A New Fluorescent "Turn-Off" Coumarin-Based Chemosensor: Synthesis, Structure and Cu-Selective Fluorescent Sensing in Water Samples

Abstract

We report the synthesis and characterization two coumarin-based fluorescence probes, N'-{[7-(diethylamino)-2-oxo-2H-chromen-3-yl]carbonyl}pyridine-3-carbohydrazide (3) and N'-benzoyl-7-(diethylamino)-2-oxo-2H-chromene-3-carbohydrazide (4), proposed as a novel fluorescent chemosensor. The two probes designed showed an instant turn-off fluorescence response to Cu²⁺ over other metal ions in ethanol-water mixture based on intramolecular charge transfer (ICT). It was found that pyridine-analogue coumarin is highly selective and sensitive sensor for Cu²⁺. The 3 sensor coordinates Cu²⁺ in 1:1 stoichiometry with a binding constant, K_a = 5.22 M^-1 and the detection limit was calculated 1.97 × 10^-9 M.

Keywords: Copper (II) sensor; Coumarin; Fluorescence; ICT.