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Creation of the cross type electron conjugated system strong fluorophore arranged donor- and acceptor- groups

Research Project

Project/Area Number 18550133
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

MATSUBARA Yoshio  Kinki University, Faculty of Science Engineering, Professor (80088450)

Project Period (FY) 2006 – 2007
Project Status Completed (Fiscal Year 2007)
Budget Amount *help
¥3,950,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2007: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2006: ¥2,000,000 (Direct Cost: ¥2,000,000)
KeywordsStrong fluorophores / Donor group / Acceptor group / Cross type / Electron conjugated system / Core part in the center / Photophysical data
Research Abstract

In this study, creation of strong fluorescence material was carried out by the constriction of π-electron conjugation system forming core part in the center, arm part having electron donor or acceptor group in four direction, and result were discussed with photophysicochemically. The design of emitted cross shaped tetrakis(phenyletylnyl)benzenes: The cross types of electron conjugative ability was advantageous than a straight line type by the investigation of HOMO-LUMO gap using AM1 calculation. Thus, compounds 1-4 were designed and synthesized. Compounds 1-4 by the reaction of halogenated 1, 4-disubstituted-benzene(core part) with p-substituted phenyl ethynyl (arm part) were synthesized using sonogashira cross coupling reaction. Photophysical data of cross shaped tetrakis(phenylethynyl)benzenes were summarized. Absorption(λ_<abs>) and absorbancy (log ε) were increase in order of non-substitution compound(1) < electron donor(core) compound(2) < electron acceptor(side arms) compound(3) < electron donor(core)/acceptor(side arms) compound(4) and emission wavelength(λ_<em>) were red-shifted above orders. The fluorescence quantum yields (Φ_f) also greatly go up by the introducing the electronic donor acceptor group . The compound 1, 2, 3 and 4 increase the k_r values, and decrease the k_d values. Relationship exists between Φ_f and kinetic parameters for the radiative and radiationless process were examined. ΔΔS^‡=ΔS_r^‡-ΔS_d^‡=1n k_r/k_d
A nice liner relationship between Φ_f and ΔΔS^‡(Φ_f= 0.092ΔΔS^‡+ 0.520). It is inferred that ΔΔS^‡ might be a measure for α-conjugation of the molecules at the exited singlet state.

Report

(3 results)
  • 2007 Annual Research Report   Final Research Report Summary
  • 2006 Annual Research Report
  • Research Products

    (13 results)

All 2007 2006

All Journal Article (11 results) (of which Peer Reviewed: 6 results) Presentation (2 results)

  • [Journal Article] Solid-state optical properties of a chiral supramolecular fluorophore consisting of chiral (1R,2R)-1,2-diphenylethylenediamine and fluorescent carboxylic acid derivatives2007

    • Author(s)
      Y.Imai
    • Journal Title

      Tetrahedron Lett. 48(16)

      Pages: 2927-2930

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Solid-state optical properties of a chiral supramolecular fluorophore consisting of chiral(1R, 2R)-1, 2-diphenylethyleneiamine and fluorescent carboxylic acid derivatives2007

    • Author(s)
      Y. Imai, K. Kawaguchi, T. Harada, T. Sato, M. Ishikawa, M. Fujiki, R. Kuroda, Y. Matsubara
    • Journal Title

      Tetrahedron Lett. 48(16)

      Pages: 2927-2930

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Solid-state optical properties of a chiral supramolecular fluorophore consisting of chiral(1R,2R)-1,2-diphenylethykenediamine and fluorescent carboxylic acid derivatives2007

    • Author(s)
      Y.Imai
    • Journal Title

      Tetrahedron Lett 48(16)

      Pages: 2927-2930

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rod-shaped oligophenyleneethynylenes modified by donor and acceptor groups inablock mamer:synthesis and light-emitting characteristics2007

    • Author(s)
      T.Ochi
    • Journal Title

      Chem.Lett 36(6)

      Pages: 794-795

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A solid-state fluorescence sensing system consisting of chiral (1R,2S)-2-amino-1,2-diphenylethanol and fluorescent 2-anthracenecarboxylic acid2007

    • Author(s)
      Y.Imai
    • Journal Title

      Org.Lett 9(17)

      Pages: 3457-3460

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] New Fluorophores with Rod-Shaped Polycyano π-Conjugated Structures:Synthesis and Photophysical Properties2006

    • Author(s)
      Y.Yamaguchi
    • Journal Title

      Org.Lett. 8(4)

      Pages: 717-720

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Rigid Molecular Architectures That Comprise a 1,3,5-Trisubstituted Benzene Core and Three Oligoaryleneethynylene Arms:Light-Emitting Characteristics and π Conjugation between the Arms2006

    • Author(s)
      Y.Yamaguchi
    • Journal Title

      J.Am.Chem.Soc. 128(14)

      Pages: 4504-4505

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [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(4)

      Pages: 717-720

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Rigid Molecular Architectures That Comprise a 1, 3, 5-Trisubstituted Benzene Core and Three Oligoarylene-ethynylene 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. Chern,Soc 128(14)

      Pages: 4504-4505

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 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(4)

      Pages: 717-720

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Rigid Molecular Architectures that Comprise a 1,3,5-Trisubstituted Benzene Core and Three Oligoarylenecthynylene Arms : Light-Emitting Characteristics and πConjugation between the Arms.2006

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

      J.Am.Chem.Soc. 128(14)

      Pages: 4504-4505

    • Related Report
      2006 Annual Research Report
  • [Presentation] 分子中央に電子吸引基を有するドナー/アクセプター置換オリゴフェニレンエチニレン類:合成と発光特性2007

    • Author(s)
      越智 剛敬
    • Organizer
      日本化学会第87春季年会
    • Place of Presentation
      関西大学 千里山キャンパス
    • Year and Date
      2007-03-26
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Donor and Acceptor-Substituted Oligo(phenylenethynylene)s Having The Acceptor Groups at The Molecular Center : Synthesis and Light-Emitting Characteristics2007

    • Author(s)
      T. Ochi, Y. Yamaguchi, T. Wakamiya, Y. Matsubara, Z. Yoshida
    • Organizer
      The 88th Spring Meeting of CSJ
    • Year and Date
      2007-03-26
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary

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Published: 2006-04-01   Modified: 2016-04-21  

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