Synthesis and Electronic Transitions of the Dye Based on 1-{2-[4-(3-Hydroxy-2-oxo-2H-chromen-4-yl)phenyl]-2-oxoethyl}-4-methylpyridinium Bromide

Abstract

4-[4-(2-Bromoacetyl)phenyl]-3-hydroxy-2H-chromen-2-one reacted with pyridine and 4-methylpyridine to give the corresponding quaternary pyridinium salts. The condensation of 1-{2-[4-(3-hydroxy-2-oxo-2H-chromen-4-yl)phenyl]-2-oxoethyl}-4-methylpyridinium bromide with 4-(dimethylamino)benzaldehyde afforded a new biscyanine dye whose electronic spectrum showed two absorption maxima originating from interactions of chromophores. The nature of electronic transitions in the dye molecule was analyzed by quantum chemical calculations.

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REFERENCES

  1. 1

    Panigrahi, M., Dash, S., Patel, S., and Mishra, B.K., Tetrahedron, 2012, vol. 68, no. 3, p. 781. https://doi.org/10.1016/j.tet.2011.10.069

    CAS  Article  Google Scholar 

  2. 2

    Shindy, H.A., Dyes Pigm., 2017, vol. 145, p. 505. https://doi.org/10.1016/j.dyepig.2017.06.029

    CAS  Article  Google Scholar 

  3. 3

    Shindy, H.A., Mini-Rev. Org. Chem., 2012, vol. 9, no. 2, p. 209. https://doi.org/10.2174/157019312800604652

    CAS  Article  Google Scholar 

  4. 4

    Kiprianov, A.I., Tsvet i stroenie tsianinovykh krasitelei (Color and Structure of Cyanine Dyes), Kiev: Naukova Dumka, 1979, p. 303.

  5. 5

    Kachkovskii, A.D., Stroenie i tsvet polimetinovykh krasitelei (Structure and Color of Cyanine Dyes), Kiev: Naukova Dumka, 1989.

  6. 6

    Mushkalo, I.L. and Shedov, I.F., Chem. Heterocycl. Compd., 1974, vol. 10, no. 11, p. 1309. https://doi.org/10.1007/BF01175085

    Article  Google Scholar 

  7. 7

    Kiprianov, A.I., Russ. Chem. Rev., 1971, vol. 40, no. 7, p. 594. https://doi.org/10.1070/RC1971v040n07ABEH001942

    Article  Google Scholar 

  8. 8

    Chernyuk, I.N., Yagodinets, P.I., and Shevchuk, M.I., Zh. Obshch. Khim., 1982, vol. 52, no. 3, p. 716.

    CAS  Google Scholar 

  9. 9

    Yagodinets, P.I., Russ. J. Gen. Chem., 1998, vol. 68, no. 8, p. 1256.

    CAS  Google Scholar 

  10. 10

    Kiprianov, A.I. and Mushkalo, I.L., Zh. Org. Khim., 1965, vol. 1, no. 4, p. 744.

    CAS  Google Scholar 

  11. 11

    Kiprianov, A.I. and Dyadyusha, G.G., Ukr. Khim. Zh., 1969, vol. 35, no. 6, p. 608.

    CAS  Google Scholar 

  12. 12

    Yelenich, O.V., Skrypska, O.V., Lytvyn, R.Z., Neshchadin, A.O., Obushak, M.D., Kachkovskii, A.D., and Yagodinets, P.I., Russ. J. Gen. Chem., 2014, vol. 84, no. 11, p. 2114. https://doi.org/10.1134/S1070363214110127

    CAS  Article  Google Scholar 

  13. 13

    Yelenich, O.V., Lytvyn, R.Z., Skrypska, O.V., Pitkovych, Kh.Ye., Kachkovskii, A.D., Obushak, M.D., and Yagodinets, P.I., Russ. J. Gen. Chem., 2016, vol. 86, no. 8, p. 1838. https://doi.org/10.1134/S1070363214110127

    CAS  Article  Google Scholar 

  14. 14

    Chernyuk, I.N., Yagodinets, P.I., and Pridan, V.E., Russ. J. Gen. Chem., 1997, vol. 67, no. 3, p. 427.

    Google Scholar 

  15. 15

    Yagodinets, P.I., Russ. J. Org. Chem., 1998, vol. 34, no. 1, p. 137.

    CAS  Google Scholar 

  16. 16

    Yagodinets, P.I., Russ. J. Gen. Chem., 1997, vol. 67, no. 9, p. 1482.

    CAS  Google Scholar 

  17. 17

    Yagodinets, P.I., Russ. J. Gen. Chem., 1998, vol. 68, no. 8, p. 1252.

    CAS  Google Scholar 

  18. 18

    Yagodinets’, P.І., Kachkovs’kii, O.D., and Skrips’ka, O.V., Zh. Org. Farm. Khіm., 2005, vol. 3, no. 2, p. 55.

    Google Scholar 

  19. 19

    Pridan, V.E., Chernyuk, I.N., Rogovik, L.I., and Bukachuk, O.M., Zh. Org. Khim., 1980, vol. 16, no. 9, p. 1973.

    CAS  Google Scholar 

  20. 20

    Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, J.A.Jr., Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., and Pople, J.A., Gaussian 03, Revision B.03, Wallingford CT: Gaussian, 2003.

  21. 21

    Hedvig, P., Experimental Quantum Chemistry, Budapest: Akadémiai Kiadó, 1975.

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Correspondence to M. D. Obushak.

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Skrypska, O.V., Lytvyn, R.Z., Rusnak, O.V. et al. Synthesis and Electronic Transitions of the Dye Based on 1-{2-[4-(3-Hydroxy-2-oxo-2H-chromen-4-yl)phenyl]-2-oxoethyl}-4-methylpyridinium Bromide. Russ J Gen Chem 90, 602–609 (2020). https://doi.org/10.1134/S1070363220040076

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Keywords:

  • cyanine dyes
  • pyridinium salts
  • coumarin derivatives
  • arylation
  • quantum chemical calculations