Study of the Counter Anions in the Host-Guest Chemistry of Cucurbit[8]uril and 1-Ethyl-1′-benzyl-4,4′-bipyridinium

Abstract

A series of 1-ethyl-1′-benzyl-4,4′-bipyridinium compounds with different counter anions (BEV-X ₂, where the X is Cl, Br, I, PF ₆, ClO ₄) were synthesized. By using of NMR, MS, electrochemistry, Na ₂S ₂O ₄-induced redox chemistry, and UV-Vis, the role of the different counter anions in the host-guest chemistry of cucurbit[8]uril (CB[8]) was studied for the first time. The result demonstrated that BEV-X ₂ can form a 1 : 1 host-guest complex with CB[8] in water. Theoretical calculation further suggested that the viologen region was threaded through the cavity of CB[8], while the corresponding counter anions were located outside the cavity. Some difference can be observed on UV-Vis titration and Na ₂S ₂O ₄-induced redox chemistry, which showed that the counter anions have some effect on the host-guest chemistry. All these provide new insights into CB[8] host-guest system.