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Studies on Molecular Devices showing Redox Response

Research Project

Project/Area Number 06640675
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field Organic chemistry
Research InstitutionHokkaido University (1995)
Tohoku University (1994)

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) 1994 – 1995
Project Status Completed (Fiscal Year 1995)
Budget Amount *help
¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1995: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1994: ¥1,000,000 (Direct Cost: ¥1,000,000)
KeywordsRedox System ; / Molecular Device ; / Electrochromism ; / Photochromism ; / Dynamic Redox Behavior / 多段階レドックス / 分子構造変化 / 応答性 / 渡環結合 / 渡環相互作用
Research Abstract

The research project is intended to construct the organic redox systems which exhibit the electrochemical response such as electrochromism. In order to realize such molecular systems a new way of molecular designing was adopted where (1) the charged species would be stabilized by formation of strong chromophores with large pi-conjugation but not by aromatization and (2) drastic structural changes should be occurred during the electron transfer. These conditions are quite different from what had been used to design the multi-stage redox systems for a long time. The "dynamic redox behavior"is the central concept in this work, thus the redox pairs were designed so as to undergo reversible C-C bond formation andcleavage upon electron transfer. Dibenzo-TTF derivatives inserted with a cycloalkane ring as well as their isomersof the tricyclic skeleton were studiedin detail as prototypes. Some molecules studies here were proven to be thereversible dynamic redox systems . In orderr to construct the electrochromic systems other molecules containing triarylmethane dye skeletons were designed. The reversible interconversion between hexaarylethane derivatives and bis (triarylmethane) dications was demonstrated .

Report

(3 results)
  • 1995 Annual Research Report   Final Research Report Summary
  • 1994 Annual Research Report
  • Research Products

    (27 results)

All Other

All Publications (27 results)

