4-Vinylphenyl Glycidyl Ether: Synthesis, RAFT Polymerization, and Postpolymerization Modifications with Alcohols

4-Vinylphenyl glycidyl ether (4VPGE), an epoxide-containing styrenic monomer, was synthesized and then polymerized in a controlled fashion under reversible addition–fragmentation chain-transfer (RAFT) polymerization conditions using butyl 1-phenylethyl trithiocarbonate as the chain-transfer agent. The high degree of chain-end functionalization of the produced polymers was confirmed by chain extension reactions with styrene that afforded well-defined block copolymers. Phenyl glycidyl ether was utilized as a model compound to identify the optimal reaction conditions for alcoholysis of the glycidyl moiety using BF3 as a Lewis acid catalyst, and postpolymerization modifications were subsequently carried out on the epoxide groups of poly4VPGE with a library of structurally diverse alcohols to yield a number of β-hydroxy ether-functionalized polymers.