Selective fluorescence sensing of polynitroaromatic explosives using triaminophenylbenzene scaffolds

Abstract

A supramolecular fluorophore, 1,3,5-tris(4'-aminophenyl)benzene (TAPB), selectively senses polynitroaromatic compounds (PNAC), viz. 2,4,6-trinitrotoluene (TNT), 2,4-dinitrotoluene (DNT), picric acid (PA), m-dinitrobenzene (m-DNB) and p-dinitrobenzene (p-DNB) through donor-acceptor complexation. Steady-state and time resolved fluorescence measurements indicate predominantly static quenching of the TAPB fluorophore with TNT, DNT, m-DNB and p-DNB. In the case of PA, a new emissive band with a marginally longer lifetime emerges due to complex formation with TAPB. The selectivity of sensing action is rationalized through computation of HOMO and LUMO energies for both the fluorophore and the analytes using the M06-2X/6-311+G(d,p) level of theory. Practical utility of the fluorophore has also been demonstrated with TNT and DNT vapour.

Luminescent Nanofibers Fabricated from Phenanthroimidazole Derivatives by Organogelation: Fluorescence Response towards Acid with High Performance

“…[18] The ,r espectively (Figure 4d,S 6d,S 7d), thus suggesting as trong interaction between the probesa nd TFA. Moreover, the detection limit (LOD = 3s/K sv )f or PCC, PDC and PSC towards TFAw ere measured to be 9.2 10…”

π-Electron rich small molecule sensors for the recognition of nitroaromatics

“…66 Very recently, 45 Murugavel and co-workers synthesized an amino-substituted triphenylbenzene supramolecular fluorophore [72; 1,3,5-tris(4'aminophenyl)benzene] that can selectively sense nitroaromatic explosives through donor-acceptor complexation. 67 In the solidstate, fluorophore 72 interconnected with each other via 50 intermolecular hydrogen-bonding interactions between ─NH 2 groups to adopt a three-dimensional supramolecular framework which is capable of encapsulating NACs analytes. The presence of ─NH 2 groups further increased the binding propensity of 72 through intermolecular hydrogen bonding interactions with ─NO 2 55 group of NACs.…”

“…B) Molecular structure of 73 and its 1:3 host-35 guest complexation with PA in solid-state. Adapted with permission from reference[67, 68]. Copyright 2013/2014 Royal Society of Chemistry.…”

Branched benzothiadiazole-cored oligomers with terminal carbazoles: Synthesis and fluorescence probing nitroaromatics

“…3 and Fig. S9, we found that the emission intensities of oligomers 1 and 2 decreased gradually with increasing the concentration of the quenchers, and the fluorescence quenching data were obtained using SterneVolmer equation: where F 0 is the initial emission intensity of the probe prior to the addition of the quencher, F is the emission intensity at given concentration of the quencher [Q], and K sv is the SterneVolmer constant [23]. It was clear that the linear SterneVolmer plots were obtained from the fluorescence quenching titration profiles, meaning that the photo-induced electron transfer happened between the emitters and the quenchers [22].…”