10.34804/SUPRA.20210928164
Combes, Sébastien
Sébastien
Combes
0000-0002-8213-2407
Institut de Chimie Radicalaire
Tran, Khoa Truong
Khoa Truong
Tran
Institut de Chimie Radicalaire
AYHAN, MEHMET MENAF
MEHMET MENAF
AYHAN
0000-0001-5367-2220
Institut de Chimie Radicalaire
Karoui, Hakim
Hakim
Karoui
Aix-Marseille University
Rockenbauer, Antal
Antal
Rockenbauer
0000-0002-2865-1599
Institute of Materials and Environmental Chemistry
Tonetto, Alain
Alain
Tonetto
French National Centre for Scientific Research
Monnier, Valérie
Valérie
Monnier
French National Centre for Scientific Research
Charles, Laurence
Laurence
Charles
0000-0003-3807-8375
Institut de Chimie Radicalaire
Rosas, Roselyne
Roselyne
Rosas
French National Centre for Scientific Research
Viel, Stéphane
Stéphane
Viel
0000-0003-3338-0559
Institut de Chimie Radicalaire
Siri, Didier
Didier
Siri
0000-0003-1561-7233
Institut de Chimie Radicalaire
Tordo, Paul
Paul
Tordo
0000-0002-4968-8841
Institut de Chimie Radicalaire
Clair, Sylvain
Sylvain
Clair
0000-0002-8751-1887
French National Centre for Scientific Research
Wang, Ruibing
Ruibing
Wang
0000-0001-9489-4241
University of Macau
Bardelang, David
David
Bardelang
0000-0002-0318-5958
Aix-Marseille University
Ouari, Olivier
Olivier
Ouari
0000-0003-4320-4313
Aix-Marseille University
Triangular Regulation of Cucurbit[8]uril 1:1 Complexes
SupraBank
2024
Interaction Data
Kang, Rui
Rui
Kang
0000-0002-5149-6443
english
10.1021/jacs.9b00150
3 interactions
text/html
Creative Commons Attribution Share Alike 4.0 International
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.