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

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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 - 31 Oct 2014

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Polymerization
Polymers
Transition Temperature
Polystyrenes
Glass
Molecular Weight
Temperature
mandelic acid
pyridine
poly(lactic acid)

Cite this

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title = "Preparation of stereoregular isotactic poly(mandelic acid) through organocatalytic ring-opening polymerization of a cyclic O-carboxyanhydride",
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.",
author = "Antoine Buchard and Carbery, {David R} and Davidson, {Matthew G} and Ivanova, {Petya K} and Jeffery, {Ben J} and Gabriele Kociok-K{\"o}hn and Lowe, {John P}",
year = "2014",
month = "10",
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doi = "10.1002/anie.201407525",
language = "English",
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TY - JOUR

T1 - Preparation of stereoregular isotactic poly(mandelic acid) through organocatalytic ring-opening polymerization of a cyclic O-carboxyanhydride

AU - Buchard, Antoine

AU - Carbery, David R

AU - Davidson, Matthew G

AU - Ivanova, Petya K

AU - Jeffery, Ben J

AU - Kociok-Köhn, Gabriele

AU - Lowe, John P

PY - 2014/10/31

Y1 - 2014/10/31

N2 - 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.

AB - 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.

U2 - 10.1002/anie.201407525

DO - 10.1002/anie.201407525

M3 - Article

VL - 53

SP - 13858

EP - 13861

JO - Angewandte Chemie-International Edition

JF - Angewandte Chemie-International Edition

SN - 1433-7851

IS - 50

ER -