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New terpyridine derivatives of thiacalix[4]arenes in solution and at the water-air interface

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Abstract

New di- and tetrasubstituted thiacalix[4]arenes in cone and 1,3-alternate configurations containing terpyridine and triazole fragments at the lower rim of the macrocycle, as well as model triazole-terpyridine, are synthesized. The structures and purity of the compounds are confirmed by NMR spectroscopy and high-resolution MALDI mass spectrometry. The compounds form luminescent complexes with lanthanide cations (europium and terbium) in a chloroform-methanol (10: 1) system during fluorimetric titration. The possibility of antenna ef ect during fluorescence sensitization in lanthanides by the thiacalixarene ligands is demonstrated. Successful immobilization of the terpyridine receptors on a solid substrate makes it possible to consider the Langmuir-Blodgett films on the basis of these receptors as promising adsorbents of lanthanide from nonaqueous media or organic salts and also provides new opportunities for the investigation of the luminescence characteristics of lanthanide complexes in thin films.

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Authors and Affiliations

  1. Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences,”, A. E. Arbuzov Institute of Organic and Physical Chemistry, 8 ul. Arbuzova, 420088, Kazan, Russian Federation

    A. A. Muravev, A. S. Agarkov, O. B. Bazanova, I. Kh. Rizvanov, A. V. Zaitseva & S. E. Solovieva

  2. Kazan (Volga Region) Federal University, 18 ul. Kremlevskaya, 420008, Kazan, Russian Federation

    F. B. Galieva, A. T. Yakupov & I. S. Antipin

  3. A. N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Build. 4, 31 Leninsky prosp., 119071, Moscow, Russian Federation

    A. V. Shokurov & S. L. Selektor

Authors
  1. A. A. Muravev
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  2. A. S. Agarkov
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  3. F. B. Galieva
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  4. A. T. Yakupov
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  5. O. B. Bazanova
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  6. I. Kh. Rizvanov
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  7. A. V. Shokurov
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  8. A. V. Zaitseva
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  9. S. L. Selektor
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  10. S. E. Solovieva
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  11. I. S. Antipin
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Corresponding author

Correspondence to A. A. Muravev.

Additional information

The authors are grateful to the Centers for Collective Use at the Kazan Scientific Center of the Russian Academy of Sciences and A. N. Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences for technical support of the studies.

This work was financially supported in the framework of the state task of the Kazan Scientific Center of the Russian Academy of Sciences (synthesis and characterization of the structures of the terpyridine ligands; A. A. Muravev, A. S. Agarkov, S. E. Solovieva, O. B. Bazanova, and I. Kh. Rizvanov) and financially supported in part by the Russian Foundation for Basic Research (Project No. 19-33-50008-mol-nr; study of the luminescence characteristics and aggregation behavior of the ligands).

Based on the materials of the International Markovnikov Congress on Organic Chemistry (June 21-28, 2019, Moscow- Kazan, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0339—0350, February, 2020.

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Muravev, A.A., Agarkov, A.S., Galieva, F.B. et al. New terpyridine derivatives of thiacalix[4]arenes in solution and at the water-air interface. Russ Chem Bull 69, 339–350 (2020). https://doi.org/10.1007/s11172-020-2766-y

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  • DOI: https://doi.org/10.1007/s11172-020-2766-y

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