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機能性π電子系の多様性指向合成

Research Project

Project/Area Number 16750119
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Functional materials chemistry
Research InstitutionNagoya University (2005)
Kyoto University (2004)

Principal Investigator

伊丹 健一郎  名古屋大学, 物質科学国際研究センター, 助教授 (80311728)

Project Period (FY) 2004 – 2005
Project Status Completed (Fiscal Year 2005)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,900,000)
Fiscal Year 2005: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 2004: ¥3,000,000 (Direct Cost: ¥3,000,000)
Keywords遷移金属触媒 / 拡張π電子系 / 多様性指向合成 / 有機蛍光材料 / π電子系 / 多置換オレフィン / 遷移全属触媒 / 蛍光性化合物
Research Abstract

本研究の目的は、π電子系における効率的多様性創出を可能にする新しい合成方法論を開発し、機能を有する新規な拡張π電子系を見出すことである。本研究では、コアとなるπ電子系プラットホームの特定の位置に置換基を段階的に導入する手法(プラットホーム型合成)を用いた拡張π電子系の構築に焦点を当て、検討を行った。
1.多置換オレフィンの一般的合成法の確立
ビニルシラン、ビニルボラン、ビニルスルフィドなどのビニル元素化合物に対する結合選択的な置換基導入反応(Pd触媒反応)を開発した。これらの反応を逐次的に集積化することで、これまで困難とされてきた多置換オレフィンの一般的合成法を確立した。
2.多置換オレフィン骨格を基盤とする拡張π電子系の合成と機能評価
上述の合成法を用いて、多置換オレフィン型拡張π電子系ライブラリーを構築し、これが蛍光性化合物のライブラリーであることを見出した。さらにこの中から、幅広い発光色の実現、非常に高い蛍光量子収率を有する化合物の発見、光特性に及ぼす特異な置換様式効果の発見、新しい蛍光性ナノ粒子や蛍光性高分子の創製にも成功した。
3.トリアリールエテン骨格を枝分かれ単位にもつ新しい共役デンドリマーの合成と機能評価
独自に開発したオレフィン合成法を駆使して、トリアリールエテン骨格を枝分かれ単位にもつ新しい共役デンドリマーの合成に成功した。また、これが高い溶解性、高い蛍光効率、幅広い発光色を実現する新しい蛍光材料であることを明らかにした。
4.ピリミジンをコアにもつ拡張π電子系の合成と機能評価
その高い電子受容性から有機材料の骨格として注目を集めているピリミジンをコアにもつ拡張π電子系の一般的合成法を確立することに成功した。さらに、電子供与性芳香環と電子求引性芳香環が適切な位置に導入されたピリミジン誘導体が強いソルバトフルオロクロミズムを示すことを見出した。

Report

(2 results)
  • 2005 Annual Research Report
  • 2004 Annual Research Report
  • Research Products

    (19 results)

All 2006 2005 2004

All Journal Article (19 results)

  • [Journal Article] Catalytic Four-Component Assembly Based on Allenylboronate Platform : New Access to Privileged Allylic Amine Structures2006

    • Author(s)
      K.Tonogaki, K.Itami, J.Yoshida
    • Journal Title

      Journal of the American Chemical Society 128/5

      Pages: 1464-1465

    • Related Report
      2005 Annual Research Report
  • [Journal Article] 2-Pyridylsilyl Group : A Useful Multifunctional Group in Organic Synthesis2006

    • Author(s)
      K.Itami, J.Yoshida
    • Journal Title

      Synlett 2006/2

      Pages: 157-180

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Palladium-Catalyzed Cross-Coupling Reactions of (2-Pyridyl)allyldimethylsilanes with Aryl Iodides2006

    • Author(s)
      T.Nokami, Y.Tomida, T.Kamei, K.Itami, J.Yoshida
    • Journal Title

      Organic Letters 8/4

      Pages: 729-731

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Platform Synthesis : A Useful Strategy for Rapid and Systematic Generation of Molecular Diversity2006

    • Author(s)
      K.Itami, J.Yoshida
    • Journal Title

      Chemistry - A European Journal 12(In press)

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Multisubstituted Olefins : Platform Synthesis and Application to Materials Science and Pharmaceutical Chemistry2006

    • Author(s)
      K.Itami, J.Yoshida
    • Journal Title

      Bulletin of the Chemical Society of Japan 79(In press)

    • NAID

      10019164962

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Novel Conjugated Dendrimers Based on Triarylethene Branching : Palladium-Catalyzed Convergent Synthesis and Interesting Properties2006

