Abstract
The molecular and crystal structure of single crystalline 5’-hydroxymethyl-1,3,3,7’, 8’-pentamethylspiro[indoline-2,2’-[2H]-pyrano[3,4-b]pyridinium] iodide (1) was studied. The crystal structure is composed of cation layers separated by iodide ions and provides a sufficient volume for the phototransformation of compound 1. The spectroscopic and photochromic properties of this compound in the crystalline state were investigated. Upon irradiation with light at 270–370 nm, up to 600 layers of single crystals are subjected to photochromic transformations. The quantum yield of formation of the open form is ∼0.1, and the quantum yield of decoloration is 0.04. After ten reversible photocyclizations, the absorption of the colored form was decreased by 10%. The photochromic properties were related to the single-crystal structure.
Similar content being viewed by others
References
Photochromism. Molecules and Systems, Eds H. Dürr and H. Bouas-Laurent, Elsevier, Amsterdam, 1990.
M. Irie, Photo-Reactive Materials for Ultrahigh Density Optical Memory, Elsevier, Amsterdam, 1994.
S. Bénard, E. Rivière, P. Yu, K. Nakatani, and J. F. Delouis, Chem. Mater., 2001, 13, 159.
R. Clément, S. Decurtins, M. Gruselle, and C. Train, Monatsh. Chem., 2003, 134, 117.
K. Nakatani and J. A. Delaire, Chem. Mater., 1997, 9, 2682.
M. Suzuki, T. Asahi, K. Takahashi, and H. Masuhara, Chem. Phys. Lett., 2003, 368, 384.
S. Bénard and P. Yu, Adv. Mater., 2000, 12, 48.
S. Bénard and P. Yu, J. Chem. Soc., Chem. Commun., 2000, 65.
Yu. N. Semenov, V. A. Smirnov, S. M. Aldoshin, and B. G. Rogachev, Izv. Akad. Nauk, Ser. Khim., 2001, 2359 [Russ. Chem. Bull., Int. Ed., 2001, 50, 2471].
G. M. Sheldrick, SHELXL-97, Program for the Refinement of Crystal Structures, Göttingen University, Göttingen (Germany), 1993.
S. M. Aldoshin, in Organic Photochromic and Thermochromic Compounds, Eds J. C. Crano and R. J. Gugliemetti, Kluwer Academic—Plenum Publishers, New York, 1999, 2, 275.
G. V. Timofeeva, N. I. Chernikova, and P. M. Zorkii, Usp. Khim., 1980, 966 [Russ. Chem. Rev., 1980, 49 (Engl. Transl.)].
Yu. V. Zefirov and P. M. Zorkii, Zh. Strukt. Khim., 1976, 17, 994 [J. Struct. Chem. (USSR), 1976, 17 (Engl. Transl.)].
N. G. Bakhshiev, M. I. Knyazhanskii, V. I. Minkin, O. A. Osipov, and G. V. Saidov, Usp. Khim., 1969, 1644 [Russ. Chem. Rev., 1969, 39 (Engl. Transl.)].
M. Irie and K. Uchida, Bull. Chem. Soc. Jpn, 1998, 71, 985.
J. Harada, H. Uekusa, and Y. Ohashi, J. Am. Chem. Soc., 1999, 121, 5809.
Author information
Authors and Affiliations
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2050–2055, September, 2005.
Rights and permissions
About this article
Cite this article
Aldoshin, S.M., Nikonova, L.A., Smirnov, V.A. et al. Structure and photochromic properties of a single-crystalline spiro[indolinepyranopyridinium] salt. Russ Chem Bull 54, 2113–2118 (2005). https://doi.org/10.1007/s11172-006-0085-6
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/s11172-006-0085-6