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Synthesis and study of N,N′-disubstituted derivatives of pyromellitic diimide

Russian Chemical Bulletin volume 69, pages 1944–1948 (2020)Cite this article

Abstract

New N, N′-bis(4,6-dimethylpyrimidin-2-yl)- and N, N′-bis(2,3,5,6-tetrafluorophenyl)-substituted pyromellitic diimides were synthesized. Their properties were studied in comparison with the previously synthesized N, N′-bis(4-fluorophenyl)pyromellitic diimide. Thermogravimetry, UV spectroscopy, cyclic voltammetry, and quantum chemical calculations in the framework of the density functional theory were used to characterize the synthesized compounds. The introduction of the pyrimidine cycle significantly decreases the energy of the lowest unoccupied molecular orbital. The highest occupied molecular orbitals in all compounds synthesized are deep-lying (about −7 eV).

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Authors and Affiliations

  1. Institute of Technical Chemistry, Ural Branch, Russian Academy of Sciences, Division of the Perm Federal Center of the Ural Branch of the Russian Academy of Sciences, 3 ul. Akad. Koroleva, 614013, Perm, Russian Federation

    E. A. Komissarova & G. G. Abashev

  2. Perm State National Research University, 15 ul. Bukireva, 614990, Perm, Russian Federation

    E. A. Komissarova, V. E. Zhulanov, I. G. Mokrushin, A. N. Vasyanin, E. V. Shklyaeva & G. G. Abashev

Authors
  1. E. A. Komissarova
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  2. V. E. Zhulanov
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  3. I. G. Mokrushin
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  4. A. N. Vasyanin
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  5. E. V. Shklyaeva
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  6. G. G. Abashev
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Corresponding authors

Correspondence to E. A. Komissarova or G. G. Abashev.

Additional information

This study was financially supported by the Russian Foundation for Basic Research (Project No. 18-33-00323mol_a).

Russian Chemical Bulletin, International Edition, Vol. 69, No. 10, pp. 1944–1948, October, 2020

Published in Russian in Izyestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1944–1948, October, 2020.

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Komissarova, E.A., Zhulanov, V.E., Mokrushin, I.G. et al. Synthesis and study of N,N′-disubstituted derivatives of pyromellitic diimide. Russ Chem Bull 69, 1944–1948 (2020). https://doi.org/10.1007/s11172-020-2983-4

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  • DOI: https://doi.org/10.1007/s11172-020-2983-4

Key words

  • pyromellitic diimide
  • pyrimidine
  • fluoroaniline
  • tetrafluoroaniline
  • highest occupied molecular orbital
  • lowest unoccupied molecular orbital
  • forbidden gap width
  • quantum chemical calculations