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Isomerization and changes of the properties of spiropyrans by mechanical stress: advances and outlook

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Chemistry of Heterocyclic Compounds Aims and scope

The review is devoted to mechanically sensitive indoline spiropyrans and their structural features. Recent advances in the study of their isomerization processes are considered, special attention is paid to the effect of pressure on the behavior of spiropyrans in the composition of various photochromic materials and dyes, as well as in the process of the formation of J-aggregates in Langmuir–Blodgett films.

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References

  1. Minkin, V. I. Chem. Rev. 2004, 104, 2751.

    Article  CAS  PubMed  Google Scholar 

  2. Lukyanov, B. S.; Lukyanova, M. B. Chem. Heterocycl. Compd. 2005, 41, 281. [Khim. Geterotsikl. Soedin. 2005, 323.]

  3. Zakhs, É. R.; Martynova, V. M.; Efros, L. S. Chem. Heterocycl. Compd. 1979, 15, 351. [Khim. Geterotsikl. Soedin. 1979, 435.]

  4. Vlasceanu, A.; Cacciarini, M.; Nielsen, M. B. Tetrahedron 2018, 74, 6635.

    Article  CAS  Google Scholar 

  5. Raymo, F. M.; Giordani, S. J. Am. Chem. Soc. 2001, 123, 4651.

    Article  CAS  PubMed  Google Scholar 

  6. Wojtyk, J. T. C.; Wasey, A.; Xiao, N.-N.; Kazmaier, P. M.; Hoz, S.; Yu, C.; Lemieux, R. P.; Buncel, E. J. Phys. Chem. A 2007, 111, 2511.

    Article  CAS  PubMed  Google Scholar 

  7. Keum, S.-R.; Lee, K.-B.; Kazmaier, P. M.; Buncel, E. Tetrahedron Lett. 1994, 35, 1015.

    Article  CAS  Google Scholar 

  8. Cui, L.; Zhang, H.; Zhang, G.; Zhou, Y.; Fan, L.; Shi, L.; Zhang, C.; Shuang, S.; Dong, C. Spectrochim. Acta, Part A 2018, 202, 13.

    Article  CAS  Google Scholar 

  9. Remón, P.; Li, S. M.; Grøtli, M.; Pischel, U.; Andréasson, J. Chem. Commun. 2016, 52, 4659.

    Article  Google Scholar 

  10. Kortekaas, L.; Chen, J.; Jacquemin, D.; Browne, W. R. J. Phys. Chem. B 2018, 122, 6423.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  11. Marini, A.; Muñoz-Losa, A.; Biancardi, A.; Mennucci, B. J. Phys. Chem. B 2010, 114, 17128.

    Article  CAS  PubMed  Google Scholar 

  12. Xu, Z.; Li, S.; Shen, Y.; Chen, M.; Shao, X. Tetrahedron Lett. 2018, 59, 3829.

    Article  CAS  Google Scholar 

  13. Zhu, S.; Li, M.; Tang, S.; Zhang, Y.-M.; Yang, B.; Zhang, S. X.-A. Eur. J. Org. Chem. 2014, 6, 1227.

    Article  Google Scholar 

  14. Ivashenko, O.; van Herpt, J. T.; Feringa, B. L.; Rudolf, P.; Browne, W. R. J. Phys. Chem. C 2013, 117, 18567.

  15. Chernyshev, A. V.; Voloshin, N. A.; Raskita, I. M.; Metelitsa, A. V.; Minkin, V. I. J. Photochem. Photobiol., A 2006, 184, 289.

