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Chemistry of Heterocyclic Compounds

, Volume 54, Issue 6, pp 604–611 | Cite as

New push–pull system based on 4,5,6-tri(het)arylpyrimidine containing carbazole substituents: synthesis and sensitivity toward nitroaromatic compounds

  • Egor V. Verbitskiy
  • Anna A. Baranova
  • Konstantin O. Khokhlov
  • Yuliya A. Yakovleva
  • Roman D. Chuvashov
  • Grigory A. Kim
  • Evgeny V. Moiseykin
  • Ekaterina M. Dinastiya
  • Gennady L. Rusinov
  • Oleg N. Chupakhin
  • Valery N. Charushin
Article
  • 56 Downloads

A sequence of microwave-assisted Suzuki cross-coupling reaction and bromination with N-bromosuccinimide was used for the synthesis of 3,3'-(5,5'-{5-[5-(9-ethyl-9H-carbazol-3-yl)-3-hexylthiophen-2-yl]pyrimidine-4,6-diyl}bis(thiophene-5,2-diyl))bis(9-ethyl-9H-carbazole). The obtained compound was characterized with regard to its optical properties, as well as possible applications in sensors for nitroaromatic compounds in acetonitrile solutions and in vapor phase.

Keywords

9-ethyl-9H-carbazole pyrimidines fluorescence quenching nitroaromatic explosives sensors 

Notes

This study (the synthetic experiments and structural characterization of the compounds) was supported by the Russian Foundation for Basic Research (grant 17-03-00011-A).

Professor V. N. Charushin gratefully acknowledges the financial support from the Ural Branch of the Russian Academy of Sciences (program No. 18-3-3-20).

The work was performed using equipment of the “Spectroscopy and analysis of organic compounds” Collective Use Center and the Uran supercomputer at the Institute of Mathematics and Mechanics, Ural Branch, Russian Academy of Sciences.

Supplementary material

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Egor V. Verbitskiy
    • 1
    • 2
  • Anna A. Baranova
    • 2
  • Konstantin O. Khokhlov
    • 2
  • Yuliya A. Yakovleva
    • 2
  • Roman D. Chuvashov
    • 2
  • Grigory A. Kim
    • 1
  • Evgeny V. Moiseykin
    • 2
  • Ekaterina M. Dinastiya
    • 1
  • Gennady L. Rusinov
    • 1
    • 2
  • Oleg N. Chupakhin
    • 1
    • 2
  • Valery N. Charushin
    • 1
    • 2
  1. 1.Postovsky Institute of Organic synthesisUral Branch of the Russian Academy of SciencesYekaterinburgRussia
  2. 2.Ural Federal University named after the first President of Russia B. N. YeltsinYekaterinburgRussia

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