Efficient RAFT polymerization of N-(3-aminopropyl)methacrylamide hydrochloride using unprotected “clickable” chain transfer agents

The reversible addition fragmentation chain transfer (RAFT) of N-(3-aminopropyl)methacrylamide hydrochloride (APMA) using unprotected “clickable” chain transfer agents in water/dioxane mixtures is reported. The controlled character of the polymerization was confirmed by the linear increase of the polymer molecular weight with monomer conversion, the narrow molecular weight distribution (Р⩽ 1.1) and by chain extension experiments. The alkyne-terminated PAPMA was further functionalized by “click” chemistry with an azido-functionalized coumarin derivative. The method reported here will be useful for the preparation of novel PAPMA based materials for biomedical applications using a strategy that does not require challenging protection/deprotection steps.