Russian Journal of General Chemistry

, Volume 86, Issue 5, pp 1054–1063 | Cite as

Absorption and luminescence spectra of 5-aryl-3-methyl-1,2,4-oxadiazoles and their chelate complexes with Zinc(II) and copper(II)

  • I. E. Mikhailov
  • N. I. Vikrishchuk
  • L. D. Popov
  • G. A. Dushenko
  • A. D. Beldovskaya
  • Yu. V. Revinskii
  • V. I. Minkin
Article

Abstract

5-(2-Hydroxyphenyl)-3-methyl-1,2,4-oxadiazole and its O-methyl and O-acyl derivatives, as well as zinc(II) and copper(II) chelates, were synthesized. All these compounds showed luminescence with the emission maxima ranging from λ = 332 to 490 nm, but only 5-(2-methoxyphenyl)- and 5-(2-acetoxyphenyl)-3-methyl-1,2,4-oxadiazoles and zinc(II) complex of 5-(2-hydroxyphenyl)-3-methyl-1,2,4-oxadiazole were characterized by high luminescence quantum yield (φ = 0.308–0.452, 0.089–0.153, and 0.115–0.334, respectively). Stable conformers of 5-(2-hydroxyphenyl)-3-methyl-1,2,4-oxadiazole with different structures of the coordination entity were identified by DFT quantum chemical calculations.

