Triangular Regulation of Cucurbit[8]uril 1:1 Complexes

Journal of the American Chemical Society
Sébastien CombesOlivier Ouari

Abstract

Triangular shapes have inspired scientists over time and are common in nature, such as the flower petals of oxalis triangularis, the triangular faces of tetrahedrite crystals, and the icosahedron faces of virus capsids. Supramolecular chemistry has enabled the construction of triangular assemblies, many of which possess functional features. Among these structures, cucurbiturils have been used to build supramolecular triangles, and we recently reported paramagnetic cucurbit[8]uril (CB[8]) triangles, but the reasons for their formation remain unclear. Several parameters have now been identified to explain their formation. At first sight, the radical nature of the guest was of prime importance in obtaining the triangles, and we focused on extending this concept to biradicals to get supramolecular hexaradicals. Two sodium ions were systematically observed by ESI-MS in trimer structures, and the presence of Na+ triggered or strengthened the triangulation of CB[8]/guest 1:1 complexes in solution. X-ray crystallography and molecular modeling have allowed the proposal of two plausible sites of residence for the two sodium cations. We then found that a diamagnetic guest with an H-bond acceptor function is equally good at forming CB[8] t...Continue Reading

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Citations

Dec 12, 2019·Chemical Communications : Chem Comm·Francesca GuagniniPeter B Crowley
Feb 15, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Fengbo LiuDavid Bardelang
Feb 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Elena V Zaytseva, Dmitrii G Mazhukin
Jan 11, 2021·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Xinyi ZhuChao Zhang
Apr 15, 2021·Organic Letters·Fengbo LiuDavid Bardelang
Aug 24, 2019·The Journal of Organic Chemistry·Hikaru HashimotoWataru Setaka

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