Cucurbit[n]urils (CB[n]) are pumpkin-shaped, water soluble molecular containers which have a hydrophobic cavity and two hydrophilic carbonylated portals. In this study, we determined the relative affinities of a series of hydrocarbons for the cavity formed by the inner wall of Cucurbit[8]uril (CB[8]) and a tolyl unit linked to an auxiliary guest. The auxiliary guest is tagged with a trifluoromethyl group for quantification by 19F NMR spectroscopy. The CB[8]/probe pair was selective for cyclic hydrocarbons (cycloheptene and cyclooctatetraene ,in particular). To the contrary, the affinity of benzene was approximately 450 times weaker than cycloheptene. Therefore, we conclude that unlike π−π interactions, CH−π interactions, as well as differences in hydrocarbon solvation, contribute significantly to the recognition process.

Hydrocarbon sensing with cucurbit[8]uril and an auxiliary probe

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

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