Chinese Journal of Organic Chemistry >
Research Progress of Solid-State Fluorescent Photoswitching Molecules
Received date: 2024-03-31
Revised date: 2024-06-30
Online published: 2024-07-18
Supported by
Natural Science Foundation of Jilin Province(20240101003JC); National Natural Science Foundation of China(52073116); Fundamental Research Funds for the Central Universities of China; Jilin University Science and Technology Innovative Research Team(2021TD-03)
Fluorescent photoswitching molecules have been explored for their potential applications in the fields of anti- counterfeiting, super-resolution imaging, optical data storage, and sensor devices due to their fast response, reversibility, and fatigue resistance. The fluorescence switch of fluorescent photoswitching molecules requires a certain degree of spatial freedom, so compared to solution, achieving solid-state fluorescence switching is somewhat difficult. An effective method is to combine aggregation induced luminescence (AIE) molecules with fluorescent switching molecules through covalent bonds or supramolecular interactions, and the distorted conformation of AIE molecules can provide enough space for the configurational changes of fluorescent photoswitching molecules after light exposure, thus realizing solid-state fluorescent photoswitching. In this paper, the application of this strategy in several typical photoswitching molecules is mainly reviewed, providing a feasible reference for the design of novel solid-state fluorescent photoswitching molecular systems, which is crucial for understanding the stimulus-response mechanism of solid-state photoswitching molecules, developing new materials, and expanding their applications.
Key words： photoswitch; aggregation-induced luminescence; fluorescence
Jiasong Hu , Chunjuan Li , Bin Xu , Wenjing Tian . Research Progress of Solid-State Fluorescent Photoswitching Molecules[J]. Chinese Journal of Organic Chemistry, 2024 , 44(8) : 2425 -2440 . DOI: 10.6023/cjoc202403056
| [1] | Natali, M.; Giordani, S. Chem. Soc. Rev. 2012, 41, 4010. |
| [2] | Arai, Y.; Ito, S.; Fujita, H.; Yoneda, Y.; Kaji, T.; Takei, S.; Kashihara, R.; Morimoto, M.; Irie, M.; Miyasaka, H. Chem. Commun. 2017, 53, 4066. |
| [3] | Chai, X. Z.; Han, H. H.; Sedgwick, A. C.; Li, N.; Zang, Y.; James, T. D.; Zhang, J. J.; Hu, X. L.; Yu, Y.; Li, Y.; Wang, Y.; Li, J.; He, X. P.; Tian, H. J. Am. Chem. Soc. 2020, 142, 18005. |
| [4] | Champagne, B.; Plaquet, A.; Pozzo, J. L.; Rodriguez, V.; Castet, F. J. Am. Chem. Soc. 2012, 134, 8101. |
| [5] | Chen, L.; Wu, J. C.; Schmuck, C.; Tian, H. Chem. Commun. 2014, 50, 6443. |
