Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 14, Issue 7, Pages 2248-2263Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200701347
Keywords
anions; calixarenes; cations; receptors; recognition
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A new family of heteroditopic calix[4]diquinone receptors capable of the cooperative recognition of ion-pair species through a contact binding mechanism has been developed. The receptors bind contact ion pairs cooperatively, with an unprecedented AND recognition phenomenon being observed to operate in certain cases in which receptors display no affinity for either of the individual free cation or anion, but bind the cation and anion ion-pair strongly. X-ray crystallographic, solution-state, and computational methods rationalize the observed recognition behavior of the receptors. It is shown that the contact ion-pair interaction occurs through a pi-stacking-mediated folding of the receptors such that the anion and cation binding sites are arranged in close proximity, while in the solid state an unusual ion-mediated receptor dimerization is observed. Molecular dynamics simulations are further used to explain the observed trends in the association constants of different ion-pair species and the mechanism of interaction.
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