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.
Similar content being viewed by others
References
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)].
B. S. Lukyanov and M. B. Lukyanova, Khim. Geterotsikl. Soedin., 323 (2005). [Chem. Heterocycl. Compd., 41, 281 (2005)].
V. I. Minkin, Chem. Rev., 104, 2751 (2004).
M. B. Lukyanova, V. A. Kogan, and B. S. Lukyanov, Khim. Geterotsikl. Soedin., 1733 (2007). [Chem. Heterocycl. Compd., 43, 1477 (2007)].
B. S. Lukyanov, D. E. Nivorozhkin, and V. I. Minkin, Khim. Geterotsikl. Soedin., 176 (1993). [Chem. Heterocycl. Compd., 29, 152 (1993)].
H. Duerr and H. Bouas-Laurent (editors), Photochromism. Molecules and Systems, Elsevier, Amsterdam (1990).
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).
J. P. Perdew, K. Burke, and M. Ernzerhof, Phys. Rev. Lett., 77, 3685 (1996).
V. Barone and M. Cossi, J. Phys. Chem. A, 102, 1995 (1998).
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).
N. E. Gel'man, Methods in Quantitative Organic Elemental Analysis [in Russian], Khimiya, Moscow (1987).
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)].
Author information
Authors and Affiliations
Corresponding author
Additional information
For Communication 38, see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1951-1958, December, 2013.
Rights 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
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-014-1433-3