Abstract
Solid-state photochromic indoline spiropyrans bearing a formyl group at the 6′ and 8′ positions of the 2H-chromene moiety of the molecules were characterized. The molecular structures of spiropyrans were established by single-crystal X-ray diffraction. Intermolecular interactions and voids in the crystals were investigated using the CrystalExplorer17 software package. Further studies of photochromism and mechanochromism of these spiropyrans in the crystalline state are shown to be promising.
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B. S. Lukyanov, M. B. Lukyanova, Chem. Heterocycl. Compd. (Engl. Transl.), 2005, 41, 281; DOI: https://doi.org/10.1007/s10593-005-0148-x.
W. Szymanski, J. M. Beierle, H. A. Kistemaker, W. A. Velema, B. L. Feringa, Chem. Rev., 2013, 113, 6114; DOI: https://doi.org/10.1021/cr300179f.
H. Bouas-Laurent, H. Dürr, Pure Appl. Chem., 2001, 73, 639; DOI: https://doi.org/10.1351/pac200173040639.
A. D. Pugachev, E. L. Mukhanov, I. V. Ozhogin, A. S. Kozlenko, A. V. Metelitsa, B. S. Lukyanov, Chem. Heterocycl. Compd. (Engl. Transl.), 2021, 57, 122; DOI: https://doi.org/10.1007/s10593-021-02881-y.
V. I. Minkin, Russ. Chem. Rev., 2013, 82, 1; DOI: https://doi.org/10.1070/RC2013v082n01ABEH004336.
I. V. Ozhogin, P. V. Zolotukhin, V. V. Tkachev, A. D. Pugachev, A. S. Kozlenko, A. A. Belanova, S. M. Aldoshin, B. S. Lukyanov, Russ. Chem. Bull., 2021, 70, 1388; DOI: https://doi.org/10.1007/s11172-021-3228-x.
R. Klajn, Chem. Soc. Rev., 2014, 43, 148; DOI: https://doi.org/10.1039/C3CS60181A.
A. R. Tuktarov, R. B. Salikhov, A. A. Khuzin, I. N. Safargalin, I. N. Mullagaliev, O. V. Venidiktova, T. M. Valova, V. A. Barachevsky, U. M. Dzhemilev, Mendeleev Commun., 2019, 29, 160; DOI: https://doi.org/10.1016/j.mencom.2019.03.014.
A. Abdollahi, H. Roghani-Mamaqani, B. Razavi, Prog. Polym. Sci., 2019, 98, 101149; DOI: https://doi.org/10.1016/j.progpolymsci.2019.101149.
W. Qiu, P. A. Gurr, G. da Silva, G. G. Qiao, Polym. Chem., 2019, 10, 1650; DOI: https://doi.org/10.1039/c9py00017h.
Y. Fang, W. Dehaen, Coord. Chem. Rev., 2021, 427, 213524; DOI: https://doi.org/10.1016/j.ccr.2020.213524.
O. G. Nikolaeva, O. Yu. Karlutova, K. S. Tikhomirova, Yu. V. Revinskii, I. V. Dorogan, A. D. Dubonosov, V. A. Bren, A. V. Metelitsa, V. I. Minkin, Russ. Chem. Bull., 2019, 68, 1223; DOI: https://doi.org/10.1007/s11172-019-2545-9.
Y. Hong, P. Zhang, H. Wang, M. Yu, Y. Gao, J. Chen, Sens. Actuators B Chem., 2018, 272, 340; DOI: https://doi.org/10.1016/j.snb.2018.05.175.
N. Xie, K. Feng, B. Chen, M. Zhao, S. Peng, L. P. Zhang, C. H. Tung, L. Z. Wu, J. Mater. Chem. B, 2014, 2, 502; DOI: https://doi.org/10.1039/C3TB21251C.
P. Q. Nhien, W. L. Chou, T. T. K. Cuc, T. M. Khang, C. H. Wu, N. Thirumalaivasan, B. T. B. Hue, J. I. Wu, S. P. Wu, H. C. Lin, ACS Appl. Mater. Interfaces, 2020, 12, 10959; DOI: https://doi.org/10.1021/acsami.9b21970.
