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Evaluation of metal ion sensing behaviour of fluorescent probe along with its precursors: PET-CHEF mechanism, molecular logic gate behaviour and DFT studies

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Abstract

For the first time, we have reported the metal ion sensing behaviour of a fluorescent probe APAP (derivative of 4-amino/4-formyl antipyrine) along with its precursors (AAP-4-Aminoantipyrine, FAP-4-Formylantipyrine) and explained the tuning of precursors resulted in difference in the sensing behaviour. The two antipyrine precursors (4-amino/4-formyl antipyrine) were condensed together to form a new host molecule APAP, which acts an effective fluorescent chemosensor for detection of Fe3+ ions. The precursors AAP and FAP would able to detect Al3+ and Cr3+ ions respectively. The antipyrine precursors as well as the antipyrine derivative showed fluorescence response towards trivalent cations when treated with various metal ions in CH3OH:H2O (1:9, v/v) medium. Binding stoichiometry between APAP and Fe3+ ion was 1:1 from Jobs’ plot and the binding constant value was calculated as 5.3 × 105 M−1 by Benesi–Hildebrand plot. Addition of Na2EDTA to the [APAP-Fe3+] complex solution quenched the fluorescence emission, indicating the reversible nature of the probe. The binding of APAP with Fe3+ was based on restricted PET with CHEF process. Quantum mechanical studies using time dependent density functional theory (TDDFT) have also been carried out to understand the mechanism of Fe3+ binding mode with APAP probe. With respect to various pH, the probe APAP exhibited an AND molecular logic gate behaviour when H+ and Fe3+ ions were given as inputs.

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For the first time, the metal recognition property of a fluorescent probe along with its precursors was studied.

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Acknowledgements

Authors sincerely acknowledge the Science and Engineering Research Board (SERB), Department of Science and Technology, India, for the financial support (Project Number SB/FT/CS-068/2012).

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Authors and Affiliations

  1. Department of Chemistry, Karunya Institute of Technology and Sciences (Deemed to be University), Coimbatore, Tamil Nadu, 641 114, India

    Chitra Varadaraju, Mosae Selvakumar Paulraj, G. Tamilselvan & I. V. Muthu Vijayan Enoch

  2. Division of Chemistry, Department of Sciences and Humanities, Vignan’s Foundation for Science, Technology and Research, Vadlamudi, Guntur, Andhra Pradesh, 522 213, India

    V. Srinivasadesikan

  3. Department of Chemistry and Biochemistry, National Chung Cheng University, Chia-Yi, 621, Taiwan

    Lee Shyi-Long

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  1. Chitra Varadaraju
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  2. Mosae Selvakumar Paulraj
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  3. G. Tamilselvan
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Correspondence to Mosae Selvakumar Paulraj.

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Varadaraju, C., Paulraj, M.S., Tamilselvan, G. et al. Evaluation of metal ion sensing behaviour of fluorescent probe along with its precursors: PET-CHEF mechanism, molecular logic gate behaviour and DFT studies. J Incl Phenom Macrocycl Chem 95, 79–89 (2019). https://doi.org/10.1007/s10847-019-00919-5

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