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Development of single-Component Organic Conductors

Research Project

Project/Area Number 03804039
Research Category

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

Allocation TypeSingle-year Grants
Research Field 有機化学一般
Research InstitutionOkazaki National Research Institutes

Principal Investigator

YAMASHITA Yoshiro  Okazaki National Inst., Inst. for Molecular Sci., Associate Professor, 分子科学研究所, 助教授 (90116872)

Co-Investigator(Kenkyū-buntansha) TANAKA Shoji  Okazaki National Inst., Inst. for Molecular Sci., Research Associate, 分子科学研究所, 助手 (20192635)
Project Period (FY) 1991 – 1992
Project Status Completed (Fiscal Year 1992)
Budget Amount *help
¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 1992: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1991: ¥1,400,000 (Direct Cost: ¥1,400,000)
KeywordsOrganic Conductor / Organic Semiconductor / Single-Component Conductor / Conducting Polymer / Molecular Crystal / Heteroatom Contact / チアジアゾール / ヘテロ環化合物 / 結晶構造 / 分子間相互作用
Research Abstract

Bis[1,2,5]thiadiazolo-p-quinobis(1,3-dithiole)(BTQBT) and its derivatives were prepared by using a Wittig-Horner reaction. The conductivity of BTQBT was good as a single component. The X-ray structural analysis reveals that the planar molecule forms a sheet-like network by short S---S contacts. The conductivities of the derivatives were poorer than that of BTQBT, indicating that the unique crystal structure of BTQBT is needed for the good conductivity. The selenadiazolo-analogues were also prepared. The conductivities were a little higher than that of BTQBT due to the stronger intermolecular interactions caused by the selenium atom.
Thieno[3,4-c][1,2,5]thiadiazole containing a hypervalent sulfur atom is a logical candidate for novel conducting polymer which would have a narrow band-gap due to the quinoid character of the thiophene ring and the S---N interactions between the polymer chains. Aromatic-quinoid copolymer systems are also promising candidates for narrow band gap materials. We have succeeded in preparing a novel conjugated copolymer containing thiophene units as an aromatic part and thieno[3,4-c][1,2,5]thiadiazole units as a quinoid part. The monomer shows a reduced HOMO-LUMO separation compared to related systems ; its lowest pi-pi^* transition is at 618 nm. The polymer was prepared by the electrochemical oxidation. The obtained polymer is easily p-doped as well as n-doped. The band gap is about 0.9 eV. This gap is about 1 eV lower than that for polythiophene.

Report

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

    (29 results)

All Other

All Publications (29 results)

  • [Publications] M.KOZAKI,S.TANAKA,Y.YAMASHITA: "Preparation and Properties of Poly-4-(1,3-dithio-2-ylidene)-4H-cyclopenta[2,1-b;3,4-b′]dithiopheve and Its Derivatives" J.Chem.Soc.,Chem.Commun.1137-1138 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.YAMASHITA,S.TANAKA,K.IMAEDA,H.INOKUCHI,M.SANO: "Preparation and Properties of Bis[1,2,5]thiadiazolo-p-quinobis-(1,3-dithiole)(BTQBT)and Its Derivatives.Novel Organic Semiconductors" J.Org.Chem.57. 5517-5522 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.TSUBATA,T.SUZUKI,T.MIYASHI,Y.YAMASHITA: "Single-Conponent Organic Condnctors Based on Neutral Radicals Containing the Pyrazino-TCNQ Skeleton" J.Org.Chem.57. 6749-6755 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.YAMASHITA,S.TANAKA: "Crystal Structures of Cation Radical Salts of a Bis(1,3-dithiole)Donor Containing a 1,2,5-Thiadiazole Unit" Chem.Lett.73-76 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M.KOZAKI,S.TANAKA,Y.YAMASHITA: "Preparation and Properties of 7-(1,3-Dithiol-2-ylidene)-7H-cyclo-penta[1,2-b;4,3-b′]dithiophenes and Their Polymers" Chem.Lett.533-536 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] S.TANAKA,Y.YAMASHITA: "Synthesis of a Narrow Band Gap Heterocyclic Polymer:Poly-4,6-di(2-thienyl)thieno[3,4-C][1,2,5]thiadiazde" Synthetic Metal. (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.Yamashita, S.Tanaka, K.Imaeda, and H.Inokuchi: "Tetrathio-Derivatives of p-Quinodimethanes Fused with 1,2,5- Thiadiazoles. A Novel Type of Organic Semiconductors" Chem. Lett.1213-1216 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.Yamashita, S.Tanaka, K.Imaeda, H.Inokuchi, and M.Sano: "5,8-Bis(1,3-dithiol-2-ylidene)-5,8-dihydroquinoxalines : Novel Electron Donors with Low Oxidation Potentials" J.Chem. Soc., Chem. Commun.1132-1133 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.Yamashita, S.Tanaka, K.Imaeda, H.Inokuchi, and M.Sano: "4,7-Bis(1,3-dithiol-2-ylidene)4,7-dihydro-2,1,3- benzothiadiazoles. A Novel Type of Electron Donors Affording Organic Metals" Chem. Lett.419-422 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T.Suzuki, H.Fujii, Y.Yamashita, C.Kabuto, S.Tanaka, M.Harasawa, T.Mukai, and T.Miyashi: "Clathrate Formation and Molecular Recognition by Novel Chalcogen-Cyano Interactions in Tetracyanoquinodimethanes Fused with Thiadiazole and Selenadiazole Rings" J.Am. Chem. Soc.114. 3034-3043 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M.Kozaki, S.Tanaka, and Y.Yamashita: "Preparation and Properties of Poly-4-(1,3-dithio-2-ylidene)-4H-cyclopenta[2,1-b ; 3,4-b']dithiophene and Its Derivatives" J.Chem. Soc., Chem. Commun.1137-1138 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.Yamashita, S.Tanaka, K.Imaeda, H.Inokuchi, and M.Sano: "Preparation and Properties of Bis[1,2,5]thiadiazolo-p- quinobis(1,3-dithiole)(BTQBT) and Its Derivatives. Novel Organic Semiconductors" J.Org. Chem.57. 5517-5522 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.Tsubata, T.Suzuki, T.Miyashi, and Y.Yamashita: "Single Component Organic Conductors Based on Neutral Radicals Containing the Pyrazino-TCNQ Skeleton" J.Org. Chem.57. 6749-6755 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.Yamashita and S.Tanaka: "Crystal Structures of Cation Radical Salts of a Bis(1,3-dithiole) Donor Containing a 1,2,5-Thiadiazole Unit" Chem. Lett.73-76 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] S.Tanaka and Y.Yamashita : Synthesis of a Narrow Band Gap Heterocyclic Polymer: "Poly-4,6-di(2-thienyl)thieno[3,4- c][1,2,5]thiadiazole" Synthetic Metal.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M.Kozaki, S.Tanaka, and Y.Yamashita: "Preparation and Properties of 7-(1,3-Dithiol-2-ylidene)-7H-cyclopenta[1,2-b : 4,3- b']dithiophenes and Their Polymers" Chem. Lett.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.Yamashita, S.Tanaka, and M.Tomura: "2,2'-(Cyclopenten-3,5- diylidene)bis(1,3-dithiole)s : Novel Electron Donors Undergoing Deprotonation by Oxidation" J.Chem. Soc., Chem. Commun.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M.Kozaki,S,Tanaka,Y.Yamashita: "Preparation and Properties of Poly-4-(1,3-dithio-2-ylidens)-4H-cyclopenta[2,1-b;3,4-b']dithiophene and Its Derivatives" J.Chem.Soc.,Chem.Commun.1137-1138 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Y.Yamashita,S.Tanaka K.Imaeda,H.Inokuchi M.Sano: "Preparation and Properties of Bis[1,2,5]thiadiazolo-p-quinobis-(1,3-dithiole)(BTQBT)and Its Derivatives. Novel Organic Semiconductors" J.Org.Chem.57. 5517-5522 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Y.Tsubata,T.Suzuki,T.Miyashi,Y.Yamashita: "Single-Component Organic Conductors Based on Neutral Radicals Containing the Pyrazino-TCNQ Skeleton" J.Org.Chem.57. 6749-6755 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Y.Yamashita,S.Tanaka: "Crystal Structures of Cation Radical Salts of a Bis(1,3-dithiolo)Ponor Containing a 1,2,5-Thiadiazole Unit" Chem.Lett.73-76 (1993)

