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Linear and V-shaped push–pull systems on a base of pyrimidine scaffold with a pyrene-donative fragment for detection of nitroaromatic compounds

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Abstract

New fluorophores based on pyrimidines, bearing a pyrene electron-donating fragment, have been designed, synthesized and characterized. The fluorescence behavior of these fluorophores has been evaluated toward nitroaromatic compounds, including such well-known explosives, as 2,4-dinitroanisole, picric and styphnic acids, 1,3,5-triethoxy-2,4,6-trinitrobenzene, 2,4-dinitrotoluene, 2,4,6-trinitrotoluene, 2,4,6-triamino-1,3,5-trinitrobenzene and nitrobenzene. The detection limits for these fluorophores in relation to nitroaromatic compounds in acetonitrile solution proved to be in the range from 10−1 to 10−7 mol/L. The sensor prototypes for handheld sniffer «Nitroscan» (Plant «Promautomatika», Ekaterinburg, Russia) based on these fluorophores have been fabricated and used for applications, as illustrated by reusable, reversible and sensitive fast detection of nitrobenzene and 2,4,6-trinitrotoluene in vapor phase concentrations up to 6 and 5 ppb, respectively.

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Acknowledgements

The authors are grateful to the Russian Foundation for Basic Research (Research Project No. 17-03-00011-A) for financial support of this work.

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Authors and Affiliations

  1. I. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskoy Str., 22, Ekaterinburg, Russia, 620990

    Egor V. Verbitskiy, Ekaterina M. Dinastiya, Gennady L. Rusinov, Oleg N. Chupakhin & Valery N. Charushin

  2. Ural Federal University, Mira St. 19, Ekaterinburg, Russia, 620002

    Egor V. Verbitskiy, Anna A. Baranova, Kseniya I. Lugovik, Konstantin O. Khokhlov, Roman D. Chuvashov, Gennady L. Rusinov, Oleg N. Chupakhin & Valery N. Charushin

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  1. Egor V. Verbitskiy
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  2. Anna A. Baranova
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  3. Kseniya I. Lugovik
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  4. Konstantin O. Khokhlov
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  5. Roman D. Chuvashov
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  6. Ekaterina M. Dinastiya
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  7. Gennady L. Rusinov
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  8. Oleg N. Chupakhin
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  9. Valery N. Charushin
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Correspondence to Egor V. Verbitskiy.

Electronic supplementary material

Details of fluorescence quenching studies and copies of 1 H and 13 C NMR spectra of the products.

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Verbitskiy, E.V., Baranova, A.A., Lugovik, K.I. et al. Linear and V-shaped push–pull systems on a base of pyrimidine scaffold with a pyrene-donative fragment for detection of nitroaromatic compounds. J IRAN CHEM SOC 15, 787–797 (2018). https://doi.org/10.1007/s13738-017-1278-7

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