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Spiropyrans: molecules in motion

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Chemistry of Heterocyclic Compounds Aims and scope

This review is devoted to the features of isomerization reactions of indoline spiropyrans and the possibilities for their applications as building blocks in the design of molecular machines and ensembles capable of self-organization. Nanoscale systems functioning on the base of changes in geometric parameters and molecular dipole moment when switching between the spirocyclic and merocyanine forms have been considered. The factors that alter the system morphology may be electromagnetic irradiation or the acidity of the medium.

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References

  1. Fischer, E.; Hirshberg, Y. J. Chem. Soc. 1952, 4522.

  2. Bouas-Laurent, H.; Dürr, H. Pure Appl. Chem. 2001, 73, 639.

    Article  CAS  Google Scholar 

  3. Hirshberg, Y. J. Am. Chem. Soc. 1956, 78, 2304.

    Article  CAS  Google Scholar 

  4. Ha, J.-W.; Ha, J.-H.; Hong, J.-N.; Cho, S.-H. WO Patent 2004011964.

  5. Kinashi, K.; Miyamae, Y.; Nakamura, R.; Sakai, W.; Tsutsumi, N.; Yamane, H.; Hatsukano, G.; Ozaki, M.; Jimbo, K.; Okabed, T. Chem. Commun. 2015, 51, 11170.

    Article  CAS  Google Scholar 

  6. Kortekaas, L.; Browne, W. R. Chem. Soc. Rev. 2019, 48, 3406.

    Article  CAS  PubMed  Google Scholar 

  7. Klajn, R. Chem. Soc. Rev. 2014, 43, 148.

    Article  CAS  PubMed  Google Scholar 

  8. Minkin, V. I. Russ. Chem. Rev. 2013, 82, 1. [Usp. Khim. 2013, 82, 1.]

  9. Feringa, B. L. Angew. Chem., Int. Ed. 2017, 56, 11060.

  10. Sauvage, J.-P. Angew. Chem., Int. Ed. 2017, 56, 11080.

  11. Stoddart, J. F. Angew. Chem., Int. Ed. 2017, 56, 11094.

  12. Yang, Z.; Liu, Z.; Yuan, L. Asian J. Org. Chem. 2021, 10, 74.

    Article  CAS  Google Scholar 

  13. Velema, W. A.; Szymanski, W.; Feringa, B. L. J. Am. Chem. Soc. 2014, 136, 2178.

    Article  CAS  PubMed  Google Scholar 

  14. Jeong, M.; Park, J.; Kwon, S. Eur. J. Org. Chem. 2020, 7254.

  15. Kholmanskii, A. S.; Zubkov, A. V.; Dyumaev, K. M. Russ. Chem. Rev. 1981, 50, 305. [Usp. Khim. 1981, 50, 569.]

  16. Selvanathan, P.; Dorcet, V.; Roisnel, T.; Bernot, K.; Huang, G.; Le Guennic, B.; Norel, L.; Rigaut, S. Dalton Trans. 2018, 4139.

  17. Naumov, P.; Yu, P.; Sakurai, K. J. Phys. Chem. A 2008, 112, 5810.

    Article  CAS  PubMed  Google Scholar 

  18. Fleming, C.; Li, S.; Grøtli, M.; Andréasson, J. J. Am. Chem. Soc. 2018, 140, 14069.

    Article  CAS  PubMed  Google Scholar 

  19. 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 

  20. Minkin, V. I.; Metelitsa, A. V.; Lukyanov, B. S.; Besugliy, S. O.; Micheau, J.-C. J. Phys. Chem. A 2005, 109, 9605.

    Article  CAS  PubMed  Google Scholar 

  21. Aakeröy, C. B.; Hurley, E. P.; Desper, J.; Natali, M.; Douglawi, A.; Giordani, S. CrystEngComm 2010, 12, 1027.

    Article  Google Scholar 

  22. Hobley, J.; Malatesta, V.; Millini, R.; Montanari, L.; Parker, W. O. N. Phys. Chem. Chem. Phys. 1999, 1, 3259.

    Article  CAS  Google Scholar 

  23. Nuernberger, P.; Ruetzel, S.; Brixner, T. Angew. Chem., Int. Ed. 2015, 54, 11368.

  24. Metelitsa, A.; Chernyshev, A.; Voloshin, N.; Solov'eva, E.; Rostovtseva, I.; Dorogan, I.; Gaeva, E.; Guseva, A. Dyes Pigm. 2021, 186, 109070.

