent diarylethene derivatives with short alkyl chain substituents Peer-reviewed

      Yuta Takagi, Tomohiro Kunishi, Tetsuro Katayama, Yukihide Ishibashi, Hiroshi Miyasaka, Masakazu Morimoto, Masahiro Irie

      PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES11 ( 11 ) 1661 - 1665   2012

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      The sulfone derivatives of 1,2-bis(2-alkyl-6-phenyl-1-benzothiophen-3-yl)perfluorocyclopentene having various short alkyl chain substituents at reactive carbons were prepared and the effect of alkyl substitution on the fluorescence property of the closed-ring isomers was studied. Upon irradiation with ultraviolet (UV) light the derivatives exhibit a brilliant green fluorescence under irradiation with visible (&gt; 400 nm) light, while the fluorescence disappears upon irradiation with visible (&gt; 400 nm) light alone. The fluorescence quantum yield of the methyl substituted derivative (1b) dramatically decreases from 0.84 to 0.15 when the solvent is changed from hexane to acetonitrile, while the changes of ethyl, n-propyl and n-butyl substituted derivatives (2b)-(4b) are moderate. The quantum yields of (2b)-(4b) are kept to values close to 0.7 even in polar acetonitrile. The fluorescence lifetime measurement revealed that efficient non-radiative decay processes took place in (1b) in polar solvent, while their contribution to the deactivation was not so large in (2b)-(4b). The neighboring short alkyl chains at the connecting carbons are considered to defend the sulfone units against the attack of polar solvent molecules and weaken the solvent polarity effect.

      DOI: 10.1039/c2pp25078k

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    • Photochromism of diarylethene derivatives bearing a benzo[b]silole unit Peer-reviewed

      Tadatsugu Yamaguchi, Manabu Hosaka, Toru Ozeki, Masakazu Morimoto, Masahiro Irie

      TETRAHEDRON LETTERS52 ( 43 ) 5601 - 5604   10 2011

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:PERGAMON-ELSEVIER SCIENCE LTD  

      Photochromic benzo[b]silole derivatives, 1-(1,1-dimethyl-2-phenylbenzo[b]silol-3-yl)-2-(2-phenylbenzo[b]thien-3-yl)perfluorocyclopentene and 1-(1,1-dimethyl-2-phenylbenzo[b]silol-3-yl)-2-(2-phenyl-1-benzofuran-3-yl)perfluorocyclopentene, were synthesized and their photochromic performance was examined in solution. (C) 2011 Elsevier Ltd. All rights reserved.

      DOI: 10.1016/j.tetlet.2011.08.063

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    • In Situ Preparation of Highly Fluorescent Dyes upon Photoirradiation Peer-reviewed

      Kakishi Uno, Hiroyuki Niikura, Masakazu Morimoto, Yukihide Ishibashi, Hiroshi Miyasaka, Masahiro Irie

      JOURNAL OF THE AMERICAN CHEMICAL SOCIETY133 ( 34 ) 13558 - 13564   8 2011

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:AMER CHEMICAL SOC  

      Photoswitchable or photoactivatable fluorescent dyes are potentially applicable to ultrahigh density optical, memory media as well as super-resolution fluorescence imaging when the dyes are highly fluorescent and have large absorption coefficients. Here, we report on highly fluorescent photochromic dyes, which are initially nonluminous in solution under irradiation with visible light but activated to emit green or red fluorescence upon irradiation with ultraviolet (UV) light. The dyes Sa-9a are sulfone derivatives of 1,2-bis(2-ethyl-6-phenyl(or thienyl)-1-benzothiophen-3-yl)perfluorocyclopentene. It was found that substitution of phenyl or thiophene rings at 6 and 6' positions of the benzothiophene-1,1-dioxide groups is effective to increase the fluorescence quantum yields of the closed-ring isomers over 0.7 and absorption coefficients over 4 x 10(4) M-1 cm(-1). The phenyl-substituted derivatives 5a-7a undergo photocyclization reactions to produce yellow closed-ring isomers 5b-7b, which emit brilliant green fluorescence at around 550 nm (Phi(F) = 0.87-0.88) under irradiation with 488 nm light. Any absorption intensity change of the closed-ring isomers was not observed even after 100 h storage in the dark at 80 degrees C. The closed-ring isomers slowly returned to the initial open-ring isomers upon irradiation with visible (lambda &gt; 480 nm) light. The ring-opening quantum yields (Phi(C -&gt; O)) were measured to be (1.6-4.0) x 10(-4). When the phenyl substituents are replaced with thiophene rings, such as compounds 8a and 9a, the absorption bands of the closed-ring isomers shift to longer than 500 nm. The closed-ring isomers exhibit brilliant red fluorescences at around 620 nm (Phi(F) = 0.61-0.78) under irradiation with 532 nm light. The ring-opening reactions are very slow (Phi(C -&gt; O) &lt; 1 x 10(-5)). The fluorescence lifetimes of these sulfone derivatives were measured to be around 2-3 ns, which is much longer than the value of the closed-ring isomer of 1,2-bis (2-methyl-1-benzothiophen-3-yl)perfluorocyclopentene (tau(F) = 4 and 22 ps). The closed-ring isomer 8b in 1,4-dioxane exhibits excellent fatigue resistant property under irradiation with visible light (lambda &gt; 440 nm) superior to the stability of Rhodamine 101 in ethanol

