• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Development of Novel Organic Conductors Based on New Electron Donors and Acceptors

Research Project

Project/Area Number 09640655
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionOkazaki National Research Institute

Principal Investigator

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

Co-Investigator(Kenkyū-buntansha) TANAKA Shoji  Okazaki Natinal Inst., Inst.for Molecular Science, Associate Professor, 分子科学研究所, 助手 (20192635)
Project Period (FY) 1997 – 1998
Project Status Completed (Fiscal Year 1998)
Budget Amount *help
¥2,700,000 (Direct Cost: ¥2,700,000)
Fiscal Year 1998: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1997: ¥1,900,000 (Direct Cost: ¥1,900,000)
KeywordsOrganic Conductor / Electron Donor / Electron Acceptor / Electro Chemical Oxidation / Cation Radical / Oxidation Potential / X-ray crystal structure / 有機半導体 / ドナー / アクセプター
Research Abstract

Novel non-planar bis (l, 3-dithiole) donors with small on-site Coulomb repulsion have been prepared by using a Wittig reaction.They afforded unusual cation radical salts as single crystals whose properties were strikingly affected by the incorporated solvent molecules.Some salts exhibited metallic behavior down to low temperature.Novel TTF vinylogues with extended pi-conjugation have been synthesized using an oxidative dimerization reaction of 1,4-dithiafulvenes with tris(4-bromophenyl)aminium hexachloroantimonate.The derivatives with omicron-substituted phenyl groups show stepwise reversible oxidation potentials, suggesting that the cation radicals are thermodynamically stable where the aryl part is twisted and the TTF vinylogue skeleton is planar.Some compounds afforded cation radical salts upon electrochemical oxidation.X-ray analysis revealed the planar structure of the TTF vinylogue part and interesting crystal structures such as a two-dimensional columnar structure.
Novel pi-extended TCNQ analogues have also been prepared.X-ray analyses of thiophene-TCNQ and bithiophene-TCNQ derivatives revealed the interesting crystal structures where intermolecular networks are formed by short S・N contacts.Some of the new acceptors afforded charge-transfer complexes with TTF whose unique structures involving S・N contacts were also revealed by X-ray.A tetracyanodipheno-quinodimethane derivative fused with thiadiazole rings is a strong electron acceptor and afforded highly conducting materials.

Report

(3 results)
  • 1998 Annual Research Report   Final Research Report Summary
  • 1997 Annual Research Report
  • Research Products

    (31 results)

All Other

All Publications (31 results)

