Synthesis of Poly(β-hydroxyketone)s with Three-Component Polymerization of Diazocarbonyl Compounds, Triethylboron, and Aldehydes

Abstract

Three-component polymerization based on the Hooz reaction has been developed for the first time. Under mild conditions (0–40 °C, catalyst-free), the reaction of dialdehydes, bisdiazocarbonyl compounds, and trialkylboron leads to the formation of poly(β-hydroxyketone)s. The number-average molecular weight (Mn) is up to 31.2 kg mol–1, and the yield is up to 97%. The β-hydroxyketone structure in poly(β-hydroxyketone)s enables highly efficient polymer degradation under alkaline conditions, with the isolation of dialdehydes for recycling. The hydroxyl groups in the polymer also provide the possibility for postpolymerization modifications, including cross-linking, acetylation, and oxidation.

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