      DOI: 10.1021/ja204583e

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    • Photochromism of 1,2-Bis(5-n-alkyl-2-phenyloxazol-4-yl)perfluorocyclopentene Derivatives in Single-crystalline Phase Peer-reviewed

      Tadatsugu Yamaguchi, Wataru Taniguchi, Tomonori Kagawa, Yusuke Kamihashi, Toru Ozeki, Masakazu Morimoto, Masahiro Irie

      CHEMISTRY LETTERS40 ( 6 ) 635 - 637   6 2011

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:CHEMICAL SOC JAPAN  

      1,2-Bis(5-n-alkyl-2-phenyloxazol-4-yl)perfluorocyclopentenes were synthesized and their photochromic performance was examined in hexane solution as well as in single-crystalline phase.

      DOI: 10.1246/cl.2011.635

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    • Reversible Photocontrol of Surface Wettability between Hydrophilic and Superhydrophobic Surfaces on an Asymmetric Diarylethene Solid Surface Peer-reviewed

      Ayaka Uyama, Seik Yamazoe, Satomi Shigematsu, Masakazu Morimoto, Satoshi Yokojima, Hiroyuki Mayama, Yuko Kojima, Shinichiro Nakamura, Kingo Uchida

      LANGMUIR27 ( 10 ) 6395 - 6400   5 2011

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:AMER CHEMICAL SOC  

      By alternate UV and visible light irradiation, reversible topographical changes were observed on a newly synthesized diarylethene microcrystalline surface between the rough crystalline surface of an open-ring isomer and flat eutectic surfaces. The contact angle changes of a water droplet between 80 and 150 and peak intensities changes of the open-ring isomer in XRD patterns within 2 h of repeating cycle were observed. The results indicated that reversibly photogenerated rod-shaped crystals on the surface were produced based on the lattice of the open-ring isomer crystals in the subphase.

      DOI: 10.1021/la2006524

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    • Copper(II)-terbium(III) Single-Molecule Magnets linked by photochromic ligands Peer-reviewed

      Takuya Shiga, Hitoshi Miyasaka, Masahiro Yamashita, Masakazu Morimoto, Masahiro Irie

      DALTON TRANSACTIONS40 ( 10 ) 2275 - 2282   2011

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:ROYAL SOC CHEMISTRY  

      Two assemblies composed of single-molecule magnets (SMMs) linked by photochromic ligands, [Cu(2)(II)Tb(2)(III)(L)(2)(NO(3))(2)(dae-o)(2)]center dot 2(n-BuOH) (1) and {[Cu(II)Tb(III)(L)(n-BuOH)(0.5)](2)(dae-c)(3)}center dot 5(DMF)center dot 4(n-BuOH)center dot 2(H(2)O) (2), were synthesized by reacting the SMM [Cu(II)Tb(III)(L)(NO(3))(3)] (H(2)L = 1,3-bis((3-methoxysalicylidene)amino)propane) and photochromic molecules, H(2)dae-o and H(2)dae-c, which are open-and closed-ring isomers of 1,2-bis(5-carboxyl-2-methyl-3-thienyl)perfluoropentene (H(2)dae), respectively. 1 has a tetranuclear ring-like structure comprised of two [CuTb] units and two dae-o(2-) ligands. On the other hand, 2 has a one-dimensional ladder-type structure involving the [CuTb] and dae-c(2-) units in a 3 : 2 ratio. Magnetic studies revealed that 1 and 2 had ferromagnetic interactions between the Cu(II) and Tb(III) ions and that both compounds exhibited frequency dependence of ac susceptibilities owing to freezing the magnetization of the [CuTb] SMM. Upon irradiation with ultraviolet light and visible light, an absorption band at similar to 600 nm changed, indicating that photochromic reactions involving the dae(2-) ligands occurred. After irradiation, the magnetic behaviour of 1 did not change, whereas magnetic behaviour of 2 changed, due to the modification of intermolecular environment.

      DOI: 10.1039/c0dt01119c

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    • Photochemical control of a highly efficient addition reaction between electron-rich alkynes and tetracyanoethylene Peer-reviewed

      Masakazu Morimoto, Kimie Murata, Tsuyoshi Michinobu

      CHEMICAL COMMUNICATIONS47 ( 35 ) 9819 - 9821   2011

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      The electron density of an alkyne moiety is enhanced by the photochromic ring closure of a diarylethene derivative, which allows the thermal addition reaction with a small pi-acceptor, tetracyanoethylene, at room temperature.

      DOI: 10.1039/c1cc13476k

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    • Photochemical control of dielectric properties based on intermolecular proton transfer in a hydrogen-bonded diarylethene crystal Peer-reviewed

      Masakazu Morimoto, Masahiro Irie

      CHEMICAL COMMUNICATIONS47 ( 14 ) 4186 - 4188   2011

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      The photochromic reaction of a diarylethene derivative having imidazoline rings reversibly modulates the dielectric properties of the crystal, which is based on the intermolecular proton transfer in one-dimensional (1D) hydrogen-bonded chains.

