Novel anionic polymethines of the fluorene series

TitleNovel anionic polymethines of the fluorene series
Publication TypeJournal Article
Year of Publication2017
AuthorsKurdyukova, IV, Ishchenko, AA, Mysyk, DD
Abbreviated Key TitleDopov. Nac. akad. nauk Ukr.
DOI10.15407/dopovidi2017.04.063
Issue4
SectionChemistry
Pagination63-69
Date Published4/2017
LanguageRussian
Abstract

The vinylogical series of anionic polymethine dyes based on tris(2,2,3,3,4,4,5,5-octafluoropenthyl)-9H-fluorene-2,4,7-trisulfonate is synthesized. It is shown that, in contrast to similar derivatives of polynitrofluorene, the most intense and long-wavelength electronic transition is the polymethine transition. It is found that the absorption band of this transition for highest vinylogies, in contrast to those of classic polymethines, is preserved very intense and narrow even in highly polar solvents.

Keywordsabsorption spectra, anionic polymethine dyes, electronic transitions, fluorescence spectra, Tris(2;2;3;3;4;4;5;5-octafluoropenthyl)-9H-fluorene-2;4;7-trisulfonate
References: 
  1. Tolmachev, A.I., Slominskii, Yu.L., & Ishchenko, A.A. (1998). New cyanine dyes absorbing in the NIR region. In Daehne, S., Resch-Genger, U., Wolfbeis, O.S. (Eds.), New Infrared Dyes for High Technology Applications, NATO ASI Series. 3, High Technology (pp. 385-415), Dordrecht, Boston, London: Kluwer, Vol. 52. https://doi.org/10.1007/978-94-011-5102-3_19
  2. Bricks, J. L., Kachkovskii, A. D., Slominskii, Yu. L., Gerasov, A. O. & Popov, S. V. (2015). Molecular design of near infrared polymethine dyes: A review. Dyes Pigments, 121. Iss. 3, pp. 238-255. https://doi.org/10.1016/j.dyepig.2015.05.016
  3. Kurdyukova, I. V., Ishchenko, A. A. (2012). Organic dyes based on fluorene and its derivatives, Uspekhi khimii, 81, No. 3, pp. 258-290 (in Russian). doi: https://doi.org/10.1070/RC2012v081n03ABEH004211
  4. Kurdyukova, I. V., Derevyanko, N. A., Ishchenko, A. A. & Mysyk, D. D. (2009). Deeply colored anionic polymethine dyes derived from bis(2,2,3,3,4,4,5,5-octafluoropentyl) 9N-fluorene-2,7-disulfonate. Izv. AN. Ser. khim., No. 4, pp. 811-820 (in Russian).
  5. Kurdyukova, I. V., Derevyanko, N. A., Ishchenko, A. A. & Mysyk, D. D. (2012). Synthesis and spectroscopic properties of the symmetric anionic polymethine dyes based on fluorene and its derivatives with electronwithdrawing substituents. Izv. AN. Ser. khim., No. 2, pp. 287-296 (in Russian).
  6. Kurdyukova, I. V., Kulinich, A. V. & Ishchenko, A. A. (2012). Near-infrared squarate and croconate dianios derived from tetranitrofluorene. New J. Chem., 36, Iss. 8, pp. 1564-1567. https://doi.org/10.1039/c2nj40303j
  7. Popov, V. I., Skripkina, V. T, Protsyk S. P., Skrynnikova, A. A., Krasovitskii, B. M. & Yagupol'skii, L. M. (1991). Electronic nature of polyfluoroalkoxysulfonyl groups and their effect on spectral characteristics of azo- and triarylpyrazoline dyes. Ukr. khim. zhurn., 57, No. 8, pp. 843-849 (in Russian).
  8. Bassin, J. P., Cremlyn, R. J. & Swinbourne, F. J. (1992). Chlorosulfonation of Some Polynuclear Heterocyclic Compounds. Phosphorus Sulfur Silicon Relat. Elem., 72, pp. 157-170. https://doi.org/10.1080/10426509208031549
  9. Dutto, P. C. & Mandal, D. (1956). Studies in indigoid dyes. Part XIX. Thiondigoid dyes derived from fluorine-2:7-disulphonic acid. J. Indian Chem. Soc., 33, No. 10, pp. 721-723.
  10. Kuhn, R., Fischer, H., Neugebauer, F. A. & Fischer, H. (1962). Über Hochacide Kohlenwasserstoffe. Liebigs Ann. Chem., 654, pp. 64-81. https://doi.org/10.1002/jlac.19626540109
  11. Kulinich, A. V., Derevyanko, N. A. & Ishchenko, A. A. (2007). Electronic structure and solvatochromism of merocyanines based on N,N-diethylthiobarbituric acid. J. Photochem. Photobiol. A., 188, No. 2-3, pp. 207-217. https://doi.org/10.1016/j.jphotochem.2006.12.014
  12. Ishchenko, A. A. (1991). Structure and spectral-luminescent properties of polymethine dyes. Russ. Chem. Rev., 60, No. 8, pp. 865–884. https://doi.org/10.1070/RC1991v060n08ABEH001116
  13. Ishchenko, A. A. (1998). Physicochemical aspects of the creation of modern light-sensitive materials based on polymethine dyes. Teoret. i eksperim. khimiia, 34, No. 4, pp. 214-232 (in Russian). https://doi.org/10.1007/bf02523249
  14. Masunov, A. E., Anderson, D., Freidzon, A. Ya. & Bagaturyants, A. A. (2015). Symmetry-Breaking in Cationic Polymethine Dyes: Pt. 2. Shape of Electronic Absorption Bands Explained by the Thermal Fluctuations of the Solvent Reaction Field. J. Phys. Chem. A., 119, Iss. 26, pp. 6807-6815. https://doi.org/10.1021/acs.jpca.5b03877