Use of a novel initiator for synthesis of amino-end functionalized polystyrene (NH2-PS) by atom transfer radical polymerization

Here we report a versatile new method for end-functionalizing polystyrene. In order to produce polystyrene with an amino end group, 2-(3-bromo-3-phenylpropyl)isoindoline-1,3-dione was synthesized and used as a novel initiator for ATRP. After ATRP polymerization, tri-n-butyltin hydride ((n-Bu)3SnH) reductively replace existing halogens on polymer chains by hydrogen. Finally, the phthaloyl groups on polymer backbone were cleaved by treatment with hydrazine yielding amino terminated polystyrene. A polymer with M n ≈ 10,350 and M w/M n = 1.17 was obtained. Therefore, this method allows the preparation of amino end functionalized polystyrene of narrow polydispersity with complete degree of functionalization.