Abstract
In order to obtain crystalline photochromic materials combining the advantages of photochroms in liquid and polymeric solutions (high quantum yields) and in the solid state (enhanced resistance to photodegradation) a photochromic adduct consisting of a metal-organic framework [Zn4(dmf)(ur)2(ndc)4] (ndc2– is 2,6-naphthalenedicarboxylate, ur is urotropine, dmf is N,N-dimethylformamide) and 2,3-bis-(2,5- dimethylthiophen-3-yl-cyclopent-2-en-1-one) is synthesized (compound 1). The photochemistry of the adduct is studied. Solid 2,3-diarylcyclopentenone exhibits photochromism typical of diarylethenes. Quantum yields of the adduct photocoloration and photobleaching turn out to be 1.5 and 3 times higher respectively than those for solid compound 1 and lower than those of solution 1 in acetonitrile by an order of magnitude. The number of photochemical cycles for compound 1 in the solution, the solid state, and the adduct composition is limited by the monomolecular side reaction.
Similar content being viewed by others
References
Organic Photochromic, Thermochromic Compounds, J. C. Сrano, R. J. Guglielmetti (eds.) V. 1, Plenum Press, London, NY (1999), pp. 2-9.
M. V. Alfimov, O. A. Fedorova, and S. P. Gromov, J. Photochem. Photobiol. A, 158, Nos. 2/3, 183 (2003).
E. Hadjoudis and I. M. Mavridis, Chem. Soc. Rev., 33, No. 9, 579 (2004).
K. Amimoto and T. Kawato, J. Photochem. Photobiol. C, 6, No. 4, 207 (2005).
S. Kobatake, Y. Tamada, K. Uchida, N. Kato, and M. Irie, J. Am. Chem. Soc., 121, No. 11, 2380 (1999).
M. Irie, Chem. Rev., 100, No. 5, 1685 (2000).
M. Morimoto, S. Kobatake, and M. Irie, J. Am. Chem. Soc., 125, No. 36, 11080 (2003).
K. Matsuda and M. Irie, J. Photochem. Photobiol. C, 5, No. 2, 169 (2004).
M. Irie, Proc. Jpn. Acad., Ser. B, 86, No. 5, 472 (2010).
S. Kobatake and M. Irie, Chem. Lett., 33, No. 7, 904 (2004).
Yu. E. Semenov, V. A. Smirnov, S. M. Aldoshin, and B. G. Rogachev, Russ. Chem. Bull. Int. Ed., 50, No. 12, 2471 (2001).
J. Harada, H. Uekusa, and Y. Ohashi, J. Am. Chem. Soc., 121, No. 24, 5809 (1999).
M. I. Nikolaeva, V. V. Korolev, E. A. Pritchina, E. M. Glebov, V. F. Plyusnin, A. V. Metelitsa, N. A. Voloshin, and V. I. Minkin, J. Phys. Org. Chem., 24, No. 9, 833 (2011).
S. Benard and P. Yu, Chem. Commun., No. 1, 65 (2000).
D. G. Patel, J. B. Benedict, R. A. Kopelman, and N. L. Frank, Chem. Commun., No. 17, 2208 (2005).
M. R. di Nunzio, P. L. Gentili, A. Romani, and G. Favaro, J. Phys. Chem. C, 114, No. 14, 6123 (2010).
V. F. Plyusnin, E. M. Glebov, V. P. Grivin, V. V. Korolev, A. V. Metelitsa, N. A. Voloshin, and V. I. Minkin, Russ. Chem. Bull. Int. Ed, 60, 124 (2011).
A. Bousseksou, G. Milnar, P. Demont, and J. Menegotto, J. Mater. Chem., 13, No. 9, 2069 (2003).
Y. Huang, Q. Pan, X. W. Dong, and Z. X. Cheng, Mater. Chem. Phys., 97, Nos. 2/3, 431 (2006).
T. He and J. Yao, Prog. Mater. Sci., 51, No. 6, 810 (2006).
M.-S. Wang, G. Xu, Z.-J. Zhang, and G.-C. Guo, Chem. Commun., No. 3, 361 (2010).
R. Pardo, M. Zayat, and D. Levy, Chem. Soc. Rev., 40, No. 2, 672 (2011).
S. Kitagawa, R. Kitaura, and S. I. Noro, Angew. Chem., Int. Ed., 43, No. 18, 2334 (2004).
R. E. Morris and P. S. Wheatly, Angew. Chem. Int. Ed., 47, No. 27, 4966 (2008).
M. P. Yutkin, D. N. Dybtsev, and V. P. Fedin, Russ. Chem. Rev., 80, No. 11, 1009 (2011).
N. Yanai, T. Uemura, M. Inoue, R. Matsuda, T. Fukushima, M. Tsujimoto, S. Isoda, and S. Kitagawa, J. Am. Chem. Soc., 134, No. 10, 4501 (2012).