M. Regehly, Y. Garmshausen, M. Reuter, N. F. König, E. Israel, D. P. Kelly, C. Y. Chou, K. Koch, B. Asfari, S. Hecht, Nature, 2020, 588, 620; DOI: https://doi.org/10.1038/s41586-020-3029-7.
M. B. Lukyanova, V. A. Kogan, B. S. Lukyanov, Chem. Heterocycl. Compd. (Engl. Transl.), 2007, 43, 1477; DOI: https://doi.org/10.1007/s10593-007-0227-2.
M. S. Attia, M. M. H. Khalil, M. S. A. Abdel-Mottaleb, M. B. Lukyanova, Yu. A. Alekseenko, B. S. Lukyanov, Int. J. Photoenergy, 2006, 42846; DOI: https://doi.org/10.1155/IJP/2006/42846.
A. V. Laptev, N. E. Belikov, A. Y. Lukin, Y. P. Strokach, V. A. Barachevsky, M. V. Alfimov, O. V. Demina, V. I. Shvets, D. A. Skladnev, A. A. Khodonov, Russ. J. Bioorg. Chem., 2008, 34, 252; DOI: https://doi.org/10.1134/S1068162008020179.
A. V. Laptev, A. Y. Lukin, N. E. Belikov, K. V. Zvezdin, O. V. Demina, V. A. Barachevsky, S. D. Varfolomeev, A. A. Khodonov, V. I. Shvets, Russ. Chem. Bull., 2014, 63, 2026; DOI:https://doi.org/10.1007/s11172-014-0695-3.
A. Laptev, A. Lukin, N. Belikov, M. Fomin, K. Zvezdin, O. Demina, V. Barachevsky, S. Varfolomeev, V. Shvets, A. Khodonov, J. Photochem. Photobiol. A, 2011, 222, 16; DOI: https://doi.org/10.1016/j.jphotochem.2011.03.014.
R. C. Bertelson, in Organic Photochromic and Thermochromic Compounds. Topics in Applied Chemistry, Eds J. C. Crano, R. J. Guglielmetti, Springer, Boston, MA, 2002, p. 11; DOI: https://doi.org/10.1007/0-306-46911-1_2.
S. Aldoshin, in Organic Photochromic and Thermochromic Compounds. Topics in Applied Chemistry, Eds J. C. Crano, R. J. Guglielmetti, Springer, Boston, MA, 2002, p. 297; DOI: https://doi.org/10.1007/0-306-46912-X_8.
A. K. Chibisov, H. Görner, J. Phys. Chem. A, 1997, 101, 4305; DOI: https://doi.org/10.1021/jp9625691.
A. D. Pugachev, I. V. Ozhogin, M. B. Lukyanova, B. S. Lukyanov, A. S. Kozlenko, I. A. Rostovtseva, N. I. Makarova, V. V. Tkachev, S. M. Aldoshin, A. V. Metelitsa, J. Mol. Struct., 2021, 1229, 129615; DOI: https://doi.org/10.1016/j.molstruc.2020.129615.
A. S. Kozlenko, N. I. Makarova, I. V. Ozhogin, A. D. Pugachev, M. B. Lukyanova, I. A. Rostovtseva, G. S. Borodkin, N. V. Stankevich, A. V. Metelitsa, B. S. Lukyanov, Mendeleev Commun., 2021, 31, 403; DOI: https://doi.org/10.1016/j.mencom.2021.05.040.
F. L. Feris, US Pat. 3346385.
K. G. Dzhaparidze, Spirokhromeny [Spirochromenes], Metsniereba, Tbilisi, 1979, 112 pp. (in Russian).
B. S. Lukyanov, A. V. Metelitsa, N. A. Voloshin, Yu. S. Alexeenko, M. B. Lukyanova, G. T. Vasilyuk, S. A. Maskevich, E. L. Mukhanov, Int. J. Photoenergy, 2005, 7, 17; DOI: https://doi.org/10.1155/S1110662X05000036.
B. S. Lukyanov, A. V. Metelitsa, Y. S. Alekseenko, M. B. Lukyanova, E. L. Mukhanov, N. I. Borisenko, S. O. Bezugliy, Mol. Cryst. Liq. Cryst., 2005, 431, 351; DOI: https://doi.org/10.1080/15421400590946730.
