Advertisement

Chemistry of Heterocyclic Compounds

, Volume 49, Issue 12, pp 1808–1814 | Cite as

Photo- and Thermochromic Spirans. 39. *Study of the Complexation of a New Crown-containing Benzoxazine Spiropyran with Metal Cations

  • M. B. Lukyanova
  • B. S. LukyanovEmail author
  • I. V. Dorogan
  • S. O. Bezuglyi
  • M. S. Korobov
Article
  • 148 Downloads

A new benzoxazinone spiropyran containing a crown ether fragment have been synthesized. This compound was studied by both experimental and theoretical methods. In contrast to previously studied analogs, photoinduced coloration is not observed. By irradiating this crown-containing spiropyran, only an E-Z isomerization reaction proceeds. Complexation of the closed spiropyran form runs in a solution containing a calcium salt. A hypsochromic shift of the long-wavelength maximum in the absorption spectrum is observed.

Keywords

crown ether spiropyran chemosensor quantum-chemical calculations 

References

  1. 1.
    E. V. Solov'eva, A. V. Chernyshev, N. A. Voloshin, A. V. Metelitsa, and V. I. Minkin, Khim. Geterotsikl. Soedin., 1645 (2013). [Chem. Heterocycl. Compd., 48, 1533 (2013)].Google Scholar
  2. 2.
    B. S. Lukyanov and M. B. Lukyanova, Khim. Geterotsikl. Soedin., 323 (2005). [Chem. Heterocycl. Compd., 41, 281 (2005)].Google Scholar
  3. 3.
    V. I. Minkin, Chem. Rev., 104, 2751 (2004).CrossRefGoogle Scholar
  4. 4.
    M. B. Lukyanova, V. A. Kogan, and B. S. Lukyanov, Khim. Geterotsikl. Soedin., 1733 (2007). [Chem. Heterocycl. Compd., 43, 1477 (2007)].Google Scholar
  5. 5.
    B. S. Lukyanov, D. E. Nivorozhkin, and V. I. Minkin, Khim. Geterotsikl. Soedin., 176 (1993). [Chem. Heterocycl. Compd., 29, 152 (1993)].Google Scholar
  6. 6.
    H. Duerr and H. Bouas-Laurent (editors), Photochromism. Molecules and Systems, Elsevier, Amsterdam (1990).Google Scholar
  7. 7.
    M. V. Alfimov, A. V. Balakin, S. P. Gromov, Yu. V. Zaushitsyn, O. A. Fedorova, N. I. Koroteev, A. V. Pakulev, Yu. V. Resnyanskii, and A. P. Shkurinov, Zh. Fiz. Khim., 73, 1884 (1999).Google Scholar
  8. 8.
    J. P. Perdew, K. Burke, and M. Ernzerhof, Phys. Rev. Lett., 77, 3685 (1996).CrossRefGoogle Scholar
  9. 9.
    V. Barone and M. Cossi, J. Phys. Chem. A, 102, 1995 (1998).CrossRefGoogle Scholar
  10. 10.
    M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kita, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cro, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al. Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and J. A. Pople, Gaussian 03, Rev. C.02, Gaussian, Inc., Wallingford, CT (2004).Google Scholar
  11. 11.
    N. E. Gel'man, Methods in Quantitative Organic Elemental Analysis [in Russian], Khimiya, Moscow (1987).Google Scholar
  12. 12.
    B. S. Lukyanov, Yu. I. Ryabukhin, G. N. Dorofeenko, L. E. Nivorozhkin, and V. I. Minkin, Khim. Geterotsikl. Soedin., 161 (1978). [Chem. Heterocycl. Compd., 14, 122 (1978)].Google Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • M. B. Lukyanova
    • 1
  • B. S. Lukyanov
    • 1
    Email author
  • I. V. Dorogan
    • 3
  • S. O. Bezuglyi
    • 2
  • M. S. Korobov
    • 1
  1. 1.Scientific-Research Institute of Physical and Organic ChemistrySouthern Federal UniversityRostov-on-the-DonRussia
  2. 2.Chemical FacultySouthern Federal UniversityRostov-on-the-DonRussia
  3. 3.Southern Scientific CenterRussian Academy of SciencesRostov-on-the-DonRussia

Personalised recommendations