A benzimidazole-based chromogenic anion receptor.
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(-).
Yu
Ming
M
Department of Chemistry, Nankai University, Tianjin 300071, China.
Lin
Hai
H
Zhao
Guanhua
G
Lin
Huakuan
H
D000838:Anions / Q000737:chemistry*; D001562:Benzimidazoles / Q000032:analysis / Q000737:chemistry*; D002863:Chromogenic Compounds / Q000032:analysis / Q000138:chemical synthesis / Q000737:chemistry*; D003124:Colorimetry; D004121:Dimethyl Sulfoxide; D007700:Kinetics; D019906:Nuclear Magnetic Resonance, Biomolecular; D013056:Spectrophotometry, Ultraviolet; D017186:Titrimetry; D014961:X-Ray Diffraction
D000838:Anions; D001562:Benzimidazoles; D002863:Chromogenic Compounds; C031000:benzimidazole; D004121:Dimethyl Sulfoxide