5-Methyl-5-propargyloxycarbonyl-1,3-dioxane-2-one is an alkyne-functionalized, cyclic carbonate monomer that can be polymerized or copolymerized to yield alkyne-functionalized polycarbonates. The incorporation of alkynes allows for rapid post-polymerization modification through reactions, such as copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) or thiol-yne click reactions. These reactions are highly preferable for functionalization due their high efficiency and the ability to easily install the corresponding functionality (e.g., azides or thiols) onto the biomolecule or small molecule of interest.
Chemical communications (Cambridge, England), (1), 114-116 (2008-04-11)
Cyclic carbonate monomers based on a single biocompatible scaffold allow for incorporation of a wide range of functional groups into macromolecules via ring-opening polymerization.
Organocatalytic synthesis and post-polymerization functionalization of propargyl-functional poly(carbonate)s.
Journal of the American Chemical Society, 132(42), 14724-14726 (2010-10-05)
An improved two-step synthetic route to functionalized cyclic carbonate monomers that features a novel cyclic carbonate intermediate with an active pentafluorophenyl ester group (MTC-OPhF(5)) has been developed. The versatile pentafluorophenyl ester intermediate can be synthesized on the gram to kilogram
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