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Synthesis and Properties of Orgamic Molecules with Small HOMO-LUMO Gaps

Research Project

Project/Area Number 07454170
Research Category

Grant-in-Aid for Scientific Research (B)

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

Principal Investigator

YAMASHITA Toshiro  Okazaki National 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 National Inst., Inst.for Molecular Science, Research Associate, 分子科学研究所, 助手 (20192635)
Project Period (FY) 1995 – 1996
Project Status Completed (Fiscal Year 1996)
Budget Amount *help
¥6,300,000 (Direct Cost: ¥6,300,000)
Fiscal Year 1996: ¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 1995: ¥4,400,000 (Direct Cost: ¥4,400,000)
KeywordsOrganic Conductor / Organic Semiconductor / Single-Component Conductor / Conducting Polymer / Thiophene Oligomer / Electron Donor / 単一成物導体 / バンドギャップ / HOMO-LUMOギャップ / ポリチオフェン
Research Abstract

Compounds containing both electron donor and acceptor units are expected to have small HOMO-LUMO gaps which lead to interesting properties such as intrinsic conductivity and nonlinear optical properties. They are also interesting as components for organic conductors because they are highly polarized and unique molecular assemblies may be formed by strong intermolecular interactions. We prepared here novel donor-acceptor compounds containing 1,2,5-thiadiazole units.
Benzobis (thiadiazole) with a nonclassical thiadiazole ring has a high electron affinity. Introduction of electron-donating groups afforded a new type of donor-acceptor compounds. Their cyclic voltammograms showed that they are easily both oxidized and reduced. Some of them have the absorption maxima above 700 nm due to the small HOMO-LUMO separation. X-ray structure analysis of the diphenyl derivative revealed the formation of a tap-like network through short S---N contacts.
A series of novel monomers containing aromatic-donor and o-quinoid-acceptor units were also prepared. One compound showed the absorption maximum at 1345 nm. Electrochemical oxidation of the monomers afforded polymers showing small bandgaps. The electrochemical bandgap of one polymer was found to be nearly zero. We have furthermore developed a new synthetic approach to precisely-defined conjugated oligomers containing various types of thiophene units. For example, a sexithiophene derivative showing an absorption maximum at 1097 nm was prepared.

Report

(3 results)
  • 1996 Annual Research Report   Final Research Report Summary
  • 1995 Annual Research Report
  • Research Products

    (30 results)

All Other

All Publications (30 results)