    Article  CAS  Google Scholar 

  25. Kim, D.; Zhang, Z.; Xu, K. J. Am. Chem. Soc. 2017, 139, 9447.

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  Google Scholar 

  27. Kovalenko, O.; Reguero, M. Phys. Scr. 2020, 95, 055402.

    Article  CAS  Google Scholar 

  28. Sheng, Y.; Leszczynski, J.; Garcia, A. A.; Rosario, R.; Gust, D.; Springer, J. J. Phys. Chem. B 2004, 108, 16233.

    Article  CAS  Google Scholar 

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

  30. Chibisov, A.; Görner, H. Photochem. Photobiol. A 1997, 105, 261.

    Article  CAS  Google Scholar 

  31. Breslin, V. M.; Barbour, N. A.; Dang, D.-K.; Lopez, S. A.; Garcia-Garibay, M. A. Photochem. Photobiol. Sci. 2018, 17, 741.

    Article  CAS  PubMed  Google Scholar 

  32. Liu, F.; Kurashige, Y.; Yanai, T.; Morokuma, K. J. Chem. Theory Comput. 2013, 9, 4462.

    Article  CAS  PubMed  Google Scholar 

  33. Roohi, H.; Rostami, T. J. Photochem. Photobiol. A 2020, 392, 112410.

    Article  CAS  Google Scholar 

  34. Brügner, O.; Reichenbach, T.; Sommer, M.; Walter, M. J. Phys. Chem. A 2017, 121, 2683.

    Article  PubMed  CAS  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  36. Balmond, E. I.; Tautges, B. K.; Faulkner, A. L.; Or, V. W.; Hodur, B. M.; Shaw, J. T.; Louie, A. Y. J. Org. Chem. 2016, 81, 8744.

    Article  CAS  PubMed  Google Scholar 

  37. Yurieva, E. A.; Aldoshin, S. M. Org. Photonics Photovoltaics 2015, 3, 42.

    Article  Google Scholar 

  38. Voloshin, N. A.; Bezugliy, S. O.; Solov’eva, E. V.; Metelitsa, A. V.; Minkin, V. I. Chem. Heterocycl. Compd. 2008, 44, 1229. [Khim. Geterotsikl. Soedin. 2008, 1513.]

  39. Kozlenko, A. S.; Makarova, N. I.; Ozhogin, I. V.; Pugachev, A. D.; Lukyanova, M. B.; Rostovtseva, I. A.; Borodkin, G. S.; Stankevich, N. I.; Metelitsa, A. V.; Lukyanov, B. S. Mendeleev Commun. 2021, 31, 403.

    Article  CAS  Google Scholar 

  40. Pugachev, A. D.; Lukyanova, M. B.; Lukyanov, B. S.; Ozhogin, I. V.; Kozlenko, A. S.; Rostovtseva, I. A.; Makarova, N. I.; Tkachev, V. V.; Aksenov, N. A. J. Mol. Struct. 2019, 1178, 590.

    Article  CAS  Google Scholar 

  41. Tyurin, R. V.; Lukyanov, B. S.; Chernyshev, A. V.; Malay, V. I.; Kozlenko, A. S.; Lukyanova, M. B.; Tkacheva, N. S.; Burov, O. N. Dokl. Chem. 2016, 470, 268. Dokl. Akad. Nauk 2016, 470, 297.]

