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Syntheses of Organic Conductive Compounds

Research Project

Project/Area Number 03650704
Research Category

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

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionHIROSHIMA UNIVERSITY

Principal Investigator

OTSUBO Tetsuo  Hiroshima Univ. Fac. of Eng. Prof., 工学部, 教授 (80029884)

Co-Investigator(Kenkyū-buntansha) ASO Yoshio  Hiroshima Univ. Fac. of Eng. Assit., 工学部, 助手 (60151065)
OGURA Fumio  Hiroshima Univ. Fac. of Eng. Prof., 工学部, 教授 (90028150)
Project Period (FY) 1991 – 1992
Project Status Completed (Fiscal Year 1992)
Budget Amount *help
¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 1992: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1991: ¥1,100,000 (Direct Cost: ¥1,100,000)
KeywordsOrganic Conductor / Complex Charge-transfer / Electron Donor / Electron Acceptor / Heteroatom / Chalcogen Atom
Research Abstract

As part of our interest to develop organic metals, we have designed two novel types of chalcogen-containing compounds, i.e., (1) peri-dichalcogen arenes and (2) fused heteroarenes. (1) Peri-dichalcogen bridged arenes represented by tetrathiotetracene are a prototype of superior electron donors. We have been interested in 1,9- and 4,10-bridged anthracenes and 1,10- and 8,10-bridged phenanthrenes. They could be improved by modifications with methyl and methylthio substitutions, readily forming a variety of conductive charge-transfer complexes with typical electron acceptors such as TCNQ, DMTCNQ, and TNAP. (2) Perylene and pyrene are typical hydrocarbons forming conductive halogen complexes. We have been interested in two novel sulfur-containing heteroarenes isoelectronic with perylene and pyrene in the neutral or oxidation state. Their structures were elucidated by an X-ray analysis to have quite planar molecular geometries. They also formed highly conductive complexes with some electron acceptors.

Report

(3 results)
  • 1992 Annual Research Report   Final Research Report Summary
  • 1991 Annual Research Report
  • Research Products

    (38 results)

All Other

All Publications (38 results)

  • [Publications] H.MIYAMOTO et al.: "Dimethyl and tetramethyl derivatives of anthra[1,9-cd:11,12-c'd']bis[1,2]dichalcogenoles." Synthetic Metals. 42. 2389-2392 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] H.ISHIDA et al.: "2,5-Bis(dicyanomethylene)-2,5-dihydrofuran and its conjugated homologues as novel oxygen-containing electron acceptors" Synthetic Metals. 41. 811-814 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K.TAKIMIYA et al.: "Syntheses and properties of dimethyl and tetramethyl anthral[1,9-cd:4,10-c'd']bis[1,2]-dichalcogenoles and their charge-transfer complexes." Bulletin of the Chemical Society of Japan. 64. 2091-2102 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] F.OGURA et al.: "Design of novel chalcogen-containing organic metals: extensively conjugated electron donors and acceptors with reduced on-site coulomb repulsion." Sulfur Reports. 11. 439-464 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K.TAKIMIYA et al.: "Phenanthro[1,10-cd:8,9-c'd']bis[1,2]-dithiole and -diselenole as novel electron donors." Journal of the Chemical Society,Chemical Communications. 278-280 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K.WATANABE et al.: "Synthesis and properties of naphtho[1,8-bc:4,5-b'c']dithiophene as a novel heterocyclic electron donor." Chemisty Letters. 1233-1236 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K.TAKIMIYA et al.: "Synthesis,molecular structure,and properties of 1,9-dithia[2.2]metacyclophane." Chemistry Express. 7. 865-868 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K.TAKIMIYA et al.: "Fecile preparation and charge-transfer complexes of naphtho[1,8-bc:4,5-b'c']dithiophene and 2,5-dimethyl and bis(methylthio) derivatives." Chemistry Letters. 365-368 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T.OTSUBO et al.: "Syntheses,structure,and properties of 2,3,6,7-tetrathiabenzo[1,3-cd:4,6-c'd']dipentalene and its methyl,ethyl,methylthio derivatives:novel fused polynuclear heteroarenes." Bulletin of the Chemical Society of Japan. 65. (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M.FUJII et al.: "2,6-Bis(dicyanomethylene)-2,6-dihydrobenzo-[1,2-b:4,5-b']dithiophene as a novel electron acceptor." Synthetic Metals. IN PRESS (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M.FUJII et al.: "Syntheses and properties of ethanediylidene-2,2'-(5-dicyanomethylene-3-thiolene) and its dibromo derivatives as new extensively conjugated electron acceptors." Synthetic Metals. (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T.YANAGIMOTO et al.: "11,11,12,12-Tetracyano-2,6-anthraquinodimethane(TANT) as a novel extensive electron acceptor." Journal of the Chemical Society,Chemical Communications. (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] H. Miyamoto et al.: "Dimethyl and tetramethyl derivatives of anthra-[1,9-cd:11,12-c'd']bis[1,2]di-chalcogenoles." Synth. Metals. Vol.42. 2389-2392 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] H. Ishida et al.: "2,5-Bis(dicyano-methylene)-2,5-dihydrofuran and its conjugated homologues as novel oxygen-containing electron acceptors." Symth. Metals. Vol.41. 811-814 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K. Takimiya et al.: "Syntheses and properties of dimethyl and tetramethyl anthra[1,9-cd:4,10-c'd']bis[1,2]di-chalcogenoles and their charge-transfer complexes." Bull. Chem. Soc. Jpn. Vol.64. 2091-2102 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] F. Ogura et al.: "Design of novel Chalcogen-containing organic metals: extensively conjugated electron donors and acceptors with reduced on-site coulomb repulsion." Sulfur Reports. Vol.11. 439-464 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K. Takimiya et al.: "Phenanthro[1,10-cd:8,9-c'd']bis[1,2]-dithiole and -diselenole as novel electron donors." J. Chem. Soc., Chem. Commun. 278-280 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K. Watanabe et al.: "Synthesis and properties of naphtho[1,8-bc:4,5-b'c']dithiophene as a novel heterocyclic electron donor." Chem. Lett.1233-1236 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K. Takimiya et al.: "Synthesis, molecular structure, and properties of 1,9- dithia[2.2]metacyclophane." Chem. Express. Vol.7. 865-868 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K. Takimiya et al.: "Facile preparation and charge-transfer complexes of naphtho[1,8-bc:4,5-b'c']dithiophenes and 2,5-dimethyl and bis(methylthio) derivatives." Chem. Lett.365-368 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T. Otsubo et al.: "Syntheses, structure, and properties of 2,3,6,7-tetrathia-benzo[1,3-cd:4,6-c'd']dipentalene and its methyl, ethyl, methylthio derivatives: novel fused polynuclear heteroarenes." Bull. Chem. Soc. Jpn.Vol.65. (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M. Fujii et al.: "2,6-Bis(dicyano-methylene)-2,6-dihydrobenzo[1,2-b:4,5-b']dithiophene as a novel electron acceptor." Synth. Metals. (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M. Fujii et al.: "Syntheses and properties of ethanediylidene-2,2'-(5-dicyanomethylene-3-thiolene) and its dibromo derivatives as new extensively conjugated electron acceptors." Synth. Metals. (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T. Yanagimoto et al.: "11,11,12,12-Tetracyano-2,6-anthraquinodimethane (TANT) as a novel extensive electron acceptor." J. Chem. Soc., Chem. Commun. (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] F. Ogura et al.: "Design of novel chalcogen-containing organic Metals: extensively conjugated electron donors and acceptors with reduced on-site coulomb repulsion." Sulfur Reports. 11. 439-464 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] K. Takimiya et al.: "Phenanthro[1,10-cd:8,9-C‘d']bis[1,2]-dithiole and -diselenole as novel electron donors." Journal of chemical Society, chemical Communications. 278-280 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] K. Watanabe et al.: "Synthesis and properties of naphtho[1,8-bc:4,5- b‘c']dithiophene as a novel heterocyclic electron donor." Chemistry Letters. 1233-1236 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] K. Takimiya et al.: "Synthesis,molecular structure, and properties of 1,9-dithia[2.2]metacyclophane." Chemistry Express. 7. 865-868 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] K. Takimiya et al.: "Facile preparation and charge-transfer complexes of naphtho[1,8-bc:4,5-b‘c']dithiophene and 2,5-dimethyl and bis(methylthio) derivatives." Chemistry Letters. 365-368 (1993)

