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An antipyrine based fluorescence “turn-on” dual sensor for Zn2+ and Al3+ and its selective fluorescence “turn-off” sensing towards 2,4,6-trinitrophenol (TNP) in the aggregated state

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Abstract

A 2,6-diformyl-p-cresol (DFC)-4-amino antipyrine (AP) based dual signaling fluorescent Schiff base ligand (DFCAP) is found to exhibit colorimetric and fluorescence turn on selective sensing towards metal ions, Zn2+ and Al3+. It also exhibits a significant aggregation induced emission (AIE) phenomenon by controlling the water–THF solvent ratio which provides robust green emissive fluorogenic aggregates with well-defined morphologies. Turn-on fluorescence enhancements as high as 195 fold and 168 fold in methanol for Al3+ and Zn2+ at 480 nm and 508 nm, respectively, were noticed. The binding constants and stoichiometry determined from the fluorescence titration data are K = 7.63 × 104 M−1 and 3.42 × 104 M−1 and 1:1 complexation for both Al3+ and Zn2+ respectively, supported by Job’s method. DFCAP shows high sensitivity towards the detection of Zn2+ and Al3+ ions with very low detection limit values of ca. ~21 nM and 30 nM respectively. Besides by applying its attractive AIE feature, the green emissive hydrosol functions as a good chemosensor with high sensitivity for a selected explosive TNP through ground state complexation with a LOD value of ca. ~1.74 µM and especially a high Stern–Volmer quenching constant of ca. ~4.14 × 105 M−1. For instant ‘naked eye’ response for the trace detection of TNP in the solution state, we fabricated a simple paper strip that could detect TNP on-site in a fast, inexpensive and simple way.

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Authors and Affiliations

  1. Department of Chemistry, Vidyasagar University, Midnapore, 721102, W.B., India

    Sudipto Dey, Ashim Maity, Milan Shyamal, Debasish Das, Samir Maity, Prabhat Kumar Giri, Naren Mudi, Shashanka Shekhar Samanta, Paresh Hazra & Ajay Misra

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  1. Sudipto Dey
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  2. Ashim Maity
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  3. Milan Shyamal
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Correspondence to Ajay Misra.

Additional information

Electronic supplementary information (ESI) available: Additional details of a FT-IR study, 1H NMR study, quantitative determination results and also the detailed characterization data to establish the sensory and AIE behavior of DFCAP. See DOI: 10.1039/c9pp00226j

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Dey, S., Maity, A., Shyamal, M. et al. An antipyrine based fluorescence “turn-on” dual sensor for Zn2+ and Al3+ and its selective fluorescence “turn-off” sensing towards 2,4,6-trinitrophenol (TNP) in the aggregated state. Photochem Photobiol Sci 18, 2717–2729 (2019). https://doi.org/10.1039/c9pp00226j

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