Abstract
The results of a study of the photochromic properties of 1´-hexadecyl-3´,3´-dimethyl-6-nitro-1´,3´-dihydrospiro[chromene-2,2´-indole] (SP) are presented. The kinetic characteristics of photophysical processes occurring in acetonitrile solution of SP upon irradiation with UV light and during dark relaxation are determined. It is shown that spiropyran modified at the nitrogen atom by a long-chain hydrocarbon radical exhibits photochromic properties in the dissolved state, with the rate of the direct photocoloration exceeding the rate of dark relaxation by an order of magnitude. Comparative studies of SP photoreaction in dissolved and 2D states are carried out. The obtained results open up broad prospects for application of such photochromes in thin-film devices obtained using the Langmuir monolayer technique.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
G. Berkovic, V. Krongauz, V. Weiss, Chem. Rev., 2000, 100, 1741–1754.
V. I. Minkin, in Molecular Switches, Wiley-VCH, Weinheim, Germany, 2011, 37–80.
V. I. Minkin, Chem. Rev., 2004, 104, 2751–2776.
X. Guo, D. Zhang, G. Zhang, D. Zhu, J. Phys. Chem. B, 2004, 108, 11942–11945.
F. M. Raymo, S. Giordani, Proc. Natl. Acad. Sci., 2002, 99, 4941–4944.
F. Ghailane, Opt. Eng., 1995, 34, 480.
S. S. Xue, G. Manivannan, R. A. Lessard, Thin Solid Films, 1994, 253, 228–232.
M.-Q. Zhu, L. Zhu, J. J. Han, W. Wu, J. K. Hurst, A. D. Q. Li, J. Am. Chem. Soc., 2006, 128, 4303–4309.
V. Z. Shirinian, A. A. Shimkin, in Heterocyclic Polymethine Dyes, Springer, Berlin-Heidelberg, 2008, pp. 75–105.
I. Zakharova, V. Pimienta, V. I. Minkin, A. V. Metelitsa, J. C. Micheau, Russ. Chem. Bull., 2009, 58, 1329–1337. aaaaaa
I. Gruda, R. M. Leblanc, Can. J. Chem., 1976, 1–5.
C. J. Drummond, D. N. Furlong, J. Chem. Soc. Faraday Trans., 1990, 86, 3613–3621.
V. Z. Shirinian, V. A. Barachevsky, A. A. Shimkin, M. M. Krayushkin, A. K. Mailian, D. V. Tsyganov, O. A. Vinter, O. V. Venidiktova, Russ. Chem. Bull., 2010, 59, 828–832.
X. Song, J. Zhou, Y. Li, Y. Tang, J. Photochem. Photobiol. A Chem., 1995, 92, 99–103.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2266–2270, December, 2018.
Based on the materials of the VII International Conference on Physical Chemistry of Crown Compounds, Porphyrins, and Phthalocyanines (September 9–14, 2018, Tuapse, Russia).
Rights and permissions
About this article
Cite this article
Ivakhnenko, D.A., Shokurov, A.V., Lyubimova, G.V. et al. Photochromic transformations of amphiphilic spiropyran in acetonitrile solutions and at the air/water interface. Russ Chem Bull 67, 2266–2270 (2018). https://doi.org/10.1007/s11172-018-2368-0
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-018-2368-0