A BODIPY/pyrene-based chemodosimetric fluorescent chemosensor for selective sensing of hydrazine in the gas and aqueous solution state and its imaging in living cells

Abstract

A BODIPY-based pyrenebutyrate-linked (BPB) chromogenic and fluorogenic probe was synthesized and characterized for the specific detection of hydrazine. In the presence of hydrazine, BODIPY-based pyrenebutyrate was selectively deprotected, producing switch off meso-phenoxyBODIPY along with a color change from yellow to brown, allowing colorimetric detection of hydrazine by the naked eye. Selectivity experiments proved BPB has excellent selectivity to hydrazine over other environmentally abundant ions and common amine-containing species. Probe BPB was also successfully applied in vapor hydrazine detection into a solid state over other interfering volatile analytes. Furthermore, the probe BPB coated with silica gel TLC plates could act as a visual and fluorimetric probe for hydrazine vapor detection. The probe (BPB) has been shown to detect hydrazine up to 1.87 μM at pH 7.4. DFT and TDDFT calculations were performed in order to demonstrate the sensing mechanism and the electronic properties of the probe and hydrazinolysis product. BPB can also be used for the detection of hydrazine in Vero cells without appreciable interference from other biologically abundant analytes.