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Fluoride detection by an AIE active pyrene functionalized imidazole-based fluorescent sensor: Real-time applications and anti-counterfeiting
  • Sathiyanarayanan Kulathu Iyer,
  • Selin Manoj Kumar
Sathiyanarayanan Kulathu Iyer
Vellore Institute of Technology

Corresponding Author:[email protected]

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Selin Manoj Kumar
Vellore Institute of Technology
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Abstract

An AIE active imidazole-based chemoreceptor, 2-(4-(1-(benzo[d]thiazol-2-yl)-4,5-diphenyl-1H-imidazol-2-yl)benzylidene)-N-(pyren-1-ylmethylene)hydrazine-1-carbothioamide ( BIPC), has been successfully synthesized and characterized by NMR and HRMS analyses. The aggregation-induced emission of BIPC in a binary solvent system is fascinating. Upon aggregation, BIPC forms nanoaggregate which is characterized by dynamic light scattering methods (DLS). Furthermore, optical experiments demonstrated that the sensor BIPC is highly selective and sensitive to F - with a low level of detection. A color change with a bathochromic shift of absorbance and a ratiometric fluorescence attributed to the induction of photoinduced electron transfer (PET) and intramolecular charge transfer (ICT) processes upon the addition of F -. In the present study Job’s plot, HRMS, DFT, and 1H NMR experiments were used to validate BIPC’s detection mechanism and binding stoichiometry with F -. Additionally, F - was successfully detected in environmental water samples by BIPC. Since BIPC emits a bright light, it can be used as a counterfeit detecting tool. It was also found that BIPC was effective for detecting F - ion in live cells with a high permeability.