[structure: see text] Novel deoxycholic acid-based cyclic receptors, 3 and 4, containing two imidazolium groups and m-xylene and p-xylene as spacers have been synthesized. These receptors bind anions through hydrogen bonds utilizing two imidazolium (C-H)(+) and inwardly directed methylene hydrogens of both acetyl groups. Receptor 3 shows a moderate selectivity for fluoride ion whereas receptor 4 shows high affinity and selectivity for chloride ion in CDCl(3).
The anion binding properties of bile acid-based cyclic bisbenzimidazolium receptors 6-8 bridged with m-xylene, p-xylene, and 2,6-dimethylpyridine have been studied. Receptors 6 and 7 exhibit much higher binding affinity for fluoride and chloride ions, respectively, as compared to the imidazolium receptors 1 and 2. Receptor 8, however, shows high selectivity but very low binding affinity for anions due to the presence of pyridyl nitrogen. The single-crystal X-ray structure of imidazolium receptor 10-(Br)2 containing pyridyl spacer reveals the binding pattern.
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