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Self-assembly via ionic interactions of calix[6]arene-based receptors displaying remarkable host-guest properties toward neutral guests |
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| Authors: | Sté phane Le Gac,Olivia Reinaud |
| Affiliation: | a URCOM, Université du Havre, Faculté des Sciences et Techniques, 25 rue Philippe Lebon, BP 540, 76058 Le Havre Cedex, France b Laboratoire de Résonance Magnétique Nucléaire Haute Résolution, Université Libre de Bruxelles (U.L.B.), Avenue F.D. Roosevelt 50, CP160/08, B-1050 Brussels, Belgium c Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, UMR CNRS 8601, Université Paris Descartes, 45 rue des Saints Pères, 75006 Paris, France d Service de Chimie Organique, Université Libre de Bruxelles (U.L.B.), Avenue F.D. Roosevelt 50, CP160/06, B-1050 Brussels, Belgium |
| Abstract: | The association of a C3v-symmetrical calix[6]tris-amine with different concave tris-carboxylic acids of various degrees of flexibility has been explored by 1H NMR spectroscopy. In all cases, self-assembled structures directed by the selective inclusion of a neutral guest molecule were obtained, the more preorganized being stable in protic solvents. With a rigid C3-symmetrical cap, chiral guest recognition in the calixarene cavity resulted. A large tris-acidic partner gave a unique molecular ditopic receptor that is able to simultaneously accommodate two neutral molecules in two distinct hydrophobic cavities with different binding processes. |
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