Y-SHAPED FLUOROPHORES BASED ON N(2)-ARYL-1,2,3-TRIAZOLES: SYNTHESIS, THEORETICAL CALCULATIONS, OPTICAL PROPERTIES, AND APPLICATION OPPORTUNITIES FOR DETECTION OF NITROAROMATICS

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription or Fee Access

Abstract

A five-stage method for the synthesis of Y-shaped push-pull fluorophores based on 2-(4′-methoxyphenyl)-1,2,3-triazole has been described. These molecules proved to possess emission in the range from 350 to 450 nm and high quantum yields QY 90–99% in solvents of various polarity. An opportunity of using the obtained compounds as chemosensors for both aromatic and aliphatic nitroanalytes at concentrations from 300 ppb has been elucidated.

About the authors

I. A. Lavrinchenko

Ural Federal University

Email: chupakhin@ios.uran.ru
Russian Federation, 620002, Yekaterinburg

T. D. Moseev

Ural Federal University

Email: chupakhin@ios.uran.ru
Russian Federation, 620002, Yekaterinburg

M. V. Varaksin

Ural Federal University; Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Author for correspondence.
Email: m.v.varaksin@urfu.ru
Russian Federation, 620002, Yekaterinburg; Russian Federation, 620990, Yekaterinburg

Y. A. Seleznev

Ural Federal University

Email: chupakhin@ios.uran.ru
Russian Federation, 620002, Yekaterinburg

L. K. Sadieva

Ural Federal University

Email: chupakhin@ios.uran.ru
Russian Federation, 620002, Yekaterinburg

G. V. Zyryanov

Ural Federal University; Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Email: chupakhin@ios.uran.ru
Russian Federation, 620002, Yekaterinburg; Russian Federation, 620990, Yekaterinburg

A. N. Tsmokaluk

Ural Federal University

Email: chupakhin@ios.uran.ru
Russian Federation, 620002, Yekaterinburg

V. N. Charushin

Ural Federal University; Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Email: chupakhin@ios.uran.ru
Russian Federation, 620002, Yekaterinburg; Russian Federation, 620990, Yekaterinburg

O. N. Chupakhin

Ural Federal University; Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

Author for correspondence.
Email: chupakhin@ios.uran.ru
Russian Federation, 620002, Yekaterinburg; Russian Federation, 620990, Yekaterinburg