J. Park, D. Yuan, K. T. Pham, J.-R. Li, A. Yakovenko, and H.-C. Zhou, J. Am. Chem. Soc., 134, No. 1, 99 (2012).
D. Hermann, H. Emerich, R. Lepski, D. Schaniel, and U. Ruschewitz, Inorg. Chem., 52, No. 5, 2744 (2013).
I. M. Walton, J. M. Cox, J. A. Coppin, C. M. Linderman, D. G. Patel, and J. B. Benedict, Chem. Commun., No. 49, 8012 (2013).
V. V. Semionova, E. M. Glebov, V. V. Korolev, S. A. Sapchenko, D. G. Samsonenko, and V. P. Fedin, Inorg. Chim. Acta, 409B, 342 (2014).
S. A. Sapchenko, D. G. Samsonenko, D. N. Dybtsev, M. S. Melgunov, and V. P. Fedin, Dalton Trans., 40, No. 10, 2196 (2011).
H. Bouas-Laurent and H. Durr, Pure Appl. Chem., 73, No. 4, 639 (2001).
M. M. Krayushkin, V. Z. Shirinian, L. I. Belen′kii, A. Yu. Shadronov, A. Y. Martynkin, and B. M. Uzhinov, Mendeleev Commun., 12, No. 4, 141 (2002).
M. M. Krayushkin, V. Z. Shirinian, L. I. Belen′kii, and A. Yu. Shadronov, Russ. Chem. Bull., Int. Ed., 51, No. 8, 1515 (2002).
A. A. Shimkin, V. Z. Shirinian, D. M. Nikalin, M. M. Krayushkin, T. S. Pivina, N. A. Troitsky, L. G. Vorontsova, and Z. A. Starikova, Eur. J. Org. Chem., No. 9, 2087 (2006).
V. Z. Shirinian, S. O. Bezugliy, A. V. Metelitsa, M. M. Krayushkin, D. M. Nikalin, and V. I. Minkin, J. Photochem. Photobiol., A, 189, Nos. 2/3, 161 (2007).
V. Z. Shirinian, A. A. Shimkin, A. K. Mailian, D. V. Tsyganov, L. D. Popov, and M. M. Krayushkin, Dyes Pigm., 84, No. 1, 19 (2009).
V. Z. Shirinian, A. A. Shimkin, D. V. Lonshakov, A. G. Lvov, and M. M. Krayushkin, J. Photochem. Photobiol. A, 233, 1 (2012).
D. V. Lonshakov, V. Z. Shirinian, A. G. Lvov, B. V. Nabatov, and M. M. Krayushkin, Dyes Pigm., 97, No. 2, 311 (2013).
V. Z. Shirinian, A. G. Lvov, M. M. Krayushkin, E. D. Lubuzh, and B. V. Nabatov, J. Org. Chem., 79, No. 8, 3440 (2014).
V. V. Semoinova, E. M. Glebov, A. B. Smolentsev, V. V. Korolev, V. P. Grivin, V. F. Plyusnin, and V. Z. Shirinian, Kinet. Catal., 56, No. 3, 316 (2015).
S. A. Sapchenko, D. G. Samsonenko, D. N. Dybtsev, and V. P. Fedin, Inorg. Chem., 52, No. 17, 9702 (2013).
D. Mendive-Tapia, A. Perrier, M. Bearpark, M. A. Robb, B. Lasorne, and D. Jacquemin, Phys. Chem. Chem. Phys., 16, No. 34, 18463 (2014).
M. Irie, T. Lifka, K. Uchida, S. Kobatake, and Yu. Shindo, Chem. Commun., No. 8, 747 (1999).
K. Higashiguchi, K. Matsuda, T. Yamada, T. Kawai, and M. Irie, Chem. Lett., 29, No. 12, 1358 (2000).
K. Shibata, K. Muto, S. Kobatake, and M. Irie, J. Phys. Chem. A, 106, No. 1, 209 (2002).
S. Kobatake, K. Uchida, E. Tsuchida, and M. Irie, Chem. Commun., No. 23, 2804 (2002).
M. Morimoto and M. Irie, Chem. Commun., No. 31, 3895 (2005).
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © 2016 V. V. Semionova1, V. V. Korolev, E. M. Glebov, V. Z. Shirinyan, and S. A. Sapchenko.
Translated from Zhurnal Strukturnoi Khimii, Vol. 57, No. 6, pp. 1279-1287, July-August, 2016.
Rights and permissions
About this article
Cite this article
Semionova, V.V., Korolev, V.V., Glebov, E.M. et al. Photochromic properties of polycrystals: 2,3-diarylcyclopentenone and its adduct with a metal-organic coordination polymer. J Struct Chem 57, 1216–1224 (2016). https://doi.org/10.1134/S0022476616060238
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0022476616060238