  42. Toppet, S.; Quintens, W.; Smets, G. Tetrahedron 1975, 31, 1957.

    Article  CAS  Google Scholar 

  43. Schulz-Senft, M.; Gates, P. J.; Sönnichsen, F. D.; Staubitz, A. Dyes Pigm. 2017, 136, 292.

    Article  CAS  Google Scholar 

  44. Hobley, J.; Malatesta, V.; Millini, R.; Montanari, L.; O Neil Parker, W. Phys. Chem. Chem. Phys. 1999, 1, 3259.

  45. Aiken, S.; Edgar, R. J. L.; Gabbutt, C. D.; Heron, B. M.; Hobson, P. A. Dyes Pigm. 2018, 149, 92.

    Article  CAS  Google Scholar 

  46. Amos, R. D.; Kobayashi, R. Mol. Phys. 2015, 113, 1674.

    Article  CAS  Google Scholar 

  47. Mukhanov, E. L.; Alekseenko, Y. S.; Dorogan, I. V.; Tkachev, V. V.; Lukyanov, B. S.; Aldoshin, S. M.; Besugliy, S. O.; Minkin, V. I.; Utenyshev, A. N.; Ryashchin, O. N. Chem. Heterocycl. Compd. 2010, 46, 279. [Khim. Geterotsikl. Soedin. 2010, 357.]

  48. Grogan, C.; Amarandei, G.; Lawless, S.; Pedreschi, F.; Lyng, F.; Benito-Lopez, F.; Raiteri, R.; Florea, L. Sensors 2020, 20, 854.

    Article  CAS  PubMed Central  Google Scholar 

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

    Article  CAS  Google Scholar 

  50. Pugachev, A. D.; Mukhanov, E. L.; Ozhogin, I. V.; Kozlenko, A. S.; Metelitsa, A. V.; Lukyanov, B. S. Chem. Heterocyl. Compd. 2021, 57, 122. [Khim. Geterotsikl. Soedin. 2021, 57, 122.]

  51. Li, T.; He, X.; Yu, P.; Mao, L. Electroanalysis 2015, 27, 879.

    Article  CAS  Google Scholar 

  52. Zhang, M.; Hou, X.; Wang, J.; Tian, Y.; Fan, X.; Zhai, J.; Jiang, L. Adv. Mater. 2012, 24, 2424.

    Article  CAS  PubMed  Google Scholar 

  53. Bhattacharyya, S.; Maity, M.; Chowdhury, A.; Saha, M. L.; Panja, S. K.; Stang, P. J.; Mukherjee, P. S. Inorg. Chem. 2020, 59, 2083.

    Article  CAS  PubMed  Google Scholar 

  54. Ma, G.; Zhou, Q.; Zhang, X.; Xu, Y.; Liu, H. New J. Chem. 2014, 38, 552.

    CAS  Google Scholar 

  55. Bletz, M.; Pfeifer-Fukumura, U.; Kolb, U.; Baumann, W. J. Phys. Chem. A 2002, 106, 2232.

    Article  CAS  Google Scholar 

  56. Levitus, M.; Glasser, G.; Neher, D.; Aramendía, P. F. Chem. Phys. Lett. 1997, 277, 118.

    Article  CAS  Google Scholar 

  57. Li, Y.; Zhang, H.; Qi, C.; Guo, X. J. Mater. Chem. 2012, 22, 4261.

    Article  CAS  Google Scholar 

  58. Tamaki, T.; Minode, K.; Numai, Y.; Ohto, T.; Yamada, R.; Masai, H.; Tada, H.; Terao, J. Nanoscale 2020, 12, 7527.

    Article  CAS  PubMed  Google Scholar 

  59. Liu, C.; Yang, D.; Jin, Q.; Zhang, L.; Liu, M. Adv. Mater. 2016, 28, 1644.

    Article  CAS  PubMed  Google Scholar 

  60. Miao, W.; Wang, S.; Liu, M. Adv. Funct. Mater. 2017, 27, 1701368.

    Article  CAS  Google Scholar 

  61. Tian, W.; Tian, J. Dyes Pigm. 2014, 105, 66.

    Article  CAS  Google Scholar 

  62. Metelitsa, A. V.; Nikolaeva, O. G.; Cheprasov, A. S.; Karlutova, O. Y.; Burtseva, A. A.; Dubonosov, A. D.; Bren, V. A.; Minkin, V. I. J. Photochem. Photobiol. A 2016, 321, 12.

