Self-Inclusion and Dissociation of a Bridging β-Cyclodextrin Triplet

To understand the self-inclusion and the dissociation in a branched β-cyclodextrin (CD) system, we designed and synthesized a β-CD trimer in which each CD group is connected to one of bridging arms of a planar triphenylbenzene core through a CuAAC click reaction. Only one rather than two or all of the three host CDs was demonstrated to be in a self-including state in water, while no self-inclusion was observed to occur in dimethylsulfoxide (DMSO) via the characterization of ¹H and NOESY NMR spectra. The configuration structures of the CD groups in the self-included state were evaluated, and the dissociation to free state in water was investigated under various conditions like heating, increased acidity, and discharging versus the addition of competitive guests. While raised temperature and increased acidity did not break the self-inclusion, two adamantane guest molecules were found to show capability in driving the equilibrium to get back to free state against the self-inclusion. The inclusion process of the added guests was believed to involve in the dissociation of the self-inclusion and the occupation of the guests in CD cavity. The results of host-guest interaction study indicated that the stable combination of guests was favorable for blocking the structural overturning of glucose toward trapping the bridging group into the cavity.