      DOI: 10.1039/c0cc05729k

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    • A Diarylethene Cocrystal that Converts Light into Mechanical Work Peer-reviewed

      Masakazu Morimoto, Masahiro Irie

      JOURNAL OF THE AMERICAN CHEMICAL SOCIETY132 ( 40 ) 14172 - 14178   10 2010

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      The photomechancial effect of a rectangular plate two-component cocrystal composed of a photochromic diarylethene derivative, 1,2-bis(2-methyl-5-(1-naphthyl)-3-thienyl)perfluorocyclopentene (1o), and perfluoronaphthalene (FN) has been examined. The crystal of 1o.FN with the size of 1-5 mm in length exhibits reversible bending motion upon alternate irradiation with ultraviolet (UV) and visible light. The reversible bending could be repeated over 250 times. In situ X-ray crystallographic analysis revealed that the deformation of the crystal is due to the elongation of the b-axis of the unit cell, which corresponds to the long axis of the plate crystal, induced by the shape change of component diarylethene molecules upon photocyclization. The bending motion was observed even at 4.7 K, and dynamic measurement of the bending proved that the anisotropic expansion of the crystal takes place in the microsecond time scale at the low temperature. Molecular crystal cantilevers made of 1o.FN can lift metal balls, the weight of which is 200-600 times heavier than the weight of the crystal, upon UV irradiation. The maximum stress generated by UV irradiation was estimated to be 44 MPa, which is 100 times larger than that of muscles (similar to 0.3 MPa) and comparable to that of piezoelectric crystals, such as lead zirconate titanate (PZT) (similar to 50 MPa).

      DOI: 10.1021/ja105356w

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    • Photochromism of dithienylethene single crystals having anthracene substituents Peer-reviewed

      Hiroki Ohara, Masakazu Morimoto, Masahiro Irie

      PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES9 ( 8 ) 1079 - 1081   2010

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      Three dithienylethene derivatives having anthracene substituents (connected at 1-, 2- and 9-positions) were prepared. Although these three derivatives exhibit photochromic reactivity in solution, only one of the derivatives (connected at 2-position) undergoes the photochromic reaction in the crystalline phase. X-Ray crystallographic analysis and DFT calculation revealed that conformation of the anthracene substituents plays an important role in the crystalline photochromism.

      DOI: 10.1039/c0pp00083c

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    • Photoinduced shape changes of diarylethene single crystals: correlation between shape changes and molecular packing Peer-reviewed

      Lumi Kuroki, Shizuka Takami, Kenji Yoza, Masakazu Morimoto, Masahiro Irie

      PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES9 ( 2 ) 221 - 225   2010

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      Correlation between the photoinduced shape changes of diarylethene single crystals and their molecular packing in the crystals was studied. Crystals of 1,2-bis(5-ethyl-2-phenyl-4-thiazolyl)perfluorocyclopentene (3a) and 1,2-bis(2-isopropyl-5-phenyl-3-thienyl)perfluorocyclopentene (4a) showed similar photoinduced deformation from square to lozenge as that of 1,2-bis(2-ethyl-5-phenyl-3-thienyl)perfluorocyclopentene (1a). Although these three diarylethenes have different electronic structures and exhibit different colours upon UV irradiation, the crystallographic structures and molecular packing of the crystals are very similar to each other. The result indicates that the deformation mode is determined by the packing mode of component molecules in the crystal. X-Ray crystallographic analysis of a micrometre-sized crystal 1a (20 x 15 x 8 mu m) prepared by sublimation revealed that the small-size crystal, which shows photoinduced deformation, has the same crystal structure as that of the large bulk crystal.

      DOI: 10.1039/b9pp00093c

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    • Photochromic diarylethene molecules and crystals Invited Peer-reviewed

      Masahiro Irie, Masakazu Morimoto

      PURE AND APPLIED CHEMISTRY81 ( 9 ) 1655 - 1665   9 2009

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:INT UNION PURE APPLIED CHEMISTRY  

      Some of the diarylethene derivatives were found to undergo photoisomerization reactions between two isomers even in the single-crystalline phase. The two isomers have different electronic as well as geometrical structures. The electronic structure change induces the reversible color change of the crystal. Single crystals composed of three different kinds of diarylethenes having similar geometrical structures, bisoxazolylethene, bisthiazolylethene, and bisthienylethene have been prepared. The crystals exhibited multicolor photochromism. The colorless crystals turned yellow, red, and blue upon irradiation with the appropriate wavelength of light. The geometrical structure change of component diarylethene molecules in crystals induces reversible surface morphology as well as shape and size changes of the crystals. The photoinduced geometrical structure changes of the molecules in the densely packed crystals were successfully linked to the macro-scale mechanical motion of the solid crystals and resulted in the net task of launching a tiny silica particle.

      DOI: 10.1351/PAC-CON-08-09-26

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    • Coordination Assemblies of [Mn-4] Single-Molecule Magnets Linked by Photochromic Ligands: Photochemical Control of the Magnetic Properties Peer-reviewed