  16. Meng, X.; Chen, C.; Qi, G.; Li, X.; Wang, K.; Zou, B.; Ma, Y. ChemNanoMat 2017, 3, 569.

    Article  CAS  Google Scholar 

  17. Funasako, Y.; Takaki, A.; Inokuchi, M.; Mochida, T. Chem. Lett. 2016, 45, 1397.

    Article  CAS  Google Scholar 

  18. Wan, S.; Ma, Z.; Chen, C.; Li, F.; Wang, F.; Jia, X.; Yang, W.; Yin, M. Adv. Funct. Mater. 2016, 26, 353.

    Article  CAS  Google Scholar 

  19. Meng, X.; Qi, G.; Li, X.; Wang, Z.; Wang, K.; Zou, B.; Ma, Y. J. Mater. Chem. C. 2016, 4, 7584.

    Article  CAS  Google Scholar 

  20. Poisson, L.; Raffael, K. D.; Soep, B.; Mestdagh, J.-M.; Buntinx, G. J. Am. Chem. Soc. 2006, 128, 3169.

    Article  CAS  PubMed  Google Scholar 

  21. Markworth, P. B.; Adamson, B. D.; Coughlan, N. J. A.; Goerigk, L.; Bieske, E. J. Phys. Chem. Chem. Phys. 2015, 17, 25676.

    Article  CAS  Google Scholar 

  22. Abdel-Mottaleb, M. S. A.; Ali, S. N. Int. J. Photoenergy 2016, 6765805.

  23. Prager, S; Burghardt, I.; Dreuw, A. J. Phys. Chem. A 2014, 118, 1339.

    Article  CAS  Google Scholar 

  24. Dorogan, I. V.; Minkin V. I. Chem. Heterocycl. Compd. 2016, 52, 730. [Khim. Geterotsikl. Soedin. 2016, 52, 730.]

  25. Patel, D. G.; Paquette, M. M.; Kopelman, R. A.; Kaminsky, W.; Ferguson, M. J.; Frank, N. L. J. Am. Chem. Soc. 2010, 132, 12568.

    Article  CAS  PubMed  Google Scholar 

  26. Che, Y.; Liu, L.; Zhao, J.; Yu, Y.; Zhao, X. Dyes Pigm. 2019, 169, 105.

    Article  CAS  Google Scholar 

  27. Sonoda, Y.; Goto, M.; Ichimura, K. Photochem. Photobiol. Sci. 2018, 17, 271.

    Article  CAS  PubMed  Google Scholar 

  28. Wu, L.; Chen, R.; Luo, Z.; Wang, P. J. Mater. Sci. 2020, 55, 12826.

    Article  CAS  Google Scholar 

  29. Mohana, K.; Umadevi, S. New J. Chem. 2019, 43, 15968.

    CAS  Google Scholar 

  30. Tan, B.-H.; Yoshio, M.; Ichikawa, T.; Mukai, T.; Ohno, H.; Kato, T. Chem. Commun. 2006, 45, 4703.

    Article  Google Scholar 

  31. Hobley, J.; Malatesta, V. Phys. Chem. Chem. Phys. 2000, 2, 57.

    Article  CAS  Google Scholar 

  32. Zanoni, M.; Coleman, S.; Fraser, K. J.; Byrne, R.; Wagner, K.; Gambhir, S.; Officer, D. L.; Wallace, G. G.; Diamond, D. Phys. Chem. Chem. Phys. 2012, 14, 9112.

    Article  CAS  PubMed  Google Scholar 

  33. Eilmes, A. J. Phys. Chem. A 2013, 117, 2629.

    Article  CAS  PubMed  Google Scholar 

  34. Rogers, R. A.; Rodier, A. R.; Stanley, J. A.; Douglas, N. A.; Li, X.; Brittain, W. J. Chem. Commun. 2014, 50, 3424.

    Article  CAS  Google Scholar 

  35. Zhai, G.-H.; Yang, P.; Wu, S.-M.; Lei, Y.-B.; Dou, Y.-S. Chin. Chem. Lett. 2014, 25, 727.

    Article  CAS  Google Scholar 

  36. Buback, J.; Nuernberger, P.; Kullmann, M.; Langhojer, F.; Schmidt, R.; Würthner, F.; Brixner, T. J. Phys. Chem. A 2011, 115, 3924.

