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(特異な非局在電子系の創出297-AO1)拡張共役電子系

Research Project

Project/Area Number 10146102
Research Category

Grant-in-Aid for Scientific Research on Priority Areas (A)

Allocation TypeSingle-year Grants
Research InstitutionOsaka University

Principal Investigator

小田 雅司  大阪大学, 大学院・理学研究科, 教授 (60004438)

Co-Investigator(Kenkyū-buntansha) 関 一彦  名古屋大学, 物質科学国際研究センター, 教授 (80124220)
小松 紘一  京都大学, 化学研究所, 教授 (70026243)
大坪 徹夫  広島大学, 工学部, 教授 (80029884)
山下 敬郎  東京工業大学, 大学院・総合理工学研究科, 教授 (90116872)
戸部 義人  大阪大学, 大学院・基礎工学研究科, 教授 (60127264)
Project Period (FY) 1998 – 2000
Project Status Completed (Fiscal Year 2000)
Budget Amount *help
¥97,400,000 (Direct Cost: ¥97,400,000)
Fiscal Year 2000: ¥33,000,000 (Direct Cost: ¥33,000,000)
Fiscal Year 1999: ¥33,000,000 (Direct Cost: ¥33,000,000)
Fiscal Year 1998: ¥31,400,000 (Direct Cost: ¥31,400,000)
Keywords一次元拡張共役系 / 二次元拡張共役系 / ベルト型共役系 / 曲面内包摂錯体 / パイ-シグマ拡張共役電子系 / 分子・結晶構造制御 / 共役系電子構造分子ワイヤー / 光応答分子素子 / 三次元ポリイン / 空孔内包摂 / 分子ワイヤー / 安定カチオンラジカル / 共役系電子構造 / 1〜3次元拡張共役系
Research Abstract

前年度に引き続き、構造・物性・機能の観点から有望な種々のタイプの新規な拡張型共役電子系の開発に向けて、分子設計、合成、構造解析、物性解析を行い、新展開を図った。
(1)環状パラフェニルアセチレン([n]CPPA)の内、[6]CPPA1のヘキサメチルベンゼンやC60誘導体との錯体のX-線構造解析に成功し、1のベルト状構造やC60が内部に包摂されていることを実証した。また1と[9]CPPAが結晶性錯体を形成すること見いだし今後の展開が予想される。新規な拡張キノン類、高極性共役系、拡張トリメチレンメタン類、三次元かご型化合物などの合成にも成功した(小田)。
(2)可溶性オリゴチオフェンの合成と機能の研究をさらに発展させ、ポーラロンパイダイマーのモデルとして[2.2]quinquethiophenophaneを合成し、近赤外部にパイダイマーの吸収を確認した。また分子ワイヤとしての機能の観点から、末端にフラーレンC60やポルフィリンをもつオリゴチオフェン類を合成し、電荷分離や光励起光電流を観測し光応答分子素子としての機能を確認した(大坪)。
(3)新規なシグマ-パイ共役系の創出をさらに推進し、シグマ-パイ共役に基づく含シリコン7員環共役カチオンの初めての合成に成功した。また、ビシクロ[2.1.1]ヘキセン導入システムのベンゼンおよびシクロオクタテトラエンの合成と性質について研究しベンゼンの高反応性など興味ある知見を得た(小松)。
(4)高反応性3次元ポリインの発生とフラーレンへの変換の研究をさらに遂行するとともに、環の内外に官能基をもつブタジイン架橋二次元大環状分子の合成と会合・包摂能等を研究し、双極子-双極子相互作用により互いに形状を認識しつつ会合する事などを明らかにした(戸部)。
(5)先にテトラチアフルバレンビニローグの構造・物性の精密制御を明らかにしたが、さらにビピリジンや1,2-ビス(2-ピリジル)エチレンの水素結合能を利用して新規な超分子体を構築した(山下)。
(6)トリアリールアミン誘導体やp-セクシフェニルなどを用いて、有機層におけるバンドの曲がり、有機/金属系と金属/有機系における膜成長モードと電子構造、また、側鎖にパイ共役系を有するポリアセチレンの電子構造、種々の炭素-フッ素系におけるパイ共役、シグマ共役などについて研究した(関)。

Report

(3 results)
  • 2000 Annual Research Report
  • 1999 Annual Research Report
  • 1998 Annual Research Report
  • Research Products

    (24 results)

All Other

All Publications (24 results)