      Masakazu Morimoto, Hitoshi Miyasaka, Masahiro Yamashita, Masahiro Irie

      JOURNAL OF THE AMERICAN CHEMICAL SOCIETY131 ( 28 ) 9823 - 9835   7 2009

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:AMER CHEMICAL SOC  

      To achieve reversible photoswitching of the magnetic properties of single-molecule magnets (SMMs), coordination assemblies of a mixed valence tetranuclear [(Mn2Mn2III)-Mn-II] complex linked by open-and closed-ring isomers of a photochromic diarylethene ligand were synthesized: [Mn-4(hmp)(6)(dae-o)(2)(ClO4)(2)]center dot 6H(2)O (open-ring form; 1o) and [Mn-4(hmp)(6)(dae-c)(2)(H2O)(2)](ClO4)(2)center dot CH3CN center dot 4H(2)O (closed-ring form; 1c), where Hhmp is 2-hydroxymethylpyridine, and H(2)dae-o and H(2)dae-c are open- and closed-ring isomers of 1,2-bis(5-caxboxyl-2-methyl-3-thienyl)perfluorocyclopentene (H(2)dae), respectively. From X-ray crystallographic analyses, 1o and 1c have one-dimensional (1-D) chain structures with a repeating unit of [-{Mn-4}-(dae)-], in which the [Mn-4] units are bridged by the diarylethene ligands coordinated to the Mn-II sites via carboxylate groups. Magnetic measurements involving direct-current (dc) and alternating-current (ac) techniques showed that each [Mn-4] cluster in the 1-D chains had an S-T = 9 ground state due to two kinds of intracluster ferromagnetic exchange interactions and behaved as SMMs. Both 1o and 1c underwent photochromic reactions in the crystalline phase, and their colors reversibly changed between reddish-brown and blue upon irradiation with ultraviolet (UV) and visible light. For 1o, no significant change in the magnetic properties was observed after the photocyclization of the dae-o moiety by UV irradiation. In contrast, the photocycloreversion of the dae-c moiety by visible irradiation enhanced inter-[Mn-4] unit interactions in 1c, which was triggered by the geometrical change in the diarylethene moiety during the photoreaction and the subsequent change in the inter-[Mn-4] arrangement between the neighboring 1-D chains. This work illustrates the usefulness of photochromic molecules for photoswitching the magnetic behavior of complexes, even superparamagnetic systems, with SMM units.

      DOI: 10.1021/ja903366d

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    • Photochromism of diarylethene derivatives having cyclohexyl and cyclohexenyl groups in single-component crystals and a two-component mixed crystal Peer-reviewed

      Masakazu Morimoto, Masahiro Irie

      TETRAHEDRON LETTERS50 ( 26 ) 3404 - 3407   7 2009

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:PERGAMON-ELSEVIER SCIENCE LTD  

      Diarylethene derivatives la having two cyclohexyl groups and 2a having a cyclohexyl and a cyclohexenyl group formed a mixed crystal composed of almost equal amounts of the two components, and underwent photochromism in the mixed crystal as well as in the single-component crystals. (C) 2009 Elsevier Ltd. All rights reserved.

      DOI: 10.1016/j.tetlet.2009.02.139

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    • Absolute asymmetric photocyclization in chiral diarylethene co-crystals with octafluoronaphthalene Peer-reviewed

      Masakazu Morimoto, Seiya Kobatake, Masahiro Irie

      CHEMICAL COMMUNICATIONS44 ( 3 ) 335 - 337   2008

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:ROYAL SOC CHEMISTRY  

      A photochromic diarylethene containing naphthyl groups formed a chiral crystal when co-crystallized with octafluoronaphthalene, although both molecules are achiral, and underwent highly enantioselective photocyclization owing to the conformational confinement in the crystal.

      DOI: 10.1039/b713694c

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    • Photochromic reactions of diarylethenes in single crystals with intermolecular O-H center dot center dot center dot N hydrogen-bonding networks Peer-reviewed

      Masakazu Morimoto, Masahiro Irie

      CHEMISTRY-A EUROPEAN JOURNAL12 ( 16 ) 4275 - 4282   5 2006

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

      The crystal structures and photochromic performance of a single crystal of a diarylethene derivative possessing carboxyl groups, 1,2-bis(5-car-boxyl-2-methyl-3-thienyl)perfluorocy- clopentene (1a), and cocrystals of 1a with 4,4 '-, 2,4 '-, and 2,2 '-bipyridines were examined. In crystal la, a discrete cyclic structure was observed, in which four 1a molecules are linked through hydrogen bonds between the carboxyl groups. In the homocrystal, photoreactive and photoinactive conformers of la exist in the ratio of 1:1. In the cocrystals of 1a with bipyridines, O-(HN)-N-...-type hydrogen bonds between 1a and pyridyl groups were formed, and all 1a molecules are fixed in a photoreactive conformation. Both the homocrystal 1a and the cocrystals showed photochromic performances, and color variation from bluish-violet to cyan was observed, depending on the conformation of the packed diarylethene molecules.

      DOI: 10.1002/chem.200501148

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    • Photochromism of a diarylethene charge-transfer complex: photochemical control of intermolecular charge-transfer interaction Peer-reviewed

      Masakazu Morimoto, Seiya Kobatake, Masahiro Irie

      CHEMICAL COMMUNICATIONS42 ( 25 ) 2656 - 2658   2006

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:ROYAL SOC CHEMISTRY  

      A diarylethene derivative bearing a phenylenediamine group formed radical ions with an electron acceptor molecule in solution, and the concentration of the radical ions was modulated by the photochromic reaction of the diarylethene, reflecting the difference in the electron-donating character between the open- and closed-ring isomers.