  • [Publications] Yoshiro Yamashita: "Novel Organic Metals Based or Nonplanar Bis(1,3-dithiolz)Donors" Synth.Metals. 84・1-3. 1795-1796 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshiro Yamashita: "Synthesis and Properties of Benzobis(thiadiazole)s with Nonclassical π-Electron Ring Systems" Tetrahedron. 53・29. 10169-10178 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshiro Yamashita: "Synthesis and Characterization on New Electron Donors Containing 1,2,5-Thiadiatore and 1,1-Dihydro-4,4-bipyridine Units" Chem.Commun.-・19. 1851-1852 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kazuharu Suzuki: "New Electron Acceptors Containing Thieno[3,4-b]pyrazine Units" J.Mater.Chem.8・5. 1117-1119 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshiro Yamashita: "Synthesis and Properties of Novel Tetrathiafulvalene Vinylogues" Chem.Commun.-・16. 1657-1658 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshiro Yamashita: "Highly Polarized Electron Donors,Acceptors,and Donor-Acceptor Compounds" J.Mater.Chem.8・9. 1933-1944 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] A.Ohta: "Preparation, Properties, and Oxidation of Novel Bis(1, 3-dithiole) Compounds Containing a Di (2-thienyl) methane Unit" Heterocycles. 44(1). 263-276 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] C.Kitamura: "Synthesis and Reactions of 3, 3'-Dibromodihydrodipyrrins" J.Chem.Soc., Perkin Trans.1(10). 1443-1447 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Yamashita: "Novel Organic Metals Based on Nonplanar Bis (1, 3-Dithiole) Donors" Synth.Met.84. 1795-1796 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Tomura: "Synthesis, Structure, and Physical Properties of Novel Component Molecules with Fused Heterocycles for Organic Conductor" Synth.Met.84. 1871-1872 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Yamashita: "Synthesis and Properties of Benzobis(thiadiazole)s with Nonclassical pi-Electron Ring Systems" Tetrahedron. 53(29). 10169-10178 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] A.Ohta: "Novel Bis (1, 3-dithiole) Electron Donors by Oxidative Intramolecular Cyclization of 2, 2'-Bis (1, 4-dithiafulven-6-y1)-3, 3'-bithienyls" Mol.Cryst.Liq.Cryst.296. 1-18 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Yamashita: "Synthesis and Characterization on New Electron Donors Containing 1, 2, 5-Thiadiazole and 1, 1-Dihydro-4, 4-bi (pyridylidene) Units" Chem.Commun.(19). 1851-1852 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] M.Uruichi: "Charge-transfer Salts of M(mnt)_2(M=Ni, Pd, Pt, Au) with BDNT : Ferromagnetic Interactions in Conductive (BDNT)_2-[Ni(mnt)_2]" J.Mater.Chem.8(1). 141-146 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] K.Ono: "Terphenyl and Poly (p-phenylene) Derivatives Containing Fused 1, 2, 5-Thiadiazole Units" Chem.Lett. (6). 545-548 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] K.Suzuki: "New Electron Acceptors Containing Thieno [3, 4-b] pyrazine Units" J.Mater.Chem.8(5). 1117-1119 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Yamashita: "Synthesis and Properties of Novel Tetrathiafulvalene Vinylogues" Chem.Commun. (16). 1657-1658 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Y.Yamashita: "Highly Polarized Electron Donors, Acceptors and Donor-Acceptor Compounds for Organic Conductors (feature article)" J.Mater.Chem.8(9). 1933-1944 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] T.Fukushima: "First Stable Tetracyanodiphenoquiodimethane with a Completely Planar Geometry : Preparation, X-ray Structure, and Highly Conductive Complexes of Bis [1, 2, 5] thiadiazolo-TCNDQ" Tetrahedron Lett.40(6). 1175-1178 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Mikio Uruichi: "Charge-Transfer Salts of M(mnt)_2(M=Ni,Pd,Pt,Au)with BDNT" J.Maten.Chem.8・1. 141-146 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Katsuhiko Ono: "Terphenyl and Poly(p-phenylene)Derivatives Containing Fused 1,2,5-Thiadiazole Units" Chem.Lett. 6. 545-548 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Kazuharu Suzuki: "New Electron Acceptors Containing Thieno[3,4-6]pyrazine Units" J.Mater.Chem.8・5. 1117-1119 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Yoshiro Yamashita: "Synthesis and Properties of Novel Tetrathiaful valene Vinylogues" Chem.Commun.16. 1657-1658 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Yoshiro Yamashita: "Highly Polarized Electron Donors,Acceptors,and Donor-Acceptor Compounds" J.Mater,Chem.8・9. 1933-1944 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Takanori Fukushima: "First Stable Tetracyanod:phenoquinodime thane with a Completely Planar Geometry." Tetrahednon Letters. 40・6. 1175-1178 (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] Akira Ohta: "Preparation,properties,and Oxidation of Novel Bis(1,3-dithiole)Compounds Containing a Di(2-thienyl)methane Unit" Heterocycles. 44・1. 263-276 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Chitoshi Kitamura: "Synthesis and Reaction of 3,3'-Dibromodihydrodipyrrins" J.Chem.Soc.,Perkin Trans.1. -・10. 1443-1447 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Shoji Tanaka: "A Nobel Candidate for Intrinsically Conductive Organic Polymers Based on Nonclassical Thiophene" Synth.Metals. 84・1-3. 229-230 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Yoshiro Yamashita: "Novel Organic Metals Based on Nonplanar Bis(1,3-dithiole)Donors" Synth.Metals. 84・1-3. 1795-1796 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Yoshiro Yamashita: "Synthesis and Properties of Benzobis(thiadiazole)s with Nonclassical π-Electron Ring Systems" Tetrahedron. 53・29. 10169-10178 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Yoshiro Yamashita: "Synthesis and Characterization on New Electron Donors Containing 1,2,5-Thiadiazole and 1,1-Dihydro-4,4-bipyridine Units" Chem.Commun.-・19. 1851-1852 (1997)

    • Related Report
      1997 Annual Research Report

URL: 

Published: 1997-04-01   Modified: 2016-04-21  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi