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Construction of Redox-type Photochromic Systems Based on Photoinduced Electron Transfer Reactions in Crystalline State

Research Project

Project/Area Number 08640664
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionHokkaido University

Principal Investigator

SUZUKI Takanori  Hokkaido University, Graduate School of Science, Associate Professor, 大学院・理学研究科, 助教授 (70202132)

Project Period (FY) 1996 – 1997
Project Status Completed (Fiscal Year 1997)
Budget Amount *help
¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 1997: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1996: ¥1,100,000 (Direct Cost: ¥1,100,000)
KeywordsPhotochromism ; / Electrochromism ; / Redox System ; / Triarylmethane / Hexaphenylethane / Molecular Device ; / Bistability ; / Functionalized Dye / ホトクロミズム / 酸化還元系 / 動的酸化還元 / 有機結晶 / 光誘起電子移動 / 固相反応
Research Abstract

The research project is intended to construct the novel redox-type photochromic systems based on the photoinduced electron transfer reactions of electron-donor-acceptor complexes in the crystalline state. In order to realize such an idea it is essential to develop a new type of redox molecules exhibiting bistability. Thus, the redox pairs were designed so as to undergo reversible C-C bond formation and cleavage upon electron transfer. The research started from examining the interconversion hexaphenylethane derivatives 1 and dicationic bis (triarylmethane) dyes 2. It has been found that they constitute the dynamic and reversible redox pair showing vivid change in color and drastic structural change upon electron transfer. They surely are the promising candidate for the present purpose. Unfortunately, however, attempts to obtain the CT crystal of 1 with a variety of electron donors have been unsuccessful, preventing me from realizing my initial proposal. Next, the biphenyl-type electron acceptors having dicyanovinyl moieties were investigated. 2,2'-Disubstituted derivative was found to undergo C-C bond formation upon two-electron reduction. By combining the further isomerization of the reduction product, the latter system constitute a prototype of the novel electrochromic system with "write protect" option.

Report

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

    (27 results)

All Other

All Publications (27 results)

  • [Publications] Takanori, Suzuki: "Photoreactions of crystalline charge-transfer complexes" Pure Appl.Chem.68. 281-284 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Yasutake, Takahashi: "Photoinduced skeltal rearrangement of 1,1-diarylspiropentane" J.Chem.Soc.,Perkin Trans.1. 319-325 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Teruo, Kurihara: "Electronic Structures and Oxidation Potentials of some Azulene Derivatives" Bull.Chem.Soc.Jpn.69. 2003-2008 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Takanori, Suzuki: "Teteracyanoquinodimethanes Fused with[1,2,5]Calcogenadiazole Ring" Mol.Cryst.Liq.Cryst.296・1. 165-180 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Takanori, Suzuki: "Hexaphenylethane Derivatives Bxhibiting Novel Electrochromic Behavior" Angew.Chem.Int.Ed.Engl. 36・12. 1329-1331 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Takanori, Suzuki: "Isolation and X-ray Structural Determination of Both Folded and Twisted Conformers of Bis{4H,8H-4-(dicyanomethylene)benzo[1,2-c;4,5-c′]bis[1,2,5]thiadiazol-8-ylidene},an Overcrowded Ethylene with High Electron Affinity" Angew.Chem.Int.Ed.Engl. 36・22. 2495-2497 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Takashi, Tsuji: "Tricyclo[4.2.2.2^<2,5>]dodeca-1,3,5,7,9,11-hexaene:generation and chemical trapping of the 3,4-dicyano derivative" J.Chem.Soc.,Chem.Commun.-・22. 2151-2152 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Takanori, Suzuki: "Dibenzotetrathiafulvalenes inserted with cycloaklanes and their tricyclic valence isomers:reversible C-C bond making/breaking upon electron transfer" J.Chem.Soc.,Chem.Commun.-・23. 2325-2326 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Hidetoshi, Kawai: "Kinetically Stabillized[1.1]Paracyclophane.Isolation and X-ray Structural Analysis" Angew.Chem.Int.Ed.Engl. 37・-(in press). (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] T.Suzuki: "Photoreactions of Crystalline Charge-Transfer Complexes" Pure Appl.Chem.68. 281-284 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Y.Takahashi: "Photoinduced skeletal rearrangement of 1,1-diarylspiropentanes" J.Chem.Soc., Perkin Trans.1. 319-325 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] T.Kurihara: "Electronic Structures and Oxidation Potentials of Some Azulene Derivatives" Bull.Chem.Soc.Jpn.69. 2003-2008 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] T.Suzuki: "Tetracyanoquinodimethanes Fused with a [1,2.5] Chalcogenadiazole Ring" Mol.Cryst.Liq.Cryst.296. 165-180 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] T.Suzuki: "Hexaphenylethane Derivatives Exhibiting Novel Electrochromic Behavior" Angew.Chem.Int.Ed.Engl.36. 1329-1331 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] T.Suzuki: "Isolation and X-ray Structural Determination of Both Folded and Twisted Conformers of Bis {4H、8H-4- (dicyanomethylene) benzo [1,2-c : 4,5-c'] bis [1,2,5] thiadiazol-8-ylidene} , an Overcrowded Ethylene with High Electron Affinity" Angew.Chem.Int.Ed.Engl.36. 2495-2497 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] T.Tsuji: "Tricyclo [4.2.2.22,5] dodeca-1,3,5,7,9,11-hexaene : generation and chemical trapping of the 3,4-dicyano derivative" J.Chem.Soc., Chem.Commun.2151-2152 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] T.Suzuki: "Dibenzotetrathiafulvalenes inserted with cycloalkanes and their tricyclic valence isomers : reversible C-C bond making/breaking upon electron transfer" J.Chem.Soc., Chem.Commun.2325-2326 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] H.Kawai: "Kinetically Stabilized [1.1] Paracyclophane. Isolation and X-ray Structural Analysis" Angew.Chem.Int.Ed.Engl.37 (in press). (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Takanori Suzuki: "Teteracyanoquinodimethanes Fused with [1,2,5]Calcogenadiazole Ring" Mol.Cryst.Liq.Cryst.296・1. 165-180 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Takanori Suzuki: "Hexaphenylethane Derivatives Exhibiting Novel Electrochromic Behavior" Angew.Chem.Int.Ed.Engl. 36・12. 1329-1331 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Takanori Suzuki: "Isolation and X-ray Structural Determination of Both Folded and Twisted Conformers of Bis{4H,8H-4-(dicyanomethylene)benzo[1,2-c:4,5-c']bis[1,2,5]thiadiazol-8-ylidene},an Overcrowded Ethylene with High Electron Affinity" Angew.Chem.Int.Ed.Engl. 36・22. 2495-2497 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Takashi Tsuji: "Tricyclo[4.2.2.2^<2,5>]dodeca-1,3,5,7,9,11-hexaene:generation and chemical trapping of the 3,4-dicyano derivative" J.Chem.Soc.,Chem,Commun.-・22. 2151-2152 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Takanori Suzuki: "Dibenzotetrathiafulvalenes inserted with cycloaklanes and their tricyclic valence isomers:reversible C-C bond making/breaking upon electron transfer" J.Chem.Soc.,Chem.Commun.-・23. 2325-2326 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Hidetoshi Kawai: "Kinetically Stabilized〔1,1〕Paracyclophane.Isolation and X-ray Structural Analysis" Angew.Chem.Int.Ed.Engl. 37・-(in press). (1998)

    • Related Report
      1997 Annual Research Report
  • [Publications] T. Kurihara: "Electronic Structures and Oxidation Potentials of some Azulene Deriratives" Bull. Chem. Soc. Jpn.69・7. 2003-2008 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] T. Suzuki: "Tetracyanoquinodime thanes fused with a 〔1,2,5〕Chalcogena diazole Ring" Mol. Cryst. Liq. Cryst.(印刷中). (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] T.Suzuki: "Hoxaphenylethane Derivatives Exhibiting Novel Electrochromic Behavior" Angew. Chem.(印刷中). (1997)

    • Related Report
      1996 Annual Research Report

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

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