Monomers derived from glucose, xylose and galactose, which contain an endocyclic alkene (in the sugar ring) and a terminal alkyne, underwent a cascade polymerization to prepare new polymers with the ring-opened sugar incorporated into the polymer backbone. Polymerizations were well-controlled, as demonstrated by a linear increase in molecular weight with monomer-to-initiator ratio and generally narrow molecular weight dispersity values. The living nature of the polymerization was supported by the preparation of a block copolymer from two different sugar-based monomers. The resulting polymers were also fully degradable. They underwent fast and complete depolymerization to small molecules under acidic conditions.Furthermore, by tuning the type of acid-sensitive linkage (hemi-aminal ether, acetal, or ether functional groups), we could change the degradation profile of the polymer and the identity of the resulting degradation products. For instance, the large difference in degradation rates between hemi-aminal ether and ether-based polymers enabled the sequential degradation of a block copolymer.

Controlled living cascade polymerization to make fully degradable sugar-based polymers

ACS Spring 2022

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