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[2+2] Photocycloaddition of Styryl Dyes in the Cucurbit[8]uril Cavity and Its Ultrafast Dynamics

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Abstract

[2+2] Photocycloaddition of a series of styryl dyes (a, b, and c, see text) in the cavity of cucurbit[8]uril (CB8) in aqueous solutions has been studied by optical spectroscopy. The complex formation constants were calculated for the 1 : 1 and 2 : 1 complexes of the styryl dyes with CB8. The optimal CB8 to dye molar ratios that correspond to the highest concentrations of the 2 : 1 complexes in the solution have been determined as 0.5, 0.3, and 1 for dyes a, b, and c, respectively. The quantum yields of photocycloaddition have been calculated from the results of dye photolysis in the presence of CB8: 0.06, 0.02, and 0.04 for a, b, and c, respectively. The fluorescence decay kinetics has been studied on the picosecond timescale. The lifetimes found are 1–2 ps, which correspond to the characteristic time of the solvation shell effect on the redistribution of the dye charge in the excited state. The long component of the fluorescence decay on the order of tens of picosecond is also observed. This component decreases in the presence of CB8, indicating the formation of dimeric state.

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ACKNOWLEDGMENTS

The study was supported by the Russian Scientific Foundation, project no. 14-13-00751, in part of time-resolved measurements; by the Russian Foundation for Basic Research, project no. 18-03-00214, in part of the synthesis of styryl dyes; and by the Ministry of Science and Higher Education under the State Program of “Crystallography and Photonics” Federal Scientific Research Center in part of steady-state measurements.

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Authors and Affiliations

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

    A. D. Svirida, D. A. Ivanov, I. V. Kryukov, Yu. A. Shandarov, N. Kh. Petrov, M. V. Alfimov, N. A. Aleksandrova, S. K. Sazonov, A. I. Vedernikov & S. P. Gromov

  2. Moscow Institute of Physics and Technology (State University), 141700, Dolgoprudnyi, Moscow oblast, Russia

    A. D. Svirida, N. Kh. Petrov, M. V. Alfimov & 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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  6. M. V. Alfimov
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  8. S. K. Sazonov
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  9. A. I. Vedernikov
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Correspondence to A. D. Svirida.

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Translated by T. Nekipelova

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Svirida, A.D., Ivanov, D.A., Kryukov, I.V. et al. [2+2] Photocycloaddition of Styryl Dyes in the Cucurbit[8]uril Cavity and Its Ultrafast Dynamics. High Energy Chem 53, 204–210 (2019). https://doi.org/10.1134/S0018143919030147

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