Synthesis and Properties of Functional π-Expanded Compounds Prepared by Thermal or Photochemical Conversion of the Precursors

  • Yamada Hiroko
    Graduate School of Material Science, Nara Institute of Science and Technology JST, CREST
  • Kuzuhara Daiki
    Graduate School of Material Science, Nara Institute of Science and Technology
  • Katsuta Shuhei
    Graduate School of Material Science, Nara Institute of Science and Technology
  • Okujima Tetsuo
    Graduate School of Science and Engineering, Ehime University
  • Uno Hidemitsu
    Graduate School of Science and Engineering, Ehime University

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Other Title
  • 前駆体法を利用した機能性π共役拡張化合物の合成と物性
  • ゼンクタイホウ オ リヨウ シタ キノウセイ パイ キョウヤク カクチョウ カゴウブツ ノ ゴウセイ ト ブッセイ
  • Synthesis and Properties of Functional π-Expanded Compounds Prepared by Thermal or Photochemical Conversion of the Precursors

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Abstract

This paper focuses on the synthesis of new aromatic compounds by thermal, photochemical, or oxidative cleavage reaction of the corresponding precursors. The precursor-methods are useful for the derivatization of the non-soluble aromatic compounds. We have applied retro Diels-Alder reactions for the preparation of new π-expanded porphyrinoid compounds such as [14]tribenzotriphyrin(2.1.1), tetrabenzoporphycene, dodecasubstituted porphycene, tetraanthraporphyin, butadiyne-linked tetrabenzoporphyrin dimer, and so on. We have investigated the photocleavage synthesis of pentacenes from the corresponding α-diketone precursors. This photoreaction enabled us to prepare 1,4,8,11-tetrasubstituted pentacene. The synthesis of new pentacene derivatives with electron-withdrawing substituents at 6,13-positions by oxidative cleavage reaction will be also reported.

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