H. Kargar, R. Behjatmanesh-Ardakani, M. Fallah-Mehrjardi, V. Torabi, K. S. Munawar, M. Ashfaq, M. N. Tahir, J. Mol. Struct., 2021, 1233, 130105; DOI: https://doi.org/10.1016/j.molstruc.2021.130105.
A. D. Pugachev, V. V. Tkachev, S. M. Aldoshin, N. I. Makarova, I. A. Rostovtseva, A. V. Metelitsa, N. V. Stankevich, G. V. Shilov, B. S. Lukyanov, Russ. J. Gen. Chem., 2021, 91, 1297; DOI: https://doi.org/10.1134/S1070363221070069.
C. Daisy, R. N. Asha, G. S. Kumar, E. Vadivel, N. Bhuvanesh, B. R. D. Nayagam, J. Mol. Struct., 2020, 1222, 128894; DOI: https://doi.org/10.1016/j.molstruc.2020.128894.
Y. Funasako, M. Ason, J. I. Takebayashi, M. Inokuchi, Cryst. Growth Des., 2019, 19, 7308; DOI: https://doi.org/10.1021/acs.cgd.9b01185.
Z. Wu, Q. Wang, P. Li, B. Fang, M. Yin, J. Mater. Chem., C, 2021; DOI: https://doi.org/10.1039/D1TC00974E.
V. K. Seiler, N. Tumanov, K. Robeyns, J. Wouters, B. Champagne, T. Leyssens, Crystals, 2017, 7, 84; DOI: https://doi.org/10.3390/cryst7030084.
S. Wan, Z. Ma, C. Chen, F. Li, F. Wang, X. Jia, W. Yang, M. Yin, Adv. Funct. Mater., 2016, 26, 353; DOI: https://doi.org/10.1002/adfm.201504048.
S. Bénard, P. Yu, Adv. Mater., 2000, 12, 48; DOI: https://doi.org/10.1016/S0143-7208(02)00022-0.
S. Kobatake, T. Yamada, K. Uchida, N. Kato, M. Irie, J. Am. Chem. Soc., 1999, 121, 2380; DOI: https://doi.org/10.1021/ja983717j.
A. Hryniewicka, J. W. Morzycki, S. Witkowski, J. Organomet. Chem., 2010, 695, 1265; DOI: https://doi.org/10.1016/j.jorganchem.2010.02.025.
N. E. Gel’man, E. A. Terent’eva, T. M. Shanina, L. M. Kiparenko, Metody kolichestvennogo organicheskogo elementnogo analiza [Methods of Quantitative Organic Elemental Analysis], Khimiya, Moscow, 1987, 296 pp. (in Russian).
SHELXTL v. 6.14, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin (USA), 2000.
M. J. Turner, J. J. McKinnon, S. K. Wolff, D. J. Grimwood, P. R. Spackman, D. Jayatilaka, M. A. Spackman, Crystal Explorer 17, University of Western (Australia), 2017.
B. S. Luk’yanov, L. E. Nivorozhkin, V. I. Minkin, Chem. Heterocycl. Compd. (Engl. Transl.), 1993, 29, 152; DOI: https://doi.org/10.1007/BF00531656.
B. Lukyanov, G. Vasilyuk, E. Mukhanov, L. Ageev, M. Lukyanova, Y. Alexeenko, S. Besugliy, V. Tkachev, Int. J. Photoenergy, 2009, 689450; DOI: https://doi.org/10.1155/2009/689450.
Funding
This work was financially supported by the Ministry of Science and Higher Education of the Russian Federation within the framework of the state assignment (No. 0852-2020-00-19). The X-ray diffraction study was performed by V. V. Tkachev and S. M. Aldoshin within the framework of the state assignment (registration number AAAA-A19-119092390076-7).
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Dedicated to Academician of the Russian Academy of Sciences O. M. Nefedov on the occasion of his 90th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2090–2099, November, 2021.
This paper does not contain descriptions of studies on animals or humans.
The authors declare no competing interests.
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Pugachev, A.D., Tkachev, V.V., Ozhogin, I.V. et al. Structures of spiropyrans exhibiting photochromic properties in the solid state. Russ Chem Bull 70, 2090–2099 (2021). https://doi.org/10.1007/s11172-021-3320-2
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DOI: https://doi.org/10.1007/s11172-021-3320-2