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DEVELOPMENT OF ELECTRONIC-AND PHOTO-FUNCTIONAL DEVICE MATERIALS VIA SYNTHESIS OF EXTENSIVELY CONJUGATED MOLECULES BEARING REDOX SYSTEMS

Research Project

Project/Area Number 10640523
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionKYUSHU UNIVERSITY

Principal Investigator

ASO Yoshio  kYushu University, Institute for Fundamental Research of Organic Chemistry, Associate Proffessor, 有機化学基礎研究センター, 助教授 (60151065)

Co-Investigator(Kenkyū-buntansha) OTSUBO tetsuo  Hiroshima University Faculty of Engineering, Professor, 工学部, 教授 (80029884)
Project Period (FY) 1998 – 1999
Project Status Completed (Fiscal Year 1999)
Budget Amount *help
¥3,200,000 (Direct Cost: ¥3,200,000)
Fiscal Year 1999: ¥1,300,000 (Direct Cost: ¥1,300,000)
Fiscal Year 1998: ¥1,900,000 (Direct Cost: ¥1,900,000)
KeywordsFunctional device material / Extensively conjugated system / Redox system / Oligothiophene / [60]Fullerene / Photo-induced electron transfer / Organic electroluminescent device / Polycyclic heteroaromatic / オリゴチオフェン / テトラセレナフルバレン / 液晶分子 / エネルギー移動
Research Abstract

1. A series of very long oligothiophenes up to 48-mer with an interval of tetraocty1-substituted septithiophene segment has been synthesized. Their electronic absorption and emission spectra vary progressively with the increasing chain length, but the spectroscopic saturation occurs at around 20-mer. On the Other hand, their cyclic voltammograms show a progressive decrease in the first oxidation peak potential up to the 34-mer, in contrast to the electronic spectra. This indicates a more extensive charge delocalization for the cationic species of the oligothiophenes.
2. [60]Fullerene-linked quarter-, octi, and duodeci-thiophenes have been synthesized, and their emission spectra demonstrate efficient intramolecular energy transfer from the thiophene moiety to the fullerene, whose rate constant largely depends on the chain length of the oligothiophene moiety. [60]Fullerene-linked quarter- and octi-thiophnes with a disulfide anchoring group have been synthesized, and a photovoltaic cell wi … More th a gold electrode modified with the octithiophene derivative showed a large photocurrent under illumination of visible light.
3. A series of oligo(2,3-thienylene ethynylene)s was synthesized by repeated application of the Pd-catalyzed coupling reaction of terminal alkynes and thieny1 iodides as an essential building step. The electronic absorption and fluorescence spectra vary progressively with the increasing chain length up to the 12-mer, indicating effective conjugations.
4. Triphenylenotrithiophene has been synthesized, and its unique bow1-shaped molecular structure and electronic spectra have been elucidated. The molecules are stacked in a concave-convex fashion with marked intermolecular S-S contacts.
5. Chalcogen-atom-introduced tripheny1 amine systems have been synthesized as a novel class of hole-transport materials and compared their properties as well as EL characteristics utilizing them with the most commonly used HT material TPD. All the devices utilizing them emitted green light and showed higher luminous efficiency than the device using TPD. Less

Report

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

    (33 results)

All Other

All Publications (33 results)

