A pyrazinium-based fluorescent chemosensor for the selective detection of 2,4,6-trinitrophenol in an aqueous medium†
Abstract
Sensing nitroaromatic explosives has gained significant attention due to both increased terrorist threats and a need for environmental protection. In this regard, a fluorescent chemosensor, 1-benzyl-3,5-di(thiophen-2-yl)pyrazin-1-ium bromide (BTPyz), was synthesized and characterized via spectroscopic methods. The photophysical properties were investigated using absorption and emission spectral analysis. As a fluorescent chemosensor, BTPyz exhibited a selective response towards 2,4,6-trinitrophenol (TNP) with a detection limit of 11.6 nM and quenching constant (KSV) of 3.8 × 104 M−1. The fluorescence quenching mechanism was attributed to ground-state charge-transfer complex formation and resonance energy transfer, as evident from Uv-visible, fluorescence and NMR spectroscopy, single-crystal XRD studies, and density functional theory calculations. BTPyz was also employed for the contact mode detection of TNP on paper strips. The detection of TNP in real water and soil samples demonstrated BTPyz to be a promising detection tool toward environmental specimens.
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