A novel 3-acetyl coumarin based AIE luminophore for colorimetric recognition of Cu2+ and F− ions

Abstract

A 3-acetyl coumarin appended probe 3-((Z)-1-((E)-((2-hydroxynaphthalen-1-yl) methylene) hydrazono)ethyl)-2H-chromen-2-one (CNH) has been successfully synthesized and characterized by different spectroscopic tools via IR, 1H & 13C NMR and HRMS. The probe displays solvent dependent colorimetric detection of Cu2+ and F− ions in THF and DMF media, respectively. CNH interacts with Cu2+ in 1:1 stoichiometry with limit of detection 1.4 × 10−6 M. The color change of probe with addition of Cu2+ ions is due to ligand to metal charge transfer (LMCT) as suggested by UV–Vis spectra and DFT studies. Furthermore, CNH interacts with F− in 1:1 stoichiometry with detection limit 1.32 × 10−6 M by proton transfer mechanism from O-H to F−, which enhances the electron density on CNH molecule as suggested by UV–Vis, NMR titration and DFT studies. In addition to intriguing colorimetric sensing applications, CNH displays remarkable aggregation induced emission (AIE) property in DMF/water binary mixture. The probe is almost non-fluorescent in solution but becomes strongly emissive in aggregate/solid state. The formation of aggregates at higher water content is confirmed by atomic force microscopy (AFM) and dynamic light scattering (DLS) studies in mixed water media. DLS measurements suggest the increase in average particle size from 100 nm to 299 nm upon increasing water fractions from (fw = 10%) to (fw = 90%). AFM studies also provide additional information about the aggregates at higher water fraction. In the range of 100–500 nm, the topography of surface shows that the aggregates are spherical in shape (fw = 90%).