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Synthesis and Photochemical Properties of 2,3;5,6-bis(cyclohexano)-BODIPY

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Abstract

The boron-dipyrromethene (BODIPY) dye containing an annelated cyclohexyl rings at the 2,3 and 5,6-positions of pyrroles has been synthesized and characterized. Photochemical properties of the obtained compound have been investigated in different individual solvents. 2,3;5,6-Bis(cyclohexano)-BODIPY exhibits intense chromophore properties with maximum of S o → S 1 band in the 543–549 nm (A from 66000 to 96000 L/mol·cm). The complex is a fluorophore with a quantum yield up to ~ 100%. The influence of solvent polarity on the spectral properties was evaluated. To better understand the spectroscopic results, quantum chemical calculations were carried out. Photostability of dye was studied.

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Acknowledgements

The reported study was funded by RFBR according to the research project No. 16-33-00611 mol_a and 16-33-00852 mol_a. We are grateful to the Interdisciplinary Supercomputer Center of the Russian Academy of Sciences (Moscow) for providing MBC 100 K cluster resources.

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  1. G.A. Krestov Institute of Solution Chemistry of Russian Academy of Sciences (ISC RAS), 1 Akademicheskaya st., 153045, Ivanovo, Russian Federation

    Anna Yu. Kritskaya, Natalia A. Bumagina, Elena V. Antina, Alexander A. Ksenofontov & Mikhail B. Berezin

  2. Ivanovo State University of Chemistry and Technology (ISUCT), 7 Sheremetevskij prosp., 153000, Ivanovo, Russian Federation

    Alexander S. Semeikin

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  1. Anna Yu. Kritskaya
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  2. Natalia A. Bumagina
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  3. Elena V. Antina
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  5. Mikhail B. Berezin
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Correspondence to Alexander A. Ksenofontov.

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Kritskaya, A.Y., Bumagina, N.A., Antina, E.V. et al. Synthesis and Photochemical Properties of 2,3;5,6-bis(cyclohexano)-BODIPY. J Fluoresc 28, 393–407 (2018). https://doi.org/10.1007/s10895-017-2201-4

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