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Keywords:

  • ABC miktoarm terpolymer;
  • atom transfer radical polymerization (ATRP);
  • click chemistry;
  • monomers;
  • PtBA;
  • Passerini reaction;
  • PEG;
  • PNIPAM;
  • PS;
  • star polymers

Abstract

In this article, we demonstrate the Passerini three-component reaction as a simple, effective method for the synthesis of polymers with double functional end groups, which are key precursors for the preparation of ABC miktoarm terpolymers. Thus, via the one-step Passerini reaction of monomethoxy poly(ethylene glycol)–propionaldehyde (PEG-CHO) with 2-bromo-2-methylpropionic acid and propargyl isocyanoacetamide, the PEG chain end was simultaneously functionalized with one atom transfer radical polymerization (ATRP) initiating site and one alkynyl group. The resulting PEG(-alkynyl)-Br was then used for the synthesis of three types of miktoarm ABC terpolymers via two approaches. First, we conducted ATRP of N-isopropylacrylamide (NIPAM), then click reaction with azido-terminated polystyrene (PS-N3) or poly(tert-butyl acrylate) (PtBA-N3) and obtained two ABC miktoarm terpolymers PEG(-b-PNIPAM)-b-PS and PEG(-b-PNIPAM)-b-PtBA. Alternatively, we conducted single electron transfer living radical polymerization of tBA and click reaction with PS-N3 simultaneously to give PEG(-b-PtBA)-b-PS. All the polymer precursors and miktoarm terpolymers have been characterized by 1H NMR, Fourier transform infrared, gel permeation chromatography, demonstrating that both approaches provided well-defined ABC miktoarm terpolymers. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013