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Preferential binding of unsaturated hydrocarbons in aryl-bisimidazolium·cucurbit[8]uril complexes furbishes evidence for small-molecule \(\Pi-\Pi\) interactions

Barrow, Steven J., Assaf, Khaleel I., Palma, Aniello, Nau, Werner M., Scherman, Oren A. (2019) Preferential binding of unsaturated hydrocarbons in aryl-bisimidazolium·cucurbit[8]uril complexes furbishes evidence for small-molecule \(\Pi-\Pi\) interactions. Chemical Science, 10 (44). pp. 10240-10246. ISSN 2041-6520. (doi:10.1039/C9SC03282G)

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Abstract

Whilst cucurbit[n]urils (CBn) have been utilized in gas encapsulation, only the smaller CBn (n = 5 and 6) have utility given their small cavity size. In this work, we demonstrate that the large cavity of CB8 can be tailored for gaseous and volatile hydrocarbon encapsulation by restricting its internal cavity size with auxiliary aryl-bisimidazolium (Bis, aryl = phenyl, naphthyl, and biphenyl) guests. The binding constants for light hydrocarbons \(C \le 4\) are similar to those measured with CB6, while larger values are obtained with Bis·CB8 for larger guests. A clear propensity for higher affinities of alkenes relative to alkanes is observed, most pronounced with the largest delocalized naphthalene residue in the auxiliary Bis guest, which provides unique evidence for sizable small-molecule \(\Pi-\Pi\) interactions.

Item Type: Article
DOI/Identification number: 10.1039/C9SC03282G
Divisions: Faculties > Sciences > School of Physical Sciences > Functional Materials Group
Depositing User: Aniello Palma
Date Deposited: 09 Dec 2019 14:13 UTC
Last Modified: 10 Dec 2019 09:25 UTC
Resource URI: https://kar.kent.ac.uk/id/eprint/79238 (The current URI for this page, for reference purposes)
Palma, Aniello: https://orcid.org/0000-0001-9626-4390
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