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Design and synthesis of nanosized conjugated π-electron molecules with specific functionarity

Research Project

Project/Area Number 10440189
Research Category

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

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionHiroshima University

Principal Investigator

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

Co-Investigator(Kenkyū-buntansha) TAKIMIYA Kazuo  Fac of Eng, Hiroshima University, Res.Ass., 工学部, 助手 (40263735)
ASO Yoshio  Fac of Eng, Hiroshima University, Assoc.Prof., 工学部, 助教授 (60151065)
Project Period (FY) 1998 – 2000
Project Status Completed (Fiscal Year 2000)
Budget Amount *help
¥5,100,000 (Direct Cost: ¥5,100,000)
Fiscal Year 2000: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1999: ¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 1998: ¥2,600,000 (Direct Cost: ¥2,600,000)
KeywordsNanoscale molecule / Oligomer / Thiophene / Molecular wire / Molecular device / Organic functional material / オリゴチオフェン / 分子ワイヤー / 分子エレクトロニクス
Research Abstract

As one of the most promising approaches for the development of functional organic materials, nanosized conjugated oligomers are of current attention. However, only few number of well-defined nanomolecules with over 10 nm length readily manipulated by modern STM techniques have not been known. In this regard, this project has aimed at the development of extraordinarily long oligothiophenes, which correspond to monodisperse polymers. A series of oligothiophenes up to the 72-mer has been synthesized. The spectroscopic studies of the homologous series of the long oligothiophenes served to clarify the concept of an effective conjugation length of α-conjugated thiophene systems, which extends to 20-30 thiophene units. The doped-conductivity studies of these oligomers were also very helpful in elucidating the conduction mechanism of conductive polythiophenes : it turned out that the conductivities are also dependent on the conjugation length, and the effective conjugation length play a critical role in determining the charge transport of polythiophenes. In addition, the spectroscopic studies of the oxidized species led to an important conclusion that the active charge carrier species are both π-dimers and bipolarons. In an extension study, long oligothiophenes were used as a molecular wire allowing photoinduced electron- and/or energy-transfer from the donating porphyrin part to the accepting fullerene part. Furthermore, the molecular-wire behavior of sophisticated oligothiophenes was successfully applied to the oligothiophene-based photovoltaic devices.

Report

(4 results)
  • 2000 Annual Research Report   Final Research Report Summary
  • 1999 Annual Research Report
  • 1998 Annual Research Report
  • Research Products

    (37 results)

All Other

All Publications (37 results)

