Force-Generated N-Heterocyclic Carbene Organocatalyst

Controlling the life cycle of polymer materials, for example, by extending their useful lifetime and by accelerating their recycling, is crucial to ensure a better future. Such properties can be introduced in an autonomous fashion with the help of force-responsive molecular devices. Mechanocatalysts make a step in this direction, as they have been shown to promote useful chemical transformations upon mechanical activation. However, most of these force-generated catalysts are built from noble metals, which precludes their wider adoption due to cost and processability constraints. Here, we demonstrate the activation, in solution and the solid state, of an N-heterocyclic carbene organocatalyst generated from a betaine mechanophore. Its activity was demonstrated in the solid state via transesterification and polymerization reactions, which are representative of potential recycling and self-healing applications. We anticipate that such metal-free, thermally stable mechanocatalysts should find applications in the control of the life cycle of polymer materials.