Selenonium Polyelectrolyte Synthesis through Post-Polymerization Modifications of Poly (Glycidyl Methacrylate) Scaffolds

Abstract

Atom transfer radical polymerization of glycidyl methacrylate monomer with poly(ethylene glycol)-based macroinitiators leads to the formation of reactive block copolymers. The epoxide side-chains of these polymers can be subjected to a regiospecific base-catalyzed nucleophilic ring-opening reaction with benzeneselenol under ambient conditions. The ß-hydroxy selenide linkages thus formed can be alkylated to access polyselenonium salts. 77Se-NMR indicates the formation of diastereomers upon alkylation. In such a manner, sequential post-polymerization modifications of poly(glycidyl methacrylate) scaffolds via selenium-epoxy and selenoether alkylation reactions furnish practical access to poly(ethylene glycol)-based cationic organoselenium copolymers.

Keywords

• selenium-epoxy reaction
• polyselenonium salts
• organoselenium polymers
• epoxide ring-opening reaction
• poly(glycidyl methacrylate)s