  • [Publications] H.Nakanishi: "Synthesis and Properties of the Longest Oligothiophenes : the Icosamer and Heptacosamer"Journal of Organic Chemistry. 63. 8632-8633 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Imamura: "Application of Flash Vacuum Pyrolysis of Sulfur-containing Heteroaromatic Systems"Tetrahedron Letters. 40. 2789-2792 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Yamashiro: "Intramolecular Energy Transfer of [60] Fullerene-linked Oligothiophenes"Chemistry Letters. 443-444 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Nakanishi: "The Longest Class of Oligothiophenes"Synthetic Metals. 101. 604-605 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Nakanishi: "Molecular and Crystal Structures of 2,2′ : 5′,2" : 5",2′"-Quaterselenophene"Synthetic Metals. 101. 639 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Imamura: "Triphenyleno [1,12-bcd : 4,5-b′c′d′ : 8,9-b"c"d"] trithiophene : the First Bowl-shaped Heteroaromatic"Chemical Communications. 1859-1860 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] S.Inoue: "Hexakis(terthiophenylthio) benzene as a New Class of Liquid Crystal Molecule"Journal of Chemical Research(S). 596-597 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] S.Inoue: "Syntheses, Spectroscopic Properties, and Polymerizations of 2,2′-Bitellurophene, 2,2′ : 5′, 2"-Tertellurophene and Related Chalcogenophenes"Heterocycles. 52. 159-170 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] D.Hirayama: "Preparation and Photoelectrochemical Properties of Gold Electrodes Modified with [60] Fullerene-Linked Oligothiophenes"Chemistry Letters. 570-571 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] M.Fujitsuka: "Solvent-Polarity-Dependence of Photoinduced Charge Separation in Tetrathiophene-C60 Dyad Studied by Pico- and Nano-second Laser Flash Photolysis"Journal of Physical Chemistry, A. 104. 4876-4881 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kaikawa: "Synthesis and Spectroscopic Properties of [2.2] Quinquethiophenophanes as an Ideal pi-Dimer Model"Organic Letters. 2. 4197-4199 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Nakanishi: "Spectral Properties of the Longest Oligothiophenes in the Oxidation States"Synthetic Metals. (in press). (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] N.Sumi: "Synthesis and Properties of a Series of the Longest Oligothiophenes up to the 48-mer"Bulletin of the Chemical Society of Japan. (in press). (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Nakanishi: "Synthesis and Properties of the Longest Oligothiophenes : the Icosamer and Heptacosamer"J.Org.Chem.. 63(24). 8632-8633 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Imamura: "Application of Flash Vacuum Pyrolysis to the Synthesis of Sulfur-containing Heteroaromatic Systems"Tetrahedron Lett.. 40(14). 2789-2792 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Yamashiro: "Intramolecular Energy Transfer of [60] Fullerene-linked Oligothiophenes"Chem.Lett.. (5). 443-444 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Nakanishi: "The Longest Class of Oligothiophnes"Synth.Met.. 101(1-3). 604-605 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Nakanishi: "Molecular and Crystal Structures of 2,2' : 5', 2" : 5", 2'''-Quaterselenophene"Synth.Met.. 101(1-3). 639 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Imamura: "Triphenyleno [1,12-bcd : 4,5-b'c'd' : 8,9-b"c"d"] trithiophene : the First Bowl-shaped Heteroaromatic"Chem.Commun.. (18). 1859-1860 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] S.Inoue: "Hexakis (terthiophenylthio) benzene as a New Class of Liqued Crystalline Molecule"J.Chem.Res. (S). (10). 596-597 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] S.Inoue: "Syntheses, Spectroscopic Properties, and Polymerizations of 2,2'-Bitellurophene, 2,2' : 5', 2"-Tertellurophene, and Related Hybrid Terchalcogenophenes"Heterocycles. 52(1). 159-170 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] D.Hirayama: "Preparation and Photoelectrochemical Properties of Gold Electrodes Modified with [60] Fullerene-Linked Oligothiophenes"Chem.Lett.. (5). 570-571 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] M.Fujitsuka: "Solvent-Polarity-Dependence of Photoinduced Charge Separation in Tetrathiophene-C60 Dyad-Studies by Pico- and Nano-second Laser Flash Photolysis in Near-IR Region"J.Phys.Chem.A. 104(21). 4876-4881 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kaikawa: "Synthesis and Spectroscopic Properties of [2.2] Quinquethiophenophane as an Ideal π-Dimer Model"Org.Lett.. 2(26). 4197-4199 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] H.Nakanishi: "Spectral Properties of the Longest Oligothiophenes in the Oxidation States"Synth.Met.. (in press). (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] N.Sumi: "Synthesis and Properties of a Series of the Longest Oligothiophenes up to the 48-mer"Bull.Chem.Soc.Jpn.. (in press). (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Tetsuo Otsubo et al.: "Syntheses, Spectroscopic Properties, and Polymerization of 2,2'-Bitellurophene"Heterocycles. 52,No.1. 159-170 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Tetsuo Otsubo et al.: "Preparation and Photoelectrochemical Properties of Gold Electrodes Modified with [60]Fullerene-Linked Oligothiophenes"Chemistry Letters. No.5. 570-571 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Tetsuo Otsubo et al.: "Solvent Polarity Dependence of Photoinduced Charge Separation in a Tetrathiophene-C60 Dyad"The Journal of Physical Chemistry A. 104 No.21. 4876-4881 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Tetsuo Otsubo et al.: "Synthesis and Spectroscopic Properties of [2.2] Quinquethiophenophane as an Ideal pi-Dimer Model"Organic Letters. 2,No.26. 4197-4199 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Y.Yamashiro: "Intramolecular Energy Transfer of [60] Fulleren-Linked Oligothiophenes"Chemistry Letters. 443-444 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] H.Nakanishi: "Molecular and Crystal Structures of 2,2':5',2'':5'',2''-Quaterselenophene"Synthetic Metals. 101. 639 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] H.Nakanishi: "The Longest Class of Oligothiophenes"Synthetic Metals. 101. 604-605 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] S.Inoue: "Hexakis(terthiophenylthio)benzene as a New Class Liguid Crystalline Molecule"J.Chem.Res.. 596-597 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Hidetake Nakanishi: "Synthesis and Properties of the Longest Oligothiophenes" Journal of The Organic Chemistry. 63(24). 8632-8633 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Hidetake Nakanishi: "The Longest Class of Oligothiophenes" Synthetic Metals. (in press). (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] Hidetaka Nakanishi: "Molecular and Crystal Structures of Quaterselenophene" Synthetic Metals. (in press). (1999)

    • Related Report
      1998 Annual Research Report

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Published: 1998-04-01   Modified: 2016-04-21  

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