    Article  CAS  PubMed  Google Scholar 

  37. Sheng, Y.; Leszczynski, J. Struct. Chem. 2014, 25, 667.

    Article  CAS  Google Scholar 

  38. Ishikawa, H.; Uemura, N.; Saito, R.; Yoshida, Y.; Mino, T.; Kasashima, Y.; Sakamoto, M. Chem.–Eur. J. 2019, 25, 9758.

    Article  CAS  PubMed  Google Scholar 

  39. Gossweiler, G. R.; Kouznetsova, T. B.; Craig, S. L. J. Am. Chem. Soc. 2015, 137, 6148.

    Article  CAS  PubMed  Google Scholar 

  40. Brewster, D. Philos. Trans. R. Soc. London 1816, 106, 156.

    Article  Google Scholar 

  41. Xue, P.; Ding, J.; Wang, P.; Lu, R. J. Mater. Chem. C 2016, 4, 6688.

    Article  CAS  Google Scholar 

  42. Wang, L.; Wang, K.; Zou, B.; Ye, K.; Zhang, H.; Wang, Y. Adv. Mater. 2015, 27, 2918.

    Article  CAS  PubMed  Google Scholar 

  43. Zhang, Y.; Wang, K.; Zhuang, G.; Xie, Z.; Zhang, C.; Cao, F.; Pan, G.; Chen, H.; Zou, B.; Ma, Y. Chem.–Eur. J. 2015, 21, 2474.

    Google Scholar 

  44. Nagura, K.; Saito, S.; Yusa, H.; Yamawaki, H.; Fujihisa, H.; Sato, H.; Shimoikeda, Y.; Yamaguchi, S. J. Am. Chem. Soc. 2013, 135, 10322.

    Article  CAS  PubMed  Google Scholar 

  45. Meng, X.; Qi, G.; Zhang, C.; Wang, K.; Zou, B.; Ma, Y. Chem. Commun. 2015, 51, 9320.

    Article  CAS  Google Scholar 

  46. Ma, Z.; Wang, Z.; Teng, M.; Xu, Z.; Jia, X. ChemPhysChem 2015, 16, 1811.

    Article  CAS  PubMed  Google Scholar 

  47. Dong, Y.; Xu, B.; Zhang, J.; Tan, X.; Wang, L.; Chen, J.; Lv, H.; Wen, S.; Li, B.; Ye, L.; Zou, B.; Tian, W. Angew. Chem., Int. Ed. Engl. 2012, 51, 10782.

  48. Abdollahi, A.; Roghani-Mamaqani, H.; Razavi, B. Prog. Polym. Sci. 2019, 98, 101149.

    Article  CAS  Google Scholar 

  49. Kojima, M.; Nakajima, K.; Tsuchimoto, M.; Treichel, P. M.; Kashino, S.; Yoshikawa, Y. Proc. Jpn. Acad., Ser. B 1995, 71, 175.

  50. Schönberg, A.; Ismail, A. F. A.; Asker, W. J. Chem. Soc. 1946, 442.

  51. Schönberg, A.; Mustafa, A.; Asker, W. J. Am. Chem. Soc. 1952, 74, 5640.

    Article  Google Scholar 

  52. McFadden, M. E.; Robb, M. J. J. Am. Chem. Soc. 2019, 141, 11388.

    Article  CAS  PubMed  Google Scholar 

  53. Sun, H.; Sun, W.-H.; Jiang, Y.; Wei, J.-H.; Zhao, Y.; Zhang, R.; Ni, Z.-H. Dyes Pigm. 2020, 173, 107938.

    Article  CAS  Google Scholar 

  54. Pucci, A. Sensors 2019, 19, 4969.

    Article  CAS  Google Scholar 

  55. Vidavsky, Y.; Yang, S. J.; Abel, B. A.; Agami, I.; Diesendruck, C. E.; Coates, G. W.; Silberstein, M. N. J. Am. Chem. Soc. 2019, 141, 10060.

