Polymer brushes based on N-methacryloxysuccinimide as platform for versatile post-polymerization modification

In this contribution we present a method for the surface-initiated atom-transfer radical polymerization of active esters based on N-methacryloxysuccinimide and post-polymerization modification in mild conditions. The obtained active ester brushes show quantitative conversion under amidation conditions with various primary amines, including 1-amino-2-propanol, fluorine containing amines and amine-containing fluorophores. Amidation reaction with propargyl amine offers the possibility to introduce a second functionality in the homopolymer brushes. This widens the ability of polymer analogous reactions with functionalized compounds. The effectiveness of the amidation reaction was deeply studied utilizing spectroscopic ellipsometry, infrared reflection-absorption and X-ray photoelectron spectroscopies, contact angle goniometry and surface energy analysis. As validated by functionalized homopolymer brushes, hierarchical block copolymer brushes containing active ester monomer units also undergo quantitative conversion with primary amines. Furthermore, resulting polymer brushes containing fluorophores were studied by fluorescent microscopy to further investigate their film structure and homogeneity.