      DOI: 10.1039/b604388g

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    • Crystal engineering of photochromic diarylethene derivatives by aryl-perfluoroaryl interaction Peer-reviewed

      MORIMOTO Masakazu, KOBATAKE Seiya, IRIE Masahiro

      Molecular Crystals & Liquid Crystals431 ( 1 ) 229 - 234   1 2005

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      DOI: 10.1080/15421400590947324

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    • Nanolayered structures in photochromic crystal of 1,2-bis-(2-methyl-5-p-methoxyphenyl-3-thienyl)perfluorocyclopentene Peer-reviewed

      KOBATAKE Seiya, MORIMOTO Masakazu, IRIE Masahiro

      Molecular Crystals & Liquid Crystals431 ( 1 ) 223 - 228   1 2005

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      DOI: 10.1080/15421400590947306

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    • Photochromism of diarylethene single crystals: crystal structures and photochromic performance Invited Peer-reviewed

      M Morimoto, M Irie

      CHEMICAL COMMUNICATIONS41 ( 31 ) 3895 - 3905   2005

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:ROYAL SOC CHEMISTRY  

      Diarylethenes undergo thermally irreversible and fatigue-resistant photochromic reactions not only in solution but also in the single-crystalline phase. This article describes recent development of the single-crystalline photochromism of diarylethene derivatives. We focused on the relationship between their crystal structures and the photochromic performance. Photocyclization/cycloreversion quantum yields, absorption spectra, the absorption anisotropies, and surface morphology changes are strongly dependent on the conformations and packing structures of the molecules in the crystals.

      DOI: 10.1039/b505256d

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    • Crystal engineering of photochromic diarylethene single crystals Invited Peer-reviewed

      M Morimoto, S Kobatake, M Irie

      CHEMICAL RECORD4 ( 1 ) 23 - 38   2004

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:JOHN WILEY & SONS INC  

      Photochromic performance of diarylethene single crystals was controlled by crystal engineering using non-covalent aromatic-aromatic interactions as the directional intermolecular force. A diarylethene derivative with two pentafluorophenyl groups, 1,2-bis(2-methyl-5-pentafluorophenyl-3-thienyl)perfluorocyclopentene (1a), formed stoichiometric co-crystals with benzene (Bz) and naphthalene (Np) by aryl-perfluoroaryl interactions. Face-to-face pi-stacking interactions between the pentafluorophenyl groups of la and the aromatic molecules are responsible for 2: 1 and 1 : 1 stoichiometric compositions in 1a/Bz and 1a/Np co-crystals, respectively. The diarylethene underwent thermally stable and photoreversible photochromic reactions in a homo-crystal of la and co-crystals 1a/Bz and 1a/Np. The absorption spectra of the photogenerated closed-ring isomers varied depending on the conformation of the diarylethene molecules packed in the crystals. The diarylethene la also formed I :1 stoichiometric co-crystals with different kinds of diarylethenes, 1,2-bis(2-ethyl-5-phenyl-3-thienyl)perfluorocyclopentene (2a) and 1,2-bis[2-methyl-5-(1-naphthyl)-3-thienyl]perfluorocyclopentene (3a). Both co-crystals 1a/2a and 1a/3a showed photochromism. Although la, 2a, and 3a underwent efficient photocyclization reactions in their homo-crystals, highly selective photocyclization reactions of 2a or 3a were observed in the co-crystals. The selective reactions were confirmed by HPLC and X-ray crystallography. Excited energy transfers from la to 2a and from la to 3a are considered to occur and cause the selective reactions. (C) 2004 The Japan Chemical Journal Forum and Wiley Periodicals, Inc.

      DOI: 10.1002/tcr.10078

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    • Aryl-perfluoroaryl interaction in photochromic diarylethene crystals Peer-reviewed

      M Morimoto, S Kobatake, M Irie

      CRYSTAL GROWTH & DESIGN3 ( 5 ) 847 - 854   9 2003

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:AMER CHEMICAL SOC  

      A diarylethene derivative with two pentafluorophenyl groups, 1,2-bis(2-methyl-5-pentafluorophenyl-3-thienyl)perfluorocyclopentene (1a), was synthesized in an attempt to prepare photochromic single crystals with well-controlled photochromic properties by utilizing intermolecular noncovalent aryl-perfluoroaryl interactions. Compound la formed stoichiometric cocrystals with aromatic hydrocarbons, benzene (Bz) and naphthalene (Np), based on aryl-perfluoroaryl interactions. In crystal 1a/Bz (la:Bz = 2:1), a linear chain structure was constructed, in which each benzene molecule is sandwiched between pentafluorophenyl rings of two la molecules. In crystal 1a/Np (la:Np = 1:1), a discrete sandwiched structure was formed, in which two la molecules sandwich two naphthalene molecules between its pentafluorophenyl groups. In the la, 1a/Bz, and 1a/Np crystals, the diarylethene molecules underwent photochromic reactions. Absorption properties of the photogenerated closed-ring isomers were different from each other depending on conformations of the diarylethene molecules packed in the crystals.

