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Creation of Novel Organic Fluorophores Containing Benzofuran Rings

Research Project

Project/Area Number 16550131
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Functional materials chemistry
Research InstitutionKinki University

Principal Investigator

YAMAGUCHI Yoshihiro  Kinki University, Department of Chemistry, Associate Professor, 理工学部理学科, 助教授 (30200637)

Project Period (FY) 2004 – 2005
Project Status Completed (Fiscal Year 2005)
Budget Amount *help
¥3,100,000 (Direct Cost: ¥3,100,000)
Fiscal Year 2005: ¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 2004: ¥1,600,000 (Direct Cost: ¥1,600,000)
KeywordsSynthesis / Organic Fluorophores / Benzofuran / Phenyleneethynylene / Molecular Function / Light-emitting Characteristics / Organic Electroluminescence Material / πConjugation
Research Abstract

Organic fluorophores are expected to play important roles in the extreme technology of 21st century as photoelectronics materials (e.g., organic electroluminescence diodes (OLEDs)). That is, these are expected to be not only the next generation of materials for the flat-panel display but also sources of light for illuminations, because the realization of white light-emitting may be possible on account of their flexibility of light-emitting color. In order to develop the further research in these fields, it is necessary to create the strongly fluorescent molecules at desired wavelength region. Under such circumstances, based on our previous results in regard to organic fluorophores, we have investigated on the creation of novel organic fluorophores and develop the general methodology. In conclusion, we have found out the following subjects.
1.Phenyleneethynylenes containing pyridine rings : we have succeeded in creating very intense blue light-emitter, and found out that banana-shaped sy … More stems (having 2,6-disubstituted pyridine rings) show the greater light-emitting efficiency than the corresponding rod-shaped systems (2,5-disubstituted pyridine rings). Thus, we proposed the new concept that the higher emissive efficiency of banana-shaped systems might depend on the movability of the dipolar structural unit in the excited singlet state. This concept will be sure to make a contribution to creation of strongly fluorescent molecules.
2.Linear-shaped systems introduced benzofuran rings to molecules : we have succeeded in the synthesis of very intense blue light-emitters having a single emissive maximum to suggest that the introduction of benzofuran rings to molecules is so effective for the creation of organic strongly fluorescent molecules.
3.Rod-shaped oligo(aryleneethynylene)s (para-substituted systems) : we investigated the light-emitting efficiency tuning of rod-shaped oligo(p-phenylene ethynylen)s (OPEs, trimeric to pentameric systems) by donor- and acceptor-groups so that they emit the very intense fluorescence (Φ_f【approximately equal】1.0, log ε【approximately equal】5) at the desired wavelength region. This goal was achieved by side modification by MeO (donor) groups and end modification by CN-substituted benzene ring (or side modification by CN (acceptor) groups and end modification by NMe_2-substituted benzene ring) of tetrameric p-phenylene ethynylene rod-shaped molecule.
4.Star-shaped oligo(aryleneethynylene)s (tiple mata-substituted systems) : we have investigated the light-emitting characteristics and occurrence of conjugation between arms of star-shaped rigid molecules that comprise a 1,3,5-tri-ethynylbenzene core, and methoxy group-substituted oligo(p-phenylethynylene)s arms. Consequently, we achieved the ultimate goal (Φ_f【approximately equal】1.0, log ε > 5) for organic molecules with respect to light-emitting ability by creating very intense violet-blue (Φ_f:0.97, log ε:5.11) and blue (Φ_f:0.98, log ε:5.29) bright light-emitters. Also π conjugation was found to occur between the arms of star-shaped rigid molecules despite the triple meta-substituted system. Less

Report

(3 results)
  • 2005 Annual Research Report   Final Research Report Summary
  • 2004 Annual Research Report
  • Research Products

    (12 results)

All 2006 2005

All Journal Article (12 results)

  • [Journal Article] New Fluorophores with Rod-Snaped Polycyano π-Conjugated Structures : Synthesis and Photophysical Properties.2006

    • Author(s)
      Y.Yamaguchi, T.Ochi, T.Wakamiya, Y.Matsubara, Z.Yoshida
    • Journal Title

      Organic Letters 8・4

      Pages: 717-720

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Rigid Molecular Architectures That Comprise a 1,3,5-Tri-Substituted Characteristics and π Conjugation between The Arms.2006

