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Synthesis of new polycyclic systems based on [1,2,5]chalcogenodiazolo[3,4-b]thieno[3,2-h]quinoxalines

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Abstract

A simple synthetic route to hard-to-prepare polycyclic (hetero)aromatic compounds with the [1,2,5]chalcogenodiazolo[3,4-b]pyrazine scaffold was developed based on the intramolecular nucleophilic aromatic hydrogen substitution reaction. Electrochemical and photophysical measurements demonstrated that the synthesized polycyclic systems can be considered as narrow-bandgap (from 1.25 to 1.44 eV) n-type organic semiconductors, the energy levels of which are comparable to those of commercially available electronic semiconductors.

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Authors and Affiliations

  1. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 ul. S. Kovalevskoy, 620137, Yekaterinburg, Russian Federation

    Yu. A. Kvashnin, E. M. Krynina, G. L. Rusinov, E. V. Verbitskiy & V. N. Charushin

  2. Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 ul. Mira, 620002, Yekaterinburg, Russian Federation

    Yu. A. Kvashnin, M. V. Medvedeva, T. S. Svalova, A. N. Kozitsina, O. S. Eltsov, G. L. Rusinov, E. V. Verbitskiy & V. N. Charushin

Authors
  1. Yu. A. Kvashnin
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  2. E. M. Krynina
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  3. M. V. Medvedeva
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  4. T. S. Svalova
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  5. A. N. Kozitsina
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  6. O. S. Eltsov
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  7. G. L. Rusinov
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  8. E. V. Verbitskiy
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  9. V. N. Charushin
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Corresponding author

Correspondence to E. V. Verbitskiy.

Additional information

Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya on the occasion of her anniversary.

The study was financially supported by the Ministry of Science and Higher Education of the Russian Federation within the framework of the Program of the Development of the Ural Federal University named after the first President of Russia B. N. Yeltsin under the Federal Academic Leadership Programme “Priority 2030”.

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 4, pp. 939–947, April, 2023.

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Kvashnin, Y.A., Krynina, E.M., Medvedeva, M.V. et al. Synthesis of new polycyclic systems based on [1,2,5]chalcogenodiazolo[3,4-b]thieno[3,2-h]quinoxalines. Russ Chem Bull 72, 939–947 (2023). https://doi.org/10.1007/s11172-023-3857-3

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  • DOI: https://doi.org/10.1007/s11172-023-3857-3

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