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Synthetic Studies on Organic Electric Conductors Containing Heteroatoms

Research Project

Project/Area Number 05453058
Research Category

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

Allocation TypeSingle-year Grants
Research Field 機能・物性・材料
Research InstitutionHIROSHIMA UNIVERSITY

Principal Investigator

OGURA Fumio  Hiroshima University, Facuty of Enngineering, Professor, 工学部, 教授 (90028150)

Co-Investigator(Kenkyū-buntansha) ASO Yoshio  Hiroshima University, Facuty of Enngineering, Associate Professor, 工学部, 助教授 (60151065)
OTSUBO Tetsuo  Hiroshima University, Facuty of Enngineering, Professor, 工学部, 教授 (80029884)
Project Period (FY) 1993 – 1994
Project Status Completed (Fiscal Year 1994)
Budget Amount *help
¥7,400,000 (Direct Cost: ¥7,400,000)
Fiscal Year 1994: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1993: ¥6,400,000 (Direct Cost: ¥6,400,000)
Keywordsorganic electric conductor / organic electron donor / organic electron acceptor / organic charge-transfer complex / heteroarene / dumbbell type TTF donor / hetero-TCNQ / anthracene-TCNQ
Research Abstract

Novel heteroarenes, naphtho [1,8-bc : 5,4-b'c'] -and Naphtho[1,8-bc : 4,5-b'c'] -dithiophenes (anti-and syn-NDT), isoelectronic with pyrene, were synthesized as new electron donors. Electron donating CT complexes with iodine and DDQ.2,3,6,7-Tetrathiabenzo [1,3-cd : 4,6-c'd'] dipentalene (TBD) was synthesized as a novel electron donor isoelectronic with perylene.TBD has about the same donor ability and formed a relativaly high conductive iodine complex. Various substitution derivatives of 2- (thiopyran-4'-ylidene) -1,3-dithiole and selenium analogues were syuthesized as novel electron donors.
Systematic studies on them afforded many highly conductive CT complexes. Pyranylidenemethy1-and thiopyranylidenemethy1-substituted furans, thiophenes, and N-methy1pyrroles were synthesized as precursors of organic metals. Both of the N-methy1pyrroles afforded highly conductive CT complexes with TCNQ.High conductivities of radical cation salts of anthra [1,9-cd : 4,10-c'd'] bis [1,2] dichacogenoles w … More ere studied with their solid structures.2,2'-Bi-and 2,2'5'2"-ter-tellurophenes were prepared as potential components of organic metals. Novel dimeric TTF donors linked with conjugative pi electron spacer were synthesized and their properties were studied. The (E) -ethenylene derivative formed high ly conducting CT complexes with TCNQF_4 and DDQ.2,7-Bis (dicyanomethylene) -2,7-dihydrobenzo- [2,1-b : 3,4-b'] dithiophene and - [1,2-b : 4,3-b'] dithiophene and 2,6-bis (dicyanomethylene) -2,6-dihydrobenzo- [1,2-b : 4,5-b'] dithiophene were synthesized as novel electron acceptors bearing a heteroquinoid system.
They behave as good electron acceptors comparable to TCNQ and have a small on-site Coulomb energy in their dianion states. 11,11,12,12-Tetracyano-2,6-anthraquinodimethane (TANT) and its 9,10-derivative s were synthesized. All of them are superior electron acceptors with small on-site Coulomb repulsion in the dianion states. The above acceptors afforded many highly conducting CT complexes with typical electron donors. Less

Report

(3 results)
  • 1994 Annual Research Report   Final Research Report Summary
  • 1993 Annual Research Report
  • Research Products

    (45 results)

All Other

All Publications (45 results)

