Ru-Catalyzed Polycondensation of Dialkyl 1,4-Phenylenebis(diazoacetate) with Dianiline: Synthesis of Well-Defined Aromatic Polyamines Bearing an Alkoxycarbonyl Group at the Adjacent Carbon of Each Nitrogen in the Main Chain Framework

  • Hiroaki Shimomoto
    Department of Materials Science and Biotechnology, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama 790-8577, Japan
  • Hiroto Mukai
    Department of Materials Science and Biotechnology, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama 790-8577, Japan
  • Hideaki Bekku
    Department of Materials Science and Biotechnology, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama 790-8577, Japan
  • Tomomichi Itoh
    Department of Materials Science and Biotechnology, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama 790-8577, Japan
  • Eiji Ihara
    Department of Materials Science and Biotechnology, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama 790-8577, Japan

書誌事項

公開日
2017-11-17
資源種別
journal article
DOI
  • 10.1021/acs.macromol.7b01994
公開者
American Chemical Society (ACS)

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説明

Transition-metal-catalyzed N–H insertion of a diazocarbonyl compound is applied for polycondensation for the first time to give a new type of aromatic polyamine. The well-defined polyamines were obtained by [RuCl2(p-cymene)]2-catalyzed reaction of diethyl 1,4-phenylenebis(diazoacetate) with dianilines bearing a variety of linkers between two aniline units. The polycondensation proceeded at 30 °C in CH2Cl2 with 5.0 mol % of the Ru metal to [NH2 or N2═C] to afford the products with Mn = 6400–28 300 in moderate to high yield. Ethoxycarbonyl groups located at an adjacent position to NH imparted solubility to the polyamines, and their glass transition temperatures can be varied depending on the linker structure in a range of 88–173 °C.

収録刊行物

  • Macromolecules

    Macromolecules 50 (23), 9233-9238, 2017-11-17

    American Chemical Society (ACS)

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