      DOI: 10.1021/cg034076t

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    • Multicolor photochromism of two- and three-component diarylethene crystals Peer-reviewed

      M Morimoto, S Kobatake, M Irie

      JOURNAL OF THE AMERICAN CHEMICAL SOCIETY125 ( 36 ) 11080 - 11087   9 2003

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:AMER CHEMICAL SOC  

      Novel photochromic single crystals composed of three different kinds of diarylethenes, 1,2-bis-(3,5-dimethyl-2-thienyl)perfluorocyclopentene (11 a), 1,2-bis(2,5-dimethyl-3-thienyl)perfluorocyclopentene (2a), and 1,2-bis(2-methyl-5-p-methoxyphenyl-3-thienyl)perfluorocyclopentene (3a), have been prepared. The three-component crystals turned yellow, orange, red, purple, blue, green, or black upon irradiation with light of appropriate wavelengths. The colors of the crystals were thermally stable in the dark and completely bleached by irradiation with visible light. Such multicolored photochromic crystals have potential for the application to optoelectronic devices, such as multifrequency three-dimensional optical memory media or full-color displays.

      DOI: 10.1021/ja035277o

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    • Polymorphism of 1,2-bis(2-methyl-5-p-methoxyphenyl-3-thienyl)perfluoro-cyclopentene and photochromic reactivity of the single crystals Peer-reviewed

      M Morimoto, S Kobatake, M Irie

      CHEMISTRY-A EUROPEAN JOURNAL9 ( 3 ) 621 - 627   2 2003

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

      Four polymorphic crystals were obtained by recrystallization of 1,2-bis(2-methyl-5-p-methoxyphenyl-3-thienyl)perfluorocyclopentene (1a) from hexane. All crystals underwent photochromic reactions upon alternate irradiation with ultraviolet (lambda = 370 nm) and visible light (lambda &gt; 500 nm). The hotocyclization quantum yields were found to be close to unity irrespective of the crystal types, while the photocycloreversion quantum yields were different as much as four times depending on the conformation of the closed-ring isomers in the crystals.

      DOI: 10.1002/chem.200390066

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    • Photochromism of diarylethenes in nanolayers of a single crystal Peer-reviewed

      M Morimoto, S Kobatake, M Irie

      PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES2 ( 11 ) 1088 - 1094   2003

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:ROYAL SOC CHEMISTRY  

      1,2- Bis( 2- methyl- 5- pentafluorophenyl- 3- thienyl) perfluorocyclopentene ( 1a) and 1,2- bis( 2- ethyl- 5- phenyl- 3- thienyl)perfluorocyclopentene ( 2a) were found to form a 1 : 1 stoichiometric co- crystal. The crystal is composed of alternate nanolayers of 1a and 2a molecular sheets. pi - pi Stacking of 1a and 2a molecules by aryl - perfluoroaryl interactions was not discerned. One- component 1a and 2a crystals and the co- crystal showed a reversible colour change from colourless to blue upon irradiation with ultraviolet and visible light. Although both 1a and 2a molecules underwent efficient photochromic reactions in the one- component crystals upon photoirradiation, only 2a underwent the reaction up to a conversion of 20% in the co- crystal, as confirmed by HPLC and X- ray crystallography. This indicates that excited energy transfer occurs from 1a to 2a in the crystal.

      DOI: 10.1039/b307999f

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    • Absorption spectra of colored isomer of diarylethene in single crystals Peer-reviewed

      S Kobatake, M Morimoto, Y Asano, A Murakami, S Nakamura, M Irie

      CHEMISTRY LETTERS31 ( 12 ) 1224 - 1225   12 2002

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      Language:English   Publishing type:Research paper (scientific journal)   Publisher:CHEMICAL SOC JAPAN  

      The colored isomer produced in 1,2-bis(2,5-dimethyl-3-thienyl)perfluorocyclopentene crystal upon irradiation with ultraviolet light showed an absorption maximum at 535 nm, which is 30 nm longer than that in hexane, 505 nm. The spectral shift is ascribed to the strained structure of the photogenerated closed-ring isomer in the crystal.

      DOI: 10.1246/cl.2002.1224

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    • Multi-colored photochromic crystals of diarylethene mixtures Peer-reviewed

      MORIMOTO Masakazu, KOBATAKE Seiya, IRIE Masahiro

      Advanced Materials14 ( 15 ) 1027 - 1029   8 2002

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

      DOI: 10.1002/1521-4095(20020805)14:15<1027::AID-ADMA1027>3.0.CO;2-F

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    Books and Other Publications

    • Photosynergetic responses in molecules and molecular aggregates (Editors: H. Miyasaka, K. Matsuda, J. Abe, T. Kawai)

      Masakazu Morimoto, Masahiro Irie( Role: Joint author)

      Springer  9 2020 

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      Language:English Book type:Scholarly book

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    • 光機能性有機・高分子材料における新たな息吹(監修: 市村 國宏)

      森本 正和, 入江 正浩( Role: Joint author)

      シーエムシー出版  4 2019 

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      Language:Japanese Book type:Scholarly book

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    • 光化学フロンティア:未来材料を生む有機光化学の基礎

      森本正和( Role: Contributor)

      化学同人  10 12 2018  ( ISBN:9784759814194

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      Language:Japanese Book type:Scholarly book

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    • 光化学フロンティア:未来材料を生む有機光化学の基礎(監修: 水野 一彦,宮坂 博,池田 浩)

      森本正和( Role: Contributor)

      化学同人  10 12 2018 

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      Language:Japanese Book type:Scholarly book

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    • Photon-Working Switches (Editors: Y. Yokoyama, K. Nakatani)

      M. Morimoto, M. Irie( Role: Joint author)

      Springer  6 2017  ( ISBN:9784431565444

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      Language:English Book type:Scholarly book

