Journal
SUPRAMOLECULAR CHEMISTRY
Volume 15, Issue 6, Pages 403-408Publisher
TAYLOR & FRANCIS LTD
DOI: 10.1080/1061027031000116001
Keywords
pH-switch; complexation; conformational transmitter; crown-ether; cyclohexane
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A new macrocyclic ligand, 3, which exhibits pH-induced conformational changes, has been prepared. This ligand consists of a crown ether derived from a trans-anti-trans 1,2,4,5-tetrasubstituted cyclohexane. Due to the stereochemistry of the substituents on the carbocyclic ring, two different low-energy conformations of the crown ether are possible. Ligand 3 has been studied in solution by H-1 NMR spectroscopy at different values of pH and temperature, showing that the conformation of the crown ether, and thus its complexing ability, is strongly pH-dependent. The solid-state structure of the ligand has been determined by X-ray diffraction.
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