Highly Selective and Sensitive Detection of Nitrite Ion by an Unusual Nitration of a Fluorescent Benzimidazole

Nitrite (NO2-) is a physiologically significant anion having implications for cellular signaling. Here we report our serendipitous discovery of highly selective fluorescence-based nitrite sensing using a benzimidazole which stems from hitherto-unknown direct nitration of a benzimidazole using sodium nitrite. Using one- and two-dimensional NMR techniques, we elucidate the chemical structures of the new nitrated benzimidazoles and show differences in the nitration products using conventional nitration with nitric acid. We also show its utility in robust sensing of nitrite-containing samples.