Skip to main content
Log in

Synthesis and spectral properties of lutetium complexes with unsymmetrical phthalocyanines and sandwich complexes based thereon containing tetraanthraquinonoporphyrazine fragments

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

Abstract

Joint condensation of 4,5-bis(4-hexadecyloxyphenoxy)phthalonitrile (A) and tetrachlorophthalonitrile (B) in boiling hexan-1-ol in the presence of lithium hexan-1-olate and subsequent reaction with LuCl3 · 6 H2O gave single-decker lutetium complexes with unsymmetrical phthalocyanines (AABB, ABAB). Reactions of the latter with 9,10-dioxo-9.10-dihydroanthraquinone-2,3-dicarbonitrile afforded mixed-ligand double-decker lutetium complexes containing tetraanthraquinonoporphyrazine as one of the ligands. Spectral properties of the synthesized complexes were studied, and all complexes were found to exhibit red fluorescence.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Berezin, B.D., Koordinatsionnye soedineniya porfirinov i ftalotsianina (Coordination Compounds of Porphyrins and Phthalocyanine), Moscow: Nauka, 1978.

    Google Scholar 

  2. Simic-Glavaski, B., Phthalocyanines: Properties and Applications, Leznoff, C.C. and Lever, A.B.P., Eds., New York: VCH, 1993, vol. 3, p. 119.

  3. Nalwa, H.S. and Shirk, J.S., Phthalocyanines: Properties and Applications, Leznoff, C.C. and Lever, A.B.P., Eds., New York: VCH, 1996, vol. 4, p. 79.

  4. Ng, D.K.P. and Jiang, J., Chem. Soc. Rev., 1997, vol. 26, p. 433.

    Article  CAS  Google Scholar 

  5. Simpson, T.R.E., Cook, M.J., Petty, M.C., Thorpe, S.C., and Russel, D.A., Analyst, 1996, vol. 121, p. 1501.

    Article  CAS  Google Scholar 

  6. Krier, A., Parr, T., Davidson, K., and Collins, R.A., Adv. Mater., 1996, vol. 6, p. 203.

    CAS  Google Scholar 

  7. Bouvet, M., Silinsh, E.A., Simon, J., Passard, M., Pauly, A., Gemmain, J.P., and Malleysson, C., Synth. Met., 1996, vol. 80, p. 25.

    Article  Google Scholar 

  8. Tomilova, L.G., Chernykh, E.V., Ioffe, N.T., and Luk’yanets, E.A., Zh. Obshch. Khim., 1983, vol. 53, p. 2594.

    CAS  Google Scholar 

  9. Balenko, V.G., Kaliya, O.G., Kirkin, A.N., Luk’yanets, E.A., Mizin, V.M., Popov, M.B., Teplyakova, N.V., Tomilova, L.G., and Chernykh, E.V., Kvant. Elektron., 1989, vol. 16, p. 615.

    CAS  Google Scholar 

  10. Lukyanets, E.A., Pukhtina, E.V., Ulanova, L.A., and Kovaleva, M.A., Appl. Radiat. Isotop., 1996, vol. 47, p. 1541.

    Article  CAS  Google Scholar 

  11. Kulinich, V.P. and Shaposhnikov, G.P., Russ. J. Gen. Chem., 2003, vol. 73, p. 794.

    Article  CAS  Google Scholar 

  12. Ceyhan, T., Yağlioğlu, G., Ünver, H., Salih, B., Erbil, M.K., Elmali, A., and Bekaroğlue, Ö., Macroheterocycles, 2008, vol. 1, p. 44.

    CAS  Google Scholar 

  13. Dubinina, T.V., Pushkarev, V.E., Trashin, S.A., Paramonova, K.V., and Tomilova, L.G., Macroheterocycles, 2012, vol. 5, p. 366.

    Article  CAS  Google Scholar 

  14. Bai, M., Bao, M., Ma, C., Arnold, D.P., Choi, M.T.M., Ng, D.K.P., and Jiang, J., J. Mater. Chem., 2003, vol. 13, p. 1333.

    Article  CAS  Google Scholar 

  15. Galanin, N.E. and Shaposhnikov, G.P., Russ. J. Org. Chem., 2012, vol. 48, p. 851.

    Article  CAS  Google Scholar 

  16. Galanin, N.E., Yakubov, L.A., and Shaposhnikov, G.P., Russ. J. Org. Chem., 2008, vol. 44, p. 921.

    Article  CAS  Google Scholar 

  17. Borisov, A.V., Maizlish, V.E., and Shaposhnikov, G.P., Russ. J. Gen. Chem., 2005, vol. 75, p. 1151.

    Article  CAS  Google Scholar 

  18. Moskalev, P.P. and Kirin, I.S., Opt. Spektrosk., 1970, vol. 29, p. 1149.

    CAS  Google Scholar 

  19. Shishkina, O.V., Maizlish, V.E., Shaposhnikov, G.P., Lyubimtsev, A.V., Smirnov, R.P., and Baran’ski, A., Russ. J. Gen. Chem., 1997, vol. 67, p. 789.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. V. Borisov.

Additional information

Original Russian Text © A.V. Borisov, M.V. Korel’chuk, E.S. Ageeva, N.E. Galanin, G.P. Shaposhnikov, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 7, pp. 1004–1010.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Borisov, A.V., Korel’chuk, M.V., Ageeva, E.S. et al. Synthesis and spectral properties of lutetium complexes with unsymmetrical phthalocyanines and sandwich complexes based thereon containing tetraanthraquinonoporphyrazine fragments. Russ J Org Chem 50, 986–992 (2014). https://doi.org/10.1134/S1070428014070094

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428014070094

Keywords

Navigation