| [6] | Irie, M.; Fulcaminato, T.; Matsuda, K.; Kobatake, S. Chem. Rev. 2014, 114, 12174. |
| [7] | Jia, C. C.; Migliore, A.; Xin, N.; Huang, S. Y.; Wang, J. Y.; Yang, Q.; Wang, S. P.; Chen, H. L.; Wang, D. M.; Feng, B. Y.; Liu, Z. R.; Zhang, G. Y.; Qu, D. H.; Tian, H.; Ratner, M. A.; Xu, H. Q.; Nitzan, A.; Guo, X. F. Scienc. 2016, 352, 1443. |
| [8] | Li, Y. H.; Duan, Y.; Li, J. S.; Zheng, J.; Yu, H.; Yang, R. H. Anal. Chem. 2012, 84, 4732. |
| [9] | Tsujioka, T.; Onishi, I.; Natsume, D. Appl. Opt. 2010, 49, 3894. |
| [10] | Yan, J.; Zhao, L. X.; Li, C.; Hu, Z.; Zhang, G. F.; Chen, Z. Q.; Chen, T.; Huang, Z. L.; Zhu, J. T.; Zhu, M. Q. J. Am. Chem. Soc. 2015, 137, 2436. |
| [11] | Han, P.; Qin, A. Chin. J. Org. Chem. 2023, 43, 2254 (in Chinese). |
| [11] | (韩鹏博, 秦安军, 有机化学, 2023, 43, 2254.) |
| [12] | Jung, H. Y.; Kim, B.; Jeon, M. H.; Kim, Y. Smal. 2022, 18, 2103523. |
| [13] | Kashihara, R.; Morimoto, M.; Ito, S.; Miyasaka, H.; Irie, M. J. Am. Chem. Soc. 2017, 139, 16498. |
| [14] | Mei, J.; Leung, N. L. C.; Kwok, R. T. K.; Lam, J. W. Y.; Tang, B. Z. Chem. Rev. 2015, 115, 11718. |
| [15] | Ranganathan, A.; Kulkarni, G. U. Proc. Indian Acad. Sci. 2003, 115, 637. |
| [16] | Luo, J.; Xie, Z.; Lam, J. W. Y.; Cheng, L.; Tang, B. Z.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhan, X.; Liu, Y.; Zhu, D. Chem. Commun. 2001, 1740. |
| [17] | Xu, H.; Han, P.; Qin, A.; Tang, B. Z. Acta Chim. Sinic. 2023, 81, 1420 (in Chinese). |
| [17] | (徐赫, 韩鹏博, 秦安军, 唐本忠, 化学学报, 2023, 81, 1420.) |
| [18] | He, J. T.; Xu, B.; Chen, F. P.; Xia, H. J.; Li, K. P.; Ye, L.; Tian, W. J. J. Phys. Chem. C 2009, 113, 9892. |
| [19] | Hong, Y. N.; Lam, J. W. Y.; Tang, B. Z. Chem. Commun. 2009, 4332. |
| [20] | Zhang, L.; Wang, Y.; Zhu, G.; Dai, W.; Zhao, Z.; Zhao, Y.; Zhi, J.; Dong, Y. Acta Chim. Sinic. 2022, 80, 282 (in Chinese). |
| [20] | (张璐璐, 王媛媛, 朱贵楠, 戴文博, 赵紫璇, 赵盈, 支俊格, 董宇平, 化学学报, 2022, 80, 282.) |
| [21] | Zhao, Y.-Q.; Zhang, X.; Yang, Y. R.; Zhu, L. P.; Zhou, Y. Acta Chim. Sinic. 2024, 82, 265 (in Chinese). |
| [21] | (赵玉强, 张霞, 杨芸如, 朱立平, 周莹, 化学学报, 2024, 82, 265.) |
| [22] | Zhao, Y.; Chen, P.; Li, G.; Niu, Z.; Wang, E. Chin. J. Org. Chem. 2023, 43, 2156 (in Chinese). |
| [22] | (赵洋, 陈盼盼, 李高楠, 钮智刚, 王恩举, 有机化学, 2023, 43, 2156.) |
| [23] | Zhang, Y.; Nie, F.; Zhou, L.; Wang, X.; Liu, Y.; Huo, Y.; Chen, W.; Zhao, Z. Chin. J. Org. Chem. 2023, 43, 3876 (in Chinese). |
| [23] | (张越华, 聂飞, 周路, 王晓烽, 刘源, 霍延平, 陈文铖, 赵祖金, 有机化学, 2023, 43, 3876.) |
| [24] | Zeng, C.; Hu, P.; Wang, B.; Fang, W.; Zhao, K.; Donnio, B. Acta Chim. Sinic. 2023, 81, 469 (in Chinese). |
| [24] | (曾崇洋, 胡平, 汪必琴, 方文彦, 赵可清, Donnio Bertrand, 化学学报, 2023, 81, 469.) |
| [25] | Liu, B.; Chen, P. Acta Chim. Sinic. 2022, 80, 929 (in Chinese). |