    Article  CAS  PubMed  Google Scholar 

  56. Qiu, W.; Gurr, P. A.; da Silva, G.; Qiao, G. G. Polym. Chem. 2019, 10, 1650.

  57. Kosuge, T.; Zhu, X.; Lau, V. M.; Aoki, D.; Martinez, T. J.; Moore, J. S.; Otsuka, H. J. Am. Chem. Soc. 2019, 141, 1898.

    Article  CAS  PubMed  Google Scholar 

  58. Ma, Z.; Meng, X.; Ji, Y.; Li, A.; Qi, G.; Xu, W.; Zou, B.; Ma, Y., Kuang, G.-C.; Jia, X. Dyes Pigm. 2019, 162, 136.

    Article  CAS  Google Scholar 

  59. Fu, Z; Wang, K.; Zou, B. Chin. Chem. Lett. 2019, 30, 1883.

    Article  CAS  Google Scholar 

  60. Liu, L.; Su, X.; Yu, Q.; Guo, H.; Wang, K.; Yu, B.; Li, M.; Zou, B.; Liu, Y.; Zhang, S. X.-A. J. Phys. Chem. C 2019, 123, 25366.

    Article  CAS  Google Scholar 

  61. Li, M.; Zhang, Q.; Zhu, S. Polymer. 2016, 99, 521.

    Article  Google Scholar 

  62. Xia, Z.; Alphonse, V. D.; Trigg, D. B.; Harrigan, T. P.; Paulson, J. M.; Luong, Q. T.; Lloyd, E. P.; Barbee, M. H.; Craig, S. L. Molecules 2019, 24, 542.

    Article  PubMed Central  Google Scholar 

  63. Zhang, H.; Chen, Y.; Lin, Y.; Fang, X.; Xu, Y.; Ruan, Y.; Weng, W. Macromolecules 2014, 47, 6783.

    Article  CAS  Google Scholar 

  64. Kim, T. A.; Robb, M. J.; Moore, J. S.; White, S. R.; Sottos, N. R. Macromolecules 2018, 51, 9177

    Article  CAS  Google Scholar 

  65. Li, M.; Zhang, Q.; Zhou, Y.-N.; Zhu, S. Prog. Polym. Sci. 2018, 79, 26.

    Article  CAS  Google Scholar 

  66. Taran, M. N.; Langer, K.; Koch-Müller, M. Phys. Chem. Miner. 2008, 35, 175.

    Article  CAS  Google Scholar 

  67. Jarrige, I.; Yamaoka, H.; Rueff, J.-P.; Lin, J.-F.; Taguchi, M.; Hiraoka, N.; Ishii, H.; Tsuei, K.D.; Imura, K.; Matsumura, T.; Ochiai, A.; Suzuki, H. S.; Kotani, A. Phys. Rev. B 2013, 87, 115107.

    Article  Google Scholar 

  68. Sousanis, A.; Smet, P. F.; Detavernier, C.; Poelman, D. 2016 IEEE Nanotechnology Materials and Devices Conference (NMDC). DOI: https://doi.org/10.1109/NMDC.2016.7777086.

