Polymethine dyes based on pyrylium salts with unsaturated cyclic groups in the 4-position

TitlePolymethine dyes based on pyrylium salts with unsaturated cyclic groups in the 4-position
Publication TypeJournal Article
Year of Publication2017
AuthorsKurdyukov, VV, Tolmachev, AI
Abbreviated Key TitleDopov. Nac. akad. nauk Ukr.
DOI10.15407/dopovidi2017.12.090
Issue12
SectionChemistry
Pagination90-96
Date Published12/2017
LanguageRussian
Abstract

2,6-Diphenyl-substituted pyrylium salts containing unsaturated cyclic groups are synthesized. They are shown to be feasible precursors for the synthesis of symmetric and unsymmetric dyes. The spectral properties of synthesized dyes are studied in solvents of different polarities.
Keywords1;5-diketones, cyclic groups, dicarbocyanines, polymethine chain, pyrylium salts, styryl dyes, tetra car bocyanines
References: 
  1. Balaban, A.T., Schroth, W. & Fischer, G. (1969). Pyrylium Salts Part I. Syntheses. Adv. Heterocycl. Chem., 10, pp. 241-326. doi: https://doi.org/10.1016/S0065-2725(08)60499-7
  2. Balaban, A. T., Dinculescu, A., Dorofeenko, G. N., Fischer, G. W., Koblik, A. V., Mezheritskii, V. V. & Schroth, W. (1982). Pyrylium Salts: Synthesis, Reaction, and Physical Properties. New York: Acad. Press.
  3. Pat. 2756227 US. Quaternary salts and method of preparation, Heseltine, D.W. Publ. 24.07.1956.
  4. Pat. 4532337 US. Preparation of 3-formyl-5,6-dihydro-2H-pyran, Eckhardt, H., Halbritter, K., Goetz, N., Heilen, G. Publ. 30.07.1985.
  5. Ohfusa, T. & Nishida, A. (2011). Reactivity and stereoselectivity of the Dielse Alder reaction using cyclic dienophiles and siloxyaminobutadienes. Tetrahedron, 67, rr. 1893-1906. doi: https://doi.org/10.1016/j.tet.2011.01.019
  6. Wizinger, R. & Ulrich, P. (1956). Über Thiopyrylocyanine. Helv. Chim. Acta., 39, Iss. 1, pp. 217-222. doi: https://doi.org/10.1002/hlca.19560390125
  7. Wizinger, R. & Ulrich, P. (1956). Zur Kenntnis der Thiopyryliumsalze. Helv. Chim. Acta., 39, Iss. 1, pp. 207-216. doi: https://doi.org/10.1002/hlca.19560390124
  8. Tolmachev, A. I., Derevyanko, N. A., Karaban, E. F. & Kudinova, M. A. (1975). Pyrylocyanines VI. Conversion of 4-pyrylocyanines to 4-pyridocyanines. Chemistry of Heterocyclic Compounds, 11, No. 5, pp. 534-538.
  9. Kudinova, M. A., Derevyanko, N. A., Dyadyusha, G. G., Ishchenko, A. A. & Tolmachev, A. I. (1980). Pyrylo-cyanines. 11. Symmetrical tetraphenyl-substituted pyrylo-2-cyanines Chemistry of Heterocyclic Compounds, 16, No. 7, pp. 691-695.
  10. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G. A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H. P., Izmaylov, A. F., Bloino, J., Zheng, G., Sonnenberg, J. L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J. A., Jr., Peralta, J. E., Ogliaro, F., Bearpark, M., Heyd, J. J., Brothers, E., Kudin, K. N., Staroverov, V. N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J. C., Iyengar, S. S., Tomasi, J., Cossi, M., Rega, N., Millam, J. M., Klene, M., Knox, J. E., 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., Martin, R. L., Morokuma, K., Zakrzewski, V. G., Voth, G. A., Salvador, P., Dannenberg, J. J., Dapprich, S., Daniels, A. D., Farkas, Ö., Foresman, J. B., Ortiz, J. V., Cioslowski, J., Fox, D. J. (2009). Gaussian 09, Revision D.01. Gaussian, Inc., Wallingford, CT.