Skip to main content
SpringerLink
Log in

Synthesis and Luminescence Spectral Properties of New Cyano-Substituted 2,2′-Bipyridine Derivatives

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Previously unknown 2-{4-aryl-5-cyano-[2,2′-bipyridin]-6(1H)-ylidene}malononitriles were synthe­sized by reaction of 3-aryl-1-(pyridin-2-yl)prop-2-en-1-ones (azachalcones) with malononitrile dimer. Their colored solutions showed fluorescence in the yellow–orange region with the emission maxima located at λ 565 to 582 nm, depending on the substituent in position 4 of the pyridine ring bearing cyano groups. The synthesized compounds are promising for further study as chemosensors due to a unique combination of 2,2′-bipyridine and buta-1,3-diene-1,1,3-tricarbonitrile fragments in their molecules.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme
Fig. 1.
Fig. 2.

Similar content being viewed by others

REFERENCES

  1. Summers, L.A., Adv. Heterocycl. Chem., 1984, vol. 35, p. 281. https://doi.org/10.1016/s0065-2725(08)60151-8

    Article  CAS  Google Scholar 

  2. Schilt, A.A., Analytical Applications of 1,10-Phenan­throline and Related Compounds, Oxford: Pergamon. 1969. https://doi.org/10.1016/c2013-0-02135-4

  3. Javaloyes, J.F.C. and Warrellow, G., Int Patent Appl. Pub. no. WO2004/072037.

  4. Blobaum, A.L. and Marnett, L.J., J. Med. Chem., 2007, vol. 50, p. 1425. https://doi.org/10.1021/jm0613166

    Article  CAS  PubMed  Google Scholar 

  5. Bagheri, M., Tabatabae Far, M.A., Mirzaei, H., and Ghasemi, F., Fundam. Clin. Pharmacol., 2019, vol. 34, p. 51. https://doi.org/10.1111/fcp.12492

    Article  CAS  PubMed  Google Scholar 

  6. Jang, J., Song, J., Lee, H., Sim, I., Kwon, Y.V., Jho, E., and Yoon, Y., Exp. Mol. Med., 2021, vol. 53, p. 407. https://doi.org/10.1038/s12276-021-00577-z

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Tang, X., Liu, P., Li, R., Jing, Q., Lv, J., Liu, L., and Liu, Y., Basic Clin. Pharmacol. Toxicol., 2015, vol. 117, p. 186. https://doi.org/10.1111/bcpt.12385

    Article  CAS  PubMed  Google Scholar 

  8. Bottorff, M.B., Rutledge, D.R., and Pieper, J.A., Pharmacotherapy, 1985, vol. 5, p. 227. https://doi.org/10.1002/j.1875-9114.1985.tb03422.x

    Article  CAS  PubMed  Google Scholar 

  9. Papadakis, R., Molecules, 2020, vol. 25, article no. 1. https://doi.org/10.3390/molecules25010001

  10. Adarsh, N.N. and Dastidar, P., Chem. Soc. Rev., 2012, vol. 41, p. 3039. https://doi.org/10.1039/C2CS15251G

    Article  CAS  PubMed  Google Scholar 

  11. Kuhn, R., Starr, M.P., Kuhn, D.A., Bauer, H., and Knackmuss, H.-J., Arch. Mikrobiol., 1965, vol. 51, p. 71. https://doi.org/10.1007/BF00406851

    Article  CAS  PubMed  Google Scholar 

  12. Kobayashi, H., Nogi, Y., and Horikoshi, K., Extremophiles, 2006, vol. 11, p. 245. https://doi.org/10.1007/s00792-006-0032-3

    Article  CAS  PubMed  Google Scholar 

  13. Constable, E.C. and Housecroft, C.E., Molecules, 2019, vol. 24, article no. 3951. https://doi.org/10.3390/molecules24213951

