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A Highly Sensitive and Selective Fluorescent Probe for the Detection of Cerium(III) Using Tridentate Based-Oxazolidine: Experimental and DFT Investigations

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Abstract

A new fluorescent sensor based on oxazolidine derivative, (2-(pyridin-2-yl)oxazolidine-4,4-diyl)dimethanol; TN), was designed and synthesized successfully in high yield (82%) under Schiff base reaction. The structural elucidation of the sensor has been confirmed by Infrared Spectroscopy, Nuclear Magnetic Resonance Spectroscopy, and High Resolution Mass Spectrometry - Electrospray Ionization - Time of Flight. The designed TN sensor exhibited high sensitivity and selectivity towards an aqueous solution of cerium(III) over various metal ions under biologically relevant conditions (100.0 mM HEPES buffer pH 7.4). The limit of detection (LOD) was reported as 54.0 nM. The geometry of tridentate based-oxazolidine (TN) and its coordination of cerium(III) (TN-Ce3+) was proven by using the density functional theory (DFT) calculations. The highest occupied molecular orbital - lowest unoccupied molecular orbital energy gap was decreased when TN-Ce3+ is formed. The results indicated that TN can be used as a fluorescent probe for high sensitivity and selectivity detection of cerium(III) ions.

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Data Availability

The characteristic 1 H, 13 C NMR, FT-IR, and mass spectra of TN are shown in Figs. S1–S4. Time response of TN probe to Ce(III) is shown in Fig. S5.

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Funding

We thank the Faculty of Science at Si Racha, Kasetsart University, Si Racha Campus, Chonburi, Thailand for financial support. Kasetsart University Research and Development Institute (P-3.2(D)155.61), National e-Science Infrastructure Consortium, National Electronics and Computer Technology Center (NECTEC) for providing computing resources.

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Authors and Affiliations

  1. Faculty of Science at Si Racha, Kasetsart University, Si Racha Campus, 20230, Chonburi, Thailand

    Malinee Promkatkaew, Kitiya Naree, Jinnapus Sillapa & Sopanat Kongsriprapan

  2. Chemistry Faculty of Science and Technology, Suratthani Rajabhat University, 272 Moo 9, Surat- Nasan Road., Khuntale, Surat Thani, 84100, Muang, Thailand

    Laksamee Chaicharoenwimolkul Chuaitammakit

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  1. Malinee Promkatkaew
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Contributions

M.P. expanded the idea, performed the theoretical calculations, wrote, and revised the manuscript. L.C.C. discussed critical ideas from the data, wrote, and revised the manuscript. K.N. and J.S. performed the experiment, measured, and collected the related data. S.K. initiated the idea, expanded the idea, discussed critical ideas from the data, wrote, and revised the manuscript.

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Correspondence to Sopanat Kongsriprapan.

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Promkatkaew, M., Chuaitammakit, L.C., Naree, K. et al. A Highly Sensitive and Selective Fluorescent Probe for the Detection of Cerium(III) Using Tridentate Based-Oxazolidine: Experimental and DFT Investigations. J Fluoresc 33, 145–152 (2023). https://doi.org/10.1007/s10895-022-03043-9

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