Chinese Journal of Organic Chemistry >
Advances in Aggregation-Induced Emission Molecules Based on Organic Photochromism
Received date: 2021-08-23
Revised date: 2021-10-02
Online published: 2022-02-24
In recent years, organic aggregation-induced emission (AIE) materials have effectively overcome the main shortcomings of traditional fluorescent materials in aggregation-caused quenching (ACQ) in solid or aggregate state, and have been widely studied and applied in cell imaging, biological probes, optical devices, anti-counterfeiting materials, etc. However, unifunctional AIE materials can’t meet the advancement of science and technology, and the increasing demands for material life. In order to expand the application range of AIE materials, the study of AIE molecules combined with multifunctional groups has further become one of the current focused topics in the field of materials. Multifunctional molecules with both photochromic and AIE properties have received extensive attention due to their promising performances in reversible control and multiple photoresponses upon external stimuli and good control properties. Based on the different isomerization mechanisms of the photochromic units in the multifunctional molecules, and combined with the research practice of our group in this topic, this presentation briefly reviews the main advances and application of AIE molecules based on the different photochromic functional units since the 21st century. It also looks forward to its future development, hoping to provide some reference and thinking for the research in this field.
Wei Ding , Bowen Cheng , Meng Wang , Qingyu Dou , Siying Li , Peng Zhang , Qianfu Luo . Advances in Aggregation-Induced Emission Molecules Based on Organic Photochromism[J]. Chinese Journal of Organic Chemistry, 2022 , 42(2) : 363 -383 . DOI: 10.6023/cjoc202108046
| [1] | Hong, Y. N.; Lam, J. W. Y.; Tang, B. Z. Chem. Soc. Rev. 2011, 40, 5361. |
| [2] | (a) Fang, X. F.; Zhang, Y. M.; Chang, K. W.; Liu, Z. H.; Su, X.; Chen, H. B.; An-Zhang, S. X.; Liu, Y. F.; Wu, C. F. Chem. Mater. 2016, 28, 6628. |
| [2] | (b) Gao, Y.; Qin, C. Y.; Nie, Y.; Liu, W.; Li, T. R.; Jiang, X. C. Chin. J. Org. Chem. 2020, 40, 2254. (in Chinese) |
| [2] | ( 高迎, 秦成远, 聂永, 刘威, 李天瑞, 蒋绪川, 有机化学, 2020, 40, 2254.) |
| [2] | (c) Tian, X. Q.; Zuo, M. Z.; Niu, P. B.; Wang, Y. K.; Hu, X. Y. Chin. J. Org. Chem. 2020, 40, 1823. (in Chinese) |
