Chinese Journal of Organic Chemistry >
Research Progress on Photochromic Spiropyrans in the Solid State
Received date: 2023-12-18
Revised date: 2024-02-01
Online published: 2024-02-28
Supported by
National Natural Science Foundation of China(22361001); Natural Science Foundation of Inner Mongolia(2023LHMS02013)
In recent years, organic photochromic materials have drawn continuous interest due to their wide application value in fields such as molecular switches, anti-counterfeiting and biological fluorescence imaging. Spiropyran (SP) compounds have the advantages of simple preparation, easy modification and good optical properties. They can undergo structural and performance changes under various external stimuli such as light, heat, electricity, acid-base, and external forces. Therefore, they can be applied in multiple fields. Solid spiropyran compounds without a matrix are difficult to undergo photochromic reactions due to their tightly packed molecules and lack of spatial free volume. Development of photochromic SP in the solid state is a significant trend in new materials. The research progress on photochromic spiropyrans in the solid state is summarized with the relationship between molecular structures and properties as an emphasis.
Key words: spiropyran; solid state; photochromism
Suhua Yang , Xiaoyin Liu , Lifei Zou , Jie Han . Research Progress on Photochromic Spiropyrans in the Solid State[J]. Chinese Journal of Organic Chemistry, 2024 , 44(6) : 1719 -1732 . DOI: 10.6023/cjoc202312017
| [1] | Duan, Y. L.; Zhao, H. Q.; Xiong, C. Y.; Mao, L. J.; Wang, D. S.; Zheng, Y. H. Chin. J. Chem. 2020, 38, 985. |
| [2] | Yang, S. H.; Yan, S. J.; Yang, J.; Zhang, C.; Han, G. Y. Chin. J. Org. Chem. 2018, 38, 425. (in Chinese) |
| [2] | (杨素华, 闫素君, 杨静, 张策, 韩国英, 有机化学, 2018, 38, 425.) |
| [3] | Fischer, E.; Hirshberg, Y. J. Chem. Soc. 1952, 4522. |
| [4] | Zuo, Y. J.; Chai, Y. F.; Liu, X. F.; Gao, Z. M.; Jin, X. F. Wang, F.; Bai, Y. J.; Zheng, Z. J. Spectrochim. Acta, Part A 2023, 291, 122338. |
| [5] | Yang, R. Q.; Ren, X.; Mei, L. J.; Pan, G. C.; Li, X. Z.; Wu, Z. Y.; Zhang, S.; Ma, W. Y.; Yu, W. L.; Fang, H. H.; Li, C.; Zhu, M. Q.; Hu, Z.; Sun, T. M.; Xu, B.; Tian, W. J. Angew. Chem., Int. Ed. 2022, 61, 202117158. |
| [6] | Zhang, R. Q.; Hu, L. P.; Xu, Z. X.; Song, Y. X.; Li, H. Q; Zhang, X.; Gao, X. C.; Wang, M. X.; Xian, C. Y. J. Mol. Struct. 2020, 1204, 127481. |