    Article  CAS  Google Scholar 

  63. Abdollahi, A.; Sahandi-Zangabad, K.; Roghani-Mamaqani, H. Langmuir 2018, 34, 13910.

    Article  CAS  PubMed  Google Scholar 

  64. Kundu, P. K.; Das, S.; Ahrens, J.; Klajn, R. Nanoscale 2016, 8, 19280.

    Article  CAS  PubMed  Google Scholar 

  65. Fukushima, K.; Vandenbos, A. J.; Fujiwara, T. Chem. Mater. 2007, 19, 644.

    Article  CAS  Google Scholar 

  66. Zhang, D.; Shah, P. K.; Culver, H. R.; David, S. N.; Stansbury, J. W.; Yin, X.; Bowman, C. N. Soft Matter 2019, 15, 3740.

    Article  CAS  PubMed  Google Scholar 

  67. Kwangmettatam, S.; Kudernac, T. Chem. Commun. 2018, 5311.

  68. Wu, Z.; Pan, K.; Lü, B.; Ma, L.; Yang, W.; Yin, M. Chem–Asian J. 2016, 11, 3102.

    Article  CAS  PubMed  Google Scholar 

  69. Ji, J.; Wu, T.; Zhang, Y.; Feng, F. ACS Appl. Mater. Interfaces 2019, 11, 15222.

    Article  CAS  PubMed  Google Scholar 

  70. Cardano, F.; Del Canto, E.; Giordani, S. Dalton Trans. 2019, 15537.

  71. Son, S.; Shin, E.; Kim, B.-S. Biomacromolecules 2014, 15, 628.

    Article  CAS  PubMed  Google Scholar 

  72. Yuan, W.; Gao, X.; Pei, E.; Li, Z. Polym. Chem. 2018, 9, 3651.

    Article  CAS  Google Scholar 

  73. Moldenhauer, D.; Fuenzalida Werner, J. P.; Strassert, C. A.; Gröhn, F. Biomacromolecules 2019, 20, 979.

    Article  CAS  PubMed  Google Scholar 

  74. Kundu, P. K.; Lerner, A.; Kučanda, K.; Leitus, G.; Klajn, R. J. Am. Chem. Soc. 2014, 136, 11276.

    Article  CAS  PubMed  Google Scholar 

  75. Bringmann, G.; Price Mortimer, A. J.; Keller, P. A.; Gresser, M. J.; Garner, J.; Breuning, M. Angew. Chem., Int. Ed. 2005, 44, 5384.

  76. Hernández-Melo, D.; Tiburcio, J. Chem. Commun. 2015, 17564.

  77. Yang, L.-P.; Jia, F.; Cui, J.-S.; Lu, S.-B.; Jiang, W. Org. Lett. 2017, 19, 2945.

    Article  CAS  PubMed  Google Scholar 

  78. Kothapalli, S. S. K.; Kannekanti, V. K.; Ye, Z.; Yang, Z.; Chen, L.; Cai, Y.; Zhu, B.; Feng, W.; Yuan, L. Org. Chem. Front. 2020, 7, 846.

    Article  CAS  Google Scholar 

  79. Silvi, S.; Arduini, A.; Pochini, A.; Secchi, A.; Tomasulo, M.; Raymo, F. M.; Baroncini, M.; Credi, A. J. Am. Chem. Soc. 2007, 129, 13378.

    Article  CAS  PubMed  Google Scholar 

  80. Ho, F.-C.; Huang, Y.-J.; Weng, C.-C.; Wu, C.-H.; Li, Y.-K.; Wu, J. I.; Lin, H.-C. ACS Appl. Mater. Interfaces 2020, 12, 53257.

    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 within the framework of State contract No. 0852-2020-00-19 for scientific research.

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Authors and Affiliations

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

    Anastasia S. Kozlenko, Artem D. Pugachev, Ilya V. Ozhogin, Islam M. El-Sewify & Boris S. Lukyanov

  2. Department of Chemistry, Faculty of Science, Ain Shams University, Cairo, 11566, Egypt

    Islam M. El-Sewify

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  1. Anastasia S. Kozlenko
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  2. Artem D. Pugachev
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  3. Ilya V. Ozhogin
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  4. Islam M. El-Sewify
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  5. Boris S. Lukyanov
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Correspondence to Boris S. Lukyanov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(10), 984–989

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Kozlenko, A.S., Pugachev, A.D., Ozhogin, I.V. et al. Spiropyrans: molecules in motion. Chem Heterocycl Comp 57, 984–989 (2021). https://doi.org/10.1007/s10593-021-03010-5

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