  14. Kaes, C., Katz, A., and Hosseini, M.W., Chem. Rev., 2000, vol. 100, p. 3553. https://doi.org/10.1021/cr990376z

    Article  CAS  PubMed  Google Scholar 

  15. Tu, T.N., Nguyen, M.V., Nguyen, H.L., Yuliarto, B., Cordova, K.E., and Demir, S., Coord. Chem. Rev., 2018, vol. 364, p. 33. https://doi.org/10.1016/j.ccr.2018.03.014

    Article  CAS  Google Scholar 

  16. Lewis, J.E.M., Bordoli, R.J., Denis, M., Fletcher, C.J., Galli, M., Neal, E.A., Rochette, E.M., and Goldup, S.M., Chem. Sci., 2016, vol. 7, p. 3154. https://doi.org/10.1039/C6SC00011H

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. Hu, Y.-Z., Bossmann, S.H., van Loyen, D., Schwarz, O., and Dürr, H., Chem. Eur. J., 1999, vol. 5, p. 1267. https://doi.org/10.1002/(SICI)1521-3765(19990401)5:4<1267::AID-CHEM1267>3.0.CO;2-T

    Article  CAS  Google Scholar 

  18. Chardon-Noblat, S., Deronzier, A., and Ziessel, R., Collect. Czech. Chem. Commun., 2001, vol. 66, p. 207. https://doi.org/10.1135/cccc20010207

    Article  CAS  Google Scholar 

  19. Johnson, S.I., Blakemore, J.D., Brunschwig, B.S., Lewis, N.S., Gray, H.B., Goddard, W.A., and Persson, P., Phys. Chem. Chem. Phys., 2021, vol. 23, p. 9921. https://doi.org/10.1039/D1CP00545F

    Article  CAS  PubMed  Google Scholar 

  20. Nguyen, P.T., Phan, T.A.P., Ngo, N.H.T., Huynh, T.V., and Lund, T., Solid State Ionics, 2018, vol. 314, p. 98. https://doi.org/10.1016/j.ssi.2017.11.023

    Article  CAS  Google Scholar 

  21. Aranyos, V., Hjelm, J., Hagfeldt, A., and Grennberg, H., Dalton Trans., 2003, p. 1280. https://doi.org/10.1039/B208807J

  22. Sánchez-Castellanos, M., Flores-Leonar, M.M., Mata-Pinzón, Z., Laguna, H.G., García-Ruiz, K.M., Rozenel, S.S., Ugalde-Saldívar, V.M., MorenoEsparza, R., Pijpers, J.J.H., and Amador-Bedolla, C., Phys. Chem. Chem. Phys., 2019, vol. 21, p. 15823. https://doi.org/10.1039/C9CP03176F

    Article  PubMed  Google Scholar 

  23. Jamshidvand, A., Keshavarzi, R., Mirkhani, V., Moghadam, M., Tangestaninejad, S., Mohammadpoor-Baltork, I., Afzali, N., Nematollahi, J., and Amini, M., J. Mater. Sci.: Mater. Electron., 2021, vol. 32, p. 9345. https://doi.org/10.1007/s10854-021-05598-y

    Article  CAS  Google Scholar 

  24. Mills, I.N., Kagalwala, H.N., Chirdon, D.N., Brooks, A.C., and Bernhard, S., Polyhedron, 2014, vol. 82, p. 104. https://doi.org/10.1016/j.poly.2014.05.012

    Article  CAS  Google Scholar 

  25. Hagimori, M., Mizuyama, N., Tominaga, Y., Mukai, T., and Saji, H., Dyes Pigm., 2015, vol. 113, p. 205. https://doi.org/10.1016/j.dyepig.2014.07.032

    Article  CAS  Google Scholar 

  26. Hagimori, M., Mizuyama, N., Yamaguchi, Y., Saji, H., and Tominaga, Y., Talanta, 2011, vol. 83, p. 1730. https://doi.org/10.1016/j.talanta.2010.12.003

    Article  CAS  PubMed  Google Scholar 

  27. Belikov, M.Yu., Fedoseev, S.V., Ershov, O.V., Ievlev, M.Yu., and Tafeenko, V.A., Tetrahedron Lett., 2016, vol. 57, p. 4101. https://doi.org/10.1016/j.tetlet.2016.07.095

