Journal
POLYMER CHEMISTRY
Volume 3, Issue 4, Pages 1007-1015Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2py00565d
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Funding
- Research Foundation-Flanders (FWO)
- Belgian State, Prime Minister's office
- P2M ESF
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A conceptual proof for the double modification (aminolysis and subsequent thiol-click modification) of thiolactone units, incorporated in linear polymer scaffolds, was elaborated. These polymers were prepared by either reversible addition-fragmentation chain transfer (RAFT) or nitroxide mediated radical polymerization (NMP) starting from a stable, readily available styrenic thiolactone monomer (St-TLa). Successful copolymerization of the latter with styrene (St) or methyl methacrylate (MMA) yielded linear polymers with varying thiolactone content (4-25%). Upon amine treatment, the ring-opening of the pendent thiolactones resulted in the formation of linear polythiols. Reaction conditions were optimized to avoid cross-linking via disulfide formation, thus preserving the linear nature of the polymer. Different primary amines (propylamine, benzylamine, ethanolamine and Jeffamine M-1000) were attached to the polymer backbone, while the PDIs remained low. The resulting polythiols are versatile scaffolds for further modification by various thiol-click reactions. In this respect, thiolmaleimide conjugation was used as a model reaction. NMR- and SEC-analyses revealed a near-quantitative double modification of thiolactone containing polystyrene (PS) and poly(methylmethacrylate) (PMMA) by subsequent treatment with propylamine and N-benzylmaleimide.
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