| [2] | ( 田雪琪, 左旻瓒, 牛蓬勃, 王开亚, 胡晓玉, 有机化学, 2020, 40, 1832.) |
| [3] | Li, Z.; Liu, P. C.; Ji, X. F.; Gong, J. Y.; Hu, Y. B.; Wu, W. J.; Wang, X. N.; Peng, H. Q.; Kwok, R. T. K.; Lam, J. W. Y.; Lu, J.; Tang, B. Z. Adv. Mater. 2020, 1906493. |
| [4] | Liu, H. C.; Gu, Y. R.; Dai, Y. X.; Wang, K.; Zhang, S. T.; Chen, G.; Zou, B.; Yang, B. J. Am. Chem. Soc. 2020, 142, 1153. |
| [5] | Feng, W. Q.; Su, Q.; Ma, Y.; Džolić, Z.; Huang, F.; Wang, Z. M.; Chen, S. M.; Tang, B. Z. J. Org. Chem. 2020, 85, 158. |
| [6] | Jia, X. R.; Yu, H. J.; Chen, J.; Gao, W. J.; Fang, J. K.; Qin, Y. S.; Hu, X. K.; Shao, G. Chem. Eur. J. 2018, 24, 19053. |
| [7] | Chen, M.; Chen, R.; Shi, Y.; Wang, J. G; Cheng, Y. H.; Li, Y; Gao, X. D.; Yan, Y.; Sun, J. Z.; Qin, A. J.; Kwok, R. T. K.; Lam, J. W. Y.; Tang, B. Z. Adv. Funct. Mater. 2018, 28, 1704689. |
| [8] | Pan, L. X.; Wu, H. Z.; Liu, J. K.; Xue, K. Q.; Luo, W. W.; Chen, P.; Wang, Z. M.; Qin, A. J.; Tang, B. Z. Adv. Optical Mater. 2019, 7, 1801673. |
| [9] | Situ, B.; Chen, S. J.; Zhao, E. G.; Leung, C. W. T.; Chen, Y. L.; Hong, Y. N.; Lam, J. W. Y.; Wen, Z. L.; Liu, W.; Zhang, W. Q; Zheng, L.; Tang, B. Z. Adv. Funct. Mater. 2016, 26, 7132. |
| [10] | Niu, G. L.; Zhang, R. Y.; Shi, X. J.; Park, H.; Xie, S.; Kwok, R. T. K.; Lam, J. W. Y.; Tang, B. Z. Trends Anal. Chem. 2020, 123, 115769. |
| [11] | Guo, X. M.; Yuan, P. S.; Qiao, X. F.; Yang, D. Z.; Dai, Y. F.; Sun, Q.; Qin, A. J.; Tang, B. Z.; Ma, D. G. Adv. Funct. Mater. 2020, 30, 1908704. |
| [12] | Wang, Y. F.; Zhang, Y. X.; Wang, J. J.; Liang, X. J. Adv. Drug Delivery Rev. 2019, 143, 161. |
| [13] | Tian, H.; Yang, S. J. Chem. Soc. Rev. 2004, 33, 85. |
| [14] | Abdollahi, A.; Mamaqani, H. R.; Razavi, B. Prog. Polym. Sci. 2019, 98, 101149. |
| [15] | Zhang, J. J.; Wang, J. X.; Tian, H. Mater. Horiz. 2014, 1, 169. |
| [16] | Kuroiwa, H.; Inagaki, Y.; Mutoh, K.; Abe, J. Adv. Mater. 2019, 31, 1805661. |
| [17] | Zhang, C.; Zhou, H. P.; Liao, L. Y.; Feng, W.; Sun, W.; Li, Z. X.; Xu, C. H.; Fang, C. J.; Sun, L. D.; Zhang, Y. W.; Yan, C. H. Adv. Mater. 2010, 22, 633. |
| [18] | Corredor, C. C.; Huang, Z. L.; Belfield, K. D.; Morales, A. R.; Bondar, M. V. Chem. Mater. 2007, 19, 5165. |
| [19] | Wang, J. X.; Gao, Y.; Zhang, J. J.; Tian, H. J. Mater. Chem. C 2017, 5, 4571. |
| [20] | Cheng, S. J.; Guo, Z. Q.; Zhu, S. Q.; Shi, W. E.; Zhu, W. H. ACS Appl. Mater. Interfaces 2013, 5, 5623. |
| [21] | 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. |
