• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Construction of Chiral Photochromic System Controlled by Steric Factors

Research Project

Project/Area Number 10640530
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionTokyo Kasei Gakuin University

Principal Investigator

YOKOYAMA Yayoi  Tokyo Kasei Gakuin University, Faculty of Home Economics, Associate Professor, 家政学部, 助教授 (70142263)

Project Period (FY) 1998 – 1999
Project Status Completed (Fiscal Year 1999)
Budget Amount *help
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 1999: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1998: ¥3,100,000 (Direct Cost: ¥3,100,000)
KeywordsPhotochromism / Steric Factors / Fulgides / Diastereoselectivity / Thermally Irreversibility / Photostationary State / 不斉 / ジアステレオ選択性 / ジアリールエテン
Research Abstract

A sterically demanding and thermally irreversible bisthienylfulgides, 3,4-bis[1-(2,5-dimenthyl-3-thienyl) ethylidene]-3,4-dihydro-2,5-furandione, was synthesized by Pd-catalyzed carbonylation of the corresponding 2-butyne-1,4-diol derivatives and their photochromic bihaviers were studied.
Treatment of trichloroethene with butyllithium followed by reaction of 3-acyl-2,5-dimenthylthiophene gave the acetylenediol in 45% yield. Reaction of acetylenediol with carbon monoxide in the presence of Pd(Oac)ィイD22ィエD2 afforded bisthienylfulgides as a mixture geometric isomers. These isomers were separated by silica gel column chromatography to obtain EE, EZ, and ZZ in 4, 3, and 1% yields, respectivity. The identification f geometric isomers was done by ィイD11ィエD1H NMR and their photochromic behaviors were studied. 366-nm light irradiation to the toluene solution of ZZ afforded EZ, EE, and two colored closed forms(CィイD2EEィエD2, CィイD2EZィエD2). Two colored closed forms changed EE and EZ upon 554-nm light irradiation. Two colored forms(CィイD2EEィエD2, CィイD2EZィエD2)obtained from EE and EZ were diastereomeic with each other. At photostationary state o 366-nm light irradiation, the ratio of concentration of the isomers, EE/EZ/ZZ/CィイD2EEィエD2/ CィイD2EZィエD2, was 17/14/8/58/3. The most notable feature is the highly diastereoselective formation of CィイD2EEィエD2 (90% de).

Report

(3 results)
  • 1999 Annual Research Report   Final Research Report Summary
  • 1998 Annual Research Report
  • Research Products

    (12 results)

All Other

All Publications (12 results)

  • [Publications] Yasushi Yokoyama: "Chiral Photochromic Compounds and Control of Functions"Enantiomer. 3. 123-132 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Yasushi Yokoyama: "Highly Diastereoselective Photochromic Cyclization of a Bisthienylfulgide"Chemistry Letters. 3. 220-221 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Yasushi Yokoyama: "Photochromism of Fulgenates Possessing Crown-Ether Moiety"Mol. Cryst. Liq. Cryst.. (印刷中).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Yasushi Yokoyama: "Photochromism and Kinetics of Heliochromic Benzothienylfulgides"Mol. Cryst. Liq. Cryst.. (印刷中).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 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
      1999 Final Research Report Summary
  • [Publications] Y.Yokoyama: "Highly Diastereoselective Photochromic Cyclization of a Bisthienylfulgide"Chemistry Letters. 2000. 220-221 (2000(3))

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Y.Yokoyama: "Photochromism of Fulgenates Possessing Crown-Ether Moiety"Molecular Crystals and Liquid Crystals. 2000. (in press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Y.Yokoyama: "Photochromism and Kinetics of Heliochromic Benzothienylfulgides"Molecular Crystals and Liquid Crystals. 2000. (in press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Yasushi Yokoyama: "Highly Diastereoselective Photochromic Cyclization of a Bisthieny Ifulgide"Chemistry Letters. 3. 220-221 (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] Yasushi Yokoyama: "Photochromism of Fulgenates Possessing Croen-Ether Moiety"Mol.Cryst.Liq.Cryst.,. (印刷中).

    • Related Report
      1999 Annual Research Report
  • [Publications] Yasushi Yokoyama: "Photochromism and Kinetics of Heliochromic Benzothieny Ifulgides"Mol.Cryst.Liq.Cryst.,. (印刷中).

    • Related Report
      1999 Annual Research Report
  • [Publications] Yasushi Yokoyama: "Chiral Photochromic Compounds and Control of Functions" Enantiomer. 3. 123-132 (1998)

    • Related Report
      1998 Annual Research Report

URL: 

Published: 1998-04-01   Modified: 2016-04-21  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi