Surfactant-induced AIE-active tin(IV) micelles for sensing naproxen residues in pharmaceutical effluents

Abstract

Nonsteroidal anti-inflammatory drugs, including naproxen (NPX), are highly consumed globally and their prolonged presence in the environment has detrimental effects on human health and aquatic ecosystems. In the present study, fluorescent micelles of thiophene appended chromone-based diorganotin(IV) crystalline solid (TBSn) have been obtained for the spectrofluorimetric detection of NPX in aqueous systems. Two diorganotin(IV) compounds, TBSn and TMSn were obtained from 2-thiocarboxaldehyde substituted 3-hydroxy-benzo-γ-pyrone and characterized by using FT-IR spectroscopy, multi-nuclear NMR (1H, 13C, and 119Sn) spectroscopy, mass spectrometry, CHN elemental analyses, and single-crystal X-ray diffraction. TBSn and TMSn molecules form brickwork architecture via C–H·····Sn, C–H·····O, C–H·····S, and π⋯π contacts which make them insoluble in water. However, the compounds form nano-aggregated AIE-active micelles with the aid of Pluronic F-127 in water. The micellar solution undergoes rapid elevation in emission intensity (within 5–7 s) in the presence of NPX, showcasing its effectiveness in analyzing NPX in the aqueous medium with the detection limit of 0.11 μM with a linear range of 0.5 to 9.5 μM. Therefore, the micellar formulation can be used as an effective chemosensor for the analysis of NPX in aqueous and pharmaceutical samples. This study marks a pioneering achievement in the spectrofluorimetric analysis based on turn-on detection of NPX utilizing TBSn micelles.