Abstract
A new 1-benzyl-3,3,5′,6′-tetramethylspiro[indoline-2,2′-[2H]pyrano[3,2-b]pyridinium] iodide, photochromic in the crystal state, was obtained. X-ray diffraction analysis was used for determination of crystal structures of the salt, its hydrate, and a neutral precursor. It was found that a replacement of the substituent in the indoline fragment leads to a considerable change in the crystal structure of both the neutral spiropyran and the salts as compared to the analogs studied earlier. Effects of crystal structure on photochromic properties were studied.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
O. Sato, J. Tao, Y.-Z. Zhang, Angew. Chem., Int. Ed., 2007, 46, 2152.
Y. Einaga, J. Photochem. Photobiol. C: Photochem. Rev., 2006, 7, 69.
S. M. Aldoshn, Izv. Akad. Nauk, Ser. Khim., 2008, 704 [Russ. Chem. Bull., Int. Ed.], 2008, 57, 718.
W. Fujita, K. Awaga, T. Yokoyama, Appl. Clay Sci., 1999, 15, 281.
H. Shimizu, M. Okubo, A. Nakamoto, M. Enomoto, N. Kojima, Inorg. Chem., 2006, 45, 10240.
S. Bénard, E. Rivière, P. Yu, K. Nakatani, J. F. Delouis, Chem. Mater., 2001, 13, 159.
S. M. Aldoshin, N. A. Sanina, V. I. Minkin, N. A. Voloshin, V. N. Ikorskii, V. I. Ovcharenko, V. A. Smirnov, N. K. Nagaeva, J. Mol. Struct., 2007, 826, 69.
S. M. Aldoshin, N. A. Sanina, V. A. Nadtochenko, E. A. Yurieva, V. I. Minkin, N. A. Voloshin, V. N. Ikorskii, V. I. Ovcharenko, Izv. Akad. Nauk, Ser. Khim., 2007, 1055 [Russ. Chem. Bull., Int. Ed., 2007, 56, 1095].
I. Kashima, M. Okubo, Y. Ono, M. Itoi, N. Kida, M. Hikita, M. Enomoto, N. Kojima, Synth. Met., 2005, 155, 703.
N. Kida, M. Hikita, I. Kashima, M. Okubo, M. Itoi, M. Enomoto, K. Kato, M. Takata, N. Kojima, J. Am. Chem. Soc., 2009, 131, 212.
N. Kida, M. Hikita, I. Kashima, M. Enomoto, M. Itoi, N. Kojima, Polyhedron, 2009, 28, 1694.
S. Bénard, A. Léaustic, E. Rivière, P. Yu, R. Clément, Chem. Mater., 2001, 13, 3709.
M. Okubo, M. Enomoto, N. Kojima, Synth. Met., 2005, 152, 461.
S. Bénard, P. Yu, Adv. Mater., 2000, 12, 48.
S. M. Aldoshin, L. A. Nikonova, V. A. Smirnov, G. V. Shilov, N. K. Nagaeva, J. Mol. Struct., 2005, 750, 158.
S. M. Aldoshin, L. A. Nikonova, V. A. Smirnov, G. V. Shilov, N. K. Nagaeva, Izv. Akad. Nauk, Ser. Khim., 2005, 2050 [Russ. Chem. Bull., Int. Ed., 2005, 54, 2113].
S. M. Aldoshin, L. A. Nikonova, G. V. Shilov, E. A. Bikanina, N. K. Artemova, V. A. Smirnov, J. Mol. Struct., 2006, 794, 103.
V. V. Tkachev, S. M. Aldoshin, N. A. Sanina, B. S. Luk’yanov, V. I. Minkin, A. N. Utenyshev, K. N. Khalanskii, Yu. S. Alekseenko, Khim. Geterotsikl. Soedin., 2007, 690 [Chem. Heterocycl. Compd. (Engl. Transl.), 2007, 43, 576].
P. Naumov, P. Yu, K. Sakurai, J. Phys. Chem. A, 2008, 112, 5810.
N. Clauson-Kaas, M. Meister, Acta Chem. Scand., 1967, 21, 1104.
C. D. Weis, J. Heterocycl. Chem., 1978, 15, 29.
C. H. Tilford, J. Med. Chem., 1971, 14, 1020.
G. M. Sheldrick, SHELXTL v. 6.14, Structure Determination Software Suite, Bruker AXS, Madison (Wisconsin, USA), 2000.
F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, R. Taylor, J. Chem. Soc., Perkin Trans. 2, 1987, S1.
G. V. Timofeeva, N. Yu. Chernikova, P. M. Zorkii, Usp. Khim., 1980, 49, 966 [Russ. Chem. Rev. (Engl. Transl.), 1980, 49, 509.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1379–1385, July, 2011.
Rights and permissions
About this article
Cite this article
Yurieva, E.A., Aldoshin, S.M., Nikonova, L.A. et al. 1-Benzyl-3,3,5′,6′-tetramethylspiro[indoline-2,2′-[2H]pyrano[3,2-b]-pyridinium] iodide, its hydrate, and a neutral precursor of the salts: synthesis, crystal structure, photochromic transformations in solutions and in crystals. Russ Chem Bull 60, 1401–1408 (2011). https://doi.org/10.1007/s11172-011-0210-z
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-011-0210-z