| [7] | Luo, X.; Chen, D. L.; Xu, Z. X.; Song, Y. X.; Li, H. Q.; Xian, C. Y. J. Rare Rarth. 2020, 38, 445. |
| [8] | Sanjabi, S.; Keyvan Rad, J.; Mahdavian, A. R. J. Photochem. Photobiol., A 2022, 424, 113626. |
| [9] | Zhang, D.; Qi, Y. G.; Li, Y. J.; Song, Y. X.; Xian, C. Y.; Li, H. Q.; Cong, P. H. J. Fluoresc. 2021, 31, 1133. |
| [10] | He, X. J.; Xu, W.; Xu, C. C.; Ding, F.; Chen, H.; Shen, J. L. Dyes Pigm. 2020, 180, 108497. |
| [11] | Liu, Q. L.; Zhao, Y.; Zhang, Y.; Xie, K. X.; Liu, R. R.; Ren, B. R.; Yan, Y. M.; Li, L. Analyst 2021, 145, 8016. |
| [12] | Kang, J.; Li, E. Z.; Cui, L.; Shao, Q. L.; Yin, C. X.; Cheng, F. Q. Sens. Actuators, B 2021, 327, 128941. |
| [13] | Barman, S.; Das, J.; Biswas, S.; Maiti, T. K.; Pradeep Singh, N. D. J. Mater. Chem. B 2017, 5, 3940. |
| [14] | Sharma, D.; Rao, D.; Saha, B. Nanoscale Horiz. 2023, 8, 543. |
| [15] | Qin, M.; Huang, Y.; Li, F. Y.; Song, Y. L. J. Mater. Chem. C 2015, 3, 9265. |
| [16] | Zhang, T. Z.; Lou, X. Y.; Li, X. Y.; Tu, X.; Han, J.; Zhao, B.; Yang, Y. W. Adv. Mater. 2023, 35, 2210551. |
| [17] | Aiken, S.; Edgar, R. J. L.; Gabbutt, C. D.; Heron, B. M.; Hobson, P. A. Dyes Pigm. 2018, 149, 92. |
| [18] | Suzuki, M.; Asahi, T.; Masuhara, H. Phys. Chem. Chem. Phys. 2002, 4, 185. |
| [19] | Asahi, T.; Suzuki, M.; Masuhara, Hiroshi. J. Phys. Chem. A 2002, 106, 2335. |
| [20] | Harada, J.; Kawazoe, Y.; Ogawa, K. Chem. Commun. 2010, 46, 2593. |
| [21] | Harada, J.; Ueki, K.; Anada, M.; Kawazoe, Y.; Ogawa, K. Chemistry 2011, 17, 14111. |
| [22] | Kozlenko, A. S.; Ozhogin, I. V.; Pugachev, A. D.; Lukyanova, M. B.; El-Sewify, I. M.; Lukyanov, B. S. Top. Curr. Chem. 2023, 381, 8. |
| [23] | Godsi, O.; Peskin, U.; Kapon, M.; Natan, E.; Eichen, Y. Chem. Commun. 2001, 2132. |
| [24] | Yang, R.-Q. Ph.D. Dissertation, Jilin University, Changchun, 2022. (in Chinese) |
| [24] | (杨润青, 博士论文, 吉林大学, 长春, 2022.) |
| [25] | Chen, X.-Z. M.S. Thesis, Hebei Normal University, Shijiazhuang, 2006. (in Chinese) |
| [25] | (陈肖卓, 硕士论文, 河北师范大学, 石家庄, 2006.) |
| [26] | Zhang, L.; Deng, Y. W.; Tang, Y. B.; Xie, C. X.; Wu, Z. T. Mater. Chem. Front. 2021, 5, 3119. |
| [27] | Mo, S. Z.; Tan, L.; Fang, B.; Wu, Z.; Su, Z. Q.; Zhang, Y. T.; Yin, M. Z. Sci. China: Chem. 2018, 61, 1587. |
| [28] | Yin, M.; Kuwabara, T.; Haramoto, Y.; Nanasawa, M. Macromol. Chem. Phys. 1996, 191, 575. |
| [29] | Wu, Z.; Wang, Q.; Li, P. Y.; Fang, B.; Yin, M. Z. J. Mater. Chem. C 2021, 9, 6290. |
