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Extension of the Application of Piers-Rubinsztajn Conditions to Produce Triarylamine Pendant Dimethylsiloxane Copolymers

Authors

  • Michael J. Gretton,

    1. Department of Chemical Engineering and Applied Chemistry, University of Toronto, 200 College St., Toronto, Ontario, Canada, M5S 3E5
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  • Brett A. Kamino,

    1. Department of Chemical Engineering and Applied Chemistry, University of Toronto, 200 College St., Toronto, Ontario, Canada, M5S 3E5
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  • Timothy P. Bender

    Corresponding author
    1. Department of Chemical Engineering and Applied Chemistry, University of Toronto, 200 College St., Toronto, Ontario, Canada, M5S 3E5
    2. Department of Chemistry, University of Toronto, 80 St. George St., Toronto, Ontario, Canada, M5S 3H6
    • Department of Chemical Engineering and Applied Chemistry, University of Toronto, 200 College St., Toronto, Ontario, Canada, M5S 3E5
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Abstract

Summary: In this paper we show how the strong organic Lewis acid catalyst, tris(pentafluorophenyl)borane (B(C6F5) or BCF), can be used to facilitate the functionalization of simple polymeric silicones with a triarylamine yielding a novel class of charge transporting materials. The reaction conditions we refer to as Piers-Rubinsztajn Conditions and we have previously shown such conditions to be suitable when using phenylated silicones as precursors. In this work we found they also work successfully for a silicone oligomer as well as cocopolymers of polymethylhydridosiloxane (PMHS) and polydimethylsiloxane (PDMS) and a PMHS homopolymer, all of which are highly abundent and available in industrial quanitities. The resulting material was either a waxy solid, viscous oil or a glass. An additional “finishing” step with anisole using the same chemistry was found necessary to prevent gelation of the copolymer and homopolymer of PMHS. Even after finishing a small fraction (<5%) of Si-H groups remained in the silicones. This nonetheless provides a rapid and mild method to synthesize functional silicones and tune their physical properties, using commonly available starting materials.

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