Highly efficient monomer and polymer synthesis using click chemistry.

摘要

In this work vinyl-triazole monomers, a new functional monomer family, were synthesized using 'click' chemistry. These new monomers possess many of the outstanding features of traditional monomers, such as styrenics, vinyl pyridines, and acrylates. These features include an aromatic core, a large dipole moment, and access to structural varieties. One of the most attractive features of vinyl-triazole based materials is the ease of functionalization for controlling polymeric properties.;The synthesis of isomeric, functionalized 4-vinyl-1,2,3-triazole and 5-vinyl-1,2,3-triazole monomers are demonstrated using copper catalyzed azide-alkyne cycloaddition (CuAAC) and ruthenium (Ru)-catalyzed azide-alkyne cycloadditions (RuAAC) protocols respectively. 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 was significantly higher that for the 1,4-derivatives while solubility was decreased. Reactivity ratios of these monomers with styrene were also evaluated.;The structures of N-vinyl monomers and polymers are limited due to a lack of viable synthetic procedures for the facile incorporation of functional groups. The orthogonal nature of click chemistry allows development of simple and versatile synthetic procedures to access functionalized N-vinyl triazoles monomers. These monomers were successfully polymerized and characterized.