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Photoprocesses in Guest–Host Complexes of a Styryl Dye Thio Derivative with Cucurbiturils

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Abstract

Photoprocesses in aqueous solutions of the styryl dye 1-ethyl-4-{(E)-2-[4(methylthio)phenyl]vinyl}pyridinium perchlorate (1) and its complexes with cucurbit[n]urils (CB[n], n = 6–8) have been studied using the methods of stationary and time-resolved optical spectroscopy. The fluorescence intensity increases by approximately 3 times in 1 : 1 complexes of 1 and CB[6], whereas CB[7] has almost no effect on the fluorescence intensity. In 2 : 1 complexes with CB[8], the photocycloaddition reaction does not occur, with strong fluorescence quenching being associated with the formation of nonreactive dimers. The fluorescence decay kinetics of 1 has two characteristic times, 1.4 and ~130 ps, and changes little in the complexes. The photoinduced intramolecular charge transfer in 1 is an order of magnitude smaller than in the well-known dye DASPI.

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ACKNOWLEDGMENTS

The authors thank A.I. Vedernikov and S.K. Sazonov for assistance in the production of dye 1.

Funding

Optical (including time-resolved fluorescence) measurements and the synthesis of 1-ethyl-4-{(E)-2-[4-(methylthio)phenyl]vinyl}pyridinium perchlorate 1 were supported by the Russian Science Foundation, project nos. 22-23-00234 and 22-13-00064, respectively, and the computational study was supported by the Russian Ministry of Science and Higher Education as part of the State Assignment of the Federal Research Center “Crystallography and Photonics” of the Russian Academy of Sciences.

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Authors and Affiliations

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

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

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

    S. P. Gromov

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  1. A. D. Svirida
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  2. D. A. Ivanov
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  3. I. V. Kryukov
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  4. N. Kh. Petrov
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  5. N. A. Aleksandrova
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  6. V. G. Avakyan
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  7. S. P. Gromov
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Correspondence to D. A. Ivanov.

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Translated by S. Zatonsky

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Svirida, A.D., Ivanov, D.A., Kryukov, I.V. et al. Photoprocesses in Guest–Host Complexes of a Styryl Dye Thio Derivative with Cucurbiturils. High Energy Chem 57, 109–115 (2023). https://doi.org/10.1134/S0018143923020145

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  • DOI: https://doi.org/10.1134/S0018143923020145

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