Formation of Bundle Assemblies of Stereoregular Polymers in Thermal Solid-State Polymerization of 7,7,8,8-Tetrakis(aryloxycarbonyl)-<i>p</i>-quinodimethanes

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  • Takahito Itoh
    Division of Chemistry for Materials, Graduate School of Engineering, Mie University, 1577 Kurima Machiya-cho, Tsu, Mie 514-8507, Japan
  • Erica Morita
    Division of Chemistry for Materials, Graduate School of Engineering, Mie University, 1577 Kurima Machiya-cho, Tsu, Mie 514-8507, Japan
  • Ryohei Takakura
    Division of Chemistry for Materials, Graduate School of Engineering, Mie University, 1577 Kurima Machiya-cho, Tsu, Mie 514-8507, Japan
  • Hiroto Nakajima
    Division of Chemistry for Materials, Graduate School of Engineering, Mie University, 1577 Kurima Machiya-cho, Tsu, Mie 514-8507, Japan
  • Takahiro Uno
    Division of Chemistry for Materials, Graduate School of Engineering, Mie University, 1577 Kurima Machiya-cho, Tsu, Mie 514-8507, Japan
  • Masataka Kubo
    Division of Chemistry for Materials, Graduate School of Engineering, Mie University, 1577 Kurima Machiya-cho, Tsu, Mie 514-8507, Japan
  • Norimitsu Tohnai
    Department of Material and Life Science, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan
  • Mikiji Miyata
    Department of Material and Life Science, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan

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Description

7,7,8,8-Tetrakis(aryloxycarbonyl)-p-quinodimethanes with bulky aryloxy groups such as benzyloxy (1a), pentafluorobenzyloxy (1b), and both benzyloxy and pentafluorobenzyloxy (1c) were synthesized. We investigated effects of these bulky groups on thermal solid-state polymerization reactivities on the basis of crystal structures of 1a–1c. Thermal polymerizations gave 1,6-trans-type stereoregular polymers in quantitative yields in 1 day at 110 °C for 1a, 1 day at 150 °C for 1b, and 6 days at 110 °C for 1c. Their initial crystal shapes were retained in appearance during polymerization to yield solid bundle assemblies of their polymeric chains. X-ray single-crystal structure analysis indicates that their crystals adopt molecular arrangements suitable for one-dimensional polymerization with the 1,6-trans-type addition along one crystallographic axis. Such arrangements led to expansion polymerization of 1b and contraction one of 1c. The resulting stereoregular polymers form less ordered bundle assemblies than tho...

Journal

  • Macromolecules

    Macromolecules 49 (13), 4802-4816, 2016-06-23

    American Chemical Society (ACS)

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