Introducing the aza-Michael addition reaction between acrylate and dihydropyrimidin-2(1H)-thione into polymer chemistry

Abstract

The preparation of polymers via multicomponent reactions (MCRs) is a rapidly growing branch in polymer chemistry; exploiting new polymers on the basis of the reactivity of multicomponent structures is critical for this field. Here, we develop methodologies for preparing polymers by using the efficient and clean aza-Michael addition reaction between acrylate and dihydropyrimidin-2(1H)-thione (DHPMT) that can be simply produced by the Biginelli reaction. Polyesters have been rapidly prepared through AB and A2 + B2 step-growth polymerization. Hydrophobic polymers with DHPMT groups in the main or side chain were highly efficiently modified to produce hydrophilic polymers. Fluorescent polyethylene glycol was facilely prepared by nearly 100% modification of the chain-end DHPMT group with a pyrene group. These findings demonstrated that the acrylate–DHPMT addition reaction is a reliable tool for fabricating polymers through different synthesis routes, which opens new opportunities for fabricating different functional polymers and may prompt thorough studies on MCRs in polymer chemistry.