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Mechanism of Complexation of Cucurbiturils with Styryl Dyes in the Presence of Sodium Cations

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Abstract

The complexation of styryl dyes 4-[(E)-2-(3,4-dimethoxyphenyl)]-1-ethylpyridinium perchlorate and trans-4-[4-(dimethylamino)styryl]-1-methylpyridinium iodide with cucurbit[n]urils (CBn) (n = 6, 7) in aqueous solutions in the presence of sodium sulfate with a concentration of 0 to 1 mol/L has been studied by stationary and time-resolved optical spectroscopy, electrochemical, and quantum chemical methods. Adding the electrolyte to the solution decomposes 1 : 1 inclusion complexes with the dyes (D+ · CBn) due to competitive formation of complexes of the cavitand with sodium cations: Na+ · CBn and Na+ · CBn · Na+. Their total formation constants have been determined to be β = 2760 and 168 600 M−2 for CB7 and CB6, respectively, which agrees with the results of quantum chemical calculations. At the same time, no evidence of the presence of Na+ · CBn · D+ type complexes has been found in solutions.

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Funding

This work was supported by the Russian Foundation for Basic Research (project no. 18-03-00214) for synthesis of the styryl dyes, the Ministry of Education and Science of the Russian Federation for works carried out under the State Assignment of Photochemistry Center of “Crystallography and Photonics” Federal Scientific Research Center on optical measurements and quantum chemical calculations, and the Program of Development of the Moscow State University for electrochemical measurements.

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Authors and Affiliations

  1. Photochemistry Center of “Crystallography and Photonics” Federal Scientific Research Center, Russian Academy of Sciences, 119421, Moscow, Russia

    I. V. Kryukov, A. D. Svirida, Yu. A. Shandarov, D. A. Ivanov, V. G. Avakyan, N. Kh. Petrov, N. A. Aleksandrova & S. P. Gromov

  2. Faculty of Chemistry, Moscow State University, 119991, Moscow, Russia

    S. P. Gromov, E. V. Stenina & L. N. Sviridova

Authors
  1. I. V. Kryukov
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  2. A. D. Svirida
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  3. Yu. A. Shandarov
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  4. D. A. Ivanov
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  5. V. G. Avakyan
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  6. N. Kh. Petrov
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  7. N. A. Aleksandrova
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  8. S. P. Gromov
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  9. E. V. Stenina
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  10. L. N. Sviridova
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Corresponding author

Correspondence to D. A. Ivanov.

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Translated by A. Tatikolov

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Kryukov, I.V., Svirida, A.D., Shandarov, Y.A. et al. Mechanism of Complexation of Cucurbiturils with Styryl Dyes in the Presence of Sodium Cations. High Energy Chem 54, 403–413 (2020). https://doi.org/10.1134/S0018143920060107

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  • DOI: https://doi.org/10.1134/S0018143920060107

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