  • [Publications] Kazuo TAKIMIYA: "Facile Preparation and Charge-Transfer Complexes of Naphtho[1,8-bc:4,5-b'c']dithiophene and 2,5-Dimethyl and Bis(methylthio)Derivatives." Chem.Lett.No.2. 365-368 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masanori FUJII: "2,6-Bis(decyanomethylene)-2,6-dihydrobenzo[1,2-b:4,5-b']dithiophene as a Novel Electron Acceptors." Synth.Metals. 56/1. 1910-1913 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masanori FUJII: "Synthesis and Properties of Ethanediylidene-2.2'-bis(5-dicyanomethylene)and Its Dibromo Derivatives as New Extensively Conjugated Electron Acceptors." Synth.Metals. 56/1. 2136-2139 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Tetsuya YANAGIMOTO: "11,11,12,12-Tetracyano-2,6-anthraquinodimethane(TANT)as a Novel Extensive Electron Acceptor." J.Chem.Soc.,Chem.Commun.,. No.6. 519-520 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Tetsuo OTSUBO: "Syntheses,Structure,and Properties of 2,3,6,7-Tetrathiabenzo[1,3-cd:4,6-c'd']dipentalene and Its Methyl,Ethyl,Methylthio,and Ethylthio Derivatives:Novel Fused Polynuclear Heteroarenes." Bull.Chem.Soc.Jpn.66. 2033-2041 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Tetsuo OTSUBO: "Synthese and Properties of Various Substitution Derivatives of 2-(Thiopyran-4'-ylidene)-1,3-dithiole and Selenium Analogues as Novel Electron Donors." J.Chem.Soc.,Perkin Trans.2. No.12. 1815-1824 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Kazuo TAKIMIYA: "Pyranylidenemethyl-and Thiopyranylidenemethyl-substituted Furans,Thiophene,and N-Methylpyrroles as Precursor of Organic Metals and Third-order Nonlinear Optical Materials." Chem.Lett.No.2. 255-258 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Kazuo TAKIMIYA: "Highly Conductive Radical Cation Salts of Anthra[1,9-cd:4,10-c'd']-bids[1,2]di-Chalcogenoles." Bull.Chem.Soc.Jpn.67. 766-772 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Shu YOSHIDA: "Novel Electron Acceptors Bearing a Heteroquinonoid System.4.Syntheses,Properties,and Charge-Transfer Complexes of 2,7-Bis-(dicyanomethylene)-2,7-dihydrobenzo[2,1-b:3,4-b']dithiophene,2,7-Bis(dicyanomethylene)-2,7-dihhydro-." J.Org.Chem.59. 3077-3081 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Kazuo TAKIMIYA: "Naphtho[1,8-bc:5,4-b'c']dithiophene:A New Heteroarene Isoelectronic with Pyrene." J.Chem.Soc.,Chem.Commun.No.16. 1859-1860 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Shinobu INOUE: "2,2'-Bitellurophene and 2,2':5'2'-Tertellurophene as Novel High Homologues of Tellurophene" Tetrahedron Lett.35. 8009-8012 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Tetsuo OTSUBO: "Syntheses and Properties of Novel Dimeric Tetrathiafulvalene Electron Donors Linked with an Ethenylene or Ethynylene Spacer:" Chem.Lett.No.11. 2047-2050 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Tetsuo OTSUBO: "Synthesis,Structure,and Polymerization of 2,2'-Bitellurophene." Synth.Metals. (in press.).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Atushi BITHO: "Synthese and Properties of 2,5-Bis[2-(tetrathiafulvalen-2-yl)ethenyl]-thiophene and Related Compounds as Novel Dumbbell-type Electron Donors." Synth.Metals. (in press.).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Kazuo TAKIMIYA: "Facile Preparation and Charge-Transfer Complexes of Naphtho [1,8-bc : 4,5-b'c'] dithiophene and 2,5-Dimethyl and Bis (methylthio) Derivatives." Chem.Lett.No.2. 365-368 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masanori FUJII: "2,6-Bis (dicyanomethylene) -2,6-dihydrobenzo [1,2-b : 4,5-b'] dithiophene as a Novel Electron Acceptors." Synth.Metals. 56/1. 1910-1913 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Masanori FUJII: "Synthesis and Properties of Ethanediylidene-2,2'-bis (5-dicyanomethylene) and Its Dibromo Derivatives as New Extensively Conjugated Electron Acceptors." Synth.Metals. 56/1. 2136-2139 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Tetsuya YANAGIMOTO: "11,11,12,12-Tetracyano-2,6-anthraquinodimethane (TANT) as a Novel Extensive Electron Acceptor." J.Chem.Soc.Chem.Commun.No.6. 