Ring-opening polymerization of an O-carboxyanhydride monomer derived from L-malic acid

Ryan J. Pounder; David J. Fox; Ian A. Barker; Michael J. Bennison; Andrew P. Dove

doi:10.1039/c1py00254f

Ring-opening polymerization of an O-carboxyanhydride monomer derived from L-malic acid

Ryan J. Pounder, David J. Fox, Ian A. Barker, Michael J. Bennison, Andrew P. Dove

Research output: Contribution to journal › Article › Research › peer-review

69 Citations (Scopus)

Abstract

The synthesis and ring-opening polymerization (ROP) of an O-carboxyanhydride (OCA) monomer derived from l-malic acid (l-malOCA) is reported. Application of 4-dimethylaminopyridine as catalyst led to the observation of a number of undesirable side products. Investigation of different para-substituted pyridines as catalysts identified 4-methoxypyridine to have the ideal balance of activity and selectivity to enable the controlled ROP of l-malOCA. Deprotection of the benzyl ester side groups of the resultant polymers was achieved by hydrogenolysis and the resulting hydrophilic poly(α-malic acid) was observed to fully degrade within 7 days in aqueous solution.

Original language	English
Pages (from-to)	2204-2212
Number of pages	9
Journal	Polymer Chemistry
Volume	2
Issue number	10
DOIs	https://doi.org/10.1039/c1py00254f
Publication status	Published - Oct 2011
Externally published	Yes

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abstract = "The synthesis and ring-opening polymerization (ROP) of an O-carboxyanhydride (OCA) monomer derived from l-malic acid (l-malOCA) is reported. Application of 4-dimethylaminopyridine as catalyst led to the observation of a number of undesirable side products. Investigation of different para-substituted pyridines as catalysts identified 4-methoxypyridine to have the ideal balance of activity and selectivity to enable the controlled ROP of l-malOCA. Deprotection of the benzyl ester side groups of the resultant polymers was achieved by hydrogenolysis and the resulting hydrophilic poly(α-malic acid) was observed to fully degrade within 7 days in aqueous solution.",

author = "Pounder, {Ryan J.} and Fox, {David J.} and Barker, {Ian A.} and Bennison, {Michael J.} and Dove, {Andrew P.}",

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AU - Pounder, Ryan J.

AU - Fox, David J.

AU - Barker, Ian A.

AU - Bennison, Michael J.

AU - Dove, Andrew P.

PY - 2011/10

Y1 - 2011/10

N2 - The synthesis and ring-opening polymerization (ROP) of an O-carboxyanhydride (OCA) monomer derived from l-malic acid (l-malOCA) is reported. Application of 4-dimethylaminopyridine as catalyst led to the observation of a number of undesirable side products. Investigation of different para-substituted pyridines as catalysts identified 4-methoxypyridine to have the ideal balance of activity and selectivity to enable the controlled ROP of l-malOCA. Deprotection of the benzyl ester side groups of the resultant polymers was achieved by hydrogenolysis and the resulting hydrophilic poly(α-malic acid) was observed to fully degrade within 7 days in aqueous solution.

AB - The synthesis and ring-opening polymerization (ROP) of an O-carboxyanhydride (OCA) monomer derived from l-malic acid (l-malOCA) is reported. Application of 4-dimethylaminopyridine as catalyst led to the observation of a number of undesirable side products. Investigation of different para-substituted pyridines as catalysts identified 4-methoxypyridine to have the ideal balance of activity and selectivity to enable the controlled ROP of l-malOCA. Deprotection of the benzyl ester side groups of the resultant polymers was achieved by hydrogenolysis and the resulting hydrophilic poly(α-malic acid) was observed to fully degrade within 7 days in aqueous solution.

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DO - 10.1039/c1py00254f

M3 - Article

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SN - 1759-9954

VL - 2

SP - 2204

EP - 2212

JO - Polymer Chemistry

JF - Polymer Chemistry

IS - 10

ER -

Ring-opening polymerization of an O-carboxyanhydride monomer derived from L-malic acid

Abstract

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