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Russian Chemical Bulletin

, Volume 67, Issue 12, pp 2246–2249 | Cite as

Perfluorinated porphyrazines

4. Alkoxyderivatives and water soluble glycoconjugates on the basis of perfluorinated zinc(II) octaphenylporphyrazine
  • S. S. IvanovaEmail author
  • I. A. Lebedeva
  • P. A. Stuzhin
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Abstract

Nucleophilic substitution of fluorine atoms in the phenyl rings by alkoxy groups was performed in perfluorosubstituted zinc(II) octaphenylporphyrazine [ZnPAF40]. Up to 12 fluorine atoms are substituted in the reaction with sodium butoxide in boiling butanol leading to the formation of [ZnPAF40-n(OBu)n] (n = 6–12). Up to eight monosaccharide groups are introduced in the reaction with 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (Gal´) in toluene in the presence of sodium hydride leading to the formation of [ZnPaF(40-n)(Gal´)n] (n = 6–8). It was possible to obtain a water-soluble glycoconjugated zinc(II) porphyrazine [ZnPaF(40-n)(Gal)n] after removal of the isopropylidene protecting groups by treatment with trifluoroacetic acid. Substitution products are characterized by electron absorption spectroscopy, NMR spectroscopy, and mass spectrometry. Substituting the fluorine atoms with monosaccharide residues leads to an increase in the fluorescence quantum yield from ФF = 0.19 for [ZnPAF40] to 0.29 for [ZnPA(Gal´)nF40-n] (n = 6–8).

Key words

perfluorinated porphyrazines nucleophilic aromatic substitution galactose water soluble porphyrazines 

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References

  1. 1.
    I. A. Yablokova (Lebedeva), S. S. Ivanova, Yu. A. Zhabanov, V. Novakova, P. A. Stuzhin, J. Fluorine Chem., 2018, 214, 86.CrossRefGoogle Scholar
  2. 2.
    S. G. DiMagno, J. C. Biffinger, H. Sun, in Fluorine in Heterocyc lic Chemistry, Ed. V. G. Nenajdenko, Vol. 1, 5-Membered Heterocycles and Macrocycles, Springer, Heidel berg, 2014, p. 589–620.Google Scholar
  3. 3.
    P. A. Stuzhin, in Fluorine in Heterocyclic Chemistry, Ed. V. G. Nenajdenko, Vol. 1, 5-Membered Heterocycles and Macrocycles, Springer, Heidelberg, 2014, p. 621–681.Google Scholar
  4. 4.
    T. Goslinski, J. Piskorz, Photochem. Photobiol., 2011, 304.Google Scholar
  5. 5.
    H. Brinkmann, C. Kelting, S. Makarov, O. Tsaryova, G. Schnurpfeil, D. Wöhrle, D. Schlettwein, Physica Status Solidi A Appl. Res., 2008, 205, 409.CrossRefGoogle Scholar
  6. 6.
    K. J. Balkus, Jr., M. Eissa, R. Levado, J. Am. Chem. Soc., 1995, 117, 10753.CrossRefGoogle Scholar
  7. 7.
    D. Dini, G. Y. Yang, M. Hanack, J. Chem. Phys., 2003, 119, 4857.CrossRefGoogle Scholar
  8. 8.
    J. I. T. Costa, A. C. Tome, M. G. Neves, J. A. S. Cavaleiro, J. Porphyrins Phthalocyanines, 2011, 15, 1116.CrossRefGoogle Scholar
  9. 9.
    P. Battioni, O. Brigaud, H. Desvaux, D. Mansuy, T. G. Traylor, Tetrahedron Lett., 1991, 32, 2893.CrossRefGoogle Scholar
  10. 10.
    M. Suzuki, S. Shimizu, J.-Y. Shin, A. Osuka, Tetrahedron Lett., 2003, 44, 4597.CrossRefGoogle Scholar
  11. 11.
    J. P. C. Tome, M. G. P. M. S. Neves, A. C. Tomé, J. A. S. Cavaleiro, A. F. Mendoncëa, I. N. Pegado, R. Duarte, M. L. Valdeira, Bioorg. Med. Chem., 2005, 13, 3878.CrossRefGoogle Scholar
  12. 12.
    J. Kralova, A. Synytsya, P. Pouckova, M. Koc, M. Dvorak, V. Kral, Photochem. Photobiol., 2006, 82, 433.CrossRefGoogle Scholar
  13. 13.
    J. Kralova, Z. Kejck, T. Brcza, P. Pouckova, A. Kral, P. Martasek, V. Kral, J. Med. Chem., 2010, 53, 128.CrossRefGoogle Scholar
  14. 14.
    T. Klein, T. Ziegler, Tetrahedron Lett., 2016, 57, 495.CrossRefGoogle Scholar
  15. 15.
    P. A. Stuzhin, M. Yu. Goryachev, S. S. Ivanova, A. Nazarova, I. Pimkov, O. I. Koifman, J. Porphyrins Phthalocyanines, 2013, 17, 905.CrossRefGoogle Scholar
  16. 16.
    P. A. Stuzhin, S. S. Ivanova, O. I. Koifman, O. A. Petrov, A. Nazarova, Inorg. Chem. Commun., 2014, 49, 72.CrossRefGoogle Scholar
  17. 17.
    K. P. R. Kartha, Tetrahedron Lett., 1986, 27, 3415.CrossRefGoogle Scholar
  18. 18.
    P. Zimcik, V. Novakova, K. Kopecky, M. Miletin, R. Z. Uslu Kobak, E. Svandrlikova, L. Váchová, K. Lang, Inorg. Chem., 2012, 51, 4215.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • S. S. Ivanova
    • 1
    Email author
  • I. A. Lebedeva
    • 1
  • P. A. Stuzhin
    • 1
  1. 1.Ivanovo State University of Chemistry and TechnologyIvanovoRussian Federation

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