| [22] | Ma, L. W.; Li, C. P.; Yan, Q.; Wang, S.; Miao, W. G.; Cao, D. R. Chin. Chem. Lett. 2020, 31, 361. |
| [23] | An, B. K.; Kwon, S. K.; Jung, S. D.; Park, S. Y. J. Am. Chem. Soc. 2002, 124, 14410. |
| [24] | An, B. K.; Lee, D. S.; Lee, J. S.; Park, Y. S.; Song, H. S.; Park, S. Y. J. Am. Chem. Soc. 2004, 126, 10232. |
| [25] | Lim, S. J.; An, B. K.; Jung, S. D.; Chung, M. A.; Park, S. Y. Angew. Chem., nt. Ed. 2004, 43, 6346. |
| [26] | Wang, S.; Wang, F.; Li, C. P.; Li, T.; Cao, D. R.; Ma, X. Sci. China Chem. 2018, 61, 1301. |
| [27] | Tu, Z. Z.; Zhang, Q.; Xu, X. X.; Wang, L. H.; Qian, Y.; Huang, W. RSC Adv. 2019, 9, 4812. |
| [28] | Chen, S. J.; Li, W. L.; Li, X.; Zhu, W. H. J. Mater. Chem. C 2017, 5, 2717. |
| [29] | Wu, B.; Xue, T. H.; Wang, W.; Li, S.; Shen, J. J.; He, Y. N. J. Mater. Chem. C 2018, 6, 8538. |
| [30] | Liu, G. X.; Zhang, Y. M.; Zhang, L.; Wang, C. H.; Liu, Y. ACS Appl. Mater. Interfaces 2018, 10, 12135. |
| [31] | Chen, L. L.; Zhang, J. Q.; Wang, Q. C.; Zou, L. Dyes Pigm. 2015, 123, 112. |
| [32] | Huang, G. X.; Xia, Q.; Huang, W. B.; Tian, J. W.; He, Z. K.; Li, B. S.; Tang, B. Z. Angew. Chem., nt. Ed. 2019, 58, 17814. |
| [33] | Ou, D. P.; Yu, T.; Yang, Z. Y.; Luan, T. G.; Mao, Z.; Zhang, Y.; Liu, S. W.; Xu, J. R.; Chi, Z. G.; Bryce, M. R. Chem. Sci. 2016, 7, 5302. |
| [34] | Yu, T.; Ou, D. P.; Wang, L. Y.; Zheng, S. Z.; Yang, Z. Y.; Zhang, Y.; Chi, Z. G.; Liu, S. W.; Xu, J. R.; Aldred, M. P. Mater. Chem. Front. 2017, 1, 1900. |
| [35] | He, Z. K.; Shan, L.; Mei, J.; Wang, H.; Lam, J. W. Y.; Sung, H. H. Y.; Williams, I. D.; Gu, X.; Miao, Q.; Tang, B. Z. Chem. Sci. 2015, 6, 3538. |
| [36] | Luo, Q. F.; Cao, F.; Xiong, C. C.; Dou, Q. Y.; Qu, D. H. J. Org. Chem. 2017, 82, 10960. |
| [37] | Wang, C.; Yan, L. Y.; Ding, W.; Luo, Q. F. Dyes Pigm. 2020, 177, 108264. |
| [38] | Cho, H.; Kim, E. Macromolecules 2002, 35, 8684. |
| [39] | Lim, S. J.; An, B. K.; Park, S. Y. Macromolecules 2005, 38, 6236. |
| [40] | Li, J.; Tian, M.; Xu, H. F.; Ding, X. K.; Guo, J. B. Part. Part. Syst. Charact. 2019, 36, 1900346. |
| [41] | Sinawang, G.; Wang, J. L.; Wu, B.; Wang, X. G.; He, Y. L. RSC Adv. 2016, 6, 12647. |
| [42] | Singh, R.; Wu, H. Y.; Dwivedi, A. K.; Singh, A.; Lin, C. M.; Raghunath, P.; Lin, M. C.; Wu, T. K.; Wei, K. H.; Lin, H. C. J. Mater. Chem. C. 2017, 5, 9952. |
| [43] | Ma, L. W.; Wang, S.; Li, C. P.; Cao, D. R.; Li, T.; Ma, X. Chem. Commun. 2018, 54, 2405. |
