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Schiff Bases Derived from 6-Formyl-3-(4-methoxyphenyl)picolinonitrile: Rational Synthetic Approach and Photophysical Properties

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Abstract

A convenient synthetic approach to Schiff bases based on 3-(4-methoxyphenyl)-6-formylpicolinonitrile as surrogates of 2,2′-bipyridine ligands is proposed. The synthesis was carried out using the “1,2,4-triazine” methodology, and a more efficient method for the preparation of 5-aryl-6-cyanopyridine-2-carbaldehydes was developed compared to the previously described one, which involves the use of isonitrosoacetophenone hydrazone and chloroacetonitrile as starting compounds. The resulting compounds exhibit fluorescence in solutions with a quantum yield of up to 15.4%, as well as a fluorescent response to the zinc cation in the form of dramatic fluorescence quenching.

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ACKNOWLEDGMENTS

The work was performed using the equipment of the “Spectroscopy and Analysis of Organic Compounds” Center for Collective Use.

Funding

The synthesis of Schiff bases and UV study of their complex formation with Zn2+ were performed under financial support of the Grants Council under the President of the Russian Federation (project no. NSh-1223.2022.1.3) and the literature search and photophysical investigations were funded by the Russian Science Foundation (project no. 23-13-00318, https://rscf.ru/project/23-13-00318/).

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Authors and Affiliations

  1. Ural Federal University named after the First President of Russia B.N. Eltsin, 620002, Yekaterinburg, Russia

    E. A. Kudryashova, M. I. Valieva, Ya. K. Shtaitz, N. N. Mochulskaya, A. P. Krinochkin, D. S. Kopchuk, G. V. Zyryanov & V. L. Rusinov

  2. Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, 620108, Yekaterinburg, Russia

    M. I. Valieva, A. P. Krinochkin, D. S. Kopchuk, G. V. Zyryanov & V. L. Rusinov

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  1. E. A. Kudryashova
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  2. M. I. Valieva
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  3. Ya. K. Shtaitz
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  4. N. N. Mochulskaya
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  5. A. P. Krinochkin
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  6. D. S. Kopchuk
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  7. G. V. Zyryanov
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  8. V. L. Rusinov
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Correspondence to M. I. Valieva.

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Kudryashova, E.A., Valieva, M.I., Shtaitz, Y.K. et al. Schiff Bases Derived from 6-Formyl-3-(4-methoxyphenyl)picolinonitrile: Rational Synthetic Approach and Photophysical Properties. Russ J Gen Chem 93 (Suppl 1), S73–S80 (2023). https://doi.org/10.1134/S107036322314013X

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