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Fluorescent chemosensor for mercury(II) cations in an aqueous solution based on 4-acetylamino-1, 8-naphthalimide derivative containing the N-phenylazadithia-15-crown-5-ether receptor

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Abstract

The 4-acetylamino-1,8-naphthalimide derivative containing the N-phenylazadithia-15-crown-5-ether fragment in the N-aryl substituent at the imide nitrogen atom of the naphthalimide core was synthesized, and its cation-dependent spectral properties were studied. The resulting compound in the photoexcited state exhibits low-intensity fluorescence due to the process of electron transfer from the N-aryl group to the naphthalimide residue, which is confirmed by the data of quantum chemical calculations performed using the PM6 method. The binding of Hg2+ in an aqueous acetate buffer solution at pH 6.0 is accompanied by the formation of a 1: 1 metal—ligand complex in which the electron transfer is suppressed leading to fluorescence enhancement. The observed spectral changes were used for the determination of the stability constant K of the complex (logK = 6.51±0.03). The found limit of Hg2+ detection using the synthesized sensor (28 nmol L−1) is fairly close the maximum permissible concentration for mercury in drinking water. The study of the selectivity of complexation showed that the presence of Cu2+, Zn2+, Ni2+, Pb2+ Cd2+, Ca2+, Mg2+, and Fe2+ cations did not impede the determination of Hg2+. The presented results indicate that the synthesized chemosensor is promising as a selective and highly sensitive fluorescent reagent for Hg2+ ions in an aqueous solution.

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Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    P. A. Panchenko, A. S. Polyakova, Yu. V. Fedorov & O. A. Fedorova

  2. D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya pl., 125047, Moscow, Russian Federation

    P. A. Panchenko, A. S. Polyakova & O. A. Fedorova

Authors
  1. P. A. Panchenko
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  2. A. S. Polyakova
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  3. Yu. V. Fedorov
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  4. O. A. Fedorova
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Correspondence to P. A. Panchenko.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1939–1945, October, 2021.

This paper does not contain descriptions of studies on animals or humans.

The authors declare no competing interests.

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Panchenko, P.A., Polyakova, A.S., Fedorov, Y.V. et al. Fluorescent chemosensor for mercury(II) cations in an aqueous solution based on 4-acetylamino-1, 8-naphthalimide derivative containing the N-phenylazadithia-15-crown-5-ether receptor. Russ Chem Bull 70, 1939–1945 (2021). https://doi.org/10.1007/s11172-021-3300-6

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