4 years ago

Probing Interactions between Hydrocarbons and Auxiliary Guests inside Cucurbit[8]uril

Probing Interactions between Hydrocarbons and Auxiliary Guests inside Cucurbit[8]uril
Ramin Rabbani, Eric Masson
The affinities of 20 hydrocarbons for the cavity formed by the inner wall of cucurbit[8]uril and a tolyl unit linked to an auxiliary guest were measured in aqueous solution. Cucurbit[8]uril and the auxiliary guest, a substituted ruthenium tris(2,2′-bipyridyl) complex bearing a trifluoromethyl 19F NMR probe, displayed perfect selectivity toward cyclic hydrocarbons, and cis- and trans-decalin, in particular. Unlike π–π interactions, CH−π interactions, as well as differences in hydrocarbon solvation, contribute significantly to the recognition process.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01966

DOI: 10.1021/acs.orglett.7b01966

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