  • [Publications] Masaji Oda et al.: "Synthesis, Structure, and Properties of Hexaaryl [3] radialenes,"Bull.Chem.Soc.Jpn.. 73. 2109-2114 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Masaji Oda et al.: "Synthesis and Characterisation of 2,6-Di-tert-butyl-1-thio-1,4-benzoquinone, the First Isolable Monothio-1,4-benzoquinone."J.Chem.Soc.Chem.Commun.. 2000. 1357-1358 (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. 2000. 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 Studied by Pico-and Nanosecond Laser Flash Photolysis in the Near-IR Region"J.Phys.Chem.A. 104. 4876-4881 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Kouichi Komatsu et al.: "The First Cyclic p-Conjugated Silylium Ion : The Silatropylium Ion Annelated with Rigid s-Framewords"J.Am.Chem.Soc.. 122. 9312-9313 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Kazuhiko Seki et al.: "Intramolecular Energy Band Dispersion in Oriented Thin Films of n-CF3 (CF2) 22CF3 Observed by Angle-Resolved Photoemission with Synchrotron Radiation"J.Chem.Phys.. 112. 3333-3338 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Yosito Tobe et al.: "[2+2] Cycloreversion of [4.3.2] Propella-1,3,11-trienes : An Approach to Cyclo [n] carbons from Propellane-Annelated Dehydro [n] annulenes,"J.Am.Chem.Soc.. 122. 1762-1775 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Yosiro Yamasita et al.: "Synthesis and Characterization of Novel Strong Electron Acceptors : Bithiazole Analogues of Tetracyanodiphenoquinodimethane (TCNDQ)"Tetrahedron Letters. 41. 8359-8364 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Masaji Oda et al.: "Dibenzoannulated 3, 5, 3", 5"-Tera(t-butyl)-p-terphenoquinone. A Reversible, Photochemical-Thermal Switching System Involving Restricted Conformational Change"Chemistry Letters. 1999. 749-750 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Masaji Oda et al.: "Generation and Reactivity of 2, 4, 6-Triphenylpyridyl Radicals Linked by Alkyl Chains"Synthetic Metals. 103. 2304-2305 (1999)

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

    • Related Report
      1999 Annual Research Report
  • [Publications] Kouichi Komatsu: "Cyclic p-conjugated Systems Annelated with Bicyclolakene Frameworks"European Journal of Organic Chemistry. 1999. 1495-1502 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Kouichi Komatsu et al.: "The First Isolation of the Hexafluoroantimonate Salt of 1, 4-Dithiin Radical Cation Stabilized by Bicyclo[2.2.2]octene Annelation"Tertrahedron Letters. 40. 4375-4378 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Kazuhiko Seki et al.: "Electronic Structure of Poly(1, 10-Phenanthroline-3, 8-diyl) and its k-doped State Studied by Photoelectron Spectroscopy"Journal of Chemical Physics. 110. 2552-2557 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Yosito Tobe et al.: "Pyridine analoue of macrocyclic polyyne C58H4N2 as a precursor to diazafullerene C58N2"J. Chem. Soc. Chem. Commun.. 1999. 1625-1626 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Yosiro Yamasita et al.: "Novel TTF Vinylogs Affording Stable Cation Radicals"Synthetic Metals. 102. 1730-1731 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Masaji Oda et al.: "Tetrakis(2-thienylallene)and 1,1,3,3,-Tetrakis(2-thienyl)allyl Cation,an Electron-rich Reactive Tetraallylallene and a Rematkably Stable Tetraaryl-substituted Allyl Cation" Tetrahedron Letters. 39. 7135-7138 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Masaji Oda,Keiji Okada et al.: "Preparation and Charactrization of Novel High-Spin Organoborane Dianions" Tetrahedron Letters. 39. 6483-6486 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Tetsuo Otsubo et al.: "Synthesis and Properties of the Longest Oligothiophenes : The Icosamer and Heptacosamer" Journal of Organic Chemistry. 63. 8632-8633 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Kouichi Komatsu et al.: "Synthesis,Structure and Properties of Naphthalene Fully Annelated with Bicyclo[2.2.2]octene Frameworks" Tetrahedron Letters. 40. 123-126 (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] Kazuhiko Seki et al.: "Electronic Structure of Organic Molecular Materials for Organic Electroluminescent Devices Studied by Ultraviolet Photoemission Spectroscopy" Journal of Applied Physics. 83. 4928-4938 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Yosito tobe etal.: "Synthesis and Association Behavior of[4.4.4.4.4.4]Metacyclophanedodecayne Derivatives with Interior Binding Groups" Angewandte Chemie,Int.Ed.Engl.37. 1285-1287 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Yosito Tobe et al.: "[16.16.16](1,3,5)Cycophanetetracosayne(C60H6) : A Precursor to C60 Fullerene" Journal of American Chemical Society. 120. 4544-4545 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Yosiro Yamasita et al.: "Highly Polarized Electron Donors,Acceptors and Donor-Acceptor Compounds for Organic Conductors" Journal of Material Chemistry. 8. 1657-1658 (1998)

    • Related Report
      1998 Annual Research Report

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

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