519-520 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Tetsuo OTSUBO: "Syntheses, Structure, and Properties of 2,3,6,7-Tetrarthiabenzo [1,3-cd : 4,6-c'd'] dipentalene and Its Methyl, Ethyl, Methylthio, and Ethylthio Derivatives : Novel Fused Polynuclear Heteroarenes." Bull.Chem.Soc.Jpn. 66. 2033-2041 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Tetsuo OTSUBO: "Synthese and Properties of Various Substitution Derivatives of 2- (Thiopyran-4'-ylidene) -1,3-dithiole and Selenium Analogues as Novel Electron Donors." J.Chem.Soc., Perkin Trans. 2, No.12. 1815-1824 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Kazuo TAKIMIYA: "Pyranylidenemethyl-and Thiopyranylidenemethyl-substituted Furans, Thiophene, and N-Methylpyrroles as Precursor of Organic Metals and Third-order Nonlinear Optical Materials." Chem.Lett.No.2. 255-258 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Kazuo TAKIMIYA: "Highly Conductive Redical Cation Salts of Anthra [1,9-cd : 4,10-c'd'] bids [1,2] dichalcogenoles." Bull.Chem.Soc.Jpn. 67. 766-772 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Shu YOSHIDA: "Novel Electron Acceptors Bearing a Heteroquinonoid System.4. Syntheses, Properties, and Charge-Transfer Complexes of 2,7-Bis (dicyanomethylene) -2,7-di-hydrobenzo [2,1-b : 3,4-b'] dithiophene, 2,7-Bis (dicyanomethylene) -2,7-dihydrobenzo [1,2-b : 4,3-b'] dithiophene and 2,6-Bis (dicynomethylene) -2,6-dihydrobenzo [1,2-b : 4,5-b'] dithiophene." J.Org.Chem. 59. 3077-3081 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Kazuo TAKIMIYA: "Naphtho[1,8-bc : 5,4-b'c'] dithiophene : A New Heteroarene Isoelectronic with Pyrene." J.Chem.Soc., Chem.Commun. No.16. 1859-1860 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Shinobu INOUE: "2,2'-Bitellurophene and 2,2' : 5', 2"-Tertellurophene as Novel High Homologues of Tellurophene." Tetrahedron Lett. 35. 8009-8012 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Tetsuo OTSUBO: "Syntheses and Properties of Novel Dimeric Tetrathiafulvalene Electron Donors Linked with an Ethenylene or Ethynylene Spacer." Chem.Lett.No.11. 2047-2050 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Tetsuo OTSUBO: "Synthesis, Structure, and Polymerization of 2,2'-Bitellurophene." Synth.Metals. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Atsushi BITHO: "Synthese and Properties of 2,5-Bis [2- (tetrathiafulvalen-2-yl) - ethenyl] thiophene and Related Compounds as Novel Dumbbell-type Electron Donors." Synth.Metals. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Kazuo TAKIMIYA: "Pyranylidenemethyl- and Thiopyranylidenemethyl-substituted Furans,Thiophene,and N-Methylpyrroles as Precursor of Organic Metals and Third-order Nonlinear Optical Materials." Chem.Lett.No.2. 225-258 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Kazuo TAKIMIYA: "Highly Conductive Radical Cation Salts of Anthra[1,9-cd:4,10-c'd']bids[1,2]di- Chalcogenoles." Bull.Chem.Soc.Jpn.67. 766-772 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Shu YOSHIDA: "Novel Electron Acceptors Bearing a Heteroquinonoid System.4.Syntheses,Properties,and Charge-Transfer Complexes of 2,7-Bis(dicyanomethylene)-2,7-di-hydrobenzo[2,1-b:3,4-b']dithiophene,2,7-Bis(dicyanomethylene)-2,7-dihhydro-----." J.Org.Chem.59. 3077-3081 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Kazuo TAKIMIYA: "Naphtho[1,8-bc:5,4-b'c']dithiophene: A New Heteroarene Isoelectronic with Pyrene." J.Chem.Soc.,Chem.Commun.No.16. 1859-1860 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Shinobu INOUE: "2,2'-Bitellurophene and 2,2':5',2'-Tertellurophene as Novel High Homologues of Tellurophene" Tetrahedron Lett.35. 8009-8012 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Tetsuo OTSUBO: "Syntheses and Properties of Novel Dimeric Tetrathiafulvalene Electron Donors Linked with an Ethenylene or Ethynylene Spacer:" Chem.Lett.No.11. 2047-2050 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Tetsuo OTSUBO: "Synthesis,Structure,and Polymerization of 2,2'-Bitelluraphene." Synth.Metals.(in press).