  • [Publications] Takanori Suzuki: "2-(Thiopyran-4′-ylidene)-1,3-dithioles fused with thiophene units : intramoleclar S ・・・ S interaction affecting the redox propertics and molecular geometries." J. Chem. Soc., Chem. Commum.1431-1432 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Yasutake Takahashi: "Cycloreversion of arene endoperoxides inducced by eletron tranfer" J. Chem. Soc., Chem. Commum.13-14 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Takanori Suzuki: "An absolute asymmetric synthesis of the [2+2] cycloadduct via single crystal-to-single crystal transformation by caherge-transfer excitation of soid-state molecular conplexes composedof arylolefins and bis [1, 2, 5] thiadiazolotetracyanoquinodimethane." J. Am. Chem. Soc.116. 2793-2803 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Yasutake Takahashi: "Photoinduced Skeletal Rearrangement of 1, 1-Diphenylspiropentanes" Tetrahedron Lett.36. 5207-5210 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Masatoshi Hirayama: "The π-trianion radical of 2, 3, 6, 7-tetracyanobenzo [1, 2-b : 4, 5-b′] bisdithiole-4, 8-dione. Observation of ESR with ^<13>C-Satellites in Natural Abundance" Chem. Lett.511-512 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Masatoshi Hirayama: "ESR of the trianion and anion radicals of benzo [g] [1, 2, 5] thiadiazolo [3, 4-b] quinoxaline-5, 10-dione and its selenium analogue" Chem. Lett.837-838 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Masatoshi Hirayama: "ESR of the π-radical formed by photoreduction of bis (1, 2, 5-selsna-diazolo) tetracyanoquinodimethane in methanol. Observation of a large ^<77> Se Hfs" Chem. Lett.1021-1022 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Masatoshi Hirayama: "ESR of the anion of 2, 6-dithioxonebzo [1, 2-d : 4, 5-d′] bis [1, 3]-dithiole-4, 8-dione. Observation of the Satellits of ^<17>O, ^<13>C, and ^<33>S and the second-generation satellits due to both ^<13>C and ^<33>S in Natural Abundance" Bull. Chem. Soc. Jpn.68. 3337-3339 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Takanori Suzuki: "Weak intermolecular interaction in crystal affecting the recognition properties and the soid-state reactivity" J. Synth. Org. Chem., Jpn.53. 403-412 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Takanori Suzuki: "Phototractions of crystalline change-transfer complexes" Pure Appl. Chem.68 (in press). (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Takanori Suzuki, Tomoo Sakimura, Shoji Tanaka, Yoshiro Yamashita, Hiroaki Shiohara, Tsutomu Miyashi: ""2-(Thiopyran-4'-yliden)-1,3-dithioles fused with thiophene units : Intramolecular S・・・S interaction affecting the redox properties and molecular geometries"" J.Chem.Soc., Chem.Commun.1431-1432 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Yasutake Takahashi, Shin-ichi Morishima, Kan Wakamatsu, Takanori Suzuki, Tsutomu Miyashi: ""Cycloreversion of arene endoperoxides induced by electron transfer"" J.Chem.Soc., Chem.Commun.13-14 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Takanori Suzuki, Takanori Fukushima, Yoshiro Yamashita, Tsutomu Miyashi: ""An absolute asymmetric synthesis of the[2+2]cycloadduct via single crystal-to-single crystal transformation by charge-transfer excitation of solid-state molecular complexes composed of arylolefins and bis[1,2,5]thiadiazolotetracyanoquinodimethane"" J.Am.Chem.Soc.116. 2793-2803 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Yasutake Takahashi, Hitoshi Ohaku, Shin-ichi Morishima, Takanori Suzuki, Tsutomu Miyashi: ""Photoinduced Skeletal Rearrangement of 1,1-Diphenylspiropentanes"" Tetrahedron Lett.36. 5207-5210 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Masatoshi Hirayama, Manabu Itasaka, Takanori Suzuki, Yoshiro Yamashita, Tsutomu Miyashi: ""The pi-trianion radical of 2,3,6,7-tetracyanobenzo[1,2, -b : 4,5-b']bisdithiole-4,8-dione. Observation of ESR with ^<13>C-Satellites in Natural Abundance"" Chem.Lett.511-512 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Masatoshi Hirayama, Toshitaka Terasaka, Manabu Itasaka, Takanori Suzuki, Yoshiro Yamashita, Tsutomu Miyashi: ""ESR of the trianion and anion radicals of benzo [g] [1,2,5]thiadiazolo-[3,4-b]-quinoxaline-5,10-dione and its selenium analogue"" Chem.Lett.837-838 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Masatoshi Hirayama, Toshitaka Terasaka, Yoichi morita, Takanori Suzuki, Yoshiro Yamashita, Tsutomu Miyashi: ""ESR of the pi-radical formed by photoreduction of bis (1,2,5-selenadiazolo) -tetracyanoquinodimethane in methanol. Observation of a large ^<77>Se Hfs"" Chem.Lett.1021-1022 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Masatoshi Hirayama, Toshitaka Terasaka, Yoshiro Yamashita, Takanori Suzuki, Tsutomu Miyashi, Yoshiharu Usui: ""ESR of the anion radical of 2,6-dithioxobenzo[1,2, d : 4,5-d']bis[1,3]-dithiole-4,8-dione. Observation of the Satellites of ^<17>O,^<13>C,and ^<33>S and the second-generation satellites due to both ^<13>SC and ^<33>S in Natural Abundance"" Bull.Chem.Soc.Jpn.68. 3337-3339 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Takanori Suzuki: ""Weak intermolecular interaction in crystal affecting the recognition properties and the solid-state reactivity"" J.Synth.Org.Chem., Jpn.53. 403-412 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Takanori Suzuki: ""Photoreactions of srystalline charge-transfer complexes"" Pure Appl.Chem.68(in press). (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Takanori Suzuki: "Photoreactions of Crystalline Charge-Transfer Complexes" Pure Appl,Chem.2(印刷). (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] 鈴木孝紀: "結晶状態に働く弱い分子間相互作用-分子認識から単結晶相反応まで-" 有機合成化学協会誌. 5. 403-412 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Masatoshi Hirayama: "The π-Trianion Radical of 2,3,6,7-Tetroyaht benzo〔1,2-b:4,5-b′〕bisdithiole-4,8-dione,observation of ESR with ^<13>C-Satellites in Natural Abundane" Chem.Lett.5. 511-512 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Masatoshi Hirayama: "ESR of the Trianion and Anion Radicals of Benzo〔j〕〔1,2,5〕thiadiazole〔3,4-D〕-quinoxaline-5,10-dione and Its Selenium Analogne" Chem.Lett.9. 837-838 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Masatoshi Hirayama: "ESR of the π-Radical Fornud by Photoreduction of BIS(1,2,5-selenadiazelo)-tetoaiyanoquinodinethane in Nethanl,Observation of a Large ^<77>Se Hfs" Chem.Lett. 11. 1021-1022 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Masatoshi Hirayama: "ESR of the Anion Radical of 2,6-Dithioxobenzo〔1,2-d:4,5-d′〕bis〔1,3〕dithiole-4,8-dione,Obsewation of the Satellite of ^<17>O,^<13>C,and^<32>S and the Secomd-Generation Satellites" Bull.Chem.Soc.Jpn.12. 3337-3339 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Takanori Suzuki: "2-(Thiopyran-4'-gliden)-1,3-dithioles fused with Thiophene Units : Intramolecular S・・・S Interaction affecting the Redox Properties and Molecular Geometries" J.Chem.Soc.,Chem.Commun.1431-1432 (1994)

    • Related Report
      1994 Annual Research Report

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Published: 1994-04-01   Modified: 2016-04-21  

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