Premium
Preparation of Stereoregular Isotactic Poly(mandelic acid) through Organocatalytic Ring‐Opening Polymerization of a Cyclic O ‐Carboxyanhydride
Author(s) -
Buchard Antoine,
Carbery David R.,
Davidson Matthew G.,
Ivanova Petya K.,
Jeffery Ben J.,
KociokKöhn Gabriele I.,
Lowe John P.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201407525
Subject(s) - dispersity , mandelic acid , tacticity , polymerization , polymer chemistry , polymer , polystyrene , ring opening polymerization , materials science , glass transition , pyridine , chemistry , organic chemistry
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 ( man OCA). 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.