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.
Highlights
Cationic polyelectrolytes find various bio-relevant applications due to their ability to interact with oppositely charged biomolecules
We have recently shown that selenium atoms appended to a polymer chain can be transformed into a cation to afford the first known family of selenonium polyelectrolytes [1]
Initially, an optimization study was carried out using atom transfer radically prepared [15] poly(glycidyl methacrylate) homopolymer 1 (Mw(GPC) = 41,900, Mn(GPC) = 36,400, Mw /Mn = 1.1) and benzeneselenol 2 (Scheme 1) [16]
Summary
Cationic polyelectrolytes find various bio-relevant applications due to their ability to interact with oppositely charged biomolecules. We have recently shown that selenium atoms appended to a polymer chain can be transformed into a cation to afford the first known family of selenonium polyelectrolytes [1]. Initially, an optimization study was carried out using atom transfer radically prepared [15] poly(glycidyl methacrylate) homopolymer 1 (Mw(GPC) = 41,900, Mn(GPC) = 36,400, Mw /Mn = 1.1) and benzeneselenol 2 (Scheme 1) [16]. Base-catalyzed ring-opening of side-chain epoxides in poly(glycidyl methacrylate)s through selenium-epoxy reaction.
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