Russian Journal of Organic Chemistry

, Volume 53, Issue 5, pp 808–811 | Cite as

Spectral luminescent properties of 2-aryl-5-(2,4,6-trimethylphenyl)-1Н-1,3,4-oxadiazoles

  • Yu. M. Artyushkina
  • I. E. Mikhailov
  • G. A. Dushenko
  • O. I. Mikhailova
  • Yu. V. Revinskii
  • O. N. Burov
  • S. V. Kurbatov
Short Communications
  • 43 Downloads

Abstract

Reaction of aroylhydrazides with 2,4,6-trimethylbenzoyl chloride in the presence of Et3N afforded N-(mesityl)aroylhydrazides, which through subsequent cyclization at treatment with SOCl2 resulted in 2-aryl-5-(2,4,6-trimethylphenyl)-1Н-1,3,4-oxadiazoles. For 2-hydroxyphenyl derivative containing a stable O–H N intramolecular bond a low quantum luminescence yield is observed (φ 0.006–0.038) due to the nonradiative deactivation of the agitated state by ESPIT mechanism.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Prakash, O., Kumar, M., Kumar, R., Sharma, C., and Aneja, K.R., Eur. J. Med. Chem., 2010, vol. 45, p. 4252.CrossRefGoogle Scholar
  2. 2.
    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, p. 1119.CrossRefGoogle Scholar
  3. 3.
    Mikhailov, I.E., Vikrishchuk, N.I., Popov, L.D., Beldovskaya, A.D., Revinskii, Yu.V., Dushenko, G.A., and Minkin, V.I., RF Patent no. 2568640, 2015, Byull. Izobret., 2015, no. 32.Google Scholar
  4. 4.
    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, p. 203. doi 10.1134/S1070363215010363CrossRefGoogle Scholar
  5. 5.
    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, p. 171. doi 10.1134/S1070363214010290CrossRefGoogle Scholar
  6. 6.
    Mikhailov, I.E., Dushenko, G.A., Starikov, D.A., Mikhailova, O.I., and Minkin, V.I., Vestn. YuNTs., 2012, vol. 6, p. 32.Google Scholar
  7. 7.
    Serdyuk, O.V., Evseenko, I.V., Dushenko, G.A., Revinskii, Yu.V., and Mikhailov, I.E., Russ. J. Org. Chem., 2012, vol. 48, p. 78. doi 10.1134/S1070428012010113CrossRefGoogle Scholar
  8. 8.
    Doroshenko, A.O., Posokhov, E.A., Verezubova, A.A., and Ptyagina, L.M., J. Phys. Org. Chem., 2000, vol. 13, p. 253. doi 10.1002/1099-1395(200005)13:5<253::AID-POC238>3.0.CO;2-DCrossRefGoogle Scholar
  9. 9.
    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, p. 1861. doi 10.1134/S1070428013120312CrossRefGoogle Scholar
  10. 10.
    Mikhailov, I.E., Artyushkina, Yu.M., Burov, O.N., Dushenko, G.A., Revinskii, Yu.V., and Minkin, V.I., Russ. J. Gen. Chem., 2016, vol. 86, p. 406. doi 10.1134/S1070363216020341CrossRefGoogle Scholar
  11. 11.
    Mikhailov, I.E., Vikrishchuk, N.I., Popov, L.D., Dushenko, G.A., Beldovskaya, A.D., Revinskii, Yu.V., and Minkin, V.I., Russ. J. Gen. Chem., 2016, vol. 86, p. 1054. doi 10.1134/S1070363216050121CrossRefGoogle Scholar
  12. 12.
    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, p. 2075. doi 10.1134/S1070363213110200CrossRefGoogle Scholar
  13. 13.
    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, p. 1074. doi 10.1134/S1070363215050126CrossRefGoogle Scholar
  14. 14.
    Mikhailov, I.E., Svetlichnyi, D.A., Burov, O.N., Dushenko, G.A., Revinskii, Yu.V., and Kurbatov, S.V., Russ. J. Gen. Chem., 2016, vol. 86, p. 989. doi 10.1134/S1070363216040393CrossRefGoogle Scholar
  15. 15.
    Hartmann, K.-P. and Heuschmann, M., Tetrahedron, 2000, vol. 56, p. 4213. doi 10.1016/S0040-4020(00)00346-XCrossRefGoogle Scholar
  16. 16.
    Feygelman, V.M., Walker, J.K., Katritzky, A.R., and Dega-Szafran, Z., Chem. Scripta., 1989, vol. 29, p. 241.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2017

Authors and Affiliations

  • Yu. M. Artyushkina
    • 1
    • 2
  • I. E. Mikhailov
    • 1
    • 3
  • G. A. Dushenko
    • 1
    • 3
  • O. I. Mikhailova
    • 3
  • Yu. V. Revinskii
    • 1
  • O. N. Burov
    • 2
  • S. V. Kurbatov
    • 2
  1. 1.Southern Scientific Center of Russian Academy of SciencesRostov-on-DonRussia
  2. 2.Southern Federal UniversityRostov-on-DonRussia
  3. 3.Research Institute of Physical and Organic ChemistrySouthern Federal UniversityRostov-on-DonRussia

Personalised recommendations