Synthesis of polymeric organic semiconductors using semifluorinated polymer precursors |
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Authors: | Nathan R. Paisley Christopher M. Tonge Ethan R. Sauvé Sarah V. Halldorson Zachary M. Hudson |
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Affiliation: | Department of Chemistry, The University of British Columbia, Vancouver, British Columbia, V6T 1Z1 Canada |
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Abstract: | The transesterification of 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA) homopolymers and block copolymers with methyl acrylate (MA) or n-butyl acrylate (n-BuA) were investigated for the efficient synthesis of p-type and n-type organic semiconductor acrylates. HFIPA, MA, and n-BuA are readily prepared in a one-pot synthesis by Cu(0) reversible deactivation radical polymerization in high yield with low dispersity to give poly(HFIPA)100, PMA100-b-poly(HFIPA)x, and PnBuA100-b-poly(HFIPA)x (x = 100, 50,25). The transesterification of poly(HFIPA)100 was also studied using 19F NMR spectroscopy. Based on this method, a series of eight homopolymers and three copolymers based on semiconductor motifs commonly found in organic light-emitting diodes, organic thin-film transistors, and organic photovoltaics were synthesized with narrow dispersity and conversions up to 99%. These experiments demonstrate that poly(HFIPA) can provide a useful building block in the synthesis of organic electronic materials, providing a simpler route to complex materials which may be challenging to access directly via controlled radical polymerization. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018 , 56, 2183–2191 |
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Keywords: | donor–acceptor polymer organic electronics post-polymerization functionalization reactive polymer transesterification |
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