Keywords

5-aryl-3-methyl-1,2,4-oxadiazoles electronic absorption and luminescence spectra luminescence quantum yield quantum chemical calculations 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Jiang, P. and Guo, Z., Coord. Chem. Rev., 2004, vol. 248, p. 205. DOI: 10.1016/jcct.2003.10.013.CrossRefGoogle Scholar
  2. 2.
    Mikhailov, I.E., Kolodina, A.A., Dushenko, G.A., Artyushkina, Yu.M., Tkachev, V.V., Aldoshin, S.M., Sayapin, Yu.A., and Minkin, V.I., Chem. Heterocycl. Compd., 2014, vol. 50, no. 6, p. 828. DOI: 10.1007/s10593-014-1537-9.CrossRefGoogle Scholar
  3. 3.
    Mikhailov, I.E., Dushenko, G.A., Starikov, D.A., Mikhailova, O.I., and Minkin, V.I., Vestn. Yuzhn. Nauch. Tsentra, 2010, vol. 6, no. 4, p. 32.Google Scholar
  4. 4.
    Mikhailov, I.E., Kolodina, A.A., Artyushkina, Yu.M., Dushenko, G.A., Sayapin, Yu.A., and Minkin, V.I., Russ. J. Org. Chem., 2015, vol. 51, no. 4, p. 595. DOI: 10.1134/S1070428015040235.CrossRefGoogle Scholar
  5. 5.
    Wang, G., Zhang, Y.G., Cheng, Y.X., Ma, D.G., Wang, L.X., Jing, X.B., and Wang, F.S., Synth. Met., 2003, vol. 137, nos. 1–3, p. 1119. DOI: 10.1016/S0379- 6779(02)01106-2.CrossRefGoogle Scholar
  6. 6.
    Pace, A. and Pierro, P., Org. Biomol. Chem., 2009, vol. 7, no. 6, p. 4337. DOI: 10.1039/b908937c.CrossRefGoogle Scholar
  7. 7.
    Ryabukhin, Yu.I., Mezheritskii, V.V., and Dorofeenko, G.N., Zh. Obshch. Khim., 1974, vol. 44, no. 12, p. 2792.Google Scholar
  8. 8.
    Da Silva, A.S., De Silva, M.A.A., Carvalho, C.E.M., Antunes, O.A.C., Herrera, J.O.M., Brinn, I.M., and Mangrich, A.S., Inorg. Chim. Acta, 1999, vol. 292, p. 1. DOI: 10.1016/S0020-1693(99)00108-5.CrossRefGoogle Scholar
  9. 9.
    Vikrishchuk, A.D., Popov, L.D., Vikrishchuk, N.I., Morozov, P.G., and Mikhailov, I.E., Russ. J. Gen. Chem., 2011, vol. 81, no. 1, p. 132. DOI: 10.1134/S107036321101021X.CrossRefGoogle Scholar
  10. 10.
    Beldovskaya, A.D., Dushenko, G.A., Vikrishchuk, N.I., Popov, L.D., Revinskii, Yu.V., and Mikhailov, I.E., Russ. J. Gen. Chem., 2013, vol. 83, no. 11, p. 2075. DOI: 10.1134/S1070363213110200.CrossRefGoogle Scholar
  11. 11.
    Doroshenko, A.O., Posokhov, E.A., Verezubova, A.A., and Ptyagina, L.M., J. Phys. Org. Chem., 2000, vol. 13, no. 5, p. 253. DOI: 10.1002/1099-1395(200005).CrossRefGoogle Scholar
  12. 12.
    Beldovskaya, A.D., Dushenko, G.A., Vikrishchuk, N.I., Popov, L.D., Revinskii, Yu.V., Mikhailov, I.E., and Minkin, V.I., Russ. J. Gen. Chem., 2014, vol. 84, no. 1, p. 171. DOI: 10.1134/S1070363214010290.CrossRefGoogle Scholar
  13. 13.
    Dushenko, G.A., Vikrishchuk, A.D., Mikhailov, I.E., and Vikrishchuk, N.I., Vestn. Yuzhn. Nauch. Tsentra, 2013, vol. 9, no. 1, p. 37.Google Scholar
  14. 14.
    Serdyuk, O.V., Evseenko, I.V., Dushenko, G.A., Revinskii, Yu.V., and Mikhailov, I.E., Russ. J. Org. Chem., 2012, vol. 48, no. 1, p. 78. DOI: 10.1134/S1070428012010113.CrossRefGoogle Scholar
  15. 15.
    Mikhailov, I.E., Svetlichnyi, D.A., Burov, O.N., Revinskii, Yu.V., Dushenko, G.A., and Minkin, V.I., Russ. J. Gen. Chem., 2015, vol. 85, no. 5, p. 1074. DOI: 10.1134/S1070363215050126.CrossRefGoogle Scholar
  16. 16.
    Beldovskaya, A.D., Dushenko, G.A., Vikrishchuk, N.I., Popov, L.D., Revinskii, Yu.V., Mikhailov, I.E., and Minkin, V.I., Russ. J. Org. Chem., 2013, vol. 49, no. 12, p. 1861. DOI: 10.1134/S1070428013120312.CrossRefGoogle Scholar
  17. 17.
    Mikhailov, I.E., Popov, L.D., Vikrishchuk, N.I., Beldovskaya, A.D., Revinskii, Yu.V., Dushenko, G.A., and Minkin, V.I., Russ. J. Gen. Chem., 2015, vol. 85, no. 1, p. 203. DOI: 10.1134/S1070363215010363.CrossRefGoogle Scholar
  18. 18.
    Zhang, H., Han, Li.-F., Zachariasse, K.A., and Jiang, Y.-B., Org. Lett., 2005, vol. 7, no. 19, p. 4217. DOI: 10.1021/ol051614h.CrossRefGoogle Scholar
  19. 19.
    Krasovitskii, B.M. and Bolotin, B.M., Organicheskie lyuminofory (Organic Luminophores), Moscow: Khimiya. 1984, p. 11.Google Scholar
  20. 20.
    Zhang, H., Wang, Q.-Li., and Jiang, Y.-B., Tetrahedron Lett., 2007, vol. 48, no. 23, p. 3959. DOI: 10.1016/jtetlet.2007.04.045.CrossRefGoogle Scholar
  21. 21.
    Kotelevskiy, S.I., J. Lumin., 1998, vol. 79, no. 3, p. 211.CrossRefGoogle Scholar
  22. 22.
    Weissberger, A., Proskauer, E.S., Riddick, J.A., and Toops, E.E., Organic Solvents: Physical Properties and Methods of Purification, New York: Intersci., 1955, 2nd ed.Google Scholar
  23. 23.
    Foresman, J.B. and Frisch, E., Exploring Chemistry with Electronic Structure Methods, Pittsburg Gaussian, 1996.Google Scholar
  24. 24.
    Ryabukhin, Yu.I., Eliseeva, A.Yu., Suzdalev, K.F., Bulgarevich, S.B., Movshovich, D.Ya., Knyazev, A.P., Terent’ev, P.V., and Yusman, T.A., Chem. Heterocycl. Compd., 1992, vol. 28, no. 4, p. 454.CrossRefGoogle Scholar
  25. 25.
    Ryabukhina, O.I., Yusman, T.A., Ryabukhin, Yu.I., Garnovskii, A.D., and Dorofeenko, G.N., Koord. Khim., 1980, vol. 6, no. 8, p. 1186.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2016

Authors and Affiliations

  • I. E. Mikhailov
    • 1
    • 2
  • N. I. Vikrishchuk
    • 3
  • L. D. Popov
    • 3
  • G. A. Dushenko
    • 1
    • 2
  • A. D. Beldovskaya
    • 4
  • Yu. V. Revinskii
    • 1
  • V. I. Minkin
    • 2
  1. 1.Southern Scientific CenterRussian Academy of SciencesRostov-on-DonRussia
  2. 2.Research Institute of Physical and Organic ChemistrySouthern Federal UniversityRostov-on-DonRussia
  3. 3.Southern Federal UniversityRostov-on-DonRussia
  4. 4.Institute of Arid Zones, Southern Scientific CenterRussian Academy of SciencesRostov-on-DonRussia

Personalised recommendations