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Synthesis, Photophysical and Redox Properties of the D–π–A Type Pyrimidine Dyes Bearing the 9-Phenyl-9H-Carbazole Moiety

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Abstract

Novel donor-π-acceptor dyes bearing the pyrimidine unit as an electron-withdrawing group have been synthesized by using combination of two processes, based on the microwave-assisted Suzuki cross-coupling reaction and nucleophilic aromatic substitution of hydrogen. Spectral properties of the obtained dyes in six aprotic solvents of various polarities have been studied by ultraviolet–visible and fluorescence spectroscopy. In contrast to the absorption spectra, fluorescence emission spectra displayed a strong dependence from their solvent polarities. The nature of the observed long wavelength maxima has been elucidated by means of quantum chemical calculations. The electrochemical properties of these dyes have been investigated by using cyclic voltammetry, while their photovoltaic performance was evaluated by a device fabrication study. The experimental and calculation data show that all of the dyes can be regarded as potentially good photosensitizers for dye-sensitized solar cells.

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Acknowledgments

This work was supported by the Russian Foundation for Basic Research (research projects No. 13-03-96049-r_ural_a, 13-03-12434 ofi_м2, 13-03-90606-Arm_a, 14-03-01017-А, 14-03-00479-А and 14-03-31040-mol_а, 13-03-12415), the Council on Grants at the President of the Russian Federation (Program of State Support for Leading Scientific Schools of the Russian Federation and Young Scientists, Grant MK-3939.2014.3). N.I. Makarova, I.V. Dorogan, A.V. Metelitsa and V.I. Minkin would like to acknowledge the financial support of absorption, fluorescence and quantum chemical studies from the Ministry of Education and Science of Russian Federation in the framework of the State Assignment for Research project № 1895.

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Authors and Affiliations

  1. I. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskoy Str., 22, Ekaterinburg, 620137, Russia

    Egor V. Verbitskiy, Aleksandr V. Schepochkin, Oleg N. Chupakhin, Gennady L. Rusinov & Valery N. Charushin

  2. Ural Federal University, Mira St. 19, Ekaterinburg, 620002, Russia

    Egor V. Verbitskiy, Oleg N. Chupakhin, Gennady L. Rusinov & Valery N. Charushin

  3. Institute of Physical and Organic Chemistry, Southern Federal University, Stachki Av., 194/2, 344090, Rostov on Don, Russia

    Nadezhda I. Makarova, Igor V. Dorogan, Anatoly V. Metelitsa & Vladimir I. Minkin

  4. Southern Scientific Center of the Russian Academy of Sciences, Chekhov St., 41, 344006, Rostov on Don, Russia

    Vladimir I. Minkin

  5. Kurnakov Institute of General and Inorganic Chemistry, RAS, Moscow, 119991, Russia

    Sergey A. Kozyukhin

  6. Frumkin Institute of Physical Chemistry and Electrochemistry, RAS, Moscow, 119071, Russia

    Victor V. Emets & Vitaly A. Grindberg

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  1. Egor V. Verbitskiy
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  2. Aleksandr V. Schepochkin
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Correspondence to Egor V. Verbitskiy.

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Verbitskiy, E.V., Schepochkin, A.V., Makarova, N.I. et al. Synthesis, Photophysical and Redox Properties of the D–π–A Type Pyrimidine Dyes Bearing the 9-Phenyl-9H-Carbazole Moiety. J Fluoresc 25, 763–775 (2015). https://doi.org/10.1007/s10895-015-1565-6

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