Well‐defined polymers with acetal side chains as reactive scaffolds synthesized by atom transfer radical polymerization

Abstract

AbstractThe synthesis of a polymer with acetal functionalized side chains, deprotection to aldehydes, and conjugation of aminooxy‐modified molecules is reported. Poly(3,3′‐diethoxypropyl methacrylate) (PDEPMA) was prepared by atom transfer radical polymerization (ATRP). Kinetic investigation of the ATRP of DEPMA from ethyl 2‐bromoisobutyrate in methanol with copper (I) bromide and 2,2′‐bipyridine (BIPY) at ambient temperature revealed a controlled polymerization. Altering the initial monomer to initiator ratios resulted in 75–93% conversion to polymers with different molecular weights and narrow molecular weight distributions (PDIs < 1.3). Reactive aldehyde groups were produced by hydrolysis of the acetals in dilute acid. Aminooxy‐functionalized oligo(ethylene glycol) and O‐(carboxymethyl)hydroxylamine were conjugated to the side chains via oxime linkages. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: 5004–5013, 2006