Preparation of stereoregular isotactic poly(mandelic acid) through organocatalytic ring-opening polymerization of a cyclic O-carboxyanhydride

Antoine Buchard; David R Carbery; Matthew G Davidson; Petya K Ivanova; Ben J Jeffery; Gabriele I Kociok-Köhn; John P Lowe

doi:10.1002/anie.201407525

Preparation of stereoregular isotactic poly(mandelic acid) through organocatalytic ring-opening polymerization of a cyclic O-carboxyanhydride

Angew Chem Int Ed Engl. 2014 Dec 8;53(50):13858-61. doi: 10.1002/anie.201407525. Epub 2014 Oct 14.

Authors

Antoine Buchard¹, David R Carbery, Matthew G Davidson, Petya K Ivanova, Ben J Jeffery, Gabriele I Kociok-Köhn, John P Lowe

Affiliation

¹ Department of Chemistry and Centre for Sustainable Chemical Technologies, University of Bath, Bath, BA2 7AY (UK).

PMID: 25314676
DOI: 10.1002/anie.201407525

Abstract

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 (T(g)) of 15 °C compared to the racemic polymer, suggesting potential future application as high-performance commodity and biomedical materials.

Keywords: organocatalysis; poly(mandelic acid); ring-opening polymerization; stereoregular polymer; sustainable chemistry.