    • Author(s)
      Y.Yamaguchi, T.Ochi, S.Miyamura, T.Tanaka, S.Kobayashi, T.Wakamiya, Y.Matsubara, Z.Yoshida
    • Journal Title

      Journal of The American Chemical Society 128

      Pages: 4504-4505

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] New Fluorophores with Rod-Shaped Polycyano π-Conjugated Structures : Synthesis and Photophysical Properties.2006

    • Author(s)
      Y.Yamaguchi, T.Ochi, T.Wakamiya, Y.Matsubara, Z.Yoshida
    • Journal Title

      Org.Lett. 8

      Pages: 717-720

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Rigid Molecular Architectures That Comprise a 1,3,5-Tri-Substituted Benzene Core and Three Oligoaryleneethynylene Arms : Light-Emitting Characteristics and π Conjugation between The Arms.2006

    • Author(s)
      Y.Yamaguchi, T.Ochi, S.Miyamura, T.Tanaka, S.Kobayashi, T.Wakamiya, Y.Matsubara, Z.Yoshida
    • Journal Title

      J.Am.Chem.Soc. 128

      Pages: 4504-4505

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] New Fluorophores with Rod-Shaped Polycyano π-Conjugated Structures : Synthesis and Photophysical Properties.2006

    • Author(s)
      Y.Yamaguchi, T.Ochi, T.Wakamiya, Y.Matsubara, Z.Yoshida.
    • Journal Title

      Organic Letters 8・4

      Pages: 717-720

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Rigid Molecular Architectures That Comprise a 1,3,5-Tri-Substituted Benzene Core and Three Oligoaryleneethynylene Arms : Light-Emitting Characteristics and π Conjugation between The Arms.2006

    • Author(s)
      Y.Yamaguchi, T.Ochi, S.Miyamura, T.Tanaka, S.Kobayashi, T.Wakamiya, Y.Matsubara, Z.Yoshida.
    • Journal Title

      Journal of The American Chemical Society 128(印刷中)

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Light-Emitting Efficiency Tuning of Rod-Shaped π Conjugated Systems by Donor and Acceptor Groups.2005

    • Author(s)
      Y.Yamaguchi, T.Tanaka, S.Kobayashi, T.Wakamiya, Y.Matsubara, Z.Yoshida
    • Journal Title

      Journal of The American Chemical Society 127・26

      Pages: 9332-9333

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Banana-Shaped Oligo(aryleneethynylene)s : Synthesis and Light-Emitting Characteristics.2005

    • Author(s)
      Y.Yamaguchi, S.Kobayashi, T.Wakamiya, Y.Matsubara, Z.Yoshida
    • Journal Title

      Angewandte Chemie International Edition 44・43

      Pages: 7040-7044

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Light-Emitting Efficiency Tuning of Rod-Shaped π Conjugated Systems by Donor and Acceptor Groups.2005

    • Author(s)
      Y.Yamaguchi, T.Tanaka, S.Kobayashi, T.Wakamiya, Y.Matsubara, Z.Yoshida
    • Journal Title

      J.Am.Chem.Soc. 127

      Pages: 9332-9333

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Banana-Shaped Oligo(aryleneethynylene)s : Synthesis and Light-Emitting Characteristics.2005

    • Author(s)
      Y.Yamaguchi, S.Kobayashi, T.Wakamiya, Y.Matsubara, Z.Yoshida
    • Journal Title

      Angew.Chem.Int.Ed. 44

      Pages: 7040-7044

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Light-Emitting Efficiency Tuning of Rod-Shaped π Conjugated Systems by Donor and Acceptor Groups.2005

    • Author(s)
      Y.Yamaguchi, T.Tanaka, S.Kobayashi, T.Wakamiya, Y.Matsubara, Z.Yoshida.
    • Journal Title

      Journal of The American Chemical Society 127・26

      Pages: 9332-9333

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Banana-Shaped Oligo(aryleneethynylene)s : Synthesis and Light-Emitting Characteristics.2005

    • Author(s)
      Y.Yamauchi, S.Kobayashi, T.Wakamiya, Y.Matsubara, Z.Yoshida.
    • Journal Title

      Angewandte Chemie International Edition 44・43

      Pages: 7040-7044

    • Related Report
      2005 Annual Research Report

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Published: 2004-04-01   Modified: 2016-04-21  

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