New polymetine dyes from furo [3,2-f]-, furo [2,3-h] flavilium and 4-methyl furo [4′, 3′] flavilium salts

1Tolmachev, AI, Kudinova, MA, 1Kurdyukov, VV
1Institute of Organic Chemistry of the NAS of Ukraine, Kyiv
Dopov. Nac. akad. nauk Ukr. 2018, 6:98-104
https://doi.org/10.15407/dopovidi2018.06.098
Section: Chemistry
Language: Ukrainian
Abstract: 

Symmetric and non-symmetric polymethine dyes based on 2,9-dimethyl-1,2-dihydrofuro[3,2-f]-, 4,8- dimethyl -8,9 dihydrofuro [2,3-h]- and 4-methylfuro[4′,3′]flavilium salts are synthesized. It is shown that the influence of the new heterocyclic residues — isomeric dihydrofuroflavilium systems — on the absorption spectra of synthesized dyes is expressed in the bathochromic shift of the long-wavelength absorption band and an increase of the absorption intensity in comparison with the corresponding 6-, 7- and 4'-methoxy substituted and unsub.

Keywords: absorption spectra, furo[3;2-f]- and furo[2;3-h] flavilium salts, polymethine dyes
References: 
  1. Tolmachev, A. I., Slominskii, Yu. L. & Ishchenko, A. A. (1998). New cyanine dyes absorbing in the NIR region. New infrared dyes for high technology applications. NATO ASI Series 3: High Technology, Vol. 52 (pp. 385-415). Dordrecht: Springer.
  2. Tatikolov, A. S., Ishchenko, A. A., Kudinova, M. A. & Panova, I. G. (2010). Study of the noncovalent interaction of squarylium dyes with serum albumins. High Energy Chem., 44. No. 4, pp. 304-310. doi: https://doi.org/10.1134/S0018143910040089
  3. Ishchenko, A. A., Kudinova, M. A., Slominskii, Yu. L. & Tolmachev, A. I. (1986). Pyrylo-polycarbocianines containing cyclic groops. Zhurn. organ. khimii, 22, Iss. 1, pp. 170-178 (in Russian).
  4. Mayboroda, E. I., Slominskii, Yu. L. & Tolmachev, A. I. (2002). Thiacarbocyanines containing ethylene or vinylene bridging groups and substituents in chromophore. Ukr. khim. zhurn., 69, No. 6, pp. 106-111 (in Russian).
  5. Kargapolova, I. Ju., Orlova, N. A., Erin, K. D. & Shelkovnikov, V. V. (2016). Synthesis of unsymmetrical thioflavilium dyes from julolidine derivatives and polifluorinated triphenyldihydropyrasoles. Russ. J. Org. Chem., 52, No. 1, pp. 37-41. doi: https://doi.org/10.1134/S1070428016010073
  6. Davidenko, I. G., Slominskii, Yu. L., Kachkovsky, A. D. & Tolmachev, A. I. (2008). Polymethine dyes — derivatives 7,8-dihydrobenzo[c,d]furo-[2,3-f]indole. Ukr. khim. zhurn., 74, No. 4, pp. 105-113 (in Russian).
  7. Gavrilyuk, I. M., Ishchenko, A. A., Kudinova, M. A. & Tolmachev, A. I. (1983). Pyrolocyanines. 17. Symmetrical flavylocyanines based on methoxy-substituted4-methylflavylium salts. Chem. Heterocycl. Compounds, No. 3, pp. 243-247. doi: https://doi.org/10.1007/BF00513252
  8. Gavrilyuk, I. M., Ishchenko, A. A., Kudinova, M. A. & Tolmachev, A. I. (1983). Pyrylocyanines. 18. Unsymmetrical flavylocyanines on the basis of methoxysubstituted 4-methylflavylium salts. Chem. He te rocycl. Compounds, No. 9, pp. 948-950.
  9. Gavriluyk, I. M., Ishchenko, A. A., Kudinova, M. A. & Tolmachev, A. I. (1983). Unsymmetrical flavylocyanines. Dokl. AN USSR. Ser. B., No. 6, pp. 28-30 (in Russian).
  10. Krupodanam, G. L. D., Srimannarayana, G. & Subba, Rao N. V. (1977). Synthesis of 2′′-Methylfuro[5′′,4′′: 7,8]flavones. Indian J. Chem., 15B, pp. 933-935.
  11. Dholakia, V. N., Trivedi, K. N. (1973). Stadies in the synthesis of coumarino-α-pyrones and furocoumarines. Part XX. Synthesis of furo(3,2-c)benzo-pyran and furo(3,2-f)benzopyran derivatives. J. Indian Chem. Soc., 50, pp. 813-815.
  12. Reynolds, G. A., Van Allan, J. A. & Daniel, D. (1970). Preparation of 4-methyl-flavilium derivatives. J. Heterocycl. Chem., 7, pp. 1395-1396. doi: https://doi.org/10.1002/jhet.5570070627