期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 22, 期 16, 页码 5756-5766出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201505089
关键词
anions; calixarenes; conformation analysis; host-guest systems; macrocycles
资金
- Agence Nationale des Bourses du Gabon (ANBG)
- Centre National de la Recherche Scientifique
- Ministere de la Recherche et des Nouvelles Technologies
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 4b 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 K-a reaching 2.5x10(6)m(-1).
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