Fluorimetric detections of nitroaromatic explosives by polyaromatic imine conjugates
Graphical abstract
Introduction
Nitro-aromatic compounds (NACs) are most commonly used organic compounds in the production of industrial products [1,2]. However, the excessive usage of these compounds results several environment issues such as pollution of soil, rivers and spring water [[3], [4], [5]]. Due to its acidic nature and high solubility in water, 2,4,6-trinitrophenol (TNP), also known as picric acid, pollutes ground water as well as irrigation lands [6]. Picric acid can result in severe health problems [7]. Nitroaromatic compounds such as nitrobenzene (NB), 4-nitrophenol (NP), 2,4-dinitrophenol (DNP), 2,4,6-trinitrophenol (TNP) and 2,4,6-trinitrotoluene (TNT) are organic compounds which have nitro groups (NO2) and the main ingredient of explosives [8]. The weapon manufacture plants and unexploded mine fields are the main cause the environmental contamination of these compounds [9]. The nitro-aromatic explosives are hazardous to human beings. Long term exposure to these compounds can lead to headache, nausea, vomiting, sweating, dizziness, liver damage and dermatitis; and they have negative impacts on central nervous and cardiovascular systems [[10], [11], [12]].
Due to the security, human health and environmental impacts, the rapid and selective sensing of nitro-aromatic explosives in the gas phase as well as in solution have received considerable attention [[13], [14], [15]]. In the field applications, sniffer dogs are usually used for the detection of nitroaromatic explosives [16]. Additionally, several instrumental methods such as liquid chromatography, mass spectrometry, fluorescence and Raman spectroscopy have been employed for the recognition of nitro-aromatic explosives [[17], [18], [19], [20]]. Recently, an interesting semiconductor-based sensor was introduced as electronic nose for the detection of nitro-aromatics [21]. The instrumental techniques have several disadvantages such as a certain cost and not conveniently applied in real field applications. Fluorescent compounds have been applied as fluorimetric probes for the recognition of nitro-aromatic compounds in both solid state and solutions [[22], [23], [24], [25]]. Due to their several advantages such as high selectivity/sensitivity, fast response, and easy preparation, tuneable fluorescent molecules show promising chemosensors properties [[26], [27], [28]]. Nitro-aromatic compounds are not inherently fluorescent, yet, these compounds quench the emission band of fluorescent materials via inter-molecular charge transfer mechanism. Several fluorophore molecules have been designed for the detection of nitro-aromatic compounds. These include monomers/oligomers/polymers with highly delocalized π-electrons, quantum/carbon dots, coordination polymers [[29], [30], [31], [32], [33]]. Pyrene, anthracene and naphthalene appended polyaromatic compounds have also used fluorescent probes for the sensitive detection of nitro-aromatic compounds [[34], [35], [36]].
In our group, we reported naphthalene group containing organic fluorescent molecules and metal organic frameworks for the selective detection of harmful nitro-aromatic compounds [37,38]. In the current study, three new polyaromatic compounds were prepared for fluorimetric detections of nitro-aromatics. The new probes were characterized by the spectroscopic and analytical methods. Molecular structures of the new compounds were investigated by X-ray diffraction studies. Fluorimetric sensing properties of the compounds towards nitrobenzene (NB), 4-nitrophenol (4-NP), 2,4-dinitrophenol (2,4-DNP) and trinitrophenol (TNP) were studied.
Section snippets
General
Starting materials and solvents (1-pyrene carboxaldehyde, 9-anthracene carboxaldehyde, 9-phenanthrene carboxaldehyde and salicylic hydrazide) were purchased from Sigma Aldrich and used as received. FT-IR spectra were measured on a Perkin Elmer Spectrum 100 FT-IR. The electronic spectra were taken on a Perkin Elmer Lambda 45 spectrophotometer. The fluorescence spectra were obtained on a Perkin Elmer LS55 luminescence spectrometer.
Synthesis of the probes (1–3)
A methanol solution (10 mL) of salicylic hydrazide (2 mmol,
Chemistry
In this work, three new polyaromatic groups containing fluorophores were synthesized and characterized by 1H NMR, FT-IR spectra and elemental analysis. Molecular structures of the compounds were determined by X-ray diffraction studies. The Schiff base condensation reaction of polyaromatic carboxaldehydes (1-pyrene carboxaldehyde, 9-anthracene carboxaldehyde or 9-phenanthrene carboxaldehyde) and salicylic hydrazide gave the compounds (1–3) and proposed structures were shown in Fig. 1. The new
Conclusions
Three new hydrazide-imine conjugates (1–3) having polyaromatic groups (pyrene, anthracene or phenanthrene) were prepared and their structures were determined by X-ray diffraction studies. The compounds were used as a fluorimetric probes for the sensing of nitroaromatic compounds [nitrobenzene (NB), 4-nitrophenol (NP), 2,4-dinitrophenol (DNP) and 2,4,6-trinitrophenol (TNP). The quenching efficiency of nitrobenzene (NB) were found to be higher than the other nitro-aromatics used. The compound (3)
Acknowledgments
We are grateful to The Research Unit of Kahramanmaras Sutcu Imam University, Turkey for the financial support for this work. The authors also acknowledge to Scientific and Technological Research Application and Research Centre, Sinop University, Turkey, for the use of the Bruker D8 QUEST diffractometer.
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