  • [Publications] Kazuo Takimiya: "Synthesis and Characterization of the First Boable-Birdged Tetraselena fulvalenophanes"Amgewandte Chemie, International Edition. 37・5. 619-622 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Hidetaka Nakaniski: "Synthesis and Properties of the Longest Oligothiophenes: the Icosamer and Heptacosamer"The Journal of Organic Chemistry. 63・24. 8632-8633 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Koichi Imamura: "Application of Flash Vacuum Pyrolysis to the Synthesis of Sulfur-containing Heteroaromatic Systems"Tetrahedran Letters. 40・41. 2789-2792 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Takashi Yamashiro: "Intramolecular Energy Transfer of [60] Fullereme-linked Oligothiophenes"Chemisty Letters. ・5. 443-444 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Hidetaka Nakaniski: "The Longest Class of Oligothiopheres"Synthetic Metals. 101・1-3. 604-606 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Hidetaka Nakaniski: "Molecular and Crystal Structures of 2.2': 5'.2": 5",2"'-Quaterselenophene"Synthetic Metals. 101・1-3. 639-639 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Yoshio Aso: "Alkylene- or Alkylenedithio-linked Dimeric Tetraselemafulvalenes"Synthetic Metals. 102・1-3. 1605-1606 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Masahika Iyoda: "Synthesis and Properties of Bitetraselenafulvalene"Tetraheadron Letters. 40・31. 5729-5730 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Koichi Imamura: "Triphenuyleno [1,12-bcd:4,5-b'c'd': 8, 9,-b"c"d"] trithiophene: the First Bowl-shaped Heteroaromatic"Chemical Communication. ・18. 1859-1860 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Shinobu Inoue: "Hexakis(terthiopherylthio) benyene as a New Class of Liquid Crystallin Molecule"Journal of Chemical Research (s). ・10. 596-597 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Shinobu Inoue: "Synthesis, Spectroscopic properties, and polymerization of 2.2'-Bitellurophence, 2,2': 5,2"- Tertellaropheme, and Related Hybid Terchalcogenophenes"Heterocycles. 52・1. 159-170 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Takimiya, A. Oharuda, A. Morikami, Y. Aso, T. Otsubo: ""Synthesis and Characterization of the First Double-Bridged Tetraselenafulvalenophanes""Angew. Chem., Int Ed. Engl.,. 37(5). 619-622 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H. Nakanishi, N. Sumi, Y. Aso, T. Otsubo: ""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
      1999 Final Research Report Summary
  • [Publications] K. Imamura, D. Hirayama, H. Yoshimura, K. Takimiya, Y. Aso, T. Otsubo: ""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
      1999 Final Research Report Summary
  • [Publications] T. Yamashiro Y. Aso, T. Otsubo, H. Tang, Y. Harima, K. Yamashita: ""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
      1999 Final Research Report Summary
  • [Publications] H. Nakanishi, Y. Aso, T. Otsubo: ""The Longest Class of Oligothiophnes""Synth. Metals. 101(1-3). 604-606 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H. Nakanishi, S. Inoue, Y. Aso, T. Otsubo: ""Molecular and Crystal Structures of 2,2':5',2":5",2"- Quaterselenophene""Synth. Metals. 101(1-3). 639 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] Y. Aso, T. Kageyama, M. Kawashima, A. Morikami, A. Oharuda, K. Takimiya, T. Otsubo: ""Alkylene-or Alkylenedithio-linked Dimeric Tetraselenafulvalenes""Synth. Metals. 102(1-3). 1605-1606 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] M. Iyoda, K. Hara, C. R. V. Rao, Y. Kuwatani, K. Takimiya, A. Morikami, Y. Aso, T. Otsubo: ""Synthesis and Properties of Bitetraselenafulvalene""Tetrahedron Lett. 40(31). 5729-5730 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Imamura, K. Takimiya, Y. Aso, T. Otsubo: ""Triphenyleno[1,12-bcd:4,5-b'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
      1999 Final Research Report Summary
  • [Publications] S. Inoue, S. Nishiguchi, S. Murakami, Y. Aso, T. Otsubo, V. Vill, A. Mori, S. Ujiie: ""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
      1999 Final Research Report Summary
  • [Publications] S. Inoue, T. Jigami, H. Nozoe, Y. Aso, F. Ogura, T. Otsubo: ""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
      1999 Final Research Report Summary
  • [Publications] Koichi Imamura: "Application of Flash Vacuum Pyrolysis to the Synthesis of Sulfur-containing Heteroaromatic Systems"Tetrahedron Letters. 40・14. 2789-2792 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Takashi Yamashiro: "Intramolecular Energy Transfer of [60] Fullerene-linked Oligothiophenes"Chemistry Letters. ・5. 443-444 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Hidetaka Nakanishi: "The Longest Class of Oligothiophenes"Synthetic Metals. 101・1-3. 604-606 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Yoshio Aso: "Alkylene- or Alkylenedithio-linked Dimeric Tetraselenafulvalenes"Synthetic Metals. 102・1-3. 1605-1606 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Hidetaka Nakanishi: "Molecular and Crystal Structures of 2,2':5',2'':5'',2'''-Quaterselenophene"Synthetic Metals. 101・1-3. 639-639 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Koichi Imamura: "Triphenyleno[1,12-bcd:4,5-b'c'd':8,9-b''c''d'']trithiophene : the First Bowl-Shaped Heteroaromatic"Chemical Communication. ・18. 1859-1860 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Shinobu Inoue: "Hexakis(terthiophenylthio) benzene as a New Class Liquid Crystalline Molecule"Journal of Chemical Research (S). ・10. 596-597 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Hidetaka Nakanishi: "Synthesis and Properties of the Lomhest Oligothiophemes : The Icosamer and Heptacosamer" The Journal of Organic Chemistry. 63・24. 8632-8633 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Yoshio Aso: "Alkylene-or Alkylenedithio-linked Dimeric Tetraselena fulvalenes" Synthetic Metals. 発表予定.

    • Related Report
      1998 Annual Research Report
  • [Publications] Hidetaka Nakanishi: "The Longest Class of Oligothiophenes" Synthetic Metals. 発表予定.

    • Related Report
      1998 Annual Research Report
  • [Publications] Hidetaka Nakanishi: "Molecular and Crgstal Structures of 2,2‘:5',2‘‘:5'',2'''-Quaterselenophene" Synthetic Metals. 発表予定.

    • Related Report
      1998 Annual Research Report

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

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