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Thiadiazole Functionalized Salicylaldehyde-Schiff Base as a pH-responsive and chemo-reversible “Turn-Off” fluorescent probe for selective cu (II) detection: Logic Gate Behaviour and Molecular Docking Studies

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Abstract

A novel thiadiazole functionalized schiff base chemoreceptor (E)-2,4-dichloro-6-(((5-mercapto-1,3,4-thiadiazol-2-yl)imino)methyl)phenol (SB-1) has been synthesized and characterized spectroscopically by using various techniques. Its photophysical behaviour was scanned towards a variety of metal ions in mixed aqueous media. The chemosensor (SB-1) displayed excellent selectivity towards Cu2+ ion through fluorescent diminishment (turn-off phenomenon). Colorimetric analyses showed a rapid colour change from yellow to dark red under visible light upon addition of Cu2+ ions. Interestingly, the original yellow colour reappeared back instantly after the addition of EDTA2− anions, thus confirming the reversible nature of SB-1. Competitive experiments validated no interference from the other co-existing metal ions in the recognition process of SB-1 towards Cu2+ ion. Job’s plot confirmed 1:1 binding stoichiometry between SB-1 and Cu2+ ion with the binding constant value of 3.87 × 104 M− 1. The limit of detection was determined to be 1.01 × 10− 7 M suggesting good sensitivity of SB-1 towards Cu2+ ions. Furthermore, pH-dependent UV-Vis spectral behaviour of SB-1 confirmed that it could act as an effective optical pH-sensor for highly acidic environment as well. Portable nature of probe SB-1 was explored by fabricating “easy-to-use” paper test strips, which allow robust and rapid detection of Cu2+ ions. Based on the multi-responsive properties of SB-1, a ‘NOR’ logic gate was constructed by applying Cu2+ and EDTA2− as chemical inputs (ln1: Cu2+, ln2: EDTA2−) while emission intensity observed at 560 nm was considered as output signal (O1). DFT optimized geometries confirmed that chemosensor SB-1 exists in Azo form (Enol form) in its ground state. Molecular docking of the SB-1 and its copper complex, into the binding site of TRK protein tyrosine kinase (PDB: 1t46) was also carried out to explore their biological activity and their potential use as TRK inhibitors.

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Data Availability

The datasets generated during and/or analyzed during the current study are available from the corresponding author on request. They will be made publicly available upon publication of this article.

Code Availability

The code used are available from the corresponding author on request. They will be made publicly available upon publication of this article.

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Acknowledgements

The authors express their sincere thanks to the Principal, Dyal Singh College, University of Delhi, and Principal, Zakir Husain College, University of Delhi for providing the necessary research facilities, USIC University of Delhi for spectroscopic studies. Two authors, Deepak Tomar and Madhuri Chaurasia thank the UGC, New Delhi for JRF, UGC award letter number 113932 and 117582, respectively.

Funding

The research was supported by UGC JRF fellowship.

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Authors and Affiliations

  1. Department of Chemistry, Dyal Singh College, University of Delhi, New Delhi, India

    Aruna Chhikara, Deepak Tomar & Sulekh Chandra

  2. Department of Chemistry, University of Delhi, New Delhi, India

    Deepak Tomar & Swarita Gopal

  3. Department of Chemistry, Indian Institute of Technology, Kanpur, Uttar Pradesh, India

    Gaurav Bartwal

  4. Department of Chemistry, Zakir Husain Delhi College, University of Delhi, New Delhi, India

    Madhuri Chaurasia

  5. Department of Chemistry, Indian Institute of Technology, Roorkee, Uttarakhand, India

    Anuj Sharma

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  1. Aruna Chhikara
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Contributions

Dr. A. Chhikara: (Supervision, designed and contributed to the interpretation of results). D. Tomar: (Investigation designed and directed the study, planned and carried out the experiments, wrote the manuscript). Dr. G. Bartwal: (Study effect of pH and practical utilization of chemosensor). Dr. M. Chaurasia: (Contributed to colorimetric studies and HOMO-LUMO analysis). Dr. A. Sharma: (Contributed to fluorescence spectra analysis). Dr. S. Gopal: (Analyzed and interpreted molecular docking simulation data). Dr. S. Chandra: (read and approved the final manuscript).

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Correspondence to Aruna Chhikara or Sulekh Chandra.

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Chhikara, A., Tomar, D., Bartwal, G. et al. Thiadiazole Functionalized Salicylaldehyde-Schiff Base as a pH-responsive and chemo-reversible “Turn-Off” fluorescent probe for selective cu (II) detection: Logic Gate Behaviour and Molecular Docking Studies. J Fluoresc 33, 25–41 (2023). https://doi.org/10.1007/s10895-022-02991-6

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