  69. Hickey, C. F.; Gibson, U. J. J. Appl. Phys. 1987, 62, 3912.

    Article  CAS  Google Scholar 

  70. Mitchell, D. J.; Drickamer, H. G.; Schuster, G. B. J. Am. Chem. Soc. 1977, 99, 7489.

    Article  CAS  Google Scholar 

  71. Okamoto, M.; Hirayama, S.; Steer, R. P. Can. J. Chem. 2007, 85, 432.

    Article  CAS  Google Scholar 

  72. Hirayama, S.; Steer, R. P. J. Chem. Educ. 2008, 85, 317.

    Article  CAS  Google Scholar 

  73. Renge, I. J. Phys. Chem. A 2000, 104, 7452.

    Article  CAS  Google Scholar 

  74. Renge, I. J. Phys. Chem. A 2001, 105, 9094.

    Article  CAS  Google Scholar 

  75. Renge, I. J. Phys. Chem. A 2000, 104, 3869.

    Article  CAS  Google Scholar 

  76. Seltzer, R. Chem. Eng. News 1991, 69, 29.

    Article  Google Scholar 

  77. Kimura, F.; Rodriguez, M.; McCann, J.; Carlson, B.; Dabiri, D.; Khalil, G. E.; Callis, J.B.; Xia, Y.; Gouterman, M. Rev. Sci. Instrum. 2008, 79, 074102.

    Article  PubMed  Google Scholar 

  78. Okamoto, B. Y.; Drickamer, H. G. J. Chem. Phys. 1974, 61, 2870.

    Article  CAS  Google Scholar 

  79. Renge, I. J. Phys. Chem. B 2004, 108, 10596.

    Article  CAS  Google Scholar 

  80. Zollfrank, J.; Friedrich, J. J. Phys. Chem. 1992, 96, 7887.

    Article  CAS  Google Scholar 

  81. Tomotsune, S.; Sekiya, T. Eur. Phys. J. B 2013, 86, 218.

    Article  Google Scholar 

  82. Asano, T.; Okada, T.; Shinkai, S.; Shigematsu, K.; Kusano, Y.; Manabe, O. J. Am. Chem. Soc. 1981, 103, 5161.

    Article  CAS  Google Scholar 

  83. Asano, T.; Okada, T. J. Org. Chem. 1984, 49, 4387.

    Article  CAS  Google Scholar 

  84. Sueishi, Y.; Ohcho, M.; Yamamoto, S.; Nishimura, N. Bull. Chem. Soc. Jpn. 1986, 59, 3666.

    Article  CAS  Google Scholar 

  85. Nishimura, N.; Miyake, J. I.; Sueishi, Y. Bull. Chem. Soc. Jpn. 1989, 62, 1777.

    Article  CAS  Google Scholar 

  86. Coughlan, N. J. A.; Wallace, C. M.; Adamson, B. D.; Bieske, E. J. J. Phys. Chem. A 2016, 120, 6557.

    Article  CAS  PubMed  Google Scholar 

  87. Scholz, M. S.; Bull, J. N.; Coughlan, N. J. A.; Carrascosa, E.; Adamson, B. D.; Bieske, E. J. J. Phys. Chem. A 2017, 121, 6413.

    Article  CAS  PubMed  Google Scholar 

  88. Petek, H.; Yoshihara, K.; Fujiwara, Y.; Frey, J. G. J. Opt. Soc. Am. B 1990, 7, 1540.

    Article  CAS  Google Scholar 

  89. Adamson, B. D.; Coughlan, N. J. A.; Continetti, R. E.; Bieske, E. J. Phys. Chem. Chem. Phys. 2013, 15, 9540.

    Article  CAS  Google Scholar 

  90. Yoshida, T.; Morinaka, A.; Funakoshi, N. Thin Solid Films 1988, 162, 343.

    Article  CAS  Google Scholar 

  91. Matsumoto, K.; Shinohara, T.; Koshiba, Y.; Ueda, Y.; Ji, Z. Mol. Cryst. Liq. Cryst. 2006, 445, 17.

    Article  CAS  Google Scholar 

  92. Ivakhnenko, D. A.; Shokurov, A. V.; Lyubimova, G. V.; Zaichenko, N. L.; Arslanov, V. V.; Raitman, O. A. Russ. Chem. Bull., Int. Ed. 2018, 67, 2266. [Izv. Akad. Nauk, Ser. Khim. 2018, 2266.]

