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

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.

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

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

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).

    CAS  Article  Google 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).

  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).

    Article  Google Scholar 

  9. 9.

    V. Barone and M. Cossi, J. Phys. Chem. A, 102, 1995 (1998).

    CAS  Article  Google 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).

  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 

Download references

Author information

Affiliations

Authors

Corresponding author

Correspondence to B. S. Lukyanov.

Additional information

For Communication 38, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1951-1958, December, 2013.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Lukyanova, M.B., Lukyanov, B.S., Dorogan, I.V. et al. Photo- and Thermochromic Spirans. 39. *Study of the Complexation of a New Crown-containing Benzoxazine Spiropyran with Metal Cations. Chem Heterocycl Comp 49, 1808–1814 (2014). https://doi.org/10.1007/s10593-014-1433-3

Download citation

Keywords

  • crown ether
  • spiropyran
  • chemosensor
  • quantum-chemical calculations