| [25] | (刘斌, 陈磅宽, 化学学报, 2022, 80, 929.) |
| [26] | Lu, H.; Ma, L.; Ma, H. Chin. J. Org. Chem. 2023, 43, 4075 (in Chinese). |
| [26] | (鲁会名, 马拉毛草, 马恒昌, 有机化学, 2023, 43, 4075.) |
| [27] | Zhao, Y.; Chen, P.; Han, L.; Wang, E. Chin. J. Org. Chem. 2023, 43, 2454 (in Chinese). |
| [27] | (赵洋, 陈盼盼, 韩立志, 王恩举, 有机化学, 2023, 43, 2454.) |
| [28] | Chen, Y.-J.; Pu, M.-Q.; Wu, L.-T.; Sun, X.-L., Wan, W.-M. Chin. J. Chem. 2023, 41, 1705. |
| [29] | Gui, Y.; Chen, K.; Sun, Y.; Tan, Y.; Luo, W.; Zhu, D.; Xiong, Y.; Yan, D.; Wang, D.; Tang, B. Z. Chin. J. Chem. 2023, 41, 1249. |
| [30] | Wang, Y.; Liu, X.; Li, H.; Liu, X.; Wang, L.; Liu, Y. Chin. J. Chem. 2022, 40, 2393. |
| [31] | Zeng, C.; Hu, P.; Wang, B.; Fang, W.; Zhao, K. Chin. J. Org. Chem. 2023, 43, 3287 (in Chinese). |
| [31] | (曾崇洋, 胡平, 汪必琴, 方文彦, 赵可清, 有机化学, 2023, 43, 3287.) |
| [32] | Feng, X.; Zhu, L.; Yue, B. Acta Chim. Sinic. 2022, 80, 647 (in Chinese). |
| [32] | (冯锡成, 朱亮亮, 岳兵兵, 化学学报, 2022, 80, 647.) |
| [33] | Zhao, Z.; Lam, J. W. Y.; Tang, B. Z. J. Mater. Chem. 2012, 22, 23726. |
| [34] | de Jong, J. J. D.; Browne, W. R.; Walko, M.; Lucas, L. N.; Barrett, L. J.; McGarvey, J. J.; van Esch, J. H.; Feringa, B. L. Org. Biomol. Chem. 2006, 4, 2387. |
| [35] | Ishibashi, Y.; Murakami, M.; Miyasaka, H.; Kobatake, S.; Irie, M.; Yokoyama, Y. J. Phys. Chem. C 2007, 111, 2730. |
| [36] | Han, M.; Morino, S. y.; Ichimura, K. Macromolecule. 2000, 33, 6360. |
| [37] | Petermayer, C.; Dube, H. Acc. Chem. Res. 2018, 51, 1153. |
| [38] | Motokura, K.; Kang, B.; Fujii, M.; Nesterenko, D. V.; Sekkat, Z.; Hayashi, S. J. Appl. Phys. 2020, 127, 073103. |
| [39] | Zhang, T.; Lou, X.-Y.; Li, X.; Tu, X.; Han, J.; Zhao, B.; Yang, Y.-W. Adv. Mater. 2023, 35, 2210551. |
| [40] | Gonzalez, A.; Kengmana, E. S.; Fonseca, M. V.; Han, G. G. D. Mater. Today Adv. 2020, 6, 100058. |
| [41] | Zhu, W.; Meng, X.; Yang, Y.; Zhang, Q.; Xie, Y.; Tian, H. Chem. Eur. J. 2010, 16, 899. |
| [42] | Li, W.; Jiao, C.; Li, X.; Xie, Y.; Nakatani, K.; Tian, H.; Zhu, W. Angew. Chem., Int. Ed. 2014, 53, 4603. |
| [43] | Strübe, F.; Rath, S.; Mattay, J. Eur. J. Org. Chem. 2011, 2011, 4645. |
| [44] | Bhattacharjee, U.; Freppon, D.; Men, L.; Vela, J.; Smith, E. A.; Petrich, J. W. ChemPhysChe. 2017, 18, 2526. |
| [45] | Liu, R. S.; Asato, A. E. Proc. Nail. Acad. Sci. 1985, 82, 259. |
| [46] | Krysanov, S. A.; Alfimov, M. V. Chem. Phys. Lett. 1982, 91, 77. |
| [47] | Harada, J.; Kawazoe, Y.; Ogawa, K. Chem. Commun. 2010, 46, 2593. |
| [48] | Klajn, R. Chem. Soc. Rev. 2014, 43, 148. |
| [49] | Hong, Y.; Zhang, P.; Wang, H.; Yu, M.; Gao, Y.; Chen, J. Sens. Actuator., B 2018, 272, 340. |
