Ratiometric orange fluorescent and colorimetric highly sensitive imidazolium-bearing naphthoquinolinedione-based probes for CN- sensing in aqueous solutions and bio-samples

Abstract

The widespread use of cyanide (CN^-) in industry results in contamination of various effluents such as drain, lake, and tap water, an imminent danger to the environment and human health. We prepared naphthoquinolinedione (cyclized; 1-5) and anthracenedione (un-cyclized) probes (6-7) for selective detection of CN^-. The addition of CN^- to the probe solutions (1-5) resulted in a color change from pale green to orange under 365 nm illumination. The nucleophilic addition of CN^- to C2 of the imidazolium ring of the probes is responsible for selective CN^- detection. Among all probes, 1 gave the lowest fluorescence-based LOD of 0.13 pM. In contrast, the un-cyclized probes (6 and 7) were substantially inferior to the cyclized counterparts (1 and 2, respectively) for detecting a trace amount of CN^-. The notably low LOD displayed by probe 1 was maintained in the detection of CN^- in real food samples, human fluids, and human brain cells. This is the first report studying imidazolium-bearing naphthoquinolinedione-based probes for CN^- sensing in 100% water.

Keywords: 100% aqueous Media; CN(−) sensing; Chromofluorogenic sensor; Imidazolium; Live cell imaging; Naphthoquinolinedione.