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    • Photochromic Materials - Preparation, Properties and Applications (Editors: H. Tian, J. Zhang)

      M. Morimoto, S. Kobatake, M. Irie, H. K. Bisoyi, Q. Li, S.Wang, H. Tian( Role: Joint author)

      Wiley  6 2016  ( ISBN:9783527337798

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    • Supramolecular photochemistry: controlling photochemical processes (Editors: V. Ramamurthy, Y. Inoue)

      Masakazu Morimoto, Masahiro Irie( Role: Joint author)

      Wiley  27 9 2011  ( ISBN:0470230533

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    • 超分子サイエンス&テクノロジー:基礎からイノベーションまで(監修:国武 豊喜)

      小畠誠也, 森本正和, 入江正浩( Role: Joint author)

      エヌ・ティー・エス  5 2009  ( ISBN:9784860433093

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      Language:Japanese Book type:Scholarly book

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    Presentations

    • Turn-on mode photoswitchable fluorescent molecules based on photochromic diarylethenes Invited International conference

      Masakazu Morimoto

      The 41st PhotonIcs & Electromagnetics Research Symposium (PIERS 2019 in Rome)  17 6 2019 

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      Language:English   Presentation type:Oral presentation (invited, special)  

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    • 超解像蛍光イメージングに向けた光スイッチ型蛍光色素の研究動向 Invited

      森本正和

      近畿化学協会機能性色素部会第95回例会  30 1 2018 

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      Language:Japanese   Presentation type:Public lecture, seminar, tutorial, course, or other speech  

      Venue:大阪科学技術センター(大阪市)  

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    • Photochromism and mechanical performance of diarylethene single crystals Invited International conference

      Masakazu Morimoto

      The 39th Progress In Electromagnetics Research Symposium (PIERS 2017 in Singapore)  19 11 2017 

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      Language:English   Presentation type:Oral presentation (invited, special)  

      Venue:Singapore  

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    • フォトクロミック分子・分子結晶の光反応と物性 Invited

      森本正和

      日本物理学会2017年秋季大会 領域5シンポジウム 光物性との連成による新分野創成  21 9 2017 

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      Language:Japanese   Presentation type:Oral presentation (invited, special)  

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    • Photomechanical performance of diarylethene single crystals Invited

      Masakazu Morimoto

      日本化学会第97春季年会 Asian International Symposium -Organic Crystals-  16 3 2017 

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      Language:English   Presentation type:Oral presentation (invited, special)  

      Venue:慶應義塾大学日吉キャンパス(神奈川県)  

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    • Making and breaking bonds with light in crystals: diarylethene crystals that convert light into mechanical work Invited International conference

      MORIMOTO Masakazu

      Gordon Research Conference "Artificial Molecular Switches and Motors"  7 6 2015 

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      Language:English   Presentation type:Oral presentation (invited, special)  

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    • ジアリールエテンフォトクロミック分子結晶の結晶構造と光機能 Invited

      森本 正和

      2014高分子・ハイブリッド材料研究センター若手フォーラム  12 12 2014 

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      Language:Japanese   Presentation type:Oral presentation (invited, special)  

      Venue:東北大学  

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    • Photochromism of diarylethene single crystals: photoinduced shape change and photomechanical performance Invited International conference

      MORIMOTO Masakazu

      Breaking and Making Bonds with Light Workshop  30 6 2014 

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      Language:English   Presentation type:Oral presentation (invited, special)  

      Venue:Telluride Intermediate School (Colorado, USA)  

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    • フォトクロミック分子結晶の結晶構造と多重機能

      森本 正和

      フォトクロミック分子結晶の結晶構造と多重機能  22 3 2013 

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      Language:Japanese   Presentation type:Oral presentation (invited, special)  

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    • ジアリールエテン単結晶のフォトクロミズム-分子の異性化反応が誘起する結晶格子変形と光機能

      森本 正和

      錯体化学会第62回討論会  21 9 2012 

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      Language:Japanese   Presentation type:Oral presentation (invited, special)  

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    • Photomechanical effect of diarylethene cocrystals International conference

      MORIMOTO Masakazu, IRIE Masahiro

      6th International Symposium on Organic Photochromism  17 10 2010 

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      Language:English   Presentation type:Oral presentation (general)  

      Venue:Yokohama, Japan  

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    • Crystal structures and photochromic performance of diarylethene single crystals International conference

      MORIMOTO Masakazu

      Second Japanese-French Workshop on NanoBioPhotonics  26 10 2009 

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      Language:English   Presentation type:Oral presentation (invited, special)  

      Venue:Marseille, France  

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    • 異種複合型フォトクロミック分子結晶の結晶構造と光機能

      森本 正和

      第58回錯体化学討論会  20 9 2008 

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      Language:Japanese   Presentation type:Oral presentation (invited, special)  

      Venue:金沢大学(石川県)  

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    • Photoactive materials based on photochromic crystals with hybrid structures International conference

      MORIMOTO Masakazu, TAKAISHI Shinya, KAJIWARA Takashi, MIYASAKA Hitoshi, YAMASHITA Masahiro, IRIE Masahiro

      Second International Symposium on Chemistry of Coordination Space (ISCCS 2006)  15 12 2006 

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      Language:English   Presentation type:Oral presentation (invited, special)  

      Venue:Fukuoka, Japan  

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    • ジアリールエテン単結晶の結晶構造とフォトクロミズム

