UM  > Institute of Chinese Medical Sciences
Residential Collegefalse
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 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 BySCIE ; IC
Language英語English
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
WOS IDWOS:000464769000042
Scopus ID2-s2.0-85063107791
Fulltext Access
Citation statistics
Document TypeJournal article
CollectionInstitute of Chinese Medical Sciences
Corresponding AuthorWang, Ruibing; Bardelang, David; Ouari, Olivier
Affiliation1.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 AffilicationInstitute 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.
Files in This Item:
There are no files associated with this item.
Related Services
Recommend this item
Bookmark
Usage statistics
Export to Endnote
Google Scholar
Similar articles in Google Scholar
[Combes, Sébastien]'s Articles
[Tran, Khoa Truong]'s Articles
[Ayhan, Mehmet Menaf]'s Articles
Baidu academic
Similar articles in Baidu academic
[Combes, Sébastien]'s Articles
[Tran, Khoa Truong]'s Articles
[Ayhan, Mehmet Menaf]'s Articles
Bing Scholar
Similar articles in Bing Scholar
[Combes, Sébastien]'s Articles
[Tran, Khoa Truong]'s Articles
[Ayhan, Mehmet Menaf]'s Articles
Terms of Use
No data!
Social Bookmark/Share
All comments (0)
No comment.
 

Items in the repository are protected by copyright, with all rights reserved, unless otherwise indicated.