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Dual in vitro and in silico analysis of thiacalix[4]arene dinaphthalene sulfonate for the sensing of 4-nitrotoluene and 2,3-dinitrotoluene

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A new fluorescent thiacalix[4]arene dinaphthalene sulfonate (TCDNS) was synthesized by a reaction of thiacalix[4]arene with naphthalene sulfonyl chloride. TCDNS was characterized by 1H-NMR, 13C-NMR, and ESI-MS spectrometric analyses. The selectivity… Click to show full abstract

A new fluorescent thiacalix[4]arene dinaphthalene sulfonate (TCDNS) was synthesized by a reaction of thiacalix[4]arene with naphthalene sulfonyl chloride. TCDNS was characterized by 1H-NMR, 13C-NMR, and ESI-MS spectrometric analyses. The selectivity of fluoroionophore was analyzed for 4-nitrotoluene (4-NT) and 2,3-dinitrotoluene (2,3-DNT) among various nitroaromatic compounds (NACs) using the spectrofluorimetric technique. 4-NT and 2,3-DNT behave as the strong emission quenchers for TCDNS. The information about the complexation of TCDNS with 4-NT and 2,3-DNT was revealed by ESI-MS and 1H NMR analysis. A standard addition method was used for the detection of 4-NT and 2,3-DNT in a water sample. The complex formation in the cases of TCDNS⊃4-NT and TCDNS⊃2,3-DNT has been demonstrated by molecular docking and dynamics simulation techniques.

Keywords: thiacalix; dinaphthalene sulfonate; dnt; nitrotoluene dinitrotoluene; arene dinaphthalene; thiacalix arene

Journal Title: New Journal of Chemistry
Year Published: 2018

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