References

  1. Bureš F. // RSC Adv. 2014. V. 4. № 102. P. 58826–58851. https://doi.org/10.1039/C4RA11264D
  2. Li K., Ren T.-B., Huan S., Yuan L., Zhang X.-B. // J. Am. Chem. Soc. 2021. V. 143. № 50. P. 21143–21160. https://doi.org/10.1021/jacs.1c10925
  3. Pucher N., Rosspeintner A., Satzinger V., Schmidt V., Gescheidt G., Stampfl J., Liska R. // Macromolecules. 2009. V. 42. № 17. P. 6519–6528. https://doi.org/10.1021/ma9007785
  4. Grabowski Z.R., Rotkiewicz K., Rettig W. // Chem. Rev. 2003. V. 103. № 10. P. 3899–4032. https://doi.org/10.1021/cr940745l
  5. Escudero D. // Acc. Chem. Res. 2016. V. 49. № 9. P. 1816–1824. https://doi.org/10.1021/acs.accounts.6b00299
  6. Sekar R.B., Periasamy A. // J. Cell Biol. 2003. V. 160. № 5. P. 629–633. https://doi.org/10.1083/jcb.200210140
  7. Shen Q., Wang S., Yang N.-D., Zhang C., Wu Q., Yu C. // J. Lumin. 2020. V. 225. P. 117338. https://doi.org/10.1016/j.jlumin.2020.117338
  8. Zheng Q., Juette M.F., Jockusch S., Wasserman M.R., Zhou Z., Altman R.B., Blanchard S.C. // Chem. Soc. Rev. 2014. V. 43. № 4. P. 1044–1056. https://doi.org/10.1039/C3CS60237K
  9. Martynov V.I., Pakhomov A.A. // Russ. Chem. Rev. 2021. V. 90. № 10. P. 1213–1262. https://doi.org/10.1070/RCR4985
  10. Misra R., Bhattacharyya S.P. Intramolecular Charge Transfer. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2018. https://doi.org/10.1002/9783527801916
  11. Long Y., Chen H., Wang H., Peng Z., Yang Y., Zhang G., Li N., Liu F., Pei J. // Anal. Chim. Acta. 2012. V. 744. P. 82–91. https://doi.org/10.1016/j.aca.2012.07.028
  12. Mauricio F.G.M., Silva J.Y.R., Talhavini M., Júnior S.A., Weber I.T. // Microchem. J. 2019. V. 150. P. 104037. https://doi.org/10.1016/j.microc.2019.104037
  13. Tretyakov E.V., Ovcharenko V.I., Terent’ev A.O., Krylov I.B., Magdesieva T.V., Mazhukin D.G., Gritsan N.P. // Russ. Chem. Rev. 2022. V. 91. № 2. RCR5025. https://doi.org/10.1070/RCR5025
  14. Fu H.-Y., Liu X.-J., Xia M. // RSC Adv. 2017. V. 7. № 80. P. 50720–50728. https://doi.org/10.1039/C7RA10432D
  15. Miura Y., Kobayashi K., Yoshioka N. // New J. Chem. 2021. V. 45. № 2. P. 898–905. https://doi.org/10.1039/D0NJ05323F
  16. Du F., Li D., Ge S., Xie S., Tang M., Xu Z., Wang E., Wang S., Tang B.Z. // Dye. Pigment. 2021. V. 194. P. 109640. https://doi.org/10.1016/j.dyepig.2021.109640
  17. Fu H.-Y., Xu N., Pan Y.-M., Lu X.-L., Xia M. // Phys. Chem. Chem. Phys. 2017. V. 19. № 18. P. 11563–11570. https://doi.org/10.1039/C7CP01281K
  18. Khamrang T., Kathiravan A., Ponraj C., Saravanan D. // J. Mol. Struct. 2021. V. 1238. P. 130442. https://doi.org/10.1016/j.molstruc.2021.130442
  19. Chen S.-H., Jiang K., Lin J.-Y., Yang K., Cao X.-Y., Luo X.-Y., Wang Z.‑Y. // J. Mater. Chem. C. 2020. V. 8. № 24. P. 8257–8267. https://doi.org/10.1039/D0TC01870H
  20. Lai Q., Liu Q., Zhao K., Shan C., Wojtas L., Zheng Q., Shi X., Song Z. // Chem. Commun. 2019. V. 55. № 32. P. 4603–4606. https://doi.org/10.1039/C9CC00262F
  21. Govdi A., Tokareva V., Rumyantsev A.M., Panov M.S., Stellmacher J., Alexiev U., Danilkina N.A., Balova I.A. // Molecules. 2022. V. 27. № 10. P. 3191. https://doi.org/10.3390/molecules27103191
  22. Wong M.Y., Leung L.M. // Dyes Pigm. 2017. V. 145. P. 542–549. https://doi.org/10.1016/j.dyepig.2017.06.054
  23. Ahmadi F., Tisseh Z.N., Dabiri M., Bazgir A. // C. R. Chim. 2013. V. 16. № 12. P. 1086–1090. https://doi.org/10.1016/j.crci.2013.05.006
  24. Chen Z., Yan Q., Yi H., Liu Z., Lei A., Zhang Y. // Chem. Eur. J. 2014. V. 20. № 42. P. 13692–13697. https://doi.org/10.1002/chem.201403515
  25. Begtrup M., Holm J. // J. Chem. Soc. Perkin Trans. 1. 1981. P. 503–513. https://doi.org/10.1039/p19810000503
  26. Beletskaya I.P., Alonso F., Tyurin V. // Coord. Chem. Rev. 2019. V. 385 P. 137–173. https://doi.org/10.1016/j.ccr.2019.01.012
  27. Chen C., Lu X., Holland M. C., Lv S., Ji X., Liu W., Liu J., Depre D., Westerduin P. // Eur. J. Org. Chem. 2020. V. 2020. № 5. P. 548–551. https://doi.org/10.1002/ejoc.201901519
  28. Gaussian 16, Revision C.01. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheese-man J.R., Scalmani G., Barone V., Petersson G.A., Nakatsuji H., Li X., Caricato M., Marenich A.V., Bloino J., Janesko B.G., Gomperts R., Mennucci B., Hratchian H.P., Ortiz J.V., Izmaylov A.F., Sonnenberg J.L., Williams-Young D., Ding F., Lipparini F., Egidi F., Goings J., Peng B., Petrone A., Henderson T., Ranasinghe D., Zakrzewski V.G., Gao J., Rega N., Zheng G., Liang W., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Throssell K., Montgomery J.A. Jr., Peralta J.E., Ogliaro F., Bearpark M.J., Heyd J.J., Brothers E.N., Kudin K.N., Staroverov V.N., Keith T.A., Kobayashi R., Normand J., Raghavachari K., Rendell A.P., Burant J.C., Iyengar S.S., Tomasi J., Cossi M., Millam J.M., Klene M., Adamo C., Cammi R., Ochterski J.W., Martin R.L., Morokuma K., Farkas O., Foresman J.B. Fox, D. J. Gaussian, Inc., Wallingford CT, 2016.
  29. Weigend F., Ahlrichs R. // Phys. Chem. Chem. Phys. 2005. V.7. P. 3297–3305.
  30. Weigend F. // Phys. Chem. Chem. Phys. 2006. V. 8. P. 1057–1065. https://doi.org/10.1039/B515623H
  31. Grimme S., Ehrlich S., Goerigk L. // Theor. J. Comput. Chem. 2011. V. 32. P. 1456–1465. https://doi.org/10.1002/jcc.21759
  32. Grimme S., Antony J., Ehrlich S., Krieg H. // J. Chem. Phys. 2010. V. 132. P. 154104. https://doi.org/10.1063/1.3382344
  33. libint2 library // Доступно по ссылке: http://libint.valeyev.net/ (ссылка активна на 09.01.2023)
  34. Libxc library // Доступно по ссылке: https://tddft.org/programs/libxc/ (ссылка активна на 09.01.2023).
  35. Lakowicz J.R. Principles of Fluorescence Spectroscopy, Third Edition. Springer New York, 2017. https://doi.org/10.1007/978-0-387-46312-4
  36. Campbell K., Zappas A., Bunz U., Thio Y.S., Buck-nall D.G. // J. Photochem. Photobiol. A Chem. 2012. V. 249. P. 41–46. https://doi.org/10.1016/j.jphotochem.2012.08.015

Supplementary files

Supplementary Files
Action
1. JATS XML
Download
2.

Download (84KB)
Indexing metadata
3.

Download (128KB)
Indexing metadata
4.

Download (63KB)
Indexing metadata
5.

Download (81KB)
Indexing metadata
6.

Download (133KB)
Indexing metadata
7.

Download (1MB)
Indexing metadata
8.

Download (262KB)
Indexing metadata
9.

Download (325KB)
Indexing metadata

Copyright (c) 2023 И.А. Лавринченко, Т.Д. Мосеев, М.В. Вараксин, Ю.А. Селезнев, Л.К. Садиева, Г.В. Зырянов, А.Н. Цмокалюк, В.Н. Чарушин, О.Н. Чупахин