Conclusions
-
1.
We have measured the energy barriers to conversion of the colorless form of five indolinospiropyrans with different 8′-substituents.
-
2.
We have measured the dependence of the angle between the oscillators of the electronic transitions of the colored form of the spiropyrans on the donor-acceptor properties of these substituents.
-
3.
The introduction of substituents into the pyran fragment of the spiropyran molecule controls the pathway for the color reaction and the equilibrium among the stereoisomers of the colored form.
Similar content being viewed by others
Literature cited
V. D. Ermakova, V. D. Arsenov, M. I. Cherkashin, and P. P. Kisilitsa, Izv. Akad. Nauk SSSR, Ser. Khim., 452 (1975).
J. B. Flannery, Jr., J. Am. Chem. Soc.,90, 5660 (1968).
V. S. Marevtsev, V. D. Ermakova, S. I. Beshenko, V. A. Linskii, A. T. Gradyushko, and M. I. Cherkashin, Izv. Akad. Nauk SSSR, Ser. Khim., 94 (1980).
I. Ya. Pavlenishvili, Dissertation, Tbilisi (1970).
S. Toppet, W. Quintens, and S. Smets, Tetrahedron,31, 1957 (1975).
S. J. Brois, Trans, New York Acad. Sci.,31, 931 (1969).
T. H. Kessler and D. Lebfriz, Tetrahedron Lett., 4289 (1970).
M. S. Gutowsky and C. H. Holm, J. Chem. Phys.,25, 1228 (1956).
J. G. Calvert and J. N. Pitts, Photochemistry, Wiley, New York (1966).
P. P. Feofilov, Polarized Luminescence of Atoms, Molecules, and Crystals [in Russian], Izd. Fiz.-Mat. Lit (1959).
A. Yu. Kryukov, V. D. Ermakova, A. V. Vannikov, S. I. Beshenko, E. I. Merkulov, A. F. Lunin, and M. I. Cherkashin, Vysokomol. Soedin.,19, 1022 (1977).
E. Berman, R. E. Fox, and F. D. Thomson, J. Am. Chem. Soc.,81, 5605 (1959).
A. I. Kiprianov, Usp. Khim.,29, 1336 (1960).
R. Heiligmann-Rim, Y. Hirschberg, and E. Fisher, J. Phys. Chem.,66, 2465 (1962).
A. Yu. Kryukov, A. V. Vannikov, S. I. Beshenko, V. D. Ermakova, A. F. Lunin, and M. I. Cherkashin, Izv. Akad. Nauk SSSR, Ser. Khim., 323 (1978).
C. D. Johnson, The Hammett Equation, Cambridge University Press, Cambridge (1973).
C. A. Heller, D. A. Fiue, and R. A. Henery, J. Phys. Chem.,65, 1908 (1961).
R. Gautron, Doctoral Thesis, Univ. Strasbourg (1967).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2272–2278, October, 1980.
Rights and permissions
About this article
Cite this article
Marevtsev, V.S., Zaichenko, N.L., Ermakova, V.D. et al. Effect of electron-donating and electron-accepting substituents on photo- and thermochromic properties of indolinospiropyrans. Russ Chem Bull 29, 1591–1596 (1980). https://doi.org/10.1007/BF00951220
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00951220