A highly sensitive and selective off-on fluorescent chemosensor for hydrazine based on coumarin β-diketone

Abstract

A coumarin-based sensor C1, namely 3-acetoacetylcoumarin was designed, synthesized and applied for hydrazine detection. Hydrazinolysis of the chemosensor gives a fluorescent coumarin-pyrazole product C1-N₂H₄ [3-(3-methyl-1H-pyrazol-5-yl)coumarin], and thus resulting in a prominent fluorescence off-on response toward hydrazine under physiological conditions. The probe is highly selective toward hydrazine over cations, anions and other biologically/environmentally abundant analytes. The detection limit of the probe is 3.2ppb. The sensing mechanism was supported by ¹H NMR, IR, MS and DFT calculation. The application of the fluorescent probe in monitoring intracellular hydrazine in glioma cell line U251 was also demonstrated.

Keywords: Cell imaging; Coumarin; Fluorescent probe; Hydrazine; β-Diketone.