| [30] | Xu, B.; Wang, X.; Yang, R. Q.; Tian, W. J. CN 114478559, 2022. |
| [31] | Yang, R. Q.; Jiao, Y.; Wang, B. Y.; Xu, B.; Tian, W. J. J. Phys. Chem. Lett. 2021, 12, 1290. |
| [32] | Qi, Q. K.; Li, C.; Liu, X. G.; Jiang, S.; Xu, Z. C.; Lee, R.; Zhu, M. Q.; Xu, B.; Tian, W. J. J. Am. Chem. Soc. 2017, 139, 16036. |
| [33] | Yang, Y. H.; He, Z.; He, J. Z.; Li, Y. Q.; Chen, Y. L; Jiang, G. H. Mater. Chem. Front. 2021, 5, 3918. |
| [34] | Oms, O.; Hakouk, K.; Dessapt, R.; Deniard, P.; Jobic, S.; Dolbecq, A.; Palacin, T.; Nadjo, L.; Keita, B.; Marrot, J.; Mialane, P. Chem. Commun. 2012, 48, 12103. |
| [35] | Yang, Y. H.; Chen, Y. L.; Li, Y. Q.; Wang, Z. H.; Zhao, H. M. Mater. Chem. Front. 2022, 6, 916. |
| [36] | Mo, S. Z.; Meng, Q. T.; Wan, S. L.; Su, Z. Q.; Yan, H.; Tang, B. Z.; Yin, M. Z. Adv. Funct. Mater. 2017, 27, 1701210. |
| [37] | Sekine, A.; Tanaka, M.; Uekusa, H.; Yasuda, N. CrystEngComm 2018, 20, 6061. |
| [38] | Wu, L.; Chen, R.; Luo, Z.; Wang, P. J. Mater. Sci. 2020, 55, 12826. |
| [39] | Yang, Y. H.; He, J. Z.; He, Z.; Jiang, G.H. Adv. Opt. Mater. 2020, 9, 2001584. |
| [40] | He, J. Z.; Zhao, H. M.; Wu, H.; Yang, Y. H.; Wang, Z. H.; He, Z.; Jiang, G. H. Phys. Chem. Chem. Phys. 2021, 23, 17939. |
| [41] | Yang, Y. H.; Wang, Z. H.; Wu, H.; Li, Y. Q.; Chen, Y. L.; Hu, L. L.; Wu, W. Mater. Chem. Front. 2022, 6, 1948. |
| [42] | Wang, Z. H.; Ding, Z.; Yang, Y. H.; Hu, L. L.; Wu, W.; Gao, Y. Y.; Wei, Y. H.; Zhang, X. Y.; Jiang, G. H. Chem. Eng. J. 2023, 457, 141293. |
| [43] | Lukyanov, B. S.; Metelitsa, A. V.; Voloshin, N. A.; Alexeenko, Y. S.; Lukyanova, M. B.; Vasilyuk, G. T.; Maskevich, S. A.; Mukhanov, E. L. Int. J. Photoenergy 2005, 7, 17. |
| [44] | Lukyanov, B. S.; Metelitsa, A. V.; Lukyanova, M. B.; Mukhanov, E. L.; Borisenko, N. I.; Alekseenko, Y. S.; Bezugliy, S. O. Mol. Cryst. Liq. Cryst. 2006, 431, 351. |
| [45] | Wu, Z.; Pan, K.; Mo, S. Z.; Wang, B. J.; Zhao, X. J.; Yin, M. Z. ACS Appl. Mater. Interfaces 2018, 10, 30879. |
| [46] | Shen, L.-Y. M.S. Thesis, Hebei normal University, Shijiazhuang, 2008. (in Chinese) |
| [46] | (沈利英, 硕士论文, 河北师范大学, 石家庄, 2008.) |
| [47] | Wang, L. Y.; Xiong, W.; Tang, H.; Cao, D. R. J. Mater. Chem. C 2019, 7, 9102. |
| [48] | Qu, L.; Xu, X. M.; Song, J. T.; Wu, D. H.; Wang, L.; Zhou, W. L.; Zhou, X. G.; Xiang, H. F. Dyes Pigm. 2020, 181, 108597. |
| [49] | Hu, W.; Sun, C.; Ren, Y. X.; Qin, S. Y.; Shao, Y.; Zhang, L. Y.; Wu, Y.; Wang, Q.; Yang, H.; Yang, D. K. Angew. Chem., Int. Ed. 2021, 60, 19406. |
