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Macromolecules. 2011 Apr 26;44(8):2660-2667.

A Versatile Monomer for Preparing Well-Defined Functional Polycarbonates and Poly(ester-carbonates).

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  • 1Department of Orthopedics and Physical Rehabilitation, Department of Cell Biology, University of Massachusetts Medical School, 55 Lake Avenue North, Worcester, MA 01655, USA.

Abstract

Despite the increasing demands for functional degradable biomaterials, strategies for generating materials with modular compositions and well-defined functionalities from common building blocks are still lacking. Here we report an azido-functionalized cyclic carbonate monomer, AzDXO, that exhibited controlled/"living" ring-opening polymerization kinetics under the catalysis of 1,8-diazabicyclo[5.4.0]-undec-7-ene. Homopolymerization of AzDXO and copolymerization of AzDXO with lactide resulted in polycarbonate and poly(ester-carbonates) with well-defined composition and narrow polydispersity. Further side-chain functionalizations of these polymers were accomplished under facile conditions via copper-catalyzed or copper-free strain-promoted azido-alkyne cyclcoaddition. This versatile monomer building block, obtainable in two steps without tedious purifications, provides a practical solution to the preparation of well-defined functional polycarbonates and poly(ester-carbonates).

PMID:
21686053
PMCID:
PMC3115654
DOI:
10.1021/ma200021m
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