Advertisement

Chemistry of Heterocyclic Compounds

, Volume 50, Issue 3, pp 379–388 | Cite as

5-[4-(N,N-Dimethylamino)Phenyl]-2-(4-Pyridyl)-1,3-Oxazole as a Fluorescent Probe for Monitoring Microheterogeneous Media

  • O. O. Borodin
  • R. Yu. Il’yashenko
  • A. O. DoroshenkoEmail author
Article

The N,N-dimethylamino-γ-pyridine analog of 2,5-diaryl-1,3-oxazole has been synthesized. Quantum-chemical modeling was carried out for the electronic absorption spectra and the effect of hydrogen bonding between the pyridine nitrogen atom and the water molecule on these spectra. The calculation results were compared with the experimental data for the solvent effect on the spectra of this compound. The feasibility of practical application of this derivative as a fluorescent probe was tested for determining the critical micelle concentration in aqueous solutions of nonionic, zwitterionic, cationic, and anionic surfactants.

Keywords

2,5-diaryl-1,3-oxazole derivatives Bader's AIM theory critical micelle concentration ESS analysis of electronic excitations fluorescent probe quantum-chemical calculations solvatochromism 

References

  1. 1.
    Yu. A. Vladimirov and G. E. Dobretsov, Fluorescence Analysis of Biological Membranes [in Russian], Nauka, Moscow (1986), p. 9.Google Scholar
  2. 2.
    W. T. Mason (editor), Fluorescent and Luminescent Probes for Biological Activity, Academic Press, San Diego (1993), p. 17.Google Scholar
  3. 3.
    J. R. Lakowicz, Principles of Fluorescence Spectroscopy, 3rd ed., Springer, New York (2006), p. 63.CrossRefGoogle Scholar
  4. 4.
    Molecular Probes Handbook. A Guide to Fluorescent Probes and Labeling Technologies, 11th ed., Molecular Probes® (2010), p. 1.Google Scholar
  5. 5.
    B. M. Krasovitskii and B. M. Bolotin, Organic Luminophores [in Russian], Khimiya, Moscow (1984), p. 71.Google Scholar
  6. 6.
    F. N. Hayes, B. S. Rogers, and D. G. Ott, J. Am. Chem. Soc., 77, 1850 (1955).CrossRefGoogle Scholar
  7. 7.
    D. G. Ott, F. N. Hayes, and V. N. Kerr, J. Am. Chem. Soc., 78, 1941 (1956).CrossRefGoogle Scholar
  8. 8.
    R. Yu. Il'yashenko, E. S. Roshchina, and A. O. Doroshenko, Vestn. Kharkovsk. Nats. Univ., 932, 9 (2010).Google Scholar
  9. 9.
  10. 10.
  11. 11.
    A. D. Becke, J. Chem. Phys., 98, 5648 (1993).CrossRefGoogle Scholar
  12. 12.
    D. E. Woon and T. H. Dunning, Jr., J. Chem. Phys., 98, 1358 (1993).CrossRefGoogle Scholar
  13. 13.
    R. F. W. Bader, Acc. Chem. Res., 18, 9 (1985).CrossRefGoogle Scholar
  14. 14.
    R. F. W. Bader, Chem. Rev., 91, 7314 (1991).CrossRefGoogle Scholar
  15. 15.
    R. F. W. Bader, J. Phys. Chem. A, 102, 7314 (1998).CrossRefGoogle Scholar
  16. 16.
    A. V. Luzanov and O. A. Zhikol, Int. J. Quantum Chem., 110, 902 (2008).Google Scholar
  17. 17.
    E. Espinosa, E. Molins, and C. Lecomte, Chem. Phys. Lett., 285, 170 (1998).CrossRefGoogle Scholar
  18. 18.
    A. V. Luzanov, Usp. Khim., 64, 2086 (1980).Google Scholar
