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Contents Vol 62(8)

RAFT Polymer End-Group Modification and Chain Coupling/Conjugation Via Disulfide Bonds

Cyrille Boyer A , Jingquan Liu A , Volga Bulmus B C and Thomas P. Davis A C
+ Author Affiliations
- Author Affiliations

A Centre for Advanced Macromolecular Design (CAMD), School of Chemical Sciences and Engineering, The University of New South Wales, Sydney, NSW 2052, Australia.

B School of Biotechnology and Biomolecular Sciences (BABS), The University of New South Wales, Sydney, NSW 2052, Australia.

C Corresponding authors. Email: t.davis@unsw.edu.au; vbulmus@unsw.edu.au

Australian Journal of Chemistry 62(8) 830-847 https://doi.org/10.1071/CH09062
Submitted: 30 January 2009  Accepted: 25 March 2009   Published: 13 August 2009

Abstract

End-group modification of polymers prepared by reversible addition–fragmentation 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 65–90% 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.


Acknowledgements

We acknowledge the Australian Research Council for the award of Discovery Grants (to V.B. and T.P.D.). In addition, we acknowledge the receipt of a Federation Fellowship (T.P.D.).


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