Competition between Oxidation and Coordination in Cross-Linking of Polystyrene Copolymer Containing Catechol Groups

Abstract

In gelation chemistry, catechol groups are used as cross-linking points. Both oxidation and coordination effects of catechol were investigated for their unique features in chemistry by spectroscopic measurements. Polystyrene copolymers containing catechol groups were synthesized by free radical copolymerization of styrene and <i>N</i>-2-(3',4'-ditriethylsilyloxyphenyl)ethyl methacrylamide, and the successive deprotection reaction was catalyzed by tetra-<i>n</i>-butylammonium fluoride. The copolymer containing catechol units afforded a dual cross-linking system based on completely different coordination and oxidation chemistries, and the competing cross-linking mechanisms are discussed. These findings are useful and important for paving the way for designing a novel bioinspired artificial adhesive surface coating and curing system.