Supramolecular Control of a Fast and Reversible Diels−Alder Reaction

A new cyclophane featuring two opposite anthracene units linked in 9,10-positions has been synthesized thanks to the template effect of the Me4N+ ion. It forms pseudorotaxane complexes with alkylviologen ions and undergoes a fast and reversible reaction with tetracyanoethylene. A quantitative analysis has been carried out of the formation of Diels−Alder adducts, whose distribution can be controlled by host−guest complexation. These findings open interesting perspectives in the field of Dynamic Covalent Chemistry.