    • Related Report
      1992 Annual Research Report
  • [Publications] M.Kozaki,S.Tanaka,Y.Yamashita: "Preparation and Properties of 7-(1,3-Dithiol-2-ylidene)-7H-Cyclopenta-[1,2-b;4,3-b']dithiophenes and Their Polymers" Chem.Lett.533-536 (1993)

    • Related Report
      1992 Annual Research Report
  • [Publications] S.Tanaka,Y.Yamashita: "Synthesis of a Narrow Band Gap Heterocyclic Polymer:Poly-4,6-di(2-thienyl)thiens[3,4-C][1,2,5]thiadiazole" Synthetic Metal. (1993)

    • Related Report
      1992 Annual Research Report
  • [Publications] Y.Yamashita;S.Tanaka,K.Inaeda;H.Inokuchi: "Tetrathio-Deriuatiues of P-Quinodimethanes fused with 1,2,5-Thiadiazoles.A Nouel Type of Organic Semiconductors" Chem.Lett.1213-1216 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Y.Yamashita;S.Tanaka;K.Imaeda;H.Inokuchi;M.Sano: "5,8-Bis(1,3-dithiol-2-ylidene)-5,8-dihydroquinoxalines:Nouel Electron Donors with Low Oxidation Potentials" J.Chem.Soc.,Chem.Commun.1132-1133 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Y.Yamashita;T.Suzuki;Y.Kobayashi;T.Mukai;T.Miyashi: "Preparation and Properties of Tetracyanoquinodimethane Radical-anion Salts with Azaazulenium and Diazaaznlenium Ions" Synth.Metals. 45. 213-220 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] K.Imaeda;Y.Yamashita;Y.Li;T.Mori;H.Inokuchi.M.sano: "Hall-effect Observation in the New Organic Semiconductor Bis(1,2,5-thiadiazolo)-P-quinobis(1,3-dithiole)(BTQBT)" J.Mater.Chem.2. 115-118 (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] Y.Yamashita;S.Tanaka;K.Imaeda;H.Imokuchi;M.Sano: "4,7-Bis(1,3-dithiol-2-ylidene)-4,7-dihydeo-2,1,3-benzothiazoles.A Novel Type of Electron Donors Affording Organic Metals" Chem.Lett.419-422 (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] Y.Yamashita;S.Tanaka;M.Tomura: "Tetrathio-Deriuatiues of P-Quinodimethanes Fusod with Selenadiazob Vnits:Novel Type of Wbctror Donors" Phosphorons,Sulfur and Silicon and the pelatad Elements. (1992)

    • Related Report
      1991 Annual Research Report

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

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