IDTI Dyes for Fluoride Anion Chemosensors

Abstract

Fluoride anions play a key role in human health and chemical engineering, such as in organic synthesis and biological processes. The development of high-sensitivity naked-eye detection sensors for fluoride anions in organic solutions is crucial and challenging. In this study, (3Z,3 ′ Z)-3,3 ′-[4,4,9,9-tetrakis(4-hexylphenyl)-4, 9-dihydro-s-indaceno(1,2-b:5,6-b ′)dithiophene]-2,7-diylbis(methan-1-yl-1-ylidene) bis (6-bromo-indolin-2-one) (IDTI) was designed and used as a fluoride chemosensor for the first time. IDTI is a highly sensitive fluoride sensor with a detection limit of as low as 1 × 10 −7 M. In addition, upon the reaction of IDTI with fluoride anions in a tetrahydrofuran (THF) solution, color changes from red to yellow under ambient light and from purple to green under UV light were detectable by the naked eye. These studies indicate that IDTI is a promising fluoride chemosensor.

Hydrogen-Bonded Colorimetric and Fluorescence Chemosensor for Fluoride Anion With High Selectivity and Sensitivity: A Review

“… (A) Two-photon excitation fluorescence spectra of mDPP in THF (1.0 × 10 −4 M) with different equivalents of fluoride ions excited at 720 nm under an input laser power of 150 mW ( Yang et al, 2013 ); (B) photographs of IDTI solutions with or without additional different eq. Fluoride anions under ambient light or 365 nm UV light ( Yuan et al, 2020 ); (C) chemical structures of the fluoride chromogenic sensors of 1 and 2; (D) color changes of the sensors in DMSO (2.0 × 10 −4 mol/L) by the addition of 50 equiv. of different anions (1.0 × 10 −2 mol/L), respectively ( Cao et al, 2020 ); (E) photographs of naphthodipyrrolidone in THF solution before and after the addition of 8 equiv.…”

“…In contrast, colorimetric fluoride chemosensors are more favorable, because they can directly monitor fluoride anions by the naked eye. Recently, Yuan et al developed (3Z,3′Z)-3,3’-(4,4,9,9-tetrakis (4-hexylphenyl)-4,9-dihydro-s-indaceno (1,2-b:5,6-b’)dithiophene]-2,7-diylbis (methan-1-yl-1-ylidene)) bis(indolin-2-one) (IDTI) and used it as a fluoride chemsensor ( Yuan et al, 2020 ). Once the IDTI detected fluoride in the THF solution, the color changed directly from purple to green under UV light, as well as from red to yellow under ambient light which were both easy to observe with the naked eye ( Figure 1B ).…”

“… (A) Fluorescent emission changes of the sensors (10 μ mol L −1 ) in the presence of increasing amounts of fluoride anions in 90% MeCN-H 2 O (v/v); (B) solid-state fluorescence response of the sensors with different concentrations of fluoride under UV illumination at 365 nm ( Yuan et al, 2020 ); (C) photograph of fluorescence/colorimetric detection of fluoride anions; (D) the proposed structure of CDs and mechanism for identifying fluoride anions; (E) normalized fluorescence intensity of the CDs in the presence of various individual ions ( Liu et al, 2021 ); (F) the photographs of ABDF in various solutions before and after the addition of 4.5 eq. of fluoride anions ( Deng et al, 2020 ).…”

Efficient Colorimetric Fluoride Anion Sensor Based on π-Conjugated Carbazole Small Molecule

“…Very recently, aminobenzodifuranone dyes for F − chemosensors were developed by our group, which could not only detect F − , but could also distinguish it from F − containing solvents (Deng et al, 2020). Yuan et al developed a new (3Z,[3][4]4,9,dithiophene)-2,7-diylbis (methan-1-yl-1-ylidene))bis (6-bromo-indolin-2-one) (IDTI) dye with a detection limitation as low as 1 × 10 -7 M for the fluoride anion (Yuan et al, 2020). Additionally, Zhang and coworkers developed a DPP-based polymer from t-butoxy carbonyl (t-Boc) units that detect fluoride anions, and also extract fluoride anions from organic solutions (Zhang et al, 2018).…”