| [50] | Nhien, P. Q.; Chou, W.-L.; Cuc, T. T. K.; Khang, T. M.; Wu, C.-H.; Thirumalaivasan, N.; Hue, B. T. B.; Wu, J. I.; Wu, S.-P.; Lin, H.-C. ACS Appl. Mater. Interface. 2020, 12, 10959. |
| [51] | Nhien, P. Q.; Chang, H.-K.; Cuc, T. T. K.; Khang, T. M.; Wu, C.-H.; Hue, B. T. B.; Wu, J. I.; Lin, H.-C. Sens. Actuator., B 2022, 372, 132634. |
| [52] | Wang, L.; Xiong, W.; Tang, H.; Cao, D. J. Mater. Chem. C 2019, 7, 9102. |
| [53] | Qi, Q.; Qian, J.; Ma, S.; Xu, B.; Zhang, S. X.-A.; Tian, W. Chem. Eur. J. 2015, 21, 1149. |
| [54] | Yu, Q.; Su, X.; Zhang, T.; Zhang, Y.-M.; Li, M.; Liu, Y.; Zhang, S. X.-A. J. Mater. Chem. C 2018, 6, 2113. |
| [55] | Wang, H.; Tang, J.; Deng, H.; Tian, Y.; Lin, Z.; Cui, J.; Chen, J. J. Mater. Chem. C 2023, 11, 15945. |
| [56] | Fang, B.; Chu, M.; Tan, L.; Li, P.; Hou, Y.; Shi, Y.; Zhao, Y. S.; Yin, M. ACS Appl. Mater. Interface. 2019, 11, 38226. |
| [57] | Qi, Q.; Li, C.; Liu, X.; Jiang, S.; Xu, Z.; Lee, R.; Zhu, M.; Xu, B.; Tian, W. J. Am. Chem. Soc. 2017, 139, 16036. |
| [58] | Yang, R.; Ren, X.; Mei, L.; Pan, G.; Li, X.-Z.; Wu, Z.; Zhang, S.; Ma, W.; Yu, W.; Fang, H.-H.; Li, C.; Zhu, M.-Q.; Hu, Z.; Sun, T.; Xu, B.; Tian, W. Angew. Chem., Int. Ed. 2022, 61, e202117158. |
| [59] | Bates, M.; Huang, B.; Zhuang, X. Curr. Opin. Chem. Biol. 2008, 12, 505. |
| [60] | Wei, Z.; Gourevich, I.; Field, L.; Coombs, N.; Kumacheva, E. Macromolecule. 2006, 39, 2441. |
| [61] | Nhien, P. Q.; Cuc, T. T. K.; Khang, T. M.; Wu, C.-H.; Hue, B. T. B.; Wu, J. I.; Mansel, B. W.; Chen, H.-L.; Lin, H.-C. ACS Appl. Mater. Interfaces. 2020, 12, 47921. |
| [62] | Yang, R. Q.; Jiao, Y.; Wang, B. Y.; Xu, B.; Tian, W. J. J. Phys. Chem. Lett. 2021, 12, 1290. |
| [63] | Guo, Y.; Zhu, W.; Tao, M.; Wu, X.; Chen, J.; Peng, X.; Zheng, S.; Zhao, Z.; Cao, Z. ACS Appl. Mater. Interface. 2022, 14, 39384. |
| [64] | Irie, M. Photochem. Photobiol. Sci. 2010, 9, 1535. |
| [65] | Poon, C.-T.; Lam, W. H.; Yam, V. W.-W. J. Am. Chem. Soc. 2011, 133, 19622. |
| [66] | Asadirad, A. M.; Boutault, S.; Erno, Z.; Branda, N. R. J. Am. Chem. Soc. 2014, 136, 3024. |
| [67] | Roubinet, B.; Weber, M.; Shojaei, H.; Bates, M.; Bossi, M. L.; Belov, V. N.; Irie, M.; Hell, S. W. J. Am. Chem. Soc. 2017, 139, 6611. |
| [68] | Yu, M.; Wang, H.; Li, Y.; Zhang, P.; Chen, S.; Zeng, R.; Gao, Y.; Chen, J. J. Appl. Polym. Sci. 2019, 136, 47466. |
| [69] | Ma, L.; Li, C.; Yan, Q.; Wang, S.; Miao, W.; Cao, D. Chin. Chem. Lett. 2020, 31, 361. |
| [70] | Liang, X.; Hu, H.; Zheng, Z.-g.; He, M.; Li, M.; Lv, N.; Shen, N.; Zhu, W.-H. Ind. Eng. Chem. Res. 2023, 62, 9961. |
| [71] | Liu, L.; Hao, T.; Wu, W.; Yang, C. Chin. J. Org. Chem. 2023, 43, 2189 (in Chinese). |
| [71] | (刘铃, 浩涛涛, 伍晚花, 杨成, 有机化学, 2023, 43, 2189.) |
