Residential College | false |
Status | 已發表Published |
Triangular Regulation of Cucurbit[8]uril 1:1 Complexes | |
Combes, Sébastien1,2; Tran, Khoa Truong1; Ayhan, Mehmet Menaf1,3; Karoui, Hakim1; Rockenbauer, Antal4,5; Tonetto, Alain6; Monnier, Valérie6; Charles, Laurence1; Rosas, Roselyne6; Viel, Stéphane1,7; Siri, Didier1; Tordo, Paul1; Clair, Sylvain8; Wang, Ruibing9; Bardelang, David1; Ouari, Olivier1 | |
2019-04-10 | |
Source Publication | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY |
ISSN | 0002-7863 |
Volume | 141Issue: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. |
DOI | 10.1021/jacs.9b00150 |
Indexed By | SCIE ; IC |
Language | 英語English |
WOS Research Area | Chemistry |
WOS Subject | Chemistry, Multidisciplinary |
WOS ID | WOS:000464769000042 |
Scopus ID | 2-s2.0-85063107791 |
Fulltext Access | |
Citation statistics | |
Document Type | Journal article |
Collection | Institute of Chinese Medical Sciences |
Corresponding Author | Wang, Ruibing; Bardelang, David; Ouari, Olivier |
Affiliation | 1.Aix Marseille Univ, CNRS, ICR, Marseille, France 2.Centre de Recherche en Cancérologie de Marseille (CRCM), CNRS UMR7258, Inserm U1068, Institut Paoli-Calmettes, Aix Marseille Univ, UM105, Marseille, 13009, France 3.Department of Chemistry, Gebze Technical University, P.K.141, Gebze, Kocaeli, 41400, Turkey 4.Institute of Materials and Environmental Chemistry, Hungarian Academy of Sciences, P.O. Box. 286, Budapest, 1519, Hungary 5.Department of Physics, Budapest University of Technology and Economics, Budapest, 1111, Hungary 6.Aix Marseille Univ, CNRS, Centrale Marseille, FSCM (FR1739), PRATIM, Marseille, F-13397, France 7.Institut Universitaire de France, Paris, F-75005, France 8.Aix Marseille Univ, University of Toulon, CNRS, IM2NP, Marseille, France 9.State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Taipa, Macao |
Corresponding Author Affilication | Institute of Chinese Medical Sciences |
Recommended Citation GB/T 7714 | Combes, Sébastien,Tran, Khoa Truong,Ayhan, Mehmet Menaf,et al. Triangular Regulation of Cucurbit[8]uril 1:1 Complexes[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141(14), 5897-5907. |
APA | Combes, Sébastien., Tran, Khoa Truong., Ayhan, Mehmet Menaf., Karoui, Hakim., Rockenbauer, Antal., Tonetto, Alain., Monnier, Valérie., Charles, Laurence., Rosas, Roselyne., Viel, Stéphane., Siri, Didier., Tordo, Paul., Clair, Sylvain., Wang, Ruibing., Bardelang, David., & Ouari, Olivier (2019). Triangular Regulation of Cucurbit[8]uril 1:1 Complexes. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 141(14), 5897-5907. |
MLA | Combes, Sébastien,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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