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2-amino-5-aryl- and 2-amino-5-hetaryl-3-cyano-6-(2-thienyl)pyridines as Organic Dyes for Dye-Sensitized Solar Cells: Synthesis, Quantum-Chemical Calculations, Spectral and Electrochemical Properties

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Chemistry of Heterocyclic Compounds Aims and scope

Novel organic dyes containing pyridine ring as the anchoring group with carbazole or triphenylamine substituents were synthesized from available 4-(2-thienyl)pyrimidine using the Kost–Sagitullin rearrangement and Suzuki cross coupling assisted by microwave irradiation. The photophysical (absorption and photoluminescence spectra) and electrochemical properties of these compounds were investigated. The data from quantum calculations show that all of the dyes are potentially good photosensitizers for dye-sensitized solar cells.

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This work was carried out in the Programs of the Ural Branch of the Russian Academy of Sciences 12-P-3-1014, 12-T-3-1025, 12-T-3-1031, Russian Foundation for Basic Research grants 13-03-96049-p_ural_a, 13-03-12434 ofi_m2, 13-03-90606-Arma, and 14-03-31040-mol_a and with the support of the Grants Council of the President of the Russian Federation (grant MK-3939.2014.3) and the Sverdlovsk Oblast Government.

The authors express their gratitude to M. L. Isenov for carrying the X-ray structural analysis of one of the compounds. Julia Subbotina thanks Compute Canada–"Calcul Canada and West Grid" (Canada) for computer resources.

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Authors and Affiliations

  1. I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, 22 S. Kovalevskoi St. /20 Akademicheskaya St., Yekaterinburg, 620041, Russia

    E. V. Verbitskiy, P. A. Slepukhin, Yu. O. Subbotina, M. S. Valova, A. V. Schepochkin, E. M. Cheprakova, G. L. Rusinov & V. N. Charushin

  2. Ural Federal University named after the First President of Russia B. N. Yeltsin, 19 Mir St., Yekaterinburg, 620002, Russia

    E. V. Verbitskiy, Yu. O. Subbotina, G. L. Rusinov & V. N. Charushin

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  1. E. V. Verbitskiy
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  2. P. A. Slepukhin
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  3. Yu. O. Subbotina
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  4. M. S. Valova
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  5. A. V. Schepochkin
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  6. E. M. Cheprakova
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  7. G. L. Rusinov
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  8. V. N. Charushin
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Correspondence to E. V. Verbitskiy.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii No. 6, pp. 883-896, June, 2014.

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Verbitskiy, E.V., Slepukhin, P.A., Subbotina, Y.O. et al. 2-amino-5-aryl- and 2-amino-5-hetaryl-3-cyano-6-(2-thienyl)pyridines as Organic Dyes for Dye-Sensitized Solar Cells: Synthesis, Quantum-Chemical Calculations, Spectral and Electrochemical Properties. Chem Heterocycl Comp 50, 814–827 (2014). https://doi.org/10.1007/s10593-014-1536-x

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