3-(Trimethylsilyl)propargyl methacrylate is a methacrylate-based monomer for use in the synthesis of alkyne-functionalized polymers and copolymers. 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. While alkynes offer great promise for post-polymerization functionalization, it is difficult to polymerize bifunctional, alkyne-containing monomers without the synthesis of branched or highly gelled products. 3-(Trimethylsilyl)propargyl methacrylate features a silyl-protected alkyne that can be easily deprotected post-polymerization to yield alkyne-functionalized polymers and copolymers.
Journal of the American Chemical Society, 128(14), 4823-4830 (2006-04-06)
The synthesis of novel well-defined alkyne side chain functional polymers featuring narrow molecular weight distributions (PDI = 1.09-1.17) by living radical polymerization is described. Grafting of protected and unprotected carbohydrates is achieved via either a C-6 or an anomeric azide
Clickable initiators, monomers and polymers in controlled radical polymerizations?a prospective combination in polymer science.
Mansfeld, U. et al
Polym. Chem., 1, 1560-1598 (2010)
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