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Issue 44, 2019
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Preferential binding of unsaturated hydrocarbons in aryl-bisimidazolium·cucurbit[8]uril complexes furbishes evidence for small-molecule π–π interactions

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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 ≤ 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 π–π interactions.

Graphical abstract: Preferential binding of unsaturated hydrocarbons in aryl-bisimidazolium·cucurbit[8]uril complexes furbishes evidence for small-molecule π–π interactions

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Publication details

The article was received on 03 Jul 2019, accepted on 07 Oct 2019 and first published on 17 Oct 2019


Article type: Edge Article
DOI: 10.1039/C9SC03282G
Chem. Sci., 2019,10, 10240-10246
  • Open access: Creative Commons BY license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Preferential binding of unsaturated hydrocarbons in aryl-bisimidazolium·cucurbit[8]uril complexes furbishes evidence for small-molecule π–π interactions

    S. J. Barrow, K. I. Assaf, A. Palma, W. M. Nau and O. A. Scherman, Chem. Sci., 2019, 10, 10240
    DOI: 10.1039/C9SC03282G

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