1. June 2020

Autocatalysis in the Room Temperature Copper(I)-Catalyzed Alkyne–Azide “Click” Cycloaddition of Multivalent Poly(acrylate)s and Poly(isobutylene)s.

Döhler, D., et al. Macromolecules 2012, 45 (8), 3335-3345, DOI:

We investigate autocatalytic effects in cross-linking processes based on the copper(I)-catalyzed alkyne-azide “click” cycloaddition reaction (CuAAC), taking advantage of the 1,3-triazole rings formed during the CuAAC-based cross-linking, which act as ligands for subsequent “click”-reactions in turn accelerating the reaction rate of subsequent CuAAC-reactions. Multivalent polymeric alkynes and azides (random poly(propargyl acrylate-co-n-butyl acrylate)s, Mn = 7000-23400 g/mol) were prepared via nitroxide mediated polymerization (NMP). The now designable significant autocatalytic effects together with the optimized reaction rate via the lowest molecular weight compounds enabled the design of a new, highly efficient and fast cross-linking system acting at room temperature. Reproduced with permission. Copyright 2012©, American Chemical Society.