Abstract
Derivatives of ethyl 2-cyano-2-[3,4-dicyanopyridin-2(1H)-ylidene]acetate have been synthesized by reaction of 2-chloropyridine-3,4-dicarbonitriles with ethyl cyanoacetate. The synthesized compounds showed solid state fluorescence with the emission maxima located in the range λ 619–641 nm; the emission maxima in solution range from λ 392 to 486 nm, depending on the solvent.
Similar content being viewed by others
REFERENCES
Deng, G., Huang, H., Si, P., Xu, H., Liu, J., Bo, Sh., Liu, X., Zhen, Z., and Qiu, L., Polymer, 2013, vol. 54, p. 6349. https://doi.org/10.1016/j.polymer.2013.09.042
Wang, L., Bo, Sh., Liu, J., Zhen, Z., and Liu, X., Polym. Sci., Ser. B, 2012, vol. 54, p. 297. https://doi.org/10.1134/S1560090412050041
Halter, M., Liao, Y., Plocinik, R.M., Coffey, D.C., Bhattacharjee, S., Mazur, U., Simpson, G.J., Robinson, B.H., and Keller, S.L., Chem. Mater., 2008, vol. 20, p. 1778. https://doi.org/10.1021/cm702267z
Zeng, Y., Wang, Y., Yang, N., and Liu, Y., Heterocycl. Commun., 2018, vol. 24, p. 67. https://doi.org/10.1515/hc-2017-0264
Wang, Y., Yang, N., and Liu, Y., Spectrochim. Acta, Part A, 2018, vol. 194, p. 45. https://doi.org/10.1016/j.saa.2018.01.017
Parthasarathy, V., Pandey, R., Das, P.K., Castet, F., and Blanchard-Desce, M., ChemPhysChem, 2018, vol. 19, p. 187. https://doi.org/10.1002/cphc.201701143
Tverdokhleb, N.M., Khoroshilov, G.E., and Dotsenko, V.V., Tetrahedron Lett., 2014, vol. 55, p. 6593. https://doi.org/10.1016/j.tetlet.2014.10.046
Liu, J., Hou, W., Feng, S., Qiu, L., Liu, X., and Zhen, Z., J. Phys. Org. Chem., 2011, vol. 24, p. 439. https://doi.org/10.1002/poc.1772
Cho, M.J., Lim, J.H., Hong, C.S., Kim, J.H., Lee, H.S., and Choi, D.H., Dyes Pigm., 2008, vol. 79, p. 193. https://doi.org/10.1016/j.dyepig.2008.02.005
Liu, J., Liu, X., and Zhen, Z., Electron. Mater. Lett., 2012, vol. 8, p. 451. https://doi.org/10.1007/s13391-012-2004-3
Bardasov, I.N., Alekseeva, A.U., Chunikhin, S.S., Tafeenko, V.A., and Ershov, O.V., Tetrahedron Lett., 2017, vol. 58, p. 3919. https://doi.org/10.1016/j.tetlet.2017.08.076
Bardasov, I.N., Alekseeva, A.Yu., Chunikhin, S.S., and Ershov, O.V., Russ. J. Org. Chem., 2018, vol. 54, p. 1161. https://doi.org/10.1134/S1070428018080079
Bardasov, I.N., Alekseeva, A.U., Chunikhin, S.S., Shishlikova, M.A., and Ershov, O.V., Tetrahedron Lett., 2019, vol. 60, p. 1170. https://doi.org/10.1016/j.tetlet.2019.03.054
Chunikhin, S.S, Ershov, O.V., Ievlev, M.Yu., Belikov, M.Yu., and Tafeenko, V.A., Dyes Pigm., 2018, vol. 156, p. 357. https://doi.org/10.1016/j.dyepig.2018.04.024
Ershov, O.V., Chunikhin, S.S., Ievlev, M.Yu., Belikov, M.Yu., and Tafeenko, V.A., CrystEngComm, 2019, vol. 21, p. 5500. https://doi.org/10.1039/c9ce01089k
Sadek, K.U., Fahmy, S.M., Mohareb, R.M., and Elnagdi, M.H., J. Chem. Eng. Data, 1984, vol. 29, p. 101. https://doi.org/10.1021/je00035a033
Koitz, G., Thlerrichter, B., and Junek, H., Heterocycles, 1983, vol. 20, p. 2405. https://doi.org/10.3987/R-1983-12-2405
Fahmy, S.M., Abd Allah, S.O., and Mohareb, R.M., Synthesis, 1984, vol. 1984, no. 11, p. 976. https://doi.org/10.1055/s-1984-31045
Beugelmans, R., Bois-Choussy, M., and Boudet, B., Tetrahedron, 1982, vol. 38, p. 3479. https://doi.org/10.1016/0040-4020(82)85032-1
Ducker, J.W. and Gunter, M.J., Aust. J. Chem., 1973, vol. 26, p. 2567. https://doi.org/10.1071/CH9732567
Lipin, K.V., Maksimova, V.N., Ershov, O.V., Eremkin, A.V., Kayukov, Ya.S., and Nasakin, O.E., Russ. J. Org. Chem., 2010, vol. 46, p. 617. https://doi.org/10.1134/S107042801004038X
Ershov, O.V., Lipin, K.V., Maksimova, V.N., Eremkin, A.V., Kayukov, Ya.S., and Nasakin, O.E., Russ. J. Org. Chem., 2009, vol. 45, p. 475. https://doi.org/10.1134/S1070428009030269
Funding
This study was performed under financial support by the Ministry of Science and Higher Education of the Russian Federation (project no. 0849-2020-0003).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare no conflict of interest.
Additional information
Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 7, pp. 1012–1018 https://doi.org/10.31857/S0514749221070119.
Rights and permissions
About this article
Cite this article
Chunikhin, S.S., Ershov, O.V. Synthesis and Optical Properties of Ethyl 2-Cyano-2-[3,4-dicyanopyridin-2(1H)-ylidene]acetate Derivatives. Russ J Org Chem 57, 1103–1108 (2021). https://doi.org/10.1134/S1070428021070113
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428021070113