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Photoswitchable functional organic materials

Research Project

Project/Area Number 08555229
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section展開研究
Research Field Synthetic chemistry
Research InstitutionTottori University

Principal Investigator

KIJI Jitsuo  Tottori University, Faculty of Engineering, Professor, 工学部, 教授 (60026002)

Co-Investigator(Kenkyū-buntansha) YOKOYAMA Yasushi  Yokohama National University, Faculty of Engineering, Associate Professor, 工学部, 助教授 (60134897)
OKANO Tamon  Tottori University, Faculty of Engineering, Associate Professor, 工学部, 助教授 (20112104)
Project Period (FY) 1996 – 1998
Project Status Completed (Fiscal Year 1998)
Budget Amount *help
¥8,700,000 (Direct Cost: ¥8,700,000)
Fiscal Year 1998: ¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 1997: ¥2,600,000 (Direct Cost: ¥2,600,000)
Fiscal Year 1996: ¥4,600,000 (Direct Cost: ¥4,600,000)
KeywordsChiral fulgide / Indolylgulgide / Photoswitchable function / Photochromism / Fluorescence / Fatigue-resistant Photochromic molecule
Research Abstract

(1) Control of the Pitch of Liquid Crystal by Photochromic Reactions
Chiral binaphthol-condensed fulgide derivatives work as the chiral dopants to induce the cholestic phases when doped with a nematic liquid crystal (LC). Their photochromic reactions induce the reversible and large change of the pitch values of the choleslic phases. Structural control of LC is possible by on/off switching of the photochromism.
(2) Control of Fluorescence by Photochromic Reactions
While the colorless form of the propyl-substituted, binaphthol-condensed indolylfulgide does not emit fluorescence, its colored form, which is generated by UV-irradiation, emits fluorescence. A perfect on/off switching system of fluorescence controlled by the photochromism was exhibited.
(3) CD Spectra and Optical Rotation of Chiral Fulgides
Resolved, optically-active indolylfulgide, and binaphthol-condensed indolylfulgides and beuzofulgides were synthesized and their CD spectra and optical rotation were measured. Large change of specific rotation values was observed by photochromic reactions.
(4) Others
(a) An indolylfulgide, which is trapped in an organic-inorganic matrix prepared by the sol-gel possess using methyltri-methoxysilane, showed photochromism.
(b) Bisthienylfulgides of C2 synimetly were prepared by the palladium-catalyzed carbonylation method and their photo-chromic reactions were studied.
(c) Crowned flilgides were prepared and their photochromic reactions were studied in the presence or absence of guest cations.

Report

(4 results)
  • 1998 Annual Research Report   Final Research Report Summary
  • 1997 Annual Research Report
  • 1996 Annual Research Report
  • Research Products

    (35 results)

All Other

All Publications (35 results)

