Journal of the American Chemical Society 2013-05-08

Synthesis of atactic and isotactic poly(1,2-glycerol carbonate)s: degradable polymers for biomedical and pharmaceutical applications.

Heng Zhang, Mark W Grinstaff

Index: J. Am. Chem. Soc. 135(18) , 6806-9, (2013)

Full Text: HTML

Abstract

The synthesis and characterization of atactic and isotactic linear poly(benzyl 1,2-glycerol carbonate)s are reported. The poly(benzyl 1,2-glycerol carbonate)s were obtained via the ring-opening copolymerization of rac-/(R)-benzyl glycidyl ether with CO2 using [SalcyCo(III)X] complexes with high carbonate linkage selectivity and polymer/cyclic carbonate selectivity (>99%). Deprotection of the resultant polymers afforded poly(1,2-glycerol carbonate)s with a functionalizable pendant primary hydroxyl group. Poly(1,2-glycerol carbonate) showed a remarkable increase in degradation rate compared to poly(1,3-glycerol carbonate) with a t1/2 ≈ 2-3 days. These polymers fulfill an unmet need for a readily degradable biocompatible polycarbonate.