Supramolecular assemblies controlled by cucurbit[n]uril size (n=6, 7, 8 and 10)

A benzyl substituted 4-pyrrolidinopyridinium salt (G) with multiple active sites including benzyl, pyridinium and pyrrole groups has been synthesized. The interaction between G and a series of cucurbit[n]urils (TMeQ[6], Q[7], Q[8], Q[10]), has been studied both in aqueous solution and in the solid state. The binding interaction site between G and the Q[n] can be controlled by the size of the cavity of the Q[n]s. In the case of TMeQ[6], the benzyl is accommodated within the cavity, whilst for Q[7] and Q[8], the pyrrole ring and the benzyl are accommodated within the cavity of the Q[7/8], and the latter can shuttle on the guest G in a state of dynamic equilibrium. For the larger cavity of Q[10], the entire G molecule is located within the cavity of the Q[10].