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Synthesis and characterization of poly(phenylacetylenes) featuring activated ester side groups

Authors

  • Anja C. Pauly,

    1. Institute of Organic Chemistry, University of Mainz, Duesbergweg 10-14, D-55099 Mainz, Germany
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  • Patrick Theato

    Corresponding author
    1. Institute of Organic Chemistry, University of Mainz, Duesbergweg 10-14, D-55099 Mainz, Germany
    2. World Class University (WCU) Program of Chemical Convergence for Energy & Environment (C2E2), School of Chemical and Biological Engineering, College of Engineering Seoul National University (SNU), Seoul, Korea
    • Institute of Organic Chemistry, University of Mainz, Duesbergweg 10-14, D-55099 Mainz, Germany
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Abstract

Four monomers based on 4-ethynylbenzoic acid have been synthesized, one of those featuring an activated ester. With the metathesis catalytic system WCl6/Ph4Sn, these acetylenic monomers could successfully be polymerized yielding conjugated polymers with molecular weights of around 10,000 to 15,000 g/mol and molecular weight distributions Mw/Mn ≤ 2.1. Also the copolymerization of phenylacetylene or methyl 4-ethynylbenzoate with pentafluorophenyl 4-ethynylbenzoate as reactive unit was conducted. Polymer analogous reactions of the reactive polymers and copolymers with amines have been investigated and it was found that poly(pentafluorophenyl 4-ethynylbenzoate) featured a significant reactivity, such that reactions proceeded quantitatively even with aromatic amines. Moreover the UV-Vis spectra of the activated ester based polymer before and after conversion with aliphatic amines showed a change, indicating an effect on the conjugated backbone of the polymers. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2010

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