    • Related Report
      1992 Annual Research Report
  • [Publications] T. Otsubo et al.: "Syntheses,structure, and properties of 2,3,6,7- tetrathiabenzo[1,3-cd:4,6-c‘d']depentalene and its methyl, ethyl, methylthio derivatives: novel fused polynuclear heteroarenes." Bulletin of the chemical society of Japan. 64. (1993)

    • Related Report
      1992 Annual Research Report
  • [Publications] M Fujii et al.: "2,6-Bis(dicyanomethelene)-2,6-dihydrobenzo- [1,2-b:4,5-b']dithiophene as a novel electron acceptor." Synthetic Metals. (1993)

    • Related Report
      1992 Annual Research Report
  • [Publications] M Fujii et al.: "Syntheses and properties of ethanediylidene- 2,2'-(5-dicyanomethylene-3-thiolene) and its dibromo derivatives as new extensively conjugated electron acceptors." Synthetic Metals. (1993)

    • Related Report
      1992 Annual Research Report
  • [Publications] T. Yanagimoto et al.: "11,11,12,12-Tetracyano-2,6-anthraquinodimethane (TANT) as a novel extensive electron acceptor." Journal of the Chemical Society,Chemical Communications. (1993)

    • Related Report
      1992 Annual Research Report
  • [Publications] H.Miyamoto et al.: "Dimethyl and tetramethyl derivatives of anthra[1,9ーcd:4,10ーc'd']ーand naphtaceno[5,6ーcd:11,12ーc'd']ーbis[1,2]ーdichalcogenoles" Syntheric Metals. 41ー43. 415-418 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] H.Ishida et al.: "2,5ーBis(dicyanomethylene)ー2,5ーdihydrofuran and its conjugated homologues as novel oxygenーcontaining electron acceptors" Synthetic Metals. 41ー43. 811-814 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] K.Takimiya et al.: "Syntheses and properties of dimethyl and tetramethyl anthra[1,9ーcd:4,10ーc'd']bis[1,2]dichalcogenoles and their chargeーtransfer complexes" Bull.Chem.Soc.Jpn.64. 2091-2102 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] K.Takimiya et aL.: "Phenanthro[1,10ーcd:8,9ーc'd']bis[1,2]ーdithiole andーdiselenole as novel electron donors" J.Chem.Soc.,Chem.Commun.(1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] F.Ogura et al.: "Design of novel chalcogenーcontaining organic metals:extensively conjugated electron donors and acceptors with reduced onーsite Coulomb repulsion" Sulphur Reports. (1992)

    • Related Report
      1991 Annual Research Report

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Published: 1991-04-01   Modified: 2016-04-21  

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