Chemistry of Heterocyclic Compounds

, Volume 48, Issue 2, pp 287–295 | Cite as

Synthesis and photoluminescent properties of new cationic carbazole-containing luminophores

  • A. BaranEmail author
  • A. Plotniece
  • A. Sobolev
  • B. Vigante
  • M. Gosteva
  • V. Olkhovik

The synthesis of a series of new π-conjugated amphiphilic derivatives of carbazole of the "stilbene" type, substituted with N-alkylpyridinium groups at positions 2 and 7, is described. Due to the presence of polar cationic groups and nonpolar alkyl substituents, the obtained compounds are potentially capable of acting as agents for the transportation of genetic material inside a cell, and the extended and effective conjugation chain leads to the appearance of intense photoluminescence both in solutions and in biological media, making it possible to use them as cell probes. The absorption maxima of the compounds are in the region of 422-450 nm, while the luminescence maxima are in the yellow-green region at 575-617 nm.


N-alkylpyridinium derivatives carbazole derivatives luminescent cell probes stilbenoids photoluminescence 


  1. 1.
    C.-C. Chang, I.-C. Kuo, J.-J. Lin, Y.-C. Lu, C.-T. Chen, H.-T. Back, and P.-J. Lou, and T.-C. Chang, Chem. Biodiversity, 1, 1377 (2004).CrossRefGoogle Scholar
  2. 2.
    C. Saengkhae, M. Salerno, D. Adès, A. Siove, L. Le Moyec, V. Migonney, and A. Garnier-Suillerot, Eur. J. Pharmacol., 559, 124 (2007).CrossRefGoogle Scholar
  3. 3.
    F. Tanious, D. Ding, D. Patrick, C. Bailly, R. Tidwell, and W. Wilson, Biochemistry, 39, 12091 (2000).CrossRefGoogle Scholar
  4. 4.
    C.-C. Chang, J.-Y. Wu, and T.-C. Chang, J. Chin. Chem. Soc., 50, 185 (2003).Google Scholar
  5. 5.
    F.-C. Huang, C.-C. Chang, P.-J. Lou, I.-C. Kuo, C.-W. Chien, C.-T. Chen, F.-Y. Shieh, T.-C. Chang, and J.-J. Lin, Mol. Cancer Res., 6, 955 (2008).CrossRefGoogle Scholar
  6. 6.
    J. Gu, W. Yulan, W.-Q. Chen, X.-Z. Dong, X.-M. Duan, and S. Kawata, New J. Chem., 31, 63 (2007).CrossRefGoogle Scholar
  7. 7.
    Z. Wang, V. N. Nesterov, O. Y. Borbulevych, R. D. Clark, M. Y. Antipin, and T. V. Timofeeva, Acta Crystallogr., C57, 1343 (2001).Google Scholar
  8. 8.
    J.-F. Morin, M. Leclerc, D. Ades, and A. Siove, Macromol. Rapid Commun., 26, 761 (2005).CrossRefGoogle Scholar
  9. 9.
    V. K. Olkhovik, D. A. Vasilevskii, A. A. Pap, G. V. Kalechyts, Y. V. Matveienko, A. G. Baran, N. A. Halinouski, and V. G. Petushok, ARKIVOC, ix, 69 (2008).Google Scholar
  10. 10.
    J. H. Felgner, R. Kumar, C. N. Sridhar, C. J. Wheeler, Y. J. Tsai, R. Border, P. Ramsey, M. Martin, and P. L. Felgner, J. Biol. Chem., 269, 2550 (1994).Google Scholar
  11. 11.
    A. P. Phillips, J. Am. Chem. Soc., 74, 3296 (1952).CrossRefGoogle Scholar
  12. 12.
    A. Baran, A. Plotniece, and V. Olkhovik, in: 4th International Symposium on Advances in Synthetic and Medicinal Chemistry (ASMC11), Materials of the Conference, St. Petersburg, Russia, August 21-25, 2011, p. 238.Google Scholar
  13. 13.
    S. Wróblewski, K. Trzebiatowska, B. Jędrzejewska, M. Pietrzak, R. Gawinecki, and J. Pączkowski, J. Chem. Soc., Perkin Trans. 2, 1909 (1999).Google Scholar
  14. 14.
    H. G. Kolloff, A. P. Wyss, R. E. Himelick, and F. Mantele, J. Am. Pharm. Assoc., 31, 51 (1942).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2012

Authors and Affiliations

  • A. Baran
    • 1
    Email author
  • A. Plotniece
    • 1
  • A. Sobolev
    • 1
  • B. Vigante
    • 1
  • M. Gosteva
    • 1
  • V. Olkhovik
    • 2
  1. 1.Latvian Institute of Organic SynthesisRigaLatvia
  2. 2.Institute of the Chemistry of Novel MaterialsNational Academy of Sciences of BelarusMinskBelarus

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