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Syntheses of New Multifunctional Viologen Derivatives and their Application for New Materials

Research Project

Project/Area Number 63550679
Research Category

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

Allocation TypeSingle-year Grants
Research Field 高分子合成
Research InstitutionTokyo Institute of Technology

Principal Investigator

ENDO Takeshi  Tokyo Institute of Technology, Research Laboratory of Resources Utilization, Professor, 資源化学研究所, 教授 (40016738)

Project Period (FY) 1988 – 1989
Project Status Completed (Fiscal Year 1989)
Budget Amount *help
¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 1989: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1988: ¥1,300,000 (Direct Cost: ¥1,300,000)
KeywordsMultifunctionality / Viologen / Dihydronicotinamide / Crown Ether / Azobenzene / Benzophenone / Charge Transfer Complex / Intramolecular Electron Relay / ジヒドロニコチンアミド / 分子内電子移動 / ビニルビオロゲン / ビルルアゾベンゼン
Research Abstract

We investigated In this research the syntheses and application of new multi-electron transfer systems related to the well-known redox function, viologen and their development to polymeric systems.
As new multi-electron transfer systems, we synthesized viologen derivatives bearing azobenzene, substituted benzophenones, dihydronicotinamidet or crown ethers linked with various spacers.
In these new systems, we could find some new behaviors based on the intramolecular interactions between functional groups, which were not observed between the corresponding intramolecular systems.
In the viologen derivatives having substituted benzophenone or dihydro- nicatinamide structure, charge transfer complexation between these functional groups were observed. In these systems, the photoinduced electron relay were observed in the aprotic medium for the first time.
By the comparison of the redox behaviors in the viologen derivatives having the azobenzene structure with various linkages, the electron relay in both groups was found to be most effective, when these groups were connected with propylene linkage due to the stacked conformation of both groups. In this case the direction of electron relay was controlled by pHs.
In the viologen derivative having the crown ether structure, the Na_2S_2O_4 reduction of vialogen part was accelerated by the crown ether part in the mixed solvent of water and acetonitrile.
In order to introduce the above-mentioned multi-electron transfer systems in the polymer, some new monomers were synthesized which have vinyl groups directly linked to the functional groups. and the copolymers were synthesized with the viologen and other functional groups having as direct pendants. In these copolymers, charge transfer complexation,and intramolecular electron transfer were also observed much extensively than those in the monomeric model systems.

Report

(3 results)
  • 1989 Annual Research Report   Final Research Report Summary
  • 1988 Annual Research Report
  • Research Products

    (35 results)

All Other

All Publications (35 results)

