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Synthesis and Application of New Conductive Compounds Bearing Ferrocene and S-Heterocycles.

Research Project

Project/Area Number 15550158
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Functional materials/Devices
Research InstitutionYAMAGATA UNIVERSITY

Principal Investigator

IZUMI Taeko  Yamagata University, Department of Chemistry and Chemical Engineering, Professor, 工学部, 教授 (10007031)

Co-Investigator(Kenkyū-buntansha) KIJIMA Taturou  Yamagata University, Department of Chemistry and Chemical Engineering, Assistant, 工学部, 助手 (50272084)
Project Period (FY) 2003 – 2004
Project Status Completed (Fiscal Year 2004)
Budget Amount *help
¥3,200,000 (Direct Cost: ¥3,200,000)
Fiscal Year 2004: ¥1,200,000 (Direct Cost: ¥1,200,000)
Fiscal Year 2003: ¥2,000,000 (Direct Cost: ¥2,000,000)
KeywordsFerrocene ring / Tetrathiafulvalene(TTF) / organic conductors / Thiophane ring / Electron donors / Charge-transfer(CT) complex
Research Abstract

Two themes were investigated, (1)synthesis of new donor compounds which have tetrathiafulvalenes (TTFs) bearing ferrocene ring derived to conducting charge transfer (CT) complex ; (2)synthesis of thiophene oligomers bearing ferrocene ring.
(1): As an example, 2-dimethoxy-phosphinyl-1,3-benzodithiole was prepared from anthranilic acid, then treatment of this phosphonate ester with ferrocenyl ketones (or phenyl keton as comparison) using the Wittig-Horner method in the presence of n-BuLi at-78 to 〜0℃ in dry THE afforded the donor compounds. New donor compounds which have ferrocene-TTFs bearing methyl, phenyl, hetero ring were synthesized by this way. The CT complexes were obtained from the reaction of the donor compounds with the well-known organic acceptor TCNQ or TCNQF_4 in CH_2Cl_2 at reflux temperature. The electrical conductivity measurement showed a substantial conductivity (σ = 0.26 S cm^<-1> ) when the case of 1,1'-disubstituted Ferrocene-TTFs-TCNQ compound.
(2)3-Substituted thiophene derivatives which bind to ferrocene ring by triple or double bond were synthesized using palladium catalytic reaction. The cuppling reaction of 2-bromothiophene and thiophane was carried out using palladium catalyst. Oligomer compounds were obtained, but separation were not succeeded. Electrochemical properties were also examined for these compounds.

Report

(3 results)
  • 2004 Annual Research Report   Final Research Report Summary
  • 2003 Annual Research Report
  • Research Products

    (12 results)

All 2004 2003 Other

All Journal Article (10 results) Publications (2 results)

  • [Journal Article] Synthesis and redox behavior of Novel benzo-1,3-dithiafulvalene Incorporating Ferrocene2004

    • Author(s)
      A.A.O.Sarhan
    • Journal Title

      Synthetic Metals 140(1)

      Pages: 95-100

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthesis and Redox Behavior of Novel Benzo-1,3-dithiafulvalenes Incorporating Ferrocene.2004

    • Author(s)
      A.A.O.Sarhan et al.
    • Journal Title

      Synthetic Metals 140(1)

      Pages: 95-100

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthesis and Electrochemical Properties of 1,1'-Bis(benzo-1,3-dithiol-2-yliden)ferrocene Derivatives as Novel Electron Donor Compounds2003

    • Author(s)
      A.Sarhan
    • Journal Title

      Journal of Organometallic Chemistry 682

      Pages: 49-58

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Design and Synthesis of new Functional Compounds Related to Ferrocene bearing heterocyclic Moieties2003

    • Author(s)
      A.A.O.Sarhan
    • Journal Title

      Journal of Organometallic Chemistry 675

      Pages: 1-12

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthesis and Electrochemical Studies of Ferrocene-Dithiafulvalenes(Fc-DTF) and 1,1'-Bis(dithiafulvalenyl) ferrocene(DTF-Fc-DTF). An Approach Towards new Conducting Organic Materials2003

    • Author(s)
      A.Sarhan
    • Journal Title

      Tetrahedron 59(33)

      Pages: 6353-6362

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthesis and Electrochemical Properties of 1,1'-Bi(benzo-1,3-dithiol-2-dithiol-2-yliden) ferrocene Derivative as Novel Electron Donor Compounds.2003

    • Author(s)
      A.Sarhan et al.
    • Journal Title

      Journal of Organometallic Chemistry 682

      Pages: 49-58

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Design and Synthesis of New Functional Compounds Related to Ferrocene Bearing Heterocyclic Moieties.2003

    • Author(s)
      A.A.O.Sarhan et al.
    • Journal Title

      Journal of Organometallic Chemistry 675

      Pages: 1-12

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthesis and Electrochemical Studies of Ferrocene-Dithiafulvalenes (Fc-DTF) and 1,1'-Bis(dithiafulvalenyl)ferrocene(DTF-Fc-DTF). An Approach Towards New Conducting Organic Materials.2003

    • Author(s)
      A.Sarhan et al.
    • Journal Title

      Tetrahedron 59(33)

      Pages: 6353-6362

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthesis and the Charge transfer Complexes of π-Extended Benzo-1,3-dithiafulvalenes Incorporating benzene ring

    • Author(s)
      T.Izumi
    • Journal Title

      Synthetic Metals (in Press)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthesis and the Charge Transfer Complexes of π-Extended Benzo-1,3-dithiafulvalenes Incorporating Benzene Ring.

    • Author(s)
      T.Izumi et al.
    • Journal Title

      (in Press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Publications] A.A.O.Sarhan, T.Izumi: "Design and synthesis of new functional compounds related to ferrocene bearing heterocyclic moieties"Journal of Organometallic Chemistry. 675. 1-12 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] A.Sarhan, T.Kijima, T.Izumi: "Synthesis and electrochemical properties of 1,1'-bis(benzo-1, 3-dithiol-2-yliden)ferrocene derivatives as novel electron donor compounds"Journal of Organometallic Chemistry. 682. 49-58 (2003)

    • Related Report
      2003 Annual Research Report

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Published: 2003-04-01   Modified: 2016-04-21  

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