  93. Das, R.; Kuehnert, M.; Kazemi, A. S.; Abdi, Y.; Schulze, A. Polymers 2019, 11, 344.

    Article  PubMed Central  Google Scholar 

  94. Kawasaki, H.; Tozawa, S.; Matani, T.; Hayashi, T.; Watanabe, S.; Shibata, H.; Matsumoto, M. J. Oleo Sci. 2014, 63, 691.

    Article  CAS  PubMed  Google Scholar 

  95. Masui, M.; Koshiba, Y.; Ueda, Y.; Ji, Z. Mol. Cryst. Liq. Cryst. 2007, 472, 123.

    Article  CAS  Google Scholar 

  96. Matsumoto, M.; Nakazawa, T.; Mallia, V. A.; Tamaoki, N.; Azumi, R.; Sakai, H.; Abe, M. J. Am. Chem. Soc. 2004, 126, 1006.

    Article  CAS  PubMed  Google Scholar 

  97. Nakazawa, T.; Azumi, R.; Sakai, H.; Abe, M.; Matsumoto, M. Langmuir 2004, 20, 5439.

    Article  CAS  PubMed  Google Scholar 

  98. Nakazawa, T.; Azumi, R.; Sakai, H.; Abe, M.; Matsumoto, M. Langmuir 2004, 20, 10583.

    Article  CAS  PubMed  Google Scholar 

  99. Yokoyama, Y.; Hara, W.; Inoue, T.; Ubukata, T.; Sakomura, M.; Tukada, H. Chem. Lett. 2005, 34, 1622.

    Article  CAS  Google Scholar 

  100. Matisova, G.; Markava, E.; Muzikante, I.; Fonavs, E.; Gerca, M. Adv. Mater. Opt. Electron. 1996, 6, 279.

    Article  CAS  Google Scholar 

  101. Li, L.; Yu, M.; Li, F. Y.; Yi, T.; Huang, C. H. Colloids Surf., A 2007, 304, 49.

  102. Zhao, W.; Quan, M.; Cao, Z.; Zhang, Y.; Wen, J.; Pan, D.; Dong, Z.; Yang, Z.; Wang, D.; Cao, H.; He, W. Colloids Surf., A 2018, 554, 93.

    Article  CAS  Google Scholar 

  103. Frolova, L. A.; Rezvanova, A. A.; Lukyanov, B. S.; Sanina, N. A.; Troshin, P. A.; Aldoshin, S. M. J. Mater. Chem. C 2015, 3, 11675.

    Article  CAS  Google Scholar 

  104. Tuktarov, A. R.; Salikhov, R. B.; Khuzin, A. A.; Popod'ko, N. R.; Safargalin, I. N.; Mullagaliev, I. N.; Dzhemilev, U. M. RSC Adv. 2019, 9, 7505.

    Article  CAS  Google Scholar 

  105. Mecheri, B.; Baglioni, P.; Pieroni, O.; Caminati, G. Mater. Sci. Eng., C 2003, 23, 893.

  106. Ramirez, A. L. B.; Kean, Z. S.; Orlicki, J. A.; Champhekar, M.; Elsakr, S. M.; Krause, W. E.; Craig, S. L. Nat. Chem. 2013, 5, 757.

    Article  CAS  PubMed  Google Scholar 

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This work was supported by a grant from the Ministry of Science and Higher Education of the Russian Federation (project 0852-2020-00-19).

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  1. Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachki Ave, Rostov-on-Don, 344090, Russia

    Artem D. Pugachev, Eugene L. Mukhanov, Ilya V. Ozhogin, Anastasia S. Kozlenko, Anatoly V. Metelitsa & Boris S. Lukyanov

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  1. Artem D. Pugachev
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  2. Eugene L. Mukhanov
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Correspondence to Boris S. Lukyanov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(2), 122–130

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Pugachev, A.D., Mukhanov, E.L., Ozhogin, I.V. et al. Isomerization and changes of the properties of spiropyrans by mechanical stress: advances and outlook. Chem Heterocycl Comp 57, 122–130 (2021). https://doi.org/10.1007/s10593-021-02881-y

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