Skip to main content
SpringerLink
Log in

Oligoether derivatives of 1-phenoxyanthraquinone: Synthesis, photochromism, and complex formation with metal cations

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

An Erratum to this article was published on 01 September 2016

Abstract

1-Phenoxyanthraquinone isomeric conjugates with tetraethylene glycol were prepared. Their photochromic properties and complex formation in solutions were quantitatively studied by spectrophotometry, quantum yields of the arylotropic photoisomerism and stability constants of complexes between para–ana-quinoid isomers and metal cations. The photochemical migration of a phenyl group considerably affects the complex stability thus providing the possibility to regard the synthesized compounds as photocontrolled ionophores. The structure of some complexes was investigated by X-ray diffraction (XRD) analysis and quantum-chemical simulation.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Velema, W.A., Szymanski, W., and Feringa, B.L., J. Am. Chem. Soc., 2014, vol. 136, p. 2178.

    Article  CAS  Google Scholar 

  2. Kimura, K., Sakamoto, H., and Nakamura, M., Bull. Chem. Soc. Jpn., 2003, vol. 76, p. 225.

    Article  CAS  Google Scholar 

  3. Shinkai, S., Pure Appl. Chem., 1987, vol. 59, p. 425.

    Article  CAS  Google Scholar 

  4. Ushakov, E.N., Alfimov, M.V., and Gromov, S.P., Russ. Chem. Rev., 2008, vol. 77, p. 39.

    Article  CAS  Google Scholar 

  5. Ushakov, E.N., Alfimov, M.V., and Gromov, S.P., Macroheterocycles, 2010, vol. 3, p. 189.

    Article  CAS  Google Scholar 

  6. Natali, M. and Giordani, S., Chem. Soc. Rev., 2012, vol. 41, p. 4010.

    Article  CAS  Google Scholar 

  7. Barachevsky, V.A., Organic Photochromic and Termochromic Compounds, Crano, J.C. and Guglielmetti, R., Eds., New York: Plenum Press, 1999, vol. 1.

  8. Fokin, E.P., Russkikh, S.A., and Klimenko, L.S., Izv. Sibir. Otdel. Akad. Nauk SSSR, Ser. Khim. Nauk, 1979, vol. 9, p. 117.

    Google Scholar 

  9. Gritsan, N.P. and Klimenko, L.S., J. Photochem. Photobiol. A, 1993, vol. 70, p. 103.

    Article  CAS  Google Scholar 

  10. Klimenko, L.S., Leonenko, Z.V., and Gritsan, N.P., Mol. Cryst. Liq. Cryst., 1991, vol. 297, p. 181.

    Article  Google Scholar 

  11. Babailov, S.P., Klimenko, L.S., and Mainagashev, I.Ya., J. Struct. Chem., 2006, vol. 47, p. 663.

    Article  CAS  Google Scholar 

  12. Eroshkin, V.P., Fokin, E.P., Volkov, A.I., Andreeva, T.A., Klimenko, L.S., Dolgikh, Yu.K., and Simonenko, A.F., Zh. Fiz. Khim., 1991, vol. 65, p. 1479.

    CAS  Google Scholar 

  13. Born, R., Fischer, W., Heger, D., Tokarczyk, B., and Wirz, J., Photochem. Photobiol. Sci., 2007, vol. 6, p. 552.

    Article  CAS  Google Scholar 

  14. Gerasimenko, Yu.E., Poteleshchenko, N.T., and Romanov, V.V., Zh. Org. Khim., 1980, vol. 16, p. 2014.

    CAS  Google Scholar 

  15. Löhr, H.-G. and Vögtle, F., Acc. Chem. Res., 1985, vol. 18, p. 65.

    Article  Google Scholar 

  16. Ushakov, E.N., Gromov, S.P., Fedorova, O.A., Pershina, Yu.V., Alfimov, M.V., Barigilletti, F., Flamigni, L., and Balzani, V., J. Phys. Chem. A, 1999, vol. 103, p. 11188.

    Article  CAS  Google Scholar 

  17. Martyanov, T.P., Ushakov, E.N., Savelyev, V.A., and Klimenko, L.S., Russ. Chem. Bull., 2012, vol. 61, p. 2282.

    Article  CAS  Google Scholar 

  18. Shannon, R.D., Acta Cryst., Sect. A, 1976, vol. 32, p. 751.

    Article  Google Scholar 

  19. Gottlieb, H.E., Kotlyar, V., and Nudelman, A., J. Org. Chem., 1997, vol. 62, p. 7512.

    Article  CAS  Google Scholar 

  20. Sheldrick, G.M., SHELXTL v. 6.14. Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA, 2000.

    Google Scholar 

  21. Halgren, T.A., J. Comput. Chem., 1996, vol. 17, p. 490.

    Article  CAS  Google Scholar 

  22. Perdew, J.P., Burke, K., and Ernzerhof, M., Phys. Rev. Lett., 1996, vol. 77, p. 3865.

    Article  CAS  Google Scholar 

  23. Laikov, D.N., Kvantovo-khimicheskaya programma Priroda (v. 2006.08.20), Moscow MGU, 2006.

    Google Scholar 

  24. Gaussian 09 (Revision D.01), Gaussian Inc., Wallingford CT, 2013.

  25. Cossi, M., Rega, N., Scalmani, G., and Barone, V., J. Comp. Chem., 2003, vol. 24, p. 669.

    Article  CAS  Google Scholar 

  26. Reed, A.E., Weinstock, R.B., and Weinhold, F., J. Chem. Phys., 1985, vol. 83, p. 735.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Problems of Chemical Physics, Russian Academy of Sciences, pr. Academika Semenova 1, Chernogolovka, Moscow oblast, 142432, Russia

    T. P. Mart’yanov & E. N. Ushakov

  2. Yugra State University, Khanty-Mansiisk, Russia

    L. S. Klimenko

Authors
  1. T. P. Mart’yanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. S. Klimenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. N. Ushakov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to T. P. Mart’yanov.

Additional information

Original Russian Text © T.P. Mart’yanov, L.S. Klimenko, E.N. Ushakov, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 8, pp. 1136–1146.

An erratum to this article can be found at http://dx.doi.org/10.1134/S1070428016090268.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mart’yanov, T.P., Klimenko, L.S. & Ushakov, E.N. Oligoether derivatives of 1-phenoxyanthraquinone: Synthesis, photochromism, and complex formation with metal cations. Russ J Org Chem 52, 1126–1136 (2016). https://doi.org/10.1134/S1070428016080066

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428016080066

Search

Navigation