Simple Bisthiocarbonohydrazone as a Sensitive, Selective, Colorimetric, and Ratiometric Fluorescent Chemosensor for Picric Acids

Abstract

A bisthiocarbonohydrazone-based chemosensor molecule (R1) containing a tetrahydro-8-hydroxyquinolizine-9-carboxaldehyde moiety has been synthesized and characterized as a new ratiometric fluorescent probe for picric acid (PA). The ratiometric probe R1 is a highly selective and sensitive colorimetric chemosensor for PA. The association between the chemosensor and PA and the ratiometric performance enabled by the key role of excited state intramolecular proton transfer in the detection process are demonstrated. Selectivity experiments proved that R1 has excellent selectivity to PA over other nitroaromatic chemicals. Importantly, the ratiometric probe exhibited a noteworthy change in both colorimetric and emission color, and this key feature enables R1 to be employed for detection of PA by simple visual inspection in silica-gelcoated thin-layer chromatography plates. Probe R1 has been shown to detect PA up to 3.2 nM at pH 7.4. Microstructural features of R1 and its PA complex have been measured by a field emission scanning electron microscope, and it clearly proves that their morphological features differ dramatically both in shape and size. Density function theory and time-dependent density function theory calculations were performed to establish the sensing mechanism and the electronic properties of probe R1. Furthermore, we have demonstrated the utility of probe R1 for the detection of PA in live Vero cells for ratiometric fluorescence imaging.

Functionalized graphene oxide materials for the fluorometric sensing of various analytes: a mini review

“…[14][15][16][17][18][19][20][21][22][23] In recent times, fluorescent chemosensors have gradually become a pace-setter compared to other traditional analytical techniques (e.g., atomic emission spectrometry, neutron activation analysis, inductively coupled plasma spectrometry, mass spectrometry, Raman scattering, electrothermal atomic absorption spectrometry, atomic absorption spectrometry, and voltammetry) because of their advantages such as high sensitivity and selectivity, a low concentration of analyte, effective, economical, trouble-free process, and naked-eye detection. [24][25][26][27][28][29][30][31][32][33] However, the design of fluorescent chemosensor for the most common binding and signalling approach required some of the crucial chemical components, which are predominantly obtained based on supramolecular chemistry principles for specific recognition in different media. Basically, the construction of a chemosensor involves the fusion of three basic units.…”

A New Compound for Sequential Sensing of Picric Acid and Aliphatic Amines: Physicochemical Details and Construction of Molecular Logic Gates

“…There are numerous small molecule sensors as well to detect PA with low LOD. [42][43][44][45][46][47][48][49][50][51][52][53][54][55][56] Zinc oxide nanomaterials and fluorescent quantum dots were also helpful in PA detection. [57,58] The fluorescent outputs due to the sensing mechanisms were effectively used to prepare logic based devices in some cases.…”

Quinoline-tagged fluorescent organic probes for sensing of nitro-phenolic compounds and Zn2+ions at the ppb level

“…Several fluorescent materials such as conjugated polymers, [16][17][18] macromolecules, 19 carbon dots, 20,21 small organic probes, [22][23][24][25][26][27][28][29][30][31][32][33] cages, 34,35 covalent organic frameworks [36][37][38][39] and metal-organic frameworks [40][41][42][43][44][45][46][47][48][49][50] have been utilized for TNP and small molecule detection. Most of these demonstrated TNP sensing in dichloromethane (DCM), dimethylformamide (DMF), tetrahydrofuran (THF) and other organic and aqueous-organic solvents, [16][17][18][19][33][34][35][36][37][38][39][40]42,…”

“…Most of these demonstrated TNP sensing in dichloromethane (DCM), dimethylformamide (DMF), tetrahydrofuran (THF) and other organic and aqueous-organic solvents, [16][17][18][19][33][34][35][36][37][38][39][40]42,43 however, for practical usage detection in water is highly in demand. 20,21,[27][28][29][30][31][44][45][46][47][48][49][50][51] Thus, efforts are still required in developing fluorescent materials with high stability in water for this detection purpose. Various analytical techniques such as surface-enhanced Raman spectroscopy, mass spectrometry, gas chromatography, cyclic voltammetry and fluorescence spectroscopy have been employed for TNP detection out of which fluorescence based sensing has gained more attention due to cost-effectiveness, high sensitivity, real-time detection and rapid response time.…”