Nitroxide-mediated polymerisation of thioacrylates and their transformation into poly(acrylamide)s

Abstract

One long-standing challenge in polymer science is the development of transformation reactions, in which the conversion of a specific functional group to another is targeted. For this purpose, a thioester polymer consisting of thioacrylate monomers has been prepared via nitroxide-mediated polymerization and its kinetics has been studied for the first time. The copolymerization behavior of butyl thioacrylate with PFS was investigated in detail and compared to the copolymerization of butyl acrylate and PFS. Finally, a series of modification reactions were carried out using different amines and alcohols, in an attempt to transform the thioacrylate monomer into an acrylamide or acrylate, respectively. The established conditions allowed one to obtain poly(acrylamide)s via post polymerization functionalization in a versatile and efficient way, which is why this process is believed to be widely used by polymer chemists.