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Triangular Regulation of Cucurbit[8]uril 1:1 Complexes
Sébastien Combes1,2; Khoa Truong Tran1; Mehmet Menaf Ayhan1,3; Hakim Karoui1; Antal Rockenbauer4,5; Alain Tonetto6; Valérie Monnier7; Laurence Charles1; Roselyne Rosas7; Stéphane Viel1,8; Didier Siri1; Paul Tordo1; Sylvain Clair9; Ruibing Wang10; David Bardelang1; Olivier Ouari1
2019-04
Source PublicationJOURNAL OF THE AMERICAN CHEMICAL SOCIETY
ISSN0002-7863
Volume141Issue:14Pages:5897-5907
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] triangles. Hence, a guest molecule containing a ketone function has been precisely triangulated thanks to CB[8] and sodium cations as determined by DOSY-NMR and DLS. A binding constant for the triangulation of 1:1 to 3:3 complexes is proposed. This concept has finally been extended to the triangulation of ditopic guests toward network formation by the reticulation of CB[8] triangles using dinitroxide biradicals.

DOI10.1021/jacs.9b00150
Indexed BySCI
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
WOS IDWOS:000464769000042
Fulltext Access
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Cited Times [WOS]:4   [WOS Record]     [Related Records in WOS]
Document TypeJournal article
CollectionInstitute of Chinese Medical Sciences
Corresponding AuthorRuibing Wang
Affiliation1.Aix Marseille Univ, CNRS, ICR, Marseille, France
2.Centre de Recherche en Cancérologie de Marseille (CRCM), CNRS UMR7258, Inserm U1068, Institut Paoli-Calmettes, AixMarseille Univ, UM105, 13009 Marseille, France
3.Department of Chemistry, Gebze Technical University, P.K.141, 41400 Gebze, Kocaeli, Turkey
4.Institute of Materials and Environmental Chemistry, Hungarian Academy of Sciences, P.O. Box. 286, 1519 Budapest, Hungary
5.Department of Physics, Budapest University of Technology and Economics, 1111 Budapest, Hungary
6.Aix Marseille Univ, CNRS, Centrale Marseille, FSCM (FR1739), PRATIM, F-13397 Marseille, France
7.Aix Marseille Univ, CNRS, Centrale Marseille, FSCM, Spectropole, Marseille, France
8.nstitut Universitaire de France, F-75005 Paris, France
9.Aix Marseille Univ, University of Toulon, CNRS, IM2NP, Marseille, France
10.State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Taipa,Macau, China
Corresponding Author AffilicationInstitute of Chinese Medical Sciences
Recommended Citation
GB/T 7714
Sébastien Combes,Khoa Truong Tran,Mehmet Menaf Ayhan,et al. Triangular Regulation of Cucurbit[8]uril 1:1 Complexes[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2019,141(14):5897-5907.
APA Sébastien Combes.,Khoa Truong Tran.,Mehmet Menaf Ayhan.,Hakim Karoui.,Antal Rockenbauer.,...&Olivier Ouari.(2019).Triangular Regulation of Cucurbit[8]uril 1:1 Complexes.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,141(14),5897-5907.
MLA Sébastien Combes,et al."Triangular Regulation of Cucurbit[8]uril 1:1 Complexes".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 141.14(2019):5897-5907.
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