Tetraphenylethylene-Substituted Bis(thienyl)imidazole (DTITPE), An Efficient Molecular Sensor for the Detection and Quantification of Fluoride Ions

Abstract

Fluoride ion plays a pivotal role in a range of biological and chemical applications however excessive exposure can cause severe kidney and gastric problems. A simple and selective molecular sensor, 4,5-di(thien-2-yl)-2-(4-(1,2,2-triphenylvinyl)-phenyl)-1H-imidazole, DTITPE, has been synthesized for the detection of fluoride ions, with detection limits of 1.37 × 10−7 M and 2.67 × 10−13 M, determined by UV-vis. and fluorescence spectroscopy, respectively. The variation in the optical properties of the molecular sensor in the presence of fluoride ions was explained by an intermolecular charge transfer (ICT) process between the bis(thienyl) and tetraphenylethylene (TPE) moieties upon the formation of a N-H---F− hydrogen bond of the imidazole proton. The sensing mechanism exhibited by DTITPE for fluoride ions was confirmed by 1H NMR spectroscopic studies and density functional theory (DFT) calculations. Test strips coated with the molecular sensor can detect fluoride ions in THF, undergoing a color change from white to yellow, which can be observed with the naked eye, showcasing their potential real-world application.