    Article  CAS  Google Scholar 

  28. Belikov, M.Yu., Ievlev, M.Yu., Fedoseev, S.V., and Ershov, O.V., New J. Chem., 2019, vol. 43, p. 8414. https://doi.org/10.1039/C9NJ01648A

    Article  CAS  Google Scholar 

  29. Chunikhin, S.S., Ershov, O.V., Ievlev, M.Y., Beli­kov, M.Y., and Tafeenko, V.A., Dyes Pigm., 2018, vol. 156, p. 357. https://doi.org/10.1016/j.dyepig.2018.04.024

    Article  CAS  Google Scholar 

  30. Arafa, W.A.A. and Hussein, M.F., Chin. J. Chem., 2020, vol. 38, p. 501. https://doi.org/10.1002/cjoc.201900494

    Article  CAS  Google Scholar 

  31. Engler, C. and Engler, A., Ber. Dtsch. Chem. Ges., 1902, vol. 35, p. 4061. https://doi.org/10.1002/cber.19020350437

    Article  CAS  Google Scholar 

  32. Li, C.-W., Shen, T.-H., and Shih, T.-L., Tetrahedron, 2017, vol. 73, p. 4644. https://doi.org/10.1016/j.tet.2017.06.033

    Article  CAS  Google Scholar 

  33. Niu, C., Tuerxuntayi, A., Li, G., Kabas, M., Dong, C.-Z., and Aisa, H.A., Chin. Chem. Lett., 2017, vol. 28, p. 1533. https://doi.org/10.1016/j.cclet.2017.03.018

    Article  CAS  Google Scholar 

  34. Liang, Z.-Q., Wang, X.-M., Dai, G.-L., Ye, C.-Q., Zhou, Y.-Y., and Tao, X.-T., New J. Chem., 2015, vol. 39, p. 8874. https://doi.org/10.1039/C5NJ01072A

    Article  CAS  Google Scholar 

  35. Qi, Q., Lv, S., Hao, M., Dong, X., Gu, Y., Wu, P., Zhang, W., Chen, Y., and Wang, C., Eur. J. Org. Chem., 2020, vol. 2020, p. 4417. https://doi.org/10.1002/ejoc.202000652

    Article  CAS  Google Scholar 

  36. Song, B., Wang, G., and Yuan, J., Chem. Commun., 2005, p. 3553. https://doi.org/10.1039/B503980K

  37. Brouwer, A.M., Pure Appl. Chem., 2011, vol. 83, p. 2213. https://doi.org/10.1351/PAC-REP-10-09-31

    Article  CAS  Google Scholar 

  38. Mittelbach, M., Monatsh. Chem., 1985, vol. 116, p. 689. https://doi.org/10.1007/BF00798796

    Article  CAS  Google Scholar 

Download references

Funding

This study was financially supported by the President of the Russian Federation (program for state support of young Russian scientists, project no. MK-708.2021.1.3, contract no. 075-15-2021-082).

Author information

Authors and Affiliations

  1. I.N. Ul’yanov Chuvash State University, 428015, Cheboksary, Russia

    M. Yu. Ievlev, N. S. Mayorov, M. A. Shishlikova, M. Yu. Belikov, I. N. Bardasov & O. V. Ershov

Authors
  1. M. Yu. Ievlev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. S. Mayorov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. A. Shishlikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. Yu. Belikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. I. N. Bardasov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. O. V. Ershov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to M. Yu. Ievlev.

Ethics declarations

The authors declare the absence of conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 12, pp. 1744–1751 https://doi.org/10.31857/S0514749221120090.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ievlev, M.Y., Mayorov, N.S., Shishlikova, M.A. et al. Synthesis and Luminescence Spectral Properties of New Cyano-Substituted 2,2′-Bipyridine Derivatives. Russ J Org Chem 57, 1961–1967 (2021). https://doi.org/10.1134/S1070428021120095

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428021120095

Keywords:

Search

Navigation