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Synthesis of end-functionalized poly(phenylacetylene)s with well-characterized palladium catalysts

Authors

  • Masashi Shiotsuki,

    Corresponding author
    1. Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura Campus, Nishikyo-ku, Kyoto 615-8510, Japan
    • Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura Campus, Nishikyo-ku, Kyoto 615-8510, Japan
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  • Atsushi Nakagawa,

    1. Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura Campus, Nishikyo-ku, Kyoto 615-8510, Japan
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  • Jesus Rodriguez Castañon,

    1. Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura Campus, Nishikyo-ku, Kyoto 615-8510, Japan
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  • Naoya Onishi,

    1. Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura Campus, Nishikyo-ku, Kyoto 615-8510, Japan
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  • Tatsurou Kobayashi,

    1. Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura Campus, Nishikyo-ku, Kyoto 615-8510, Japan
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  • Fumio Sanda,

    1. Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura Campus, Nishikyo-ku, Kyoto 615-8510, Japan
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  • Toshio Masuda

    1. Department of Environmental and Biological Chemistry, Faculty of Engineering, Fukui University of Technology, 3-6-1 Gakuen, Fukui 910-8505, Japan
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Abstract

End-functionalized poly(phenylacetylene)s were synthesized by the polymerization of phenylacetylene (PA) using the well-defined palladium catalysts represented as [(dppf)PdBr(R)] {dppf = 1,1′-bis(diphenylphosphino)ferrocene}. The Pd catalysts having a series of R groups such as o-tolyl, mesityl, C(Ph)[DOUBLE BOND]CPh2, C6H4-o-CH2OH, C6H4-p-CN, and C6H4-p-NO2 in conjunction with silver triflate polymerized PA to give end-functionalized poly(PA)s bearing the corresponding R groups in high yields. The results of IR and NMR spectroscopies and MALDI-TOF mass analyses proved the introduction of these R groups at one end of each polymer chain. The poly(PA) bearing a hydroxy end group was applied as a macroinitiator to the synthesis of a block copolymer composed of poly(PA) and poly(β-propiolactone) moieties. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2010

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