  19. 19.
    W. Rettig, Angew. Chem., Int. Ed. Engl., 25, 971 (1986)CrossRefGoogle Scholar
  20. 20.
    E. Lippert, W. Rettig, V. Bonacic-Koutecky, F. Heisel, and J. A. Miehe, Adv. Chem. Phys., 68, 1 (1987).Google Scholar
  21. 21.
    A. O. Doroshenko and V. G. Pivovarenko, J. Photochem. Photobiol., A, 156, 55 (2003).Google Scholar
  22. 22.
    C. Reichardt, Chem. Rev., 94, 2319 (1994).CrossRefGoogle Scholar
  23. 23.
    S. B. Savvin, R. K. Chernova, and S. N. Shtykov, Surfactants [in Russian], Nauka, Moscow (1991).Google Scholar
  24. 24.
    V. S. Bel'skii, Izv. Akad. Nauk, Ser. Khim., 248 (2000) [Russ. Chem. Bull., 49, 251 (2000)].Google Scholar
  25. 25.
    N. O. Mchedlov-Petrosyan, L. P. Loginova, and V. N. Kleshchevnikova, Zh. Fiz. Khim., 67, 1649 (1993).Google Scholar
  26. 26.
    N. O. Mchedlov-Petrosyan, A. V. Plichko, and A. S. Shumakher, Khim. Fiz., 15, 105 (1996).Google Scholar
  27. 27.
    N. Schenfeld, Ethylene Oxide Surfactants [Russian translation], Khimiya, Moscow (1982), p. 331.Google Scholar
  28. 28.
    N. A. Vodolazkaya, P. V. Shakhova, and N. O. Mchedlov-Petrossyan, Zh. Obshch. Khim., 79, 1081 (2009).Google Scholar
  29. 29.
    A. A. Abramzon, Surfactants: Properties and Applications [in Russian], Khimiya, Leningrad (1981), p. 35.Google Scholar
  30. 30.
    W. H. Melhuish, J. Res. Natl. Bur. Stand., Sect. A, 76A, 547 (1972)CrossRefGoogle Scholar
  31. 31.
    V. V. Aleksandrov, Acidity of Nonaqueous Solutions [in Russian], Vishcha Shkola, Kharkov (1981), p. 78.Google Scholar
  32. 32.
    M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, V. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, Gaussian 09, B.01, Gaussian Inc., Wallingford (2010)Google Scholar
  33. 33.
    E. J. Bylaska, W. A. de Jong, N. Govind, K. Kowalski, T. P. Straatsma, M. Valiev, D. Wang, E. Apra, T. L. Windus, J. Hammond, P. Nichols, S. Hirata, M. T. Hackler, Y. Zhao, P.-D. Fan, R. J. Harrison, M. Dupuis, D. M. A. Smith, J. Nieplocha, V. Tipparaju, M. Krishman, Q. Wu, T. Van Voorhis, A. A. Auer, M. Nooijen, E. Brown, G. Cisneros, G. I. Fann, H. Fruchtl, J. Garza, K. Hirao, R. Kendall, J. A. Nichols, K. Tsemekhman, K. Wolinski, J. Anchell, D. Bernholdt, P. Borowski, T. Clark, D. Clerc, H. Dachnel, M. Deegan, K. Dyall, D. Elwood, E. Glendening, M. Gutowski, A. Hess, J. Jaffe, B. Johnson, J. Ju, R. Kobayashi, R. Kutteh, Z. Lin, R. Littlefield, X. Long, B. Meng, T. Nakajima, S. Niu, L. Pollack, M. Rosing, G. Sandrone, M. Stave, H. Taylor, G. Thomas, J. van Lenthe, A. Wong, and Z. Zhang, NWChem. A Computational Chemistry Package for Parallel Computers, Version 5.1, Pacific Northwest National Laboratory, Richland, Washington (2007)Google Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • O. O. Borodin
    • 1
  • R. Yu. Il’yashenko
    • 1
  • A. O. Doroshenko
    • 1
    Email author
  1. 1.V. N. Karazin Kharkiv National UniversityKharkivUkraine

Personalised recommendations