| [50] | Benard, S.; Yu, P. Adv. Mater. 2000, 12, 48. |
| [51] | Léaustic, A.; Dupont, A.; Yu, P.; Clément, R. New J. Chem. 2001, 25, 1297. |
| [52] | Benard, S.; Riviere, E.; Yu, P. Chem. Mater. 2001, 13, 159. |
| [53] | Yurieva, E. A.; Aldoshin, S. M.; Nikonova, L. A.; Shilov, G. V.; Nadtochenko, V. A. Russ. Chem. Bull., Int. Ed. 2011, 60, 1401. |
| [54] | Funasako, Y.; Ason, M.; Takebayashi, J.-I.; Inokuchi, M. Cryst. Growth Des. 2019, 19, 7308. |
| [55] | Funasako, Y.; Miyazaki, H.; Sasaki, T.; Goshima, K.; Inokuchi, M. J. Phys. Chem. B 2020, 124, 7251. |
| [56] | Aldoshin, S. M.; Sanina, N. A.; Minkin, V. I.; Voloshin, N. A.; Ikorskii, V. N.; Ovcharenko, V. I.; Smirnov, V. A.; Nagaeva, N. K. J. Mol. Struct. 2007, 826, 69. |
| [57] | Guo, X. F.; Zhou, Y. C.; Zhang, D. Q.; Yin, B.; Liu, Z. L.; Liu, C. M.; Lu, Z. L.; Huang, Y. H.; Zhu, D. B. J. Org. Chem. 2004, 69, 8924. |
| [58] | D’Cruz, B.; Amin, M. O.; Al-Hetlani, E. Ind. Eng. Chem. Res. 2021, 60, 10960. |
| [59] | Colovic, M. B.; Lackovic, M.; Lalatovic, J.; Mougharbel, A. S.; Kortz, U.; Krstic, D. Z. Curr. Med. Chem. 2020, 27, 362. |
| [60] | Mialane, P.; Zhang, G. J.; Mbomekalle, I. M.; Yu, P.; Compain, J. D.; Dolbecq, A.; Marrot, J.; Secheresse, F.; Keita, B.; Nadjo, L. Chemistry 2010, 16, 5572. |
| [61] | Compain, J. D.; Deniard, P.; Dessapt, R.; Dolbecq, A.; Oms, O.; Secheresse, F.; Marrot, J.; Mialane, P. Chem. Commun. 2010, 46, 7733. |
| [62] | Yang, S. H.; Pang, M. L.; Guo, X. F.; Huo, X. L.; Han, J.; Meng, J. B. Chem. J. Chin. Univ. 2009, 30, 1135. (in Chinese) |
| [62] | (杨素华, 庞美丽, 郭心富, 霍晓莲, 韩杰, 孟继本, 高等化学学报, 2009, 30, 1135.) |
| [63] | Saad, A.; Oms, O.; Marrot, J.; Dolbecq, A.; Hakouk, K.; El Bekkachi, H.; Jobic, S.; Deniard, P.; Dessapt, R.; Garrot, D.; Boukheddaden, K.; Liu, R. J.; Zhang, G. J.; Keita, B.; Mialane, P. J. Mater. Chem. C 2014, 2, 4748. |
| [64] | Parrot, A.; Izzet, G.; Chamoreau, L. M.; Proust, A.; Oms, O.; Dolbecq, A.; Hakouk, K.; El Bekkachi, H.; Deniard, P.; Dessapt, R.; Mialane, P. Inorg. Chem. 2013, 52, 11156. |
| [65] | Hakouk, K.; Oms, O.; Dolbecq, A.; Marrot, J.; Saad, A.; Mialane, P.; El Bekkachi, H.; Jobic, S.; Deniard, P.; Dessapt, R. J. Mater. Chem. C 2014, 2, 21628. |
| [66] | Menet, C.; Serier-Brault, H.; Oms, O.; Dolbecq, A.; Marrot, J.; Saad, A.; Mialane, P.; Jobic, S.; Deniard, P.; Dessapt, R. RSC Adv. 2015, 5, 79635. |
