1,3-Alternate Tetraamido-Azacalix[4]arenes as Selective Anion Receptors.
Fiche publication
Date publication
avril 2016
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
Auteurs
Membres identifiés du Cancéropôle Est :
Dr ELHABIRI Mourad
Tous les auteurs :
Canard G, Edzang JA, Chen Z, Chessé M, Elhabiri M, Giorgi M, Siri O
Lien Pubmed
Résumé
Six tetraaza[1.1.1.1]cyclophane derivatives bearing peripheral amide groups were prepared according to two distinct synthetic strategies that depend on the connection pattern between the aryl units. NMR experiments combined with the X-ray structures of two tetraamide derivatives 4 b and 10 show that these cavitands adopt a 1,3-alternate conformation both in solution and in the solid state. Consequently, the four amide groups of the aza[1.1.1.1]-m,m,m,m-cyclophane isomer 10 can contribute to the same recognition process towards neutral water molecules or anion guests. NMR experiments, mass spectrometry analyses and single-crystal X-ray structures confirm the anion-binding ability of this receptor. Absorption spectrophotometric titrations in nonpolar solvents provided evidence for the selectivity of 10 to chloride anions in the halide series, with a corresponding association constant Ka reaching 2.5 × 10(6) m(-1).
Mots clés
anions, calixarenes, conformation analysis, host-guest systems, macrocycles
Référence
Chemistry. 2016 Apr 11;22(16):5756-66