  • [Publications] Chitoshi Kitamura: "New Narrow-Bandgap Polyners Composud of [1,2,5] Thiadiazolo [ 3,4,-g ] quinoxaline and Aromatic Heterocycles" Chemistry Letters. 63-64 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Chitoshi Kitamura: "Design of Narrow-Bandgap Polymers. Synthesis and Properties of Monomers and Polymers Containing Aromatic Donor and O-Quinoid Acceptor Units" Chemistry of Materials. 8. 570-578 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Kyuya Yakushi: "Spectroscopic Studies on BDNT Having a Property of One-Step Two-Electron Dxidation,BDNT^0,BDNT^<+1>,and BDNT^<2+>" Mol. Cryst. Lig. Cryst.284. 223-234 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Yoshiro Yamashita: "Unusual Cation Radical Salts of Nonplanar Bis (1,3-dithiole) Donors Incorporating Solvent Molecules" Chemical Communications. 2021-2022 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Akira Ohta: "Prepanation,Properties,and Oxidation of Novel Bis (1,3-dithiole) Compounds Containing a Di (2-thienyl) methane Unit" Heterocycles. 44. 263-276 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Yoshiro Yamashita: "Synthesis and Properties of Renzobis (thiadiazole)s with Norclessical π-Electron Ring Systems" Tetrahedron. (印刷中). (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] A.Ohta and Y.Yamashita: "Preparation and Properties of Bis [5-(6-methyl-1,4-dithiafulven-6-yl)-2-thienyl] methanes Affording Near-Infrared Absorbing Cations by Oxidation" J.Chem.Soc., Chem.Commun.(5). 557-558 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] S.Tanaka and Y.Yamashita: "Syntheses of Narrow Bandgap Heterocyclic Copolymers of Aromatic-Donor and Quinonoid-Acceptor Units" Synth.Met.69. 599-600 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Y.Yamashita, S.Tanaka, and K.Imaeda: "Organic Metals Based on Butterfly-Shaped Donor Molecules" Synth.Met.71. 1965-1966 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M.Karikomi, C.Kitamura, S.Tanaka, and Y.Yamashita: "New Narrow-Bandgap Polymer Composed of Benzobis (1,2,5-thiadiazole) and Thiophenes" J.Am.Chem.Soc.117(25). 6791-6792 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] A.Ohta and Y.Yamashita: "Oxidative Intramolecular Cyclization of 2,2'-Bis (1,4-dithiafulven-6-yl)-3,3'-bithienyls affording Novel Bis (1,3-dithiole) Electron Donors" J.Chem.Soc., Chem.Commun.(17). 1761-1762 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M.Tomura and Y.Yamashita: "Syntheses and Properties of Novel Conducting Dithiolato-Metal Complexes Having Peripheral Heteroatoms and Extended pi-Conjugated Systems" J.Mater.Chem.5(10). 1753-1754 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] C.Kitamura, S.Tanaka, and Y.Yamashita: "New Narrow-Bandgap Polymers Composed of [1,2,5] Thiadiazolo [3,4-g] quinoxaline and Aromatic Heterocycles" Chem.Lett.(1). 63-64 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] C.Kitamura, S.Tanaka, and Y.Yamashita: "Design of Narrow-Bandgap Polymers. Syntheses and Properties of Monomers and Polymers Containing Aromatic-Donor and o-Quinoid-Acceptor Units" Chem.Mater.8(2). 570-578 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Y.Yamashita, M.Tomura, and K.Imaeda: "Unusual Cation Radical Salts of Nonplanar Bis (1,3-dithiole) Donors Incorporating Solvent Molecules" Chem.Commun.(17). 2021-2022 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] A.Ohta and Y.Yamashita: "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
      1996 Final Research Report Summary
  • [Publications] Y.Yamashita, K.Ono, M.Tomura, and S.Tanaka: "Synthesis and Properties of Benzobis (thiadiazole) s with Nonclassical pi-Electron Ring Systems" Tetrahedron. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] A.Ohta and Y.Yamashita: "Novel Bis (1,3-dithiole) Electron Donors by Oxidative Intramolecular Cyclization of 2,2'-Bis (1,4-dithiafulven-6-yl)-3,3'-bithienyls" Mol.Cryst.Liq.Cryst.(in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Chitoshi Kitamura: "New Narrow-Bandgap Polymers Composed of 〔1,2,5〕 Thiadiazolo 〔3.4-8〕 quinoxaline and Aromatic Heterocycles" Chem.Lett.1. 63-64 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Chitishi Kitamura: "Design of Narrow-Bandgap Polymers,Synthesis and Properties of Monomers and Polymers Containing Aromatic-Donor and o-Quinoid-Acceptor Units" Chem.Mater.8・2. 570-578 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Kyuya Yakushi: "Spectroscopic Studies on BDNT Having a Property of One-Step Two-Electron Oxidation" Mol.Cryst.Lig.Cryst.284. 223-234 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Yoshiro Yamashita: "Unusual Cation Radical Salts of Nonplanar Bis (1,3-dithiole) Donors Incorporating Solvent Molecules" Chem.Commun.17. 2021-2022 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Akira Ohta: "Preparation,Properties,and Oxidation of Novel Bis (1,3-dithiole) Conpounds Containing a Di (2-thienyl) methane Unit" Heterocycles. 44・1. 263-276 (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] Yoshiro Yamashita: "Synthesis and Properties of Benzobis (thiadiazole) s with Nonclassical Tc-Electron Ring Systems" Tetrahedron. (印刷中). (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] Akira Ohta: "Preparation and Properties of Bis[5-(6methyl-1,4-dithiafulven-6-yl)-2-thieryl]-methanes Affording Near-Infrared Absorbing Cations by Oxidation" J.Chem.Soc.,Chem.Commun.557-558 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Shoji Tanaka: "Syntheses of Narrow Bandgap Heterocyclic Copolymers of Aromatic-Donor and Quinonoid-Acceptor Units" Synth.Metals. 69. 599-600 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Yoshiro Yamashita: "Organic metals Based on Butterfly-Shaped Donor Molecules" Synth.metals. 71. 1965-1966 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Kenichi Imaeda: "Temperature Dependence of Hall Mobility in a Single Crystal of Organic Semiconductor BTQBT" J.mater.Chem.5. 861-863 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Michinori Karikomi: "New Narrow-Bandgap Polymer Composed of Benzobis (1,2,5-thiadiazole) and Thiophenes" J.Am.Chem.Soc.117. 6791-6792 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Masaaki Tomura: "Syntheses and Properties of Novel Conducting Dithiolato-Metal Complexes Having Peripheral Heteroatoms and Extended π-Conjugated Systems" J.mater.Chem.5. 1753-1754 (1995)

    • Related Report
      1995 Annual Research Report

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Published: 1995-04-01   Modified: 2016-04-21  

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