Pyrogallolarene self-assembles in non-polar organic solvents to form hexamers of octahedral symmetry. Recently, our group has shown that the versatility of these capsules can be dramatically extended by inducing the self-assembly using a procedure of melting and cooling mixtures of pyrogallolarene and a desired guest under solvent-free conditions. This approach provides efficient encapsulation of many guest molecules and, remarkably, often provides kinetically trapped complexes that are indefinitely stable at room temperature and that do not form when solvent is present. Using these assembly conditions, we have carried out detailed studies on the interactions between host and guest, and have found that these interactions are strongly dependent on the guest's size, shape, and functional groups. The results reveal that an increasingly good fit of host and guest reduces the rate of guest tumbling, slows guest exchange from the capsules, and even increases the communication between host and guest. 

NMR reveals variable degrees of order inside the cavity of pyrogallolarene hexamers

243rd National Meeting (2012)

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