Controlling the Reactivity of the Se-Se Bond by the Supramolecular Chemistry of Cucurbituril

We describe a new strategy to control the reactivity of SeSe bond by using supramolecular chemistry of cucurbituril. We have demonstrated that selenocystamine (SeCy) and cucurbit[6]uril (CB[6]) can form a stable supramolecular complex (K-a=5.5x10(6)M(-1)). Before complexation, the free SeSe bond in SeCy is rather sensitive to redox stimuli and gets disrupted quickly with addition of reductant or oxidant. However, after binding with CB[6], the SeSe bond becomes quite inert and hardly reacts with reductant or oxidant. One advantage of this supramolecular protection is that it can be applied in a wide pH range from weakly acidic to basic. Additionally, the supramolecular complex formed by SeCy and CB[6] can be reversibly dissociated simply with addition of Ba2+.