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Chalcone-based Turn-Off Chemosensor for Selective and Susceptible Detection of Fe2+ Ions: Spectroscopic and DFT Investigations

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Abstract

Herein, in this report we are introducing newly synthesized chalcone derivative, “(E)-1-phenyl-3-(4-((5-(((Z)-thiophen-2-ylmethylene)amino)-1,3,4-thiadiazol-2-yl)thio)phenyl)prop-2-en-1-one” (5), as a chemosensor to detect Fe2+ metal ions in HEPES buffer solution of pH 7.5. Spectroscopic techniques were used to confirm the synthesized sensor. To determine the chemical reactivity and molecular stability of the probe, a frontier molecular orbitals investigation was carried out. A molecular electrostatic potential map was investigated to know the binding site of 5 for metal ion coordination. The theoretical absorption and fluorescence emission properties were estimated and correlated with the experimental observations. The sensor showed excellent selectivity for Fe2+ compared to all other studied metal ions. The fluorescence binding studies were carried out by adding different amounts of Fe2+ ions for a fixed concentration of probe 5. The inclusion of Fe2+ ions resulted in a decrease in fluorescence intensity with a bathochromic shift of emission wavelength of 5 due to the 5-Fe2+ complexation. The binding affinity value for the probe was found to be 576.2 M−1 with the help of the Stern–Volmer plot. The Job's plot and mass spectra supported the 2:1 (5: Fe2+) stoichiometry of complex formation. The detection limit and limit of quantification of 5 for Fe2+ were calculated to be 4.79 × 10–5 M and 14.54 × 10–5 M. Further, in addition to this, the photophysical parameters such as fluorescence lifetime of 5 and 5-Fe2+ complex measured to be 0.1439 and 0.1574 ns. The quantum yield of 5 and 5-Fe2+ was found to be 0.0398 and 0.0376. All these experimental findings revealed that probe 5 has excellent selectivity and sensitivity for Fe2+ ions.

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Acknowledgements

The Department of Science and Technology (DST), the Government of Karnataka, and the Karnataka Science and Technology Promotion Society (K-STePS) are all acknowledged for their financial support of this study on behalf of the author, Bhavya N.R. The FT-IR, lifetime and ESI-MS data were provided by the Sophisticated Analytical Instrumentation facility (SAIF), Indian Institute of Technology, Madras, for which the authors are grateful. Additionally, University of Mysore, a University with Potential for Excellence (UPE), for providing facilities for fluorescence and UV-absorption spectroscopy. We appreciate Dr. Jeyaseelan S. for providing the computational resources.

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Authors and Affiliations

  1. Department of Physics, Vidyavardhaka College of Engineering, Mysuru, 570002, Karnataka, India

    Bhavya Nelligere Revanna

  2. Department of Chemistry, Mangalore University, Mangalagangothri, Mangalore, 574199, Karnataka, India

    Vinuta Kamat & Boja Poojary

  3. Department of Studies in Physics, University of Mysore, Mysuru , Manasagangotri, 570006, Karnataka, India

    Bhavya Nelligere Revanna, Ananda Swamynayaka, Keshav Kumar Harish, Keerthikumara Venkatesha & Mahendra Madegowda

  4. School of Physical Sciences, Amrita Vishwa Vidyapeetham, Mysuru Campus, Mysuru, 570026, Karnataka, India

    Sanjay S. Majani & Shiva Prasad Kollur

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  1. Bhavya Nelligere Revanna
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Contributions

All authors contributed to the study's conception and design. Methodology, Validation, Investigation, Software, Formal analysis, and writing – Original draft by Bhavya Nelligere Revanna. Conceptualization, Methodology, Supervision, writing-Review & Editing by Mahendra Madegowda. Investigations, Resources, and data collection were performed by Vinuta Kamat, Ananda Swamynayaka, Keshav Kumar Harish, Keerthikumara Venkatesha, Boja Poojary, Sanjay S. Majani and Shiva Prasad Kollur. All authors read and approved the final manuscript.

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Correspondence to Mahendra Madegowda.

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Revanna, B.N., Kamat, V., Swamynayaka, A. et al. Chalcone-based Turn-Off Chemosensor for Selective and Susceptible Detection of Fe2+ Ions: Spectroscopic and DFT Investigations. J Fluoresc (2024). https://doi.org/10.1007/s10895-024-03646-4

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