    • Related Report
      1994 Annual Research Report
  • [Publications] Atsushi BITHO: "Synthese and Properties of 2,5-Bis[2-(tetrathiafulvalen-2-yl)ethenyl]thiophene and Related Compounds as Novel Dumbbell-type Electron Donors." Synth.Metals.(in press).

    • Related Report
      1994 Annual Research Report
  • [Publications] M.Fujii: "2,6-Bis(dicyanomethylene)-2,6-dihydrobenzo[1,2-b:4,5-b']dithiophene as a Novel Electron Acceptor." Synthetic Metals. 56/1. 1910-1913 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] M.Fujii: "Synthesis and Properties of Ethanediylidene-2,2'-Bis(5-dicyanomethylene) and Its Dibromo Derivatives as New Extensively Conjugated Electron Acceptors." Synthetic Metals. 56/1. 2136-2139 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] K.Takimiya: "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. 2. 365-368 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] T.Yanagimoto: "11,11,12,12-Tetracyano-2,6-anthraquinodimethane (TANT) as a Novel Extensive Electron Acceptor." J.Chem.Soc.,Chem.Commun.6. 519-520 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] T.Otsubo: "Syntheses,Structure,and Properties of 2,3,6,7-Tetrathiabenzo[1,3-c,d:4,6-c',d']dipentalene and Its Methyl,Ethyl,Methylthio Derivatives:Novel Fused Polynuclear Heteroarenes." Bull.Chem.Soc.Jpn.66(7). 2033-2041 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] T.Otsubo: "Syntheses and Properties of Various Substitution Dervatives of 2-(Thiopyrn-4'-ylidene)-1,3-dithiole and Selenium Analogues as Novel Unsymmetrical Electron Donors." J.Chem.Soc.,Perkin Trans.2.2. 1815-1824 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] F.Ogura: "Design and Synthesis of Novel Chalcogen-Containg Organic Metals." Pure and Applied Chemistry. 65(4). 683-690 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] K.Takimiya: "Pyranylidenemethyl- and Thiopyranylidenemethyl-substituted Furans,Thiophenes and N-Methylpyrroles as Precursor of Organic Metals and Third-order Nolinear Optical Materials." Chemistry Letters. No.2. 255-258 (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] K.Takimiya: "Highly Conductive Radical Cation Salts of Anthra[1,9-cd:4,10-c'd']bis[1,2]-dichalcogenoles." Bull.Chem.Soc.Jpn.(in press).

    • Related Report
      1993 Annual Research Report

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Published: 1993-04-01   Modified: 2016-04-21  

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