| [67] | Dridi, H.; Boulmier, A.; Bolle, P.; Dolbecq, A.; Rebilly, J.-N.; Banse, F.; Ruhlmann, L.; Serier-Brault, H.; Dessapt, R.; Mialane, P.; Oms, O. J. Mater. Chem. C 2020, 8, 637. |
| [68] | Truong, V. X.; Ehrmann, K.; Seifermann, M.; Levkin, P. A.; Barner-Kowollik, C. Chem.-Eur. J. 2022, 28, 202104466. |
| [69] | Schwartz, H. A.; Olthof, S.; Schaniel, D.; Meerholz, K.; Ruschewitz, U. Inorg. Chem. 2017, 56, 13100. |
| [70] | Martin, C. R.; Park, K. C.; Corkill, R. E.; Kittikhunnatham, P.; Leith, G. A.; Mathur, A.; Abiodun, S. L.; Greytak, A. B.; Shustova, N. B. Faraday Discuss. 2021, 231, 266. |
| [71] | Williams, D. E.; Martin, C. R.; Dolgopolova, E. A.; Swifton, A.; Godfrey, D. C.; Ejegbavwo, O. A.; Pellechia, P. J.; Smith, M. D.; Shustova, N. B. J. Am. Chem. Soc. 2018, 140, 7611. |
| [72] | Martin, C. R.; Park, K. C.; Leith, G. A.; Yu, J. R.; Mathur, A.; Wilson, G. R.; Gange, G. B.; Barth, E. L.; Ly, R. T.; Manley, O. M.; Forrester, K. L.; Karakalos, S. G.; Smith, M. D.; Makris, T. M.; Vannucci, A. K.; Peryshkov, D. V.; Shustova, N. B. J. Am. Chem. Soc. 2022, 144, 4457. |
| [73] | Wang, M. J.; Li, B.; Wei, Y. L.; Zhao, S. N.; Zang, S. Q. Chin. Chem. Lett. 2023, 35, 108491. |
| [74] | Kida, N.; Hikita, M.; Kashima, I.; Okubo, M.; Itoi, M.; Enomoto, M.; Kato, K.; Takata, M.; Kojima, N. J. Am. Chem. Soc. 2009, 131, 212. |
| [75] | Howlader, P.; Mondal, B.; Purba, P. C.; Zangrando, E.; Mukherjee, P. S. J. Am. Chem. Soc. 2018, 140, 7952. |
| [76] | Mondal, B.; Ghosh, A. K.; Mukherjee, P. S. J. Org. Chem. 2017, 82, 7783. |
| [77] | Kundu, P. K.; Olsen, G. L.; Kiss, V.; Klajn, R. Nat. Commun. 2014, 5, 3588. |
| [78] | Sch?ller, K.; Küpfer, S.; Baumann, L.; Hoyer, P. M.; de Courten, D.; Rossi, R. M.; Vetushka, A.; Wolf, M.; Bruns, N.; Scherer, L. Adv. Funct. Mater. 2014, 24, 5194. |
| [79] | Huang, Z. Z.; Hu, Y.; Jin, X.; Zhao, Y. H.; Su, J. H.; Ma, X. Adv. Opt. Mater. 2021, 9. 2100135. |
| [80] | Jiang, J. W.; Zhang, P. S.; Liu, L.; Li, Y. Q.; Zhang, Y. B.; Wu, T. C.; Xie, H. L.; Zhang, C. H.; Cui, J. X.; Chen, J. Chem. Eng. J. 2021, 425. 131557. |
| [81] | Yang, Y. H.; Zhao, H. M.; Li, Y. Q.; Chen, Y. L.; Wang, Z. H.; Wu, W.; Hu, L. L.; Zhu, J. K. ACS Omega 2023, 8, 16459. |
| [82] | Breslin, V. M.; Garcia-Garibay, M. A. Cryst. Growth Des. 2017, 17, 637. |
| [83] | Abdollahi, A.; Ghasemi, B.; Nikzaban, S.; Sardari, N.; Jorjeisi, S.; Dashti, A. ACS Appl. Mater. Interfaces 2023, 15, 7466. |
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