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Study of Synthesis and Physical Properties of New Electron Donor Compounds Incorporating Ferrocene Moiety as New Conductors

Research Project

Project/Area Number 12650844
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionYamagata University

Principal Investigator

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

Co-Investigator(Kenkyū-buntansha) KIJIMA Taturou  Yamagata University, Chemistry and Chemical Engineering, Assisstant, 工学部, 助手 (50272084)
Project Period (FY) 2000 – 2001
Project Status Completed (Fiscal Year 2001)
Budget Amount *help
¥3,800,000 (Direct Cost: ¥3,800,000)
Fiscal Year 2001: ¥1,200,000 (Direct Cost: ¥1,200,000)
Fiscal Year 2000: ¥2,600,000 (Direct Cost: ¥2,600,000)
KeywordsFerrocene ring / Anthraquinone / Organic onducting materials / tetrathiafulvalene(TTF) compound / UV-Vis Spectra / Cyclic Voltammetry(CV) spectra / Oxidation reduction potentials / 有機導電性化合物 / TCNQ構造
Research Abstract

The search for new electro active materials is nowadays very active field of research topic for chemists. Recently, the synthesis of new π-extended donors has become a great area of interest for many chemists. A number of π-extended conjugated tetrathiafulvalen (TTF) analogues separated by a conjugated spacer incorporating ferrocene moiety were successively synthesized as new π-donors and their structure and physical properties were characterized both by experimental techniques and spectral analysis. UV-Vis spectra and cyclic voltammetry of the π-extended ferrocenyl donor were studied in comparison with ferrocene, and ferrocenylquinone. A three-electron redox behavior was observed as a single wave. The absorption spectrum showed a slight red-shift and slight increase in the intensity.
On the other hand, a simple route for synthesis of new tetrathiafulvalene dimethyl ester (TTF-DME) is reported. The tetrathifulvalene dimethylester TTF-DME has been prepared by introducing an ester coordination function as a bifunctional new donor. The redox behavior of the TTF-DME was investigated in comparison to the well-known DB-TTF by cyclic voltammetry. A two-electron redox behavior was observed as a two waves.
Moreover, the synthesis of ferrocenylketone compounds and conducted to be a starting for the Wittig-Horner reaction is the aim of our topic. The ferrocenylketones have been synthesized via described methods, and allowed to react with l,3-benzodithiole-2-phosphonate ester in the presence of n-BuLi at - 78℃ in dry THF to afford the corresponding ferrocene-dithiafulvalenes (Fc-DTF's) and ferrocene-tetrathiafulvalene (Fc-TTF). Electrochemical properties of the new donor compounds were studied using UV-Vis spectra and cyclic voltamogram spectrophotometer (CV). Cyclic voltammetry (CV) and absorption spectra of the new compounds were studied in comparison with ferrocene and dibenzo-tetrathiafulvalene. A two-electron and three-electron redox behavior was observed as a two waves.

Report

(3 results)
  • 2001 Annual Research Report   Final Research Report Summary
  • 2000 Annual Research Report
  • Research Products

    (7 results)

All Other

All Publications (7 results)

  • [Publications] Abd El-Wareth Sarhan, Taeko Izumi: "An efficient synthesis of 2-(3-methylbutoxy)-1, 3-benzodithiole"J.Chem.Research (S). 11-12 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Abd El-Wareth A.O.Sarhan, Makoto Murakami, Taeko Izumi: "Synthesis of new Functionalized Compounds Related to π-Extended Tetrathiafulvalenes with Quinonoidal Structures Bearing a Ferrocene moiety"Monatshefte for Chemie. (in press).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Abd El-Wareth A.O.Sarhan, Makoto Murakami, Taeko Izumi: "Synthesis and Electrochemical Studies of tetrathiafulvalene Derivatives (TTF's) as Redox Active Ligands"Journal of Heterocyclic Chemistry. (in press).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Abd EL-Wareth Sarhan and Taeko Izumi: "An Efficient synthesis of 2-(3-methylbutoxy)-1, 3-benzodithiole"J. Chem, Research. (S). 11-12 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Abd El-Wareth A. O. Sarhan, Makoto Murakami, and Taeko Izumi: "Synthesis of new functionalized compounds related to π-extened tetrathiafulvalenes with quinonoidal structures bearing a ferrocene moiety"Monatsshefte fur Chemie. (in Press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Abd El-Wareth A. O. sarhan, Makoto Murakami, and Taeko Izumi: "Synthesis and electrochemical studies of tetrathiafulvalene derivatives(TTF's) as redox active ligands"Journal of Heterocyclic Chemistry. (in Press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Abd El-wareth sarhan, Taeko Izumi: "An efficient synthesis of 2-(3-methylbutoxy)-1,3-benzodithiole"J.Chem.Research(S).. 11-12 (2002)

    • Related Report
      2001 Annual Research Report

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Published: 2000-04-01   Modified: 2016-04-21  

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