Stability and utility of pyridyl disulfide functionality in RAFT and conventional radical polymerizations |
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| Authors: | Cyrille Boyer Jingquan Liu Lingjiun Wong Michael Tippett Volga Bulmus Thomas P Davis |
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| Institution: | 1. Centre for Advanced Macromolecular Design (CAMD), School of Chemical Sciences and Engineering, The University of NSW, Sydney, New South Wales 2052, Australia;2. Centre for Advanced Macromolecular Design (CAMD), School of Biotechnology and Biomolecular Sciences, The University of NSW, Sydney, New South Wales 2052, Australia |
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| Abstract: | Two RAFT agents, suitable for inducing living radical polymerization in water, have been synthesized. Both RAFT agents were shown to be effective over the temperature range 25–70 °C. One RAFT agent was functionalized with a pyridyl disulfide group. RAFT efficacy was demonstrated for the polymerizations of N‐isopropyl acrylamide (NIPAAM) and poly(ethylene oxide)‐acrylate (PEG‐A) in both water and acetonitrile. The kinetic data indicates that the pyridyl disulfide functionality is largely benign in free radical polymerizations, remaining intact for subsequent reaction with thiol groups. This result was confirmed by studying conventional radical polymerizations in the presence of hydroxyethyl pyridyl disulfide. The utility of the pyridyl disulfide functionality at the terminus of the polymers was demonstrated by synthesizing polymer‐BSA conjugates. © 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 7207–7224, 2008 |
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| Keywords: | bioconjugation chemical modification conjugated polymers functionalization of polymers radical polymerization reversible addition fragmentation chain transfer (RAFT) |
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