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Propylimidazole Functionalized Coumarin Derivative as Dual Responsive Fluorescent Chemoprobe for Picric Acid and Fe3+ Recognition: DFT and Natural Spring Water Applications

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Abstract

A propylimidazole functionalized coumarin derivative (IPC) was fabricated for the first time and applied as a dual responsive fluorescent chemoprobe for sensitive and selective recognition of picric acid (PA) and Fe3+. Strong fluorescence quenching phenomena of the IPC were observed in H2O/ACN (5/95, v/v) medium (λem=408 nm) upon the additions of Fe3+or PA. The fabricated dual responsive IPC offered good selectivity and sensitivity with the low limit of detection values (0.92 µM for PA and 0.22 µM for Fe3+) lower than the acceptable amounts of Fe3+ and PA by the international official authorities. The validation study for the chemoprobe IPC for PA and Fe3+ was also performed. The interaction phenomena of IPC with PA and Fe3+ based on the findings of a range of experiments were considered and DFT computations were done to verify their recognition mechanisms. The sensing phenomena of IPC towards PA (1:1) and Fe3+ (3:1) were confirmed by the MALDI TOF–MS, FT–IR, 1H–NMR titration and Job's methods. Furthermore, the compound IPC was effectively applied as a fluorescent sensor for Fe3+ and PA detection in real natural spring water samples.

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Data Availability

The data sets generated during the current study are available from the corresponding author on reasonable request.

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Funding

This study was supported by the KMU with the financial support (KMU BAP–Grant Numbers: 06–M–20, 02-YL-19 and 13-YL-15).

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Authors and Affiliations

  1. Department of Chemistry, Kamil Ozdag Science Faculty, Karamanoglu Mehmetbey University, 70200, Karaman, Turkey

    Sukriye Nihan Karuk Elmas, Abdurrahman Karagoz, Fatma Nur Arslan & Ibrahim Yilmaz

  2. Department of Chemistry and Chemical Processing Technologies, Vocational School of Technical Sciences, Karamanoglu Mehmetbey University, 70200, Karaman, Turkey

    Abdurrahman Karagoz

Authors
  1. Sukriye Nihan Karuk Elmas
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  3. Fatma Nur Arslan
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  4. Ibrahim Yilmaz
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Contributions

All authors contributed in the planning, editing and writing of the manuscript. SN KE: Resource, Methodology, Investigation, Software, Data curation. A K: Methodology, Investigation, Software, Data curation. FN A: Data curation, Writing-review and Editing. I Y: Data curation, Writing-review and Editing

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Correspondence to Sukriye Nihan Karuk Elmas.

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A licensed version of Gaussian-09 software is used in computational study

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Karuk Elmas, S.N., Karagoz, A., Arslan, F.N. et al. Propylimidazole Functionalized Coumarin Derivative as Dual Responsive Fluorescent Chemoprobe for Picric Acid and Fe3+ Recognition: DFT and Natural Spring Water Applications. J Fluoresc 32, 1357–1367 (2022). https://doi.org/10.1007/s10895-022-02936-z

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