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

Abstract

We present the synthesis of a new oxacalix[4]arene system, DMANSOC, wherein two 5-(dimethylamino)-1naphthalene 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 e cient uorescent sensor for 2,4,6trinitrophenol 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 a nity of 2.45 × 10 4 M towards TNP. Furthermore, the e ciency 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 uorescence quenching of DMANSOC in the presence of TNP.