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 Kociok-Köhn, John P Lowe

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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 (Tg ) of 15 °C compared to the racemic polymer, suggesting potential future application as high-performance commodity and biomedical materials.
Original languageEnglish
Pages (from-to)13858-13861
Number of pages4
JournalAngewandte Chemie-International Edition
Volume53
Issue number50
Early online date14 Oct 2014
DOIs
Publication statusPublished - 2 Dec 2014

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