RAFT polymer end-group modification and chain coupling/conjugation via disulfide bonds

Cyrille Boyer, Jingquan Liu, Volga Bulmus, Thomas Paul Davis

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85 Citations (Scopus)

Abstract

End-group modification of polymers prepared by reversible additionfragmentation chain transfer (RAFT) polymerization was accomplished by the conversion of trithiocarbonate or dithioester end-groups into a pyridyl disulfide (PDS) functionality. Several different polymers, such as poly(methyl methacrylate), polystyrene, poly(oligoethylene glycol-acrylate), poly(hydroxypropylacrylamide), and poly(N-isopropylacrylamide) were prepared by RAFT polymerization, and subjected to aminolysis in the presence of 2,2 -dithiodipyridine to yield thiol-terminated polymers with yields in the range 6590 dependent on the polymer structure. Furthermore, this PDS end-group was utilized to generate higher-order architectures, such as diblock copolymers with high yields and selectively. In addition, the PDS end-groups were used for the bioconjugation of different biomolecules, such as oligonucleotides, carbohydrates, and peptides. The successful modification of well-defined polymers was confirmed by a combination of UV-vis, NMR spectroscopy, and gel permeation chromatography.
Original languageEnglish
Pages (from-to)830 - 847
Number of pages18
JournalAustralian Journal of Chemistry
Volume62
Issue number8
DOIs
Publication statusPublished - 2009
Externally publishedYes

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