Reversible Complexation of Iminophenylboronates with Mono- and Dihydroxy Methacrylate Monomers and Their Polymerization at Low Temperature by Photoinduced ATRP in One Pot

Abstract

The unique ability of boronic acids to form reversible covalent linkages to 1,2- and 1,3-diols creating boronate ester rings and the pH-sensitiveness of their dissociation have stimulated the development of boron-containing polymers having phenylboronate moieties intended to be detached by competitive binding of sugars. Typically, they are synthesized by postpolymerization reactions on hydroxy-functional polymers, which cannot guarantee a quantitative functionalization, or from monomers containing the phenylboronate moiety synthesized through multiple reaction/separation/purification steps. A handy strategy for the synthesis of monomers containing an iminophenylboronate (IPB) side-chain moiety derived from glycerol monomethacrylate (GMA) or 2-hydroxyethyl methacrylate (HEMA) and their polymerization in one pot is presented, which solves these issues and is flexible enough to be extended to a variety of hydroxy-functional monomers. First, a family of IPB methacrylates was synthesized through complexation o...