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Keywords:

  • activated ester;
  • conjugated polymers;
  • copolymerization;
  • functionalization of polymers;
  • metathesis;
  • metathesis polymerization;
  • substituted poly(phenylacetylene)s

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