A benzimidazole-based anion receptor 1 has been designed and synthesized. The structure of 1 is confirmed through single crystal X-ray diffraction analysis. Anion-binding studies carried out using (1)H NMR and UV-visible revealed that this compound exhibits selective recognition toward F(-) over other halide anions. The highest selectivity for F(-) among the halides is attributed mainly to the strongest hydrogen-bond interaction of the receptor with F(-); in addition, the higher match in geometry between the receptor and F(-) also plays a role in the selective recognition of the receptor for F(-). Receptor 1 (1 x 10(-5) M) shows dramatic color change from light-yellow to red in the presence of tetrabutylammonium fluoride (TBAF) (1 x 10(-5) M). Moreover, F(-)-induced color changes remain the same even in the presence of a large excess of Cl(-), Br(-), I(-).
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Yu et al. (2006) studied this question.
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