In Silico Studies and Design of Scrupulous Novel Sensor for Nitro Aromatics Compounds and Metal Ions Detection

Abstract

A Novel Calix[4]pyrrole system bearing carboxylic acid functionality [ABuCP] has been synthesized and its interaction towards various nitroaromatics compounds [NACs] were investigated. ABuCP showed significant color change with 1,3-dinitro benzene (1,3-DNB) in comparison to the solution of other nitroaromatic compounds such as 2,3-dinitro toluene (2,3-DNT), 2,4-dinitro toluene (2,4-DNT), 2,6-dinitro toluene (2,6-DNT), 4-NBB (4-nitrobenzyl bromide) and 4-nitro toluene (4-NT). The ABuCP-1,3-DNB complex produces a red shift in absorption spectra based on charge transfer mediated recognition. Additionally, the density functional theory calculation confirmed the possible mechanism for the binding of 1,3-DNB as a guest is well supported by the calculation of other parameters such as hardness, stabilization energy, softness, electrophilicity index and chemical potential. The TDDFT calculation facilitates the understanding of the proper binding mechanism in reference to experimental results. Additionally we have also developed its derivative which acts as a new fluorescent sensor which can selectively recognize Sr(II) ion. In this view its aminoanthraquinone derivative of calix[4]pyrrole i.e. ABuCPTAA is synthesized which also results in generation of high fluorescence capability sensor.

Recent developments in calix[4]pyrrole (C4P)-based supramolecular functional systems

“…It was observed that the C4P unit in these nanofilms exhibited noteworthy mechanical and separation properties, and hence can play an important role in wastewater treatment. In another study, Fang and teammates also reported robust and defect-free C4P-based nanofilms via dynamic condensation between C4P-tetrahydrzide (98) and aldehyde 97 at the air-DMSO interface (Fig. 15).…”

“…7). 98 According to the experimental studies, they evaluated the sensing potential of 64 towards NACs such as dinitrotoluene (DNT), 4-nitrobenzyl bromide, and 4-nitrotoluene. Receptor 65 acted as a fluorescent sensor, which selectively sensed the Sr 2+ metal ion in the presence of various other competing metal ions such as Mg 2+ , Pb 2+ , Cd 2+ , Pb 2+ , Cr 3+ , and Al 3+ .…”

A Quenched Fluorescence‐based Assay for Selective Detection of Nitroaromatic Compounds using Pyrene‐Appended Oxacalix[4]arene Host

“…For explosive detection, oxacalixarene can be functionalized with specific chemical groups that interact specifically with nitroaromatic explosives through hydrogen bonding, electrostatic interactions, and van der Waals forces. This interaction can cause a change in the fluorescence or absorption spectra of the oxacalixarene, which can be measured and used to detect the presence of the explosive [15–18] …”

“…Pyrene is a polycyclic aromatic hydrocarbon that has a large conjugated pi‐electron system and can undergo pi‐pi stacking interactions with other aromatic molecules, including nitroaromatic explosives. This property makes pyrene a useful fluorescent probe for the detection of explosives [15–18] . Another compound that has been widely explored for the detection of explosives is oxacalix[4]arene, a type of calixarene with a central annulus and upper and lower rims that can be functionalized with different chemical groups to create a highly selective sensor.…”

“…This property makes pyrene a useful fluorescent probe for the detection of explosives. [15][16][17][18] Another compound that has been widely explored for the detection of explosives is oxacalix- [4]arene, a type of calixarene with a central annulus and upper and lower rims that can be functionalized with different chemical groups to create a highly selective sensor. For explosive detection, oxacalixarene can be functionalized with specific chemical groups that interact specifically with nitroaromatic explosives through hydrogen bonding, electrostatic interactions, and van der Waals forces.…”