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New Schiff base ligand N-(2-hydroxy-1-naphthylidene)-2-methyl aniline and its nano-sized copper(II) complex: synthesis, characterization, crystal structure and application as an electrochemical sensor of 2-phenylphenol in the presence of 4-chlorophenol

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Abstract

A new bidentate Schiff base ligand [HL = N-(2-hydroxy-1-naphthylidene)-2-methyl aniline] and its mononuclear Cu(II) complex with formula [CuL2] were prepared and characterized by Fourier-transform infrared (FT-IR), Nuclear Magnetic Resonance [1H and 13C{1H} NMR], Ultraviolet–visible (UV–Vis) spectroscopic methods, and elemental analysis. The Schiff base ligand [HL] and Cu(II) complex [CuL2] crystal structures were determined using the single crystal X-ray diffraction method. The data of crystal structure indicated a bidentate method of coordination for the Schiff base by NO donor sets in a regular square-planar fashion. The nano-sized [CuL2] was synthesized by the sonochemical method and was detected by X-ray powder diffraction (XRD), Field Emission Scanning Electron Microscopes (FE-SEM), and FT-IR spectroscopy. The average particle size in nano-sized [CuL2] was approximately 55 nm. The nano-complex [CuL2] was used in a modified screen-printed electrode (modified SPE) as an electrochemical sensor for the detection of 2-phenylphenol. The oxidation reaction of 2-phenylphenol at the modified electrode indicated a linear range of 0.01–600.0 µM and the recognition limit was 8.0 nM. The proposed electrode shows two well-separated oxidation signals for 2-phenylphenol and 4-chlorophenol, which makes it suitable for the simultaneous determination of these analytes. The fabricated sensor was successfully applied for the designation of 2-phenylphenol in lemon rind, orange rind, and water samples with satisfactory recovery.

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Acknowledgements

The authors thank the University of Sistan and Baluchestan and the Graduate University of Advanced Technology, Kerman, Iran for the support of this research work. The crystallographic part was supported by the project 18-10504S of the Czech Science Foundation using the CzechNanoLab Research Infrastructure supported by MEYS CR (LM2018110).

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  1. Department of Chemistry, University of Sistan and Baluchestan, P.O. Box 98135-674, Zahedan, Iran

    Mahbubeh Fazli & Niloufar Akbarzadeh-T

  2. Environment Department, Institute of Science and High Technology and Environmental Sciences, Graduate University of Advanced Technology, Kerman, Iran

    Hadi Beitollahi

  3. Institute of Physics, Academy of Sciences of the Czech Republic, Na Slovance 2, 182 21, Praha, Czech Republic

    Michal Dušek & Václav Eigner

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Fazli, M., Akbarzadeh-T, N., Beitollahi, H. et al. New Schiff base ligand N-(2-hydroxy-1-naphthylidene)-2-methyl aniline and its nano-sized copper(II) complex: synthesis, characterization, crystal structure and application as an electrochemical sensor of 2-phenylphenol in the presence of 4-chlorophenol. J Mater Sci: Mater Electron 32, 25118–25136 (2021). https://doi.org/10.1007/s10854-021-06967-3

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