| [72] | Li, C.; Gong, W.-L.; Hu, Z.; Aldred, M. P.; Zhang, G.-F.; Chen, T.; Huang, Z.-L.; Zhu, M.-Q. RSC Adv. 2013, 3, 8967. |
| [73] | Li, C.; Xiong, K.; Chen, Y.; Fan, C.; Wang, Y.-L.; Ye, H.; Zhu, M.-Q. ACS Appl. Mater. Interface. 2020, 12, 27651. |
| [74] | Yang, H.; Li, M.; Li, C.; Luo, Q.; Zhu, M.-Q.; Tian, H.; Zhu, W.-H. Angew. Chem., Int. Ed. 2020, 59, 8560. |
| [75] | Wu, Y.; Zhan, J.; Han, Z.; Liu, W.; Qian, Z.; Feng, H. J. Mater. Chem. C 2024, 12, 2552. |
| [76] | Zhu, Q.; Zuo, J.; Ping, X.; Zhu, Y.; Cai, X.; Xiong, Z.; Qian, Z.; Feng, H. J. Mater. Chem. C 2022, 10, 8674. |
| [77] | Zhou, S.; Guo, S.; Liu, W.; Ding, R.; Sun, H.; Chen, J.; Qian, Z.; Feng, H. J. Mater. Chem. C 2021, 9, 8249. |
| [78] | Zhou, S.; Guo, S.; Liu, W.; Yang, Q.; Sun, H.; Ding, R.; Qian, Z.; Feng, H. J. Mater. Chem. C 2020, 8, 13197. |
| [79] | Guo, S.; Zhou, S.; Chen, J.; Guo, P.; Ding, R.; Sun, H.; Feng, H.; Qian, Z. ACS Appl. Mater. Interface. 2020, 12, 42410. |
| [80] | Yang, H.; Li, M.; Zhao, W.; Guo, Z.; Zhu, W.-H. Chin. Chem. Lett. 2021, 32, 3882. |
| [81] | Khang, T. M.; Nhien, P. Q.; Cuc, T. T. K.; Weng, C.-C.; Wu, C.-H.; Wu, J. I.; Hue, B. T. B.; Li, Y.-K.; Lin, H.-C. Smal. 2023, 19, 2205597. |
| [82] | Alene, D. Y.; Srinivasadesikan, V.; Lin, M.-C.; Chung, W.-S. J. Org. Chem. 2023, 88, 5530. |
| [83] | Li, J.-J.; Zhang, H.-Y.; Liu, G.; Dai, X.; Chen, L.; Liu, Y. Adv. Opt. Mater. 2021, 9, 2001702. |
| [84] | Han, M. N.; Cho, S. J.; Norikane, Y.; Shimizu, M.; Kimura, A.; Tamagawa, T.; Seki, T. Chem. Commun. 2014, 50, 15815. |
| [85] | Jerca, F. A.; Jerca, V. V.; Hoogenboom, R. Nat. Rev. Chem. 2022, 6, 51. |
| [86] | Zhou, L.; Retailleau, P.; Morel, M.; Rudiuk, S.; Baigl, D. J. Am. Chem. Soc. 2019, 141, 9321. |
| [87] | Sekine, A.; Yamagiwa, H.; Uekusa, H. Chem. Lett. 2012, 41, 795. |
| [88] | Baroncini, M.; d'Agostino, S.; Bergamini, G.; Ceroni, P.; Comotti, A.; Sozzani, P.; Bassanetti, I.; Grepioni, F.; Hernandez, T. M.; Silvi, S.; Venturi, M.; Credi, A. Nat. Chem. 2015, 7, 634. |
| [89] | Qi, Q.; Huang, S.; Liu, X.; Aprahamian, I. J. Am. Chem. Soc. 2024, 146, 6471. |
| [90] | Wu, B.; Wang, W.; Wang, J.; Li, S.; He, Y. Dyes Pigm. 2018, 157, 290. |
| [91] | Yu, X.; Chen, H.; Shi, X.; Albouy, P.-A.; Guo, J.; Hu, J.; Li, M.-H. Mater. Chem. Front. 2018, 2, 2245. |
| [92] | You, J.; Zhang, S.; Li, Q.; Zhang, W.; Ma, H.; Hou, J.; Zhao, E.; He, Z. Dyes Pigm. 2023, 220, 111662. |
| [93] | Jiao, Y.; Yang, R.; Luo, Y.; Liu, L.; Xu, B.; Tian, W. CCS Chem. 2022, 4, 132. |
| [94] | Weerasekara, R. K.; Uekusa, H.; Hettiarachchi, C. V. Cryst. Growth Des. 2017, 17, 3040. |
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