  • [Publications] Naoya Kitamura: "Preparation of a Polymeric Membrane Crosslinked by the Viologen Structure from a Cyanopyridinium Salt Polymer" J.Polym.Sci.,Polym.Chem.Ed.26. 992-1001 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Toshihiko Sato: "Preparation of Cellulose Derivatives Containing the Viologen Moiety" J.Polym.Sci.,Polym.Lett.Ed.26. 341-345 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 南部洋子: "電子伝達機能団をもつ高分子の合成と応用-電子伝達膜への展開" 表面. 26. 630-640 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kazunori Ishikawa: "Electron Transport Membrane:Preparation of Polypeptide Membrane with Spacers between the Ploymer Matrix and Viologen Moiety and their Application to an Electron Transfer Reaction" J.Polym.Sci.,Polym.Chem.Ed.27. 1625-1629 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Toshihiko Sato: "Incorporation of Viologen Moiety as Redox Function into Hydroxypropyl Cellulose" J.Polym.Sci.,Polym.Lett.Ed.27. 289-293 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Yoko Nambu: "First Observation of an Intramolecular Charge Transfer and Electron Relay between the Viologen and Ester Groups in a New Copolymer System" Macromolecules. 22. 3530-3532 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Naoya Kitamura: "Synthesis and Radical Copolymerization of a New Type Pyridinium Monomer and Redox Behavior of its Polymers" J.Polym.Sci.,Polym.Chem.Ed.28. 345-352 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Yoko Nambu: "Unusual Photoreduction of Viologen by Dimethyl Sulfoxide on a New Polymer Having Direct Pendants of Viologen and Benzophenone Structures" Tetrahedron Lett.31. 891-894 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Naoya Kitamura: "Redox Behavior of Pyridinium Salts and Their Polymers Having Radical Stabilizing Groups" J.Polym.Sci.,Polym.Chem.Ed.in press.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Takeshi Endo: "Synthesis of Polyethers Containing Viologen Moiety and Their Application to Electron Transfer Catalyst" J.Polym.Sci.,Polym.Chem.Ed.in press.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 遠藤剛: "新しい電子伝達系の開発と有機合成への応用" 触媒. 30. 255-261 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 遠藤剛: "多機能性高分子の合成" 高分子. 37. 662-665 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Naoya Kitamura, Yoko Nambu, and T. Endo: "Preparation of a Polymeric Membrane Crosslinked by the Viologen Structure from a Cyanopyridinium Salt Polymer" J. Polym. Sci., Polym. Chem. Ed., 26(4), 992-1001 (1988).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Toshihiko Sato, Yoko Nambu, and Takeshi Endo: "Preparation of Cellulose Derivatives Containing the Viologen Moiety" J. Polym. Sci., Polym. Lett. Ed., 26(8), 341-345 (1988).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Yoko Nambu and Takeshi Endo: "Synthesis and Application of Polymers Bearing Electron Transfer Functions: Development for Electron Transport Membrane" Hyoumen, 26(9), 630-640 (1988).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Takeshi Endo: "Design of New Electron Transfer Systems and their Application for Organic Synthesis" Shokubai, 30(3), 255-261 (1988).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Takeshi Endo and Toshikazu Takata: "Syntheses of Multifunctionalized Polymers" Kobunshi, 37(9), 662-665 (1988).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kazunori Ishikawa, Yoko Nambu, and Takeshi Endo: "Electron Transport Membrane: Preparation of Polypeptide Membrane with Spacers Between the Polymer Matrix and Viologen Moiety and Their Application to an Electron Transfer Reaction" J. Polym. Sci., Polym. Chem. Ed., 27(5), 1625-1629 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Toshihiko Sato, Yoko Nambu, and Takeshi Endo: "Incorporation of Viologen Moiety as Redox Function into Hydroxypropyl Cellulose" J. Polym. Sci., Polym. Lett. Ed., 28(9), 289-292 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Yoko Nambu, Kazutoshi Yamamoto, and Takeshi Endo: "First Observation of an Intramolecular Charge Transfer and Electron Relay between the Viologen and Ester Groups in a New Copolymer System" Macromolecules, 22(9), 3530-3532 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Naoya Kitamura, Yoko Nambu, and Takeshi Endo: "Synthesis and Radical Copolymerization of a New Type Pyridinium Monomer and Redox Behavior of Its Polymers" J. Polym. Sci., Polym. Chem. Ed., 28(2), 345-352 (1990).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Yoko Nambu, Yokeai Gan, Chiho Tanaka, and Takeshi Endo: "Unusual Photoreduction of Viologen by Dimethyl Sulfoxide on a New Polymer Having Direct Pendants of Viologen and Benzophenone Structures" Tetrahedron Lett., 31(6), 891-894 (1990).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Naoya Kitamura, Yoko Nambu, and Takeshi Endo: "Redox Behavior of Pyridinium Salts and Their Polymers Having Radical Stabilizing Groups" J. Polym. Sci., Polym. Chem. Ed.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Takeshi Endo, Atsushi Kameyama, Yoko Nambu, Yasuro Kashi, and Makoto Okawara: "Synthesis of Polyethers Containing Viologen Moiety and Their Application to Electron Transfer Catalyst" J. Polym. Sci., Polym. Chem. Ed.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kazunori Ishikawa: "Electron Transport Membrane:Preparation of Polypeptide Membrane with Spacers Between the Polymer Matrix and Viologen Moiety and Their Applycation to an Electron Transrer Reaction" J.Polym.Sci.,Polym.Chem.Ed.27. 1625-1629 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Toshihiko Sato: "Incorporation of Viologen Moiety as Redox Function into Hydroxypropyl Cellulose" J.Polym.Sci.,Polym.Lett.Ed.28. 289-292 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Yoko Nambu: "First Observation of an Intramolecular Charge Transfer and Electron Relay between the Viologen and Ester Groups in a New Copolymer System" Macromolecules. 22. 3530-3532 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Yoko Nambu: "Unusual Photoreduction of Viologen by Dimethl Sufoxide on a New Polymer Having Direct Pendants of Viologen and Benzophenone" Tetrahedron Lett.31. 891-894 (1990)

    • Related Report
      1989 Annual Research Report
  • [Publications] Naoya Kitamura: "Synthesis and Radical Copolymerization of a New Type Pyridinium Monomer and Redox Behavior of Its Polymers" J.Polym.Sci.,Polym.Chem.Ed.

    • Related Report
      1989 Annual Research Report
  • [Publications] Naoya Kitamura: "Redox Behvior of Pyridinium Salts and Their Polymers Having Radical Stabilizing Groups" J.Polym.Sci.,Poly.Chem.Ed.

    • Related Report
      1989 Annual Research Report
  • [Publications] Naoya Kitamura: J.Polym.Sci.Polym.Chem.Ed.26. 993-1001 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Toshihiko.Sato: J.Polym.Sci.Polym.Lett.Ed.26. 341-345 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Toshihiko Sato: J.Appl.Polym.Sci.Cell.Symp.

    • Related Report
      1988 Annual Research Report
  • [Publications] Tohihiko Sato: J.Polym.Sci.Polym.Chem.Ed.

    • Related Report
      1988 Annual Research Report
  • [Publications] Kazunori Ishikawa: J.Polym.Sci.Polym.Chem.Ed.

    • Related Report
      1988 Annual Research Report

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Published: 1988-04-01   Modified: 2016-04-21  

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