      森本 正和

      光エネルギーと物質変換シンポジウム:光合成・光触媒・太陽電池および関連化学の革新  26 11 2004 

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      Language:Japanese   Presentation type:Oral presentation (invited, special)  

      Venue:金沢大学(石川県)  

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    Professional Memberships

    Research Projects

    • Development of advanced photochromic molecules and materials

      JST Basic Research Programs (Precursory Research for Embryonic Science and Technology :PRESTO) 

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      4 2007 - Present

      Grant type:Competitive

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    • ポリマーメカノケミストリーにおける結合切断点ナノ可視化技術の構築

      日本学術振興会  科学研究費助成事業 

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      4 2018 - 3 2022

      Grant type:Competitive

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    • 分子結晶の発動に基づく新奇固体物性変換機構の開拓

      文部科学省  科学研究費助成事業 

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      4 2019 - 3 2021

      Grant type:Competitive

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    • 水素移動と光化学反応の強結合による高次機能分子デバイスの創出

      文部科学省  科学研究費助成事業 

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      4 2019 - 3 2021

      Grant type:Competitive

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    • 複合応答蛍光スイッチング分子システムを用いた超解像機能イメージング

      文部科学省  科学研究費助成事業 

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      4 2017 - 3 2019

      Grant type:Competitive

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    • プロトン移動現象と光異性化反応の融合による光応答性有機強誘電体の創出

      文部科学省  科学研究費助成事業 

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      4 2016 - 3 2018

      Grant type:Competitive

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    • フォトクロミズムを用いた複合応答蛍光スイッチング分子システムの創出

      文部科学省  科学研究費助成事業 

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      4 2015 - 3 2017

      Grant type:Competitive

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    • 光により変形するフォトクロミック圧電結晶を用いた光電変換

      日本学術振興会  科学研究費助成事業 

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      4 2014 - 3 2017

      Grant type:Competitive

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    • 光応答性分子結晶の構造変化による固体物性制御

      文部科学省  科学研究費助成事業 

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      4 2014 - 3 2016

      Grant type:Competitive

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    • 光が内包する波長情報を読み取り多彩に運動する有機結晶アクチュエーターの開発

      民間財団等  徳山科学技術振興財団 研究助成 

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      5 2014 - 5 2015

      Grant type:Competitive

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    • フォトクロミック反応とプロトン移動現象の融合による光応答性強誘電体の開発

      民間財団等  池谷科学技術振興財団 単年度研究助成 

      森本正和

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      4 2014 - 3 2015

      Authorship:Principal investigator  Grant type:Competitive

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    • 単分子メモリ機能を指向した光応答性金属錯体の開発

      民間財団等  倉田記念日立科学財団 倉田奨励金 

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      4 2013 - 3 2015

      Grant type:Competitive

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    • フォトクロミック反応による有機強誘電体の光応答機能の創出

      民間財団等  住友財団 基礎科学研究助成 

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      11 2012 - 5 2014

      Grant type:Competitive

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    • 水素結合性フォトクロミック分子を用いた有機強誘電体結晶の光制御

      日本学術振興会  科学研究費助成事業 

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      4 2012 - 3 2014

      Grant type:Competitive

      光により固体物性を制御できる機能性分子結晶材料へ向けての基礎として、フォトクロミック分子の光異性化反応により強誘電物性を可逆的に変化させる有機分子結晶を創製することを目的とする。

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    • フォトクロミック分子の光異性化反応が誘起する結晶格子変形を利用した物性制御

      立教大学  立教大学学術推進特別重点資金(立教SFR) 

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      4 2011 - 3 2012

      Grant type:Competitive

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    • 光機能性有機強誘電結晶の創製

      科学技術振興機構  科学技術振興機構 戦略的創造研究推進事業 さきがけ 

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      4 2007 - 3 2011

      Grant type:Competitive

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    • フォトクロミック電荷移動錯体結晶の光誘起電荷移動量変化による固体物性制御

      日本学術振興会  科学研究費助成事業 

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      4 2007 - 3 2009

      Grant type:Competitive

      フォトクロミック電荷移動錯体結晶の光誘起電荷移動量変化による固体物性制御

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    • 超高密度メモリデバイスを指向した単分子磁性光スイッチングシステムの構築

      立教大学  立教大学学術推進特別重点資金(立教SFR) 

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      6 2007 - 3 2008

      Grant type:Competitive

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    • フォトクロミック反応による金属錯体ナノ量子磁石の光スイッチング

      東北大学  東北大学若手研究者萌芽研究育成プログラム 

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      9 2006 - 3 2007

      Grant type:Competitive

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    • Photochemical switching of magnetic properties of photochromic metal complexes

      The Other Research Programs 

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      4 2006 - 3 2007

      Grant type:Competitive

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    • 異種分子複合型光機能性フォトクロミック単結晶の開発

      科学研究費助成事業 

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      4 2004 - 3 2006

      Grant type:Competitive

      異種分子複合型光機能性フォトクロミック単結晶の開発

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    • Crystal structures and photochromic performance of diarylethene single crystals

      Grant-in-Aid for Scientific Research 

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      4 2000 - 3 2006

      Grant type:Competitive

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    Social Contribution

    • 神奈川県立川和高等学校 出張授業

      11 2012

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    • 豊島区理科実験実技研修会

      8 2008

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