Simple Bisthiocarbonohydrazone as a Sensitive, Selective, Colorimetric, and Ratiometric Fluorescent Chemosensor for Picric Acids.

A bisthiocarbonohydrazone-based chemosensor molecule () containing a tetrahydro-8-hydroxyquinolizine-9-carboxaldehyde moiety has been synthesized and characterized as a new ratiometric fluorescent probe for picric acid (PA). The ratiometric probe is a highly selective and sensitive colorimetric chemosensor for PA. The association between the chemosensor and PA and the ratiometric performance enabled by the key role of excited state intramolecular proton transfer in the detection process are demonstrated. Selectivity experiments proved that has excellent selectivity to PA over other nitroaromatic chemicals. Importantly, the ratiometric probe exhibited a noteworthy change in both colorimetric and emission color, and this key feature enables to be employed for detection of PA by simple visual inspection in silica-gel-coated thin-layer chromatography plates. Probe has been shown to detect PA up to 3.2 nM at pH 7.4. Microstructural features of and its PA complex have been measured by a field emission scanning electron microscope, and it clearly proves that their morphological features differ dramatically both in shape and size. Density function theory and time-dependent density function theory calculations were performed to establish the sensing mechanism and the electronic properties of probe . Furthermore, we have demonstrated the utility of probe for the detection of PA in live Vero cells for ratiometric fluorescence imaging.