Measuring the strength of intermolecular bonds in supramolecular assemblies is of critical importance to understand the non-covalent interactions that occur in nature. To evaluate the magnitude of π-π interactions in the non-polar and non-polarizable environment of the Cucurbituril family of macrocycles (CB[n]), we prepared eight dibenzyl ammonium guests, and titrated them with CB[8]. <sup>1</sup>H NMR spectroscopy reveals that the 1:1 “U” shape conformation of the guest inside the cavity of CB[8] is the dominant adduct even in sub-stoichiometric amounts of the host. The binding affinity of the guests towards CB[8] were measured by isothermal titration calorimetry (ITC). Intramolecular interactions (i.e. between the aryl substituents), intermolecular ones between the guests and the inner wall of CB[8], as well as differential solvation effects will be isolated and discussed carefully.

Guest folding inside cucurbit[8]uril

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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