    • Author(s)
      K.Itami, K.Tonogaki, T.Nokami, Y.Ohashi, J.Yoshida
    • Journal Title

      Angewandte Chemie International Edition 45(In press)

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Triarylethene-Based Extended π-Systems : Programmable Synthesis and Photophysical Properties2005

    • Author(s)
      K.Itami, Y.Ohashi, J.Yoshida
    • Journal Title

      The Journal of Organic Chemistry 70/7

      Pages: 2778-2792

    • Related Report
      2005 Annual Research Report
  • [Journal Article] "Cation Pool" Method Based on C-C Bond Dissociation. Effective Generation of Monocations and Dications2005

    • Author(s)
      M.Okajimas S.Suga, K.Itami, J.Yoshida
    • Journal Title

      Journal of the American Chemical Society 127/19

      Pages: 6930-6931

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Iron-Catalyzed Cross-Coupling of Alkenyl Sulfides with Grignard Reagents2005

    • Author(s)
      K.Itami, S.Higashi, M.Mineno, J.Yoshida
    • Journal Title

      Organic Letters 7/7

      Pages: 1219-1222

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Versatile Synthesis of 1,1-Diaryl-1-alkenes Using Vinylboronate Ester as a Platform2005

    • Author(s)
      K.Tonogaki, K.Soga, K.Itami, J.Yoshida
    • Journal Title

      Synlett 2005/11

      Pages: 1802-1804

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Rapid Synthesis of CDP840 with 2-Pyrimidyl Vinyl Sulfide as a Platform2005

    • Author(s)
      N.Muraoka, M.Mineno, K.Itami, J.Yoshida
    • Journal Title

      The Journal of Organic Chemistry 70/7

      Pages: 6933-6936

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Copper-Catalyzed Allylation of Carbonyl Derivatives Using Allyl(2-pyridyl)silanes2005

    • Author(s)
      T.Kamei, K.Fujita, K.Itami, J.Yoshida
    • Journal Title

      Organic Letters 7/21

      Pages: 4725-4728

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Sequential Pd- and Rh-Catalyzed Three-Component Cyclization with Allenylboronate Platform2005

    • Author(s)
      K.Tonogaki, K.Itami, J.Yoshida
    • Journal Title

      The Journal of Organic Chemistry 70/7

      Pages: 2778-2792

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Catalytic Intermolecular Pauson-Khand-type Reaction : Strong Directing Effect of Pyridylsilyl and Pyrimidylsilyl Groups and Isolation of Ru Complexes Relevant to Catalytic Reaction2004

    • Author(s)
      K.Itami, K.Mitsudo, K.Fujita, Y.Ohashi, J.Yoshida
    • Journal Title

      J.Am.Chem.Soc. 126

      Pages: 11058-11066

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Sequential Assembly Strategy for Tetrasubstituted Olefin Synthesis Using Vinyl 2-Pyrimidyl Sulfide as a Platform2004

    • Author(s)
      K.Itami, M.Mineno, N.Muraoka, J.Yoshida
    • Journal Title

      J.Am.Chem.Soc. 126

      Pages: 11778-11779

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Stereoselective Synthesis of Multisubstituted Butadienes through Directed Mizoroki-Heck Reaction and Homocoupling Reaction of Vinyl(2-pyridyl)silane2004

    • Author(s)
      K.Itami, Y.Ushiogi, T.Nokami, Y.Ohashi, J.Yoshida
    • Journal Title

      Org.Lett. 6

      Pages: 3695-3698

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Rapid Construction of Multisubstituted Olefin Structures Using Vinylboronate Ester Platform Leading to Highly Fluorescent Materials2004

    • Author(s)
      K.Itami, K.Tonogaki, Y.Ohashi, J.Yoshida
    • Journal Title

      Org.Lett. 6

      Pages: 4093-4096

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Pyrimidine-Core Extended n-Systems : General Synthesis and Interesting Fluorescent Properties2004

    • Author(s)
      K.Itami, D.Yamazaki, J.Yoshida
    • Journal Title

      J.Am.Chem.Soc. 126

      Pages: 15396-15397

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Catalytic Carbometalation/Cross-Coupling Sequence Across Alkynyl(2-pyridyl)silanes Leading to a Diversity-Oriented Synthesis of Tamoxifen-type Tetrasubstituted Olefins2004

    • Author(s)
      T.Kamei, K.Itami, J.Yoshida
    • Journal Title

      Adv.Synth.Catal. 346

      Pages: 1824-1835

    • Related Report
      2004 Annual Research Report

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

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