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Design and Synthesis of an Efficient Fluorescent Probe Based on Oxacalix[4]arene for the Selective Detection of Trinitrophenol (TNP) Explosives in Aqueous System

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Abstract

We present the synthesis of a new oxacalix[4]arene system, DMANSOC, wherein two 5-(dimethylamino)-1-naphthalene sulfonamide subunits are attached to the lower rims of the basic oxacalix[4]arene platform. Extensive spectrophotometric studies were conducted to investigate the selectivity and sensitivity of DMANSOC towards nitroaromatic explosives. Detailed analysis of spectrophotometric data, utilizing techniques such as Stern-Volmer, Benesi-Hildebrand, Job’s plot, and interference study, unequivocally demonstrated the effectiveness of DMANSOC as a highly efficient fluorescent sensor for 2,4,6-trinitrophenol explosive (TNP) detection in an aqueous medium. The sensor exhibited a linear concentration range of 7.5 μM to 50 μM, with a low detection limit of 4.64 μM and a high binding affinity of 2.45 × 104 M towards TNP. Furthermore, the efficiency of the sensor in environmental samples contaminated with TNP was evaluated, yielding excellent recovery rates. Complementary DFT calculations and molecular dynamics simulations were performed to elucidate the mechanism behind the selective fluorescence quenching of DMANSOC in the presence of TNP.

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Funding

The authors thank the financial assistance provided by LSRBDRDO, New Delhi, through the project scheme REF. No (LSRB-01/15001/M/LSRB-373/BTB/2020). B. K. S. thanks UGC: Dr. D. S. Kothari Post-Doctoral Fellowship (Project No: F4-2/2006(BSR)/CH/20–21/0113) for financial support.

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Authors and Affiliations

  1. Department of Chemistry, School of Sciences, Gujarat University, Ahmedabad, Gujarat, 380009, India

    Vishv Desai, Falak Panjwani, Banabithi Koley Seth & Vinod Kumar Jain

  2. Department of Humanities and Science, School of Engineering, Indrashil University, Mehsana, Gujarat, 382740, India

    Krunal Modi

  3. Chemical Engineering Department, Institute of Technology, Nirma University, Ahmedabad, Gujarat, 382481, India

    Manoj Vora

  4. Department of Chemistry, Faculty of Science, Ganpat University, Kherva, Gujarat, 384012, India

    Jaymin Parikh

Authors
  1. Vishv Desai
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  2. Krunal Modi
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  4. Banabithi Koley Seth
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  5. Manoj Vora
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Contributions

Vishv Desai: Lead, Data curation, Writing- Original draft Preparation (First author). Krunal Modi: Formal analysis, Software. Falak Panjwani: Methodology, Visualization. Banabithi Koley Seth: Validation, Investigation. Manoj Vora: Writing- Reviewing and Editing. Jaymin Parikh: Computational study (writing). Vinod K Jain: Supervision, Project administration, Funding acquisition.

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Correspondence to Krunal Modi or Vinod Kumar Jain.

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Desai, V., Modi, K., Panjwani, F. et al. Design and Synthesis of an Efficient Fluorescent Probe Based on Oxacalix[4]arene for the Selective Detection of Trinitrophenol (TNP) Explosives in Aqueous System. J Fluoresc 34, 1219–1228 (2024). https://doi.org/10.1007/s10895-023-03352-7

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