Colorimetric N-butyl-3,6-diamidecarbazole-based chemosensors for detection of fluoride and cyanide anions

Colorimetric sensors from N-butyl-3,6-disubstituted carbazole derivatives containing nitroazobenzene (1) and nitrobenzene (2) were designed, synthesized and compared for their anion sensing ability. Computational simulations were undertaken to determine the optimum geometry of 1. Anion sensing studies revealed that selectivity in anion detection depended on the polarity of solvent, acidity of binding unit and basicity of the anion. The ability to sense via naked eye observations using the strong basic anions (F- and CN-) for both sensors arises from a deprotonation process at the binding sites attributed to the intramolecular charge transfer transition at the sensory unit. The discrimination of F- from CN- has been achieved by the optimization of solvent polarity. Sensor 1 offers a promising property over sensor 2 with a lower detection limit, a few of anion interference and higher stability.