ATRP of MIDA Boronate-Containing Monomers as a Tool for Synthesizing Linear Phenolic and Functionalized Polymers.

Abstract

Despite numerous novel polymeric materials that have been produced by incorporating boronic acid or ester groups into polymers, it remains a challenge to prepare well-defined boronate-containing polymers due to their inherent instability. Herein, we used N-methyliminodiacetic acid (MIDA) to stabilize the reactive organoboron structure. MIDA boronate-containing polymers were synthesized in a good control by initiators for continuous activator regeneration atom transfer radical polymerization (ICAR ATRP). Oxidation and Suzuki-Miyaura coupling were conducted to prepare linear phenol-containing polymers and aromatic functionalized polymers. Upon comparison of similar polymers prepared by reversible addition-fragmentation chain transfer (RAFT) polymerization, of which the chain transfer agent (CTA) end groups cause multiple undesired side reactions, the halogen end groups of polymers prepared by ATRP are nontoxic to metal catalysts and stable during the postmodifications, thus providing a more facile tool for synthesizing various functionalized polymers with great potentials in advanced materials.