Chinese Journal of Organic Chemistry >
Research Progress of Aggregation-Caused Quenching (ACQ) to Aggregation-Induced Emission (AIE) Transformation Based on Organic Small Molecules
Received date: 2022-01-05
Revised date: 2022-01-25
Online published: 2022-02-18
Supported by
Guangdong Basic and Applied Basic Research Foundation(2021A1515012342); Guangdong Provincial Science and Technology Project(2017A010103016)
Most of the traditional organic fluorescent molecules have notorious aggregation-induced quenching (ACQ) effect, which limits their application in many fields. Therefore, how to achieve the transition from ACQ to aggregation-induced emission (AIE) while maintaining the functional properties of traditional conjugated molecules is of great significance. In recent years, many research groups have done a lot of breakthrough works in this field. According to the construction method and structural characteristics of AIE luminogen (AIEgen), the ACQ to AIE transformation strategy can be divided into two types. Based on the restriction of intramolecular motion (RIM) mechanism, the first one is to decorate ACQphore with typical AIEgen (e.g. tetraphenylethene unit). As the second one, some functional units (e.g. triphenylamine and cyanoethylene moiety) are introduced to realize the construction of AIE molecules from zero starting point as the RIM mechanism. In the latter, the construction of other AIEgen systems involving isomerism and excited-state intramolecular proton transfer (ESIPT) mechanisms has also been prominent recently. Thus, according to these classifications, the new progress on the construction strategy of ACQ-to-AIE transformation in the past five years is summarized from the four aspects of AIEgens’ structure, performance, mechanism and application.
Sihong Chen , Jiamin Xu , Yuemei Li , Baoru Peng , Lingyu Luo , Huiye Feng , Zhaohua Chen , Zhaoyang Wang . Research Progress of Aggregation-Caused Quenching (ACQ) to Aggregation-Induced Emission (AIE) Transformation Based on Organic Small Molecules[J]. Chinese Journal of Organic Chemistry, 2022 , 42(6) : 1651 -1666 . DOI: 10.6023/cjoc202201007
| [1] | Luo, J. D.; Xie, Z. L.; Lam, J. W. Y.; Cheng, L.; Chen, H. Y.; Qiu, C. F.; Kwok, H. S.; Zhan, X. W.; Liu, Y. Q.; Zhu, D. B.; Tang, B. Z. Chem. Commun. 2001, 18, 1740. |
| [2] | Mei, J.; Leung, N. L. C.; Kwok, R. T. K.; Lam, J. W. Y.; Tang, B. Z. Chem. Rev. 2015, 115, 11718. |
| [3] | Kenry; Tang, B.; Liu, B. Chem 2020, 6, 1195. |
| [4] | Wang, B.-W.; Jiang, K.; Li, J.-X.; Luo, S. H.; Wang, Z.-Y.; Jiang, H.-F. Angew. Chem., Int. Ed. 2020, 59, 2338. |
| [5] | Wang, Y. J.; Nie, J. Y.; Fang, W.; Yang, L.; Hu, Q. L.; Wang, Z. K.; Sun, J. Z.; Tang, B. Z. Chem. Rev. 2020, 120, 4534. |
| [6] | Mei, J.; Hong, Y. N.; Lam, J. W. Y.; Qin, A. J.; Tang, Y. H.; Tang, B. Z. Adv. Mater. 2014, 26, 5429 |
| [7] | Liu, Y. Y.; Zhang, X.; Li, K.; Peng, Q. C.; Qin, Y. J.; Hou, H. W.; Zang, S. Q.; Tang, B. Z. Angew. Chem., Int. Ed. 2021, 60, 22417. |
| [8] | Oshchepkov, A. S.; Oshchepkov, M. S.; Oshchepkova, M. V.; Al-Hamry, A.; Kanoun, O.; Kataev, E. A. Adv. Opt. Mater. 2021, 9, 2001913. |
| [9] | Singh, V. D.; Dwivedi, B. K.; Kumar, Y.; Pandey, D. S. Dyes Pigm. 2021, 184, 108812. |
| [10] | Chen, H.; Fan, Y. J.; Zhang, N.; Trepout, S.; Ptissam, B.; Brulet, A.; Tang, B. Z.; Li, M. H. Chem. Sci. 2021, 12, 5495. |
| [11] | Li, Z. Z.; Huo, Y. P.; Yang, X. H.; Ji, S. M. Chin. J. Org. Chem. 2016, 36, 2317. (in Chinese) |
| [11] | ( 李宗植, 霍延平, 阳香华, 籍少敏, 有机化学, 2016, 36, 2317.) |
| [12] | Chen, Y. X.; Min, X. H.; Zhang, X. Q.; Zhang, F. L.; Lu, S. M.; Xu, L. P.; Lou, X. D.; Xia, F.; Zhang, X. J.; Wang, S. T. Biosens. Bioelectron. 2018, 111, 124. |
| [13] | Huang, Y. L.; Bisoyi, H. