Synthesis of thermoresponsive oxazolone end-functional polymers for reactions with amines using thiol-Michael addition "click" chemistry

The Hien Ho, Martin Levere, Jean Claude Soutif, Véronique Montembault, Sagrario Pascual, Laurent Fontaine

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23 Citations (Scopus)

Abstract

Well-defined poly(N-isopropylacrylamide) (PNIPAM) polymers with an oxazolone ring at the chain end have been synthesized by combining controlled radical polymerization and thiol-Michael addition "click" chemistry. First, PNIPAM was synthesized using reversible addition-fragmentation chain transfer (RAFT) polymerization to afford polymers of controlled molecular weight and molecular weight distribution (Mn (1H NMR) = 3200 g mol -1; PDISEC = 1.05). The chain end was quantitatively converted to a thiol by aminolysis. Then, the functional monomer vinyl azlactone (VDM) was quantitatively "clicked" onto the chain end using a thiol-Michael addition reaction. The polymers were reacted with a model amine in order to demonstrate the potential of these polymers for bioconjugation.

Original languageEnglish
Pages (from-to)1258-1260
Number of pages3
JournalPolymer Chemistry
Volume2
Issue number6
DOIs
Publication statusPublished - 1 Jun 2011

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Biochemistry
  • Biomedical Engineering
  • Bioengineering

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