Synthesis and Characterization of Isomeric Vinyl-1,2,3-triazole Materials by Azide-Alkyne Click Chemistry.

graphical abstract
Nulwala, H.; Takizawa, K.; Odukale, A.; Khan, A.; Thibault, R.J.; Taft, B.R.; Lipshutz, B.H.; Hawker, C.J.
Macromolecules,
2009
42, 6068-6074.

The synthesis of isomeric, functionalized 4-vinyl-1,2,3-triazole and 5-vinyl-1,2,3-triazole monomers is demonstrated using heterogeneous copper (copper-in-charcoal)-catalyzed azide−alkyne cycloaddition (CuAAC) or homogeneous ruthenium (Ru)-catalyzed azide−alkyne cycloadditions (RuAAC) “click” protocols. These reactions are regiospecific, exclusively forming 1,4- and 1,5-disubstituted triazoles as determined by 1H NMR, 13C NMR, and X-ray crystallography analysis. Polymerizations were performed using living free radical procedures to yield materials with divergent properties. In the case of the 1,5-triazole materials, glass transition temperature were significantly higher that for the 1,4-derivatives while solubility was decreased.