Supramolecular catalysis is a promising area of study. Host-guest systems that use noncovalent bonds to fine-tune catalyst/substrate interactions are unique. Typically the substrate is a guest for the host and the reaction is accelerated by increasing the effective concentration or stabilizing the transition state. Unfortunately, the product is often a superior guest which results in product inhibition. Here we detail an alternative strategy where the bound guest is an organocatalyst in a deep cavitand. The cavitand contains an azobenzene wall that adopts an introverted shape when irradiated with UV light. This invaginated conformation has been characterized in solution and the solid state   and is used to control guest binding. By incorporating an organocatalyst guest, the rate of the Knoevenagel condensation is controlled with light.

Supramolecular catalysis with a light-responsive cavitand

243rd National Meeting (2012)

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