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.