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Heteropentacyclic quinoxalino[2,3-b]phenoxazines: the synthesis, optoelectronic, and electrochemical properties

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Abstract

A series of new derivatives comprising heteropentacyclic 12H-quinoxalino[2,3-b]-phenoxazine (QOPO) system and functionalized with arylamide anchoring groups was synthesized. Their photostability as well as the spectral, luminescent, electrochemical, and optoelectronic properties were studied both in composites prepared by adsorption of QOPO onto the TiO2 surface and in solution. Attachment of the amide anchoring groups to the QOPO core provides high adsorption of the compounds and the onset of photovoltaic properties that were not observed in the unfunctionalized precursors. However, these groups do not provide efficient injection of excited electrons into the conduction band of the semiconductor. According to B3LYP/6-311++G(d,p) density functional calculations of the model nanoclusters QOPO/(TiO2)10, efficient electron injection and, as a consequence, high photovoltaic conversion efficiency of dye-sensitized solar cells require delocalization of the LUMO of the QOPO/TiO2 system over both structural fragments. Relevant anchoring groups are proposed.

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Authors and Affiliations

  1. Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 prosp. Stachki, 344091, Rostov-on-Don, Russian Federation

    V. I. Minkin, P. A. Knyazev, N. I. Omelichkin, N. I. Makarova, G. S. Borodkin, A. G. Starikov & E. P. Ivakhnenko

  2. North Caucasus Federal University, 1 ul. Pushkina, 355017, Stavropol, Russian Federation

    O. P. Demidov

Authors
  1. V. I. Minkin
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  2. P. A. Knyazev
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  3. N. I. Omelichkin
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  4. N. I. Makarova
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  5. G. S. Borodkin
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  6. A. G. Starikov
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  7. O. P. Demidov
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  8. E. P. Ivakhnenko
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Corresponding authors

Correspondence to V. I. Minkin, P. A. Knyazev or O. P. Demidov.

Additional information

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

This work was financially supported by the Russian Science Foundation (Project No. 19-13-00022, https://rscf.ru/project/19-13-00022/).

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. 3, pp. 669–680, March, 2023.

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Minkin, V.I., Knyazev, P.A., Omelichkin, N.I. et al. Heteropentacyclic quinoxalino[2,3-b]phenoxazines: the synthesis, optoelectronic, and electrochemical properties. Russ Chem Bull 72, 669–680 (2023). https://doi.org/10.1007/s11172-023-3831-4

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  • DOI: https://doi.org/10.1007/s11172-023-3831-4

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