Colorimetric sensor based on hydrazine moiety for rapid and selective detection of fluoride ion via intramolecular charge transfer

Abstract

ABSTRACT A colorimetric anion sensor (E)-3-((2-((4-(4-Methoxyphenyl)thiophen-2- yl)methyl)hydrazono)methyl)-1 H-indole ATH was synthesised and confirmed by different spectroscopic methods, such as 1 H NMR, 13 C NMR, ESI-Mass and FT-IR spectroscopy. The ATH sensor revealed the spectral change and detection in the presence of fluoride ion over the other anions such as OH−, Cl−, AcO−, I−, HSO4 −, NO3 −, Br−, S2-, CN− & NO2 −. Interestingly, sensor ATH exhibited highly selective fluoride ion detection with significant changes in the colour from light yellow to dark yellow in ACN and ACN: H2O (8:2, v/v) medium. The colorimetric sensor effectively responds to fluoride ion stimulation through deprotonation and (ICT) intramolecular charge transfer sensing mechanism. The fluoride sensing mechanism was confirmed by 1 H NMR titration and was supported by density functional theory (DFT) and electrochemical studies. In this study, the B–H plot calculates the stoichiometry and binding constant (Ka) of the host-guest complex and strong interaction between the probe ATH with fluoride ions forming a 1:2 binding ratio. Furthermore, the test strips based on the probe ATH were used to detect F- ions qualitatively and quantitatively in 100% aqueous solution.