Poly(mandelic acid) (PMA) is an aryl analogue of poly(lactic acid) (PLA) and a biodegradable analogue of polystyrene. The preparation of stereoregular PMA was realized using a pyridine/mandelic acid adduct (Py⋅MA) as an organocatalyst for the ring-opening polymerization (ROP) of the cyclic O-carboxyanhydride (manOCA). Polymers with a narrow polydispersity index and excellent molecular-weight control were prepared at ambient temperature. These highly isotactic chiral polymers exhibit an enhancement of the glass-transition temperature (Tg ) of 15 °C compared to the racemic polymer, suggesting potential future application as high-performance commodity and biomedical materials.
Buchard, A., Carbery, D. R., Davidson, M. G., Ivanova, P. K., Jeffery, B. J., Kociok-Köhn, G., & Lowe, J. P. (2014). Preparation of stereoregular isotactic poly(mandelic acid) through organocatalytic ring-opening polymerization of a cyclic O-carboxyanhydride. Angewandte Chemie-International Edition, 53(50), 13858-13861. https://doi.org/10.1002/anie.201407525