Supramolecular control over recognition and efficient detection of picric acid (original) (raw)
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ACS Omega
A hydrazone-based N ′ 1 , N ′ 3-b i s ((E)-4-(diethylamino)-2 − hydroxybenzylidene)isophthalohydrazide (NDHIPH), has been synthesized, characterized, and assessed for its highly selective and sensitive (limit of detection, 2.53 nM) response toward Al(III) via fluorescence enhancement in 95% aqueous medium. All experimental results of analytical studies are in good consonance with the theoretical studies performed. Further, this NDHIPH-Al(III) ensemble is used for selective and sensitive (12.15 nM) detection of explosive picric acid (PA) via fluorescence quenching. This reversible behavior of NDHIPH toward Al(III) and PA is used for the creation of a molecular logic gate.
ACS Omega
A bisthiocarbonohydrazone-based chemosensor molecule (R1) containing a tetrahydro-8-hydroxyquinolizine-9carboxaldehyde 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.
ChemistrySelect, 2019
Rhodamine dye containing Isonicotinic hydrazide (RBN-1) is synthesized for the sensing of nitro aromatics, the probe showed turn-on fluorescence with Picric acid in coexistence with other interfering nitro aromatics. The sensor RBN-1 can be used for naked eye detection of picric acid with the detection limit of 37.3 nM in solution. The RBN-1 + PA complexation involves intermolecular hydrogen bonding between the pyridine N and the hydroxyl group of PA. The observed photophysical changes of RBN-1 with Picric acid is attributed to the spirolactam ring opening. The effective sensing ability of RBN-1 is tested in real water samples and paper strip experiments, the results are in good agreement with the pilot analysis.
SSRN Electronic Journal
In this paper, we developed a bis-triazole-pyrene sugar derivative 1 to recognize PA and Au(III) in an 80 % aqueous ethanol system. The recognition ability of 1 toward PA and Au(III) was evaluated from spectroscopic studies and DFT calculations. The dynamic excimer emission of 1 was reduced efficiently with PA and Au(III) ions compared to other NACs, metal species and anions. The sugar backbone provides the actual stereochemistry for forming dynamic excimer in aqueous ethanol medium after excitation at 345 nm. The bis-pyrene system 1 generated intramolecular pyrene dynamic excimer emission in the aqueous system. After interacting with PA, the excimer quenching was attributed to the charge and energy shifting from electron-dense pyrene units to electronlacking PA in the ground state. Receptor 1 demonstrated a 1:1 stoichiometric ratio for PA and Au(III) ion with low micromolar detection limits (0.05 µM for PA and 0.75 µM for Au 3+). The quenching and interaction mechanisms were demonstrated from DFT calculations. The recognition property of 1 for PA was also executed in the solid-supported system. Finally, the practical usefulness of the proposed method was described by the PA and Au(III) recovery abilities in various environmental water systems.
tAggregates of hexaphenylbenzene derivatives 3, having pyrene groups form network of fluorescentnanofibres in presence of mercury ions. Further, fluorescent nanofibres of 3-Hg2+supramolecular ensem-ble exhibit sensitive and pronounced response towards the picric acid. In addition, the solution coatedpaper strips of 3-Hg2+supramolecular ensemble can detect picric acid in the range of 2.29 fg/cm2, thus,providing a simple, portable and low cost method for detection of picric acid in solution and in contactmode.