Synthesis and Photodegradation Efficiency of Polyfluorotriphenylpyrazolines Containing Cationic Centers in the Presence of Borate Anion

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Abstract

A number of polyfluorinated triarylpyrazolines containing cationic centers in the form of piperazinium salts in fluorinated rings have been obtained. The synthesis is based on the substitution reaction of fluorine atoms with a 1-methylpiperazino group followed by quaternization of the nitrogen atom in the piperazine cycle. The effect of the salt structures on the spectral characteristics is investigated, and the quantum yields of photobleaching in the presence of triphenylbutyl borate are measured.

About the authors

I. N Gavrilov

Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS; Novosibirsk National Research State University

Author for correspondence.
Email: gavrilov@nioch.nsc.ru
ORCID iD: 0009-0007-5747-7992
Novosibirsk, Russia; Novosibirsk, Russia

N. A Orlova

Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS

Email: gavrilov@nioch.nsc.ru
ORCID iD: 0009-0008-1228-8423
Novosibirsk, Russia

E. V Vasilyev

Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS

Email: gavrilov@nioch.nsc.ru
ORCID iD: 0000-0002-8083-4034
Novosibirsk, Russia

V. V Shelkovnikov

Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS; Novosibirsk State Technical University

Email: gavrilov@nioch.nsc.ru
ORCID iD: 0009-0001-3364-668X
Novosibirsk, Russia; Novosibirsk, Russia

I. Y Kargapolova

Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS

Email: gavrilov@nioch.nsc.ru
ORCID iD: 0000-0003-1347-999X
Novosibirsk, Russia

A. V Ishchenko

Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS

Email: gavrilov@nioch.nsc.ru
Novosibirsk, Russia

A. S Bayrash

Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS

Email: gavrilov@nioch.nsc.ru
ORCID iD: 0009-0004-1658-3316
Novosibirsk, Russia

References

  1. Шелковников В.В., Каргаполова И.Ю., Орлова Н.А., Коротаев С.В., Симанчук А.Э., Микерин С.Л. Изв. АH. Сер. хим. 2019, 68, 92–98. Shelkovnikov V.V., Kargapolova I.Yu., Orlova N.A., Korotaev S.V., Simanchuk A.E., Mikerin S.L. Russ. Chem. Bull. 2019, 68, 92–98. https://doi.org/10.1007/s11172-019-2421-7
  2. Ishchenko R.A., Kargapolova I.Yu., Orlova N.A., Shelkovnikov V.V., Maksimov A.М., Ryazanov N.D., Berezhnaya V.N., Chernonosov А.A. J. Fluor. Chem. 2021, 248, 109841–109849. https://doi.org/10.1016/j.jfluchem.2021.109841
  3. Шелковников В.В., Микерин С.Л., Симанчук А.Э., Чубаков П.А., Коротаев С.В., Орлова Н.А., Бережная В.Н., Каргаполова И.Ю., Максимов А.М., Ищенко Р.А., Рязанов Н.Д. Автометрия. 2021, 57, 60−66. Shelkovnikov V.V., Mikerin S.L., Simanchuk A.E., Chubakov P.A., Korotaev S.V., Orlova N.A., Berezhnaya V.N., Kargapolova I.Yu., Maksimov A.M., Ishchenko R.A., Ryazanov N.D. Optoelectron. Instrum. Data Process. 2021, 57, 611–617. https://doi.org/10.15372/AUT20210606
  4. Verma M., Chaudhry A.F., Fahrni C.J. Org. Biomol. Chem. 2009, 7, 1536–1546. https://doi.org/10.1039/b821042j
  5. Chen Sh., Zhao X., Jin M., Huang W., Ye G., Pan H., Wan D. J. Polym. Sci. 2021, 59, 1899–1911. https://doi.org/10.1002/pol.20210333
  6. Chen Sh., Pan H., Wan D., Jin M. Prog. Org. Coat. 2021, 161, 106460. https://doi.org/10.1016/j.porgcoat.2021.106460
  7. Ye P., Wang D.H., Chen B., Meng Q.Y., Tung C.H., Wu L.Z. Sci. China Chem. 2016, 59, 175–179. https://doi.org/10.1007/s11426-016-5554-7
  8. Traven V.F., Ivanov I.V., Dolotov S.M., Semakin A.N., Cheptsov D.A., Mamirgova Z.Z. Photochem. Photobiol. 2019, 95, 924–930. https://doi.org/10.1111/php.13082
  9. Traven V.F., Cheptsov D.A., Vershinina G.V., Solovjeva N.P., Chibisova T.A., Dolotov S.M., Ivanov I.V. J. Photochem. Photobiol. A: Chemistry. 2018, 351, 8–15. https://doi.org/10.1016/j.jphotochem.2017.09.072
  10. Mella M., Fagnoni M., Viscardi G., Savarino P., Elisei F., Albini A. J. Photochem. Photobiol. A: Chemistry. 1997, 108, 143–148. https://doi.org/10.1016/S1010-6030(97)00097-X
  11. Kabatc J., Kaczorowska M., Jȩdrzejewska B., Pa̧czkowski J. J. Appl. Polym. Sci. 2008, 108, 1636–1645. https://doi.org/10.1002/APP.27821
  12. Filler R., Beaucaire V.D., Kang H.H. J. Org. Chem. 1975, 40, 935–939. https://doi.org/10.1021/jo00895a027 40
  13. Соболева Е.А., Орлова Н.А., Шелковников В.В. ЖОрХ. 2017, 53, 400–407. Soboleva E.A., Orlova N.A., Shelkovnikov V.V. Russ. J. Org. Chem. 2017, 53, 398–406. https://doi.org/10.1134/S1070428017030149.41
  14. Ishchenko R.A., Orlova N.A., Shelkovnikov V.V., Maksimov A.M., Ryazanov N.D., Berezhnaya V.N., Chernonosov A.A. Russ. J. Org. Chem. 2025, 61, 184–189. https://doi.org/10.1134/S1070428024604722
  15. Liao H.H., Lee S.C., Kao H., Hsu Y.L., Hsu C.M., Tsao Y.T., Minoza S., Li L.Y., Tsai Z.N., Chang K.C. Cell Rep. Phys. Sci. 2022, 3, 101010. https://doi.org/10.1016/j.xcrp.2022.101010
  16. Charles R.H. Tetrahedron. 1987, 28, 4135–4138. https://doi.org/10.1016/s0040-4039(00)95559-x
  17. Kabatc J., Jurek K., Czech Z., Kowalczyk A. Dyes Pigments. 2015, 114, 144–145. https://doi.org/10.1016/j.dyepig.2014.10.023
  18. Kabatc J., Jurek K. Polymer. 2012, 53, 1973–1980. https://doi.org/10.1016/j.polymer.2012.03.027
  19. Шелковников В.В., Васильев Е.В., Русских В.В. Оптический ж. 2025, 92, 102–115. Shelkovnikov V.V., Vasiliev E.V., Russkih V.V. J. Opt. Technol. 2025, 92, 102–115. https://doi.org/10.17586/1023-5086-2025-92-07-102-115

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