| [44] | Chung, J. W.; Yoon, S. J.; Lim, S. J.; An, B. K.; Park, S. Y. Angew. Chem., nt. Ed. 2009, 48, 7030. |
| [45] | Kim, D. J.; Kwon, J. E.; Park, S. Y. Adv. Funct. Mater. 2018, 28, 1706213. |
| [46] | Qi, Q. K.; Qian, J. Y.; Ma, S. Q.; Xu, B.; An-Zhang, S. X.; Tian, W. J. Chem. Eur. J. 2015, 21, 1149. |
| [47] | Wu, Z.; Pan, K.; Mo, S. Z.; Wang, B. J.; Zhao, X. J.; Yin, M. Z. ACS Appl. Mater. Interfaces 2018, 10, 30879. |
| [48] | Wang, L. Y.; Xiong, W.; Tang, H.; Cao, D. R. J. Mater. Chem. C 2019, 7, 9102. |
| [49] | Hong, Y. X.; Zhang, P. S.; Wang, H.; Yu, M. L.; Gao, Y.; Chen, J. Sens. Actuators, B 2018, 272, 340. |
| [50] | 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. |
| [51] | Peng, S. C.; Wen, J. H.; Hai, M. T.; Yang, Z.; Yuan, X. T.; Wang, D.; Cao, H.; He, W. L. New J. Chem. 2019, 43, 617. |
| [52] | Huang, L. L.; Qiu, Y. X.; Wu, C. Y.; Ma, Z. Y.; Shen, Z. H.; Jia, X. R. J. Mater. Chem. C 2018, 6, 10250. |
| [53] | Zhong, W. B.; Zeng, X. Y.; Chen, J.; Hong, Y. X.; Xiao, L. H.; Zhang, P. S. Polym. Chem. 2017, 8, 4849. |
| [54] | Ji, J. K.; Li, X.; Wu, T. T.; Feng, F. D. Chem. Sci. 2018, 9, 5816. |
| [55] | Bhattacharyya, S.; Chowdhury, A.; Saha, R.; Mukherjee, P. S. Inorg. Chem. 2019, 58, 3968. |
| [56] | Chen, Q.; Zhang, D. Q.; Zhang, G. X.; Yang, X. Y.; Feng, Y.; Fan, Q. H.; Zhu, D. B. Adv. Funct. Mater. 2010, 20, 3244. |
| [57] | Zeng, Z. Q.; Wu, J. C.; Chen, Q. J.; Shi, Y. C.; Zheng, J. M.; Xu, C. Y. Dyes Pigm. 2019, 170, 107649. |
| [58] | Wang, L. L.; Li, Y. Y.; You, X. J.; Xu, K.; Feng, Q.; Wang, J. M.; Liu, Y. Y.; Li, K.; Hou, H. W. J. Mater. Chem. C 2017, 5, 65. |
| [59] | Sun, H.; Li, J. Y.; Han, F. F.; Zhang, R.; Zhao, Y.; Miao, B. X.; Ni, Z. H. Dyes Pigm. 2019, 167, 143. |
| [60] | Chai, J.; Wu, Y. B.; Yang, B. S.; Liu, B. J. Mater. Chem. C 2018, 6, 4057. |
| [61] | Liu, X. D.; Li, A. S.; Xu, W. Q.; Ma, Z. Y.; Jia, X. R. Mater. Chem. Front. 2019, 3, 620. |
| [62] | Ning, T. Z.; Liu, L.; Jia, D. Z.; Xie, X. L.; Wu, D. L. J. Photochem. Photobiol.,A 2014, 291, 48. |
| [63] | Abe, I.; Hara, M.; Seki, T.; Cho, S. J.; Shimizu, M.; Matsuura, K.; Cheong, H. K.; Kim, J. Y.; Oh, J.; Jung, J.; Han, M. J. Mater. Chem. C 2019, 7, 2276. |
| [64] | Abe, I.; Han, M. New J. Chem. 2019, 43, 19014. |
| [65] | Yu, X.; Chen, H.; Shi, X.; Albouy, P. A.; Guo, J.; Hu, J.; Li, M. H. Mater. Chem. Front. 2018, 2, 2245. |
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