  • [Publications] Y.Yokoyama: "Diasterseoselective Photochromism of (R)-Binaphthol-condensed Indolylfulgide." J.Am.Chem.Soc.118(13). 3100-3107 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Yokoyama: "Photpchromism of 4-Substituted Phenoxynaphthacenequinones." Chem.Lett.1996(6). 355-356 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Yokoyama: "Study on the Conformation of an Isopropyl-substituted Furylfulgide. Photochromic Coloring Reaction and Thermal Racemization." Bull.Chem.Soc.Jpn.69(6). 1605-1612 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Yokoyama: "Role of the Methoxy Substituents on the Photochromic Indolylfulgides. Absorption Maximum vs. Molar Absorption Coefficient of the Colored Form." Chem.Lett.1996(8). 587-588 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Yokoyama: "Trifluoromethyl-substituted Photochromic Indolylfulgide. A Remarkably Durable Fulgide towards Photochemical and Thermal Treatments." Chem.Lett.1996(12). 1037-1038 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] T.Inada: "Perfect On/Off Switching of Emission of Fluorescence by Photochromic Reaction of a Binaphthol-Condensed Fulgide Derivative." Chem.Lett.1997(4), (9). 321-322,961 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Yokoyama: "Reversible Control of Pitch of Induced Cholesteric Liquid Ceystal by Optically Active Photochromic Fulgide Derivatives." Chem.Lett.1997(8). 687-688 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] J.Biteau: "Photochromism of an Indolyfulgide Trapped in a Hybrid sol-Gel Matrix." Chem.Lett.1998(4). 359-360 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Yokoyama: "Absoluts Stereochemistry and CD Spectra of Resolved Enantiomers of the Colored Form of a Photochromic Diarylethene." Chem.Lett.1998(11). 1093-1094 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Yokoyama: "Chiral Photochromic Compounds and Control of Functions." Enantiomes. 3(2). 123-132 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Yokoyama: "Diastereoselective Photochromism of (R) -Binaphthol-condensed Indolylfulgide." J.Am.Chem.Soc.118 (13). 3100-3107 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Yokoyama: "Photochromism of 4-Substituted Phenoxy-naphthacenequinones." Chem.Lett.1996 (6). 355-356 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Yokoyama: "Study on the Conformation of an Isopropyl-substituted Furylfulgide. Photochromic Coloring Reaction and Thermal Racemization." Bull.Chem.Soc.Jpn.69 (6). 1605-1612 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Yokoyama: "Role of the Methoxy Substituents on the Photochromic Indolylfulgides. Absorption Maximum vs.Molar Absorption Coefficient of the Colored Form." Chem.Lett.1996 (8). 587-588 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Yokoyama: "Trifluoromethyl-substituted Photochromic Indolylfulgide. A Remarkably Durable Fulgide towards Photochemical and Thermal Treatments." Chem.Lett.1996 (12). 1037-1038 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] T.Inada: "Perfect On/Off Switching of Emission of Fluorescence by Photochromic Reaction of a Binaphthol-Condensed Fulgide Derivative." Chem.Lett.1997 (4), (9). 321-322,961 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Yokoyama: "Reversible Control of Pitch of Induced Cholesteric Liquid Crystal by Optically Active Photochromic Fulgide Derivatives." Chem.Lett.1997 (8). 687-688 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] J.Biteau: "Photochromism of an Indolylfulgide Trapped in a Hybrid Sol-Gel Matrix." Chem.Lett.1998 (4). 359-360 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Yokoyama: "Absolute Stereochemistry and CD Spectra of Resolved Enantiomers of the Colored Form of a Photochromic Diarylethene." Chem.Lett.1998 (11). 1093-1094 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Yokoyama: "Chiral Photochromic Compounds and Control of Functions." Enantiomer.3 (2). 123-132 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] J.Biteau, F.Chaput, Y.Yokoyama,and J.Boilot: "Photochromism of an Indolylfulgide Trapped in a Hybrid Sol-Gel Matrix" Chem.Lett.359-360 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Y.Yokoyama, S.Uchida, Y.Yokoyama T.Sagisaka, Y.Uchida,and T.Inada: "Chiral Photochromic Compounds and Control of Functions." Enantiomer. 3. 123-132 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Y.Yokoyama, N.Hosoda, Y.T.Osano,and C.Sasaki: "Absolute Stereochemistry and CD Spectra of Resolved Enantiomers of the Colored Form of a Photochromic Dithienylethene." Chem.Lett.1093-1094 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] T.Inada, S.Uchida and, Y.Yokoyama: "Perfect On/Off Switching of Emission of Fluorescence by Photochromic Reaction of a Binaphthol-Condensed Fulgide Derivative" Chem.Lett.4. 321-322 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Y.Yokoyama and T.Sagisaka: "Reversible Control of Pitch of Induced Cholesteric Liquid Crystal by Optically Active Photochromic Fulgide Derivatives" Chem.Lett.8. 687-688 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Y.Yokoyama, S.Uchida, Y.Shimizu, and Y.Yokoyama: "Photochromism of Fulgides Possessing Chiral Properties" Mol.Cryst.Liq.Cryst.,Sect.A,Special Topics 86. 297. 85-91 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] J.Biteau, F.Chaput, Y.Yokoyama, and J.Boilot: "Photochromism of an Indolylfulgide Trapped in a Hybrid Sol-Gel Matrix" Chem.Lett.(in press). (1998)

    • Related Report
      1997 Annual Research Report
  • [Publications] Y.Yokoyama, S.Uchida, Y.Yokoyama, T.Sagisaka, Y.Uchida, and T.Inada: "Chiral Photochromic Compounds and Control of Functions." Enantiomer. (in press). (1998)

    • Related Report
      1997 Annual Research Report
  • [Publications] Yasushi Yokoyama: "Diastereoselective Photochromism of(R)-Binaphthol-condensed Indolylfulgide" Journal of American Chemical Society. 118・13. 3100-3107 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Yasushi Yokoyama: "Photochromism of 4-Substituted Phenoxynaphthacenequinones" Chemistry Letters. 1996・6. 355-356 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Yayoi Yokoyama: "Study on the Conformation of an Isopropyl-substituted Furylfulgide" Bulletin of Chemical Society of Japan. 69・6. 1605-1612 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Yasushi Yokoyama: "Role of the Methoxy Substltuents on the Photochromic Indolylfulgides" Chemistry Letters. 1996・8. 1037-1038 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] T Inada: "Perfect On/Off Switching of Emission of Fluorescence by Photochromic Reaction" Chemistry Letters. 1997・4(in press). (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] 横山 泰: "有機フォトクロミズムの化学" 学会出版センター, 110-128 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] 横山 泰・稲田妙子: "機能性色素の最新技術" シ-エムシ-, 272-291 (1996)

    • Related Report
      1996 Annual Research Report

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Published: 1996-04-01   Modified: 2016-04-21  

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