Selenolactone as a Building Block toward Dynamic Diselenide-Containing Polymer Architectures with Controllable Topology.

Abstract

A versatile protocol for the synthesis of a variety of multiresponsive diselenide-containing polymeric architectures was investigated. It consists of a one-pot, two-step process with the generation of a selenol by in situ nucleophilic ring opening of selenolactone with a broad range of amine-containing structures, followed by the transformation of the obtained compounds to the corresponding diselenide through a spontaneous oxidation coupling reaction. After elaboration of this one-pot reaction, a number of routes based on selenolactones have been developed for the successful synthesis of functional, linear, branched, cyclic, and cross-linked polymers via a mild, straightforward process. Moreover, the polymer end groups can be easily modified by changing the ratio of amine and selenolactone or sequential Michael addition of selenol to the methacrylic ester. At last, the self-healing properties of the diselenide-containing networks were determined by exposing a cut sample of the polymer to UV light.