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Modification of Phosphoryl Substituents of Phthalocyanines As a Route to Targeted Tuning of Lipophilic-Hydrophilic Properties

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Abstract

О′,О′-Diethyl-[2-(3,4-dicyanophenoxy)phenyl]phosphonate has been synthesized for the first time and introduced in template condensation on lithium and zinc cations to prepare a series of new neutral and acidic phthalocyanines containing four fragments of 2-oxyphenylphosphonic acid. A scheme of modification of the peripheral substituents at the phosphoryl group was developed allowing a targeted synthesis of phthalocyanine ligands and complexes soluble in organic solvents or aqueous media.

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References

  1. Tsivadze, A.Yu., Russ. Chem. Rev., 2004, vol. 73, no. 1, p. 1. doi 10.1070/RC2004v073n01ABEH000863

    Article  CAS  Google Scholar 

  2. Baulin, V.E., Ovsyannikova, E.V., Kalashnikova, I.P., Girina, G.P., Andreev, V.N., Alpatova, N.M., and Tsivadze, A.Yu., Fizikokhim. Poverkhn. Zaschita Material., 2013, vol. 49, no. 1, p. 7.

    Google Scholar 

  3. Zampa, M.F., de Brito, A.C.F., Kitagawa, I.L., Constantino, C.J.L., Oliveira, O.N., da Cunha, H.N., Zucolotto, V., dos Santos, J.R., and Eiras, C., Biomacromolecules, 2007, vol. 8, no. 11, p. 3408. doi 10.1021/bm700528u

    Article  CAS  PubMed  Google Scholar 

  4. Zuev, K.V., Smrchek, V.A., Fedoseeva, M.S., Koldaeva, T.Yu., and Perevalov, V.P., Khim. Prom–t’ Segodnya, 2015, no. 8, p. 24.

    Google Scholar 

  5. Makhseed, S., Machacek, M., Alfadly, W., Tuhl, A., Vinodh, M., Simunek, T., Novakova, V., Kubat, P., Rudolf, E., and Zimcik, P., Chem. Commun., 2013, vol. 49, p. 11149. doi 10.1039/C3CC44609C

    Article  CAS  Google Scholar 

  6. Lang, K., Kubat, P., Mosinger, J., and Wagnerová, D.M., J. Photochem. Photobiol. (A), 1998, vol. 119, no. 1, p. 47. doi 10.1016/S1010-6030(98)00380-3

    Article  CAS  Google Scholar 

  7. Quirk, B.J., Brandal, G., Donlon, S., Vera, J.C., Mang, T.S., Foy, A.B., Lew, S.M., Girotti, A.W., Jogal, S., La Violette, P.S., Connelly, J.M., and Whelan, H.T., Photodiagn. Photodyn. Ther., 2015, vol. 12, no. 3, p. 530. doi 10.1016/j.pdpdt.2015.04.009

    Article  Google Scholar 

  8. Dumoulin, F., Durmus, M. Ahsen, V., and Nyokong, T., Coord. Chem. Rev., 2010, vol. 254, nos. 23–24, p. 2792. doi 10.1016/j.ccr.2010.05.00

  9. Sharman, W.M., Kudrevich, S.V., and van Lier, J.E., Tetrahedron Lett., 1996, vol. 37, no. 33, p. 5831. doi 10.1016/0040-4039(96)01243-9

    Article  CAS  Google Scholar 

  10. Märkl, G., Gschwendner, K., Rötzer, I., and Kreitmeier, P., Helv. Chim. Acta, 2004, vol. 87, no. 4, p. 825. doi.1002/hlca.200490081

    Article  Google Scholar 

  11. Komissarov, A.N., Makarov, D.A., Yuzhakova, O.A., Savvina, L.P., Kuznetsova, N.A., Kaliya, O.L., Lukyanets, E.А.,and Negrimovsky V.M., Macroheterocycles, 2012, vol. 5, no. 2, p. 169.

    Article  CAS  Google Scholar 

  12. Wolleb, H., Preiswerk, H., Schmidhalter, B., and Spahni, H., US Patent 5641879, 1997.

    Google Scholar 

  13. Ivanov, A.V., Kabanova, K.V., Breusova, M.O., Zhukov, I. V. Tomilova, L.G., and Zefirov, N.S., Russ. Chem. Bull., 2008, vol. 57, no. 8, p. 1665. doi 10.1007/s11172-008-0218-1

    Article  CAS  Google Scholar 

  14. Baulin, V.E., Kalashnikova, I.P., Pyatova, E.N., Ivanova, I.S., Ragulin, V.V., and Tsivadze, A.Yu., Fizikokhi. Poverkhn. Zaschita Material., 2011, vol. 47, no. 4, p. 41.

    Google Scholar 

  15. Baulin, V.E., Syundyukova, V.Kh., and Tsvetkov, E.N., Zh. Obshch. Khim., 1989, vol. 59, no. 1, p. 62.

    CAS  Google Scholar 

  16. Rabinowitch, R., J. Am. Chem. Soc., 1960, vol. 82, no. 17, p. 4564. doi 10.1021/ja01502a030

    Article  Google Scholar 

  17. Khimicheskaya entsiklopediya (Chemical Encyclopedia), Zefirov, N.S., Ed., Moscow: Bol’shaya Rossiyskaya Entsiklopediya, 1998, vol. 5, p. 1011.

  18. Organic Phosphorus Compounds, Kosolapoff, G.M. and Maier, L., Eds., New-York: Wiley, 1976, vol. 7, p. 86.

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Correspondence to I. P. Kalashnikova.

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Dedicated to the 110th anniversary of M.I. Kabachnik’s birth

Original Russian Text © I.P. Kalashnikova, D.V. Baulin, V.E. Baulin, A.Yu. Tsivadze, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 9, pp. 1510–1516.

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Kalashnikova, I.P., Baulin, D.V., Baulin, V.E. et al. Modification of Phosphoryl Substituents of Phthalocyanines As a Route to Targeted Tuning of Lipophilic-Hydrophilic Properties. Russ J Gen Chem 88, 1853–1859 (2018). https://doi.org/10.1134/S1070363218090153

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  • DOI: https://doi.org/10.1134/S1070363218090153

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