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

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 illumi-nation. 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.

Automated summary

The widespread use of cyanide in industry leads to contamination of various effluents, posing an imminent threat to the environment and human health. In this study, naphthoquinolinedione and anthracenedione probes were prepared for selective detection of cyanide. The addition of cyanide to the probe solutions resulted in a color change, and the nucleophilic addition of cyanide to the probes was responsible for selective detection. Among all probes, probe 1 showed the lowest fluorescence-based limit of detection and maintained its performance in detecting cyanide in real samples.