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Published on: September 25, 2017
Novel Coumarin-Substituted Cyclophosphazene as a Fluorescent Probe for Highly Selective Detection of
Ishanki Sharma1, Rajeev Kumar Sinha2, Suranjan Shil3
1Department of Chemistry, Manipal Institute of Technology, Manipal Academy of Higher Education, Manipal 576104, India.
Abstract:
Nitroaromatic compounds (NACs) such as 2,4,6-trinitrophenol (TNP), commonly known as picric acid (PA), hold widespread application in industries such as dyestuff production, wood preservation, explosives manufacturing, insect control, and photographic development. In this study, the organic-inorganic hybrid 4,4',4″,4‴,4″″,4‴″-((1,3,5,2λ5,4λ5,6λ5-triazatriphosphinine-2,2,4,4,6,6-hexayl)hexakis(oxy))hexakis(2H-chromen-2-one) (Cpz-4-HC) was synthesized via the nucleophilic substitution reaction of 4-hydroxycoumarin (4-HC) with hexachlorocyclotriphosphazene (HCCP). The structure of Cpz-4-HC was fully characterized by Fourier transform infrared (FT-IR), 1H-, 13C-, and 31P NMR, and HRMS. Cpz-4-HC is used as a chemical fluorescence sensor for the detection of TNP, with a K SV value of 4.71 × 104 M-1 and a low limit of detection (LOD) of 0.334 ppm over some other analytes such as 2,4-DNP, 4-NP, 2-NP, 1,3-DNB, 2,4-DNT, and 2,6-DNT in water. The sensing mechanism was elucidated through spectral overlap analysis, indicating the resonance energy transfer as the dominant quenching process. Dynamic quenching was established through fluorescence lifetime studies, further affirming Cpz-4-HC capability for environmental monitoring. Experimental and theoretical analyses underscored TNP's strong interaction with Cpz-4-HC, corroborating its suitability for sensing applications. Their recyclable nature and ultrafast response time make them highly suitable for detecting TNP, even in the presence of other interfering nitroaromatics. This study provides novel perspectives on the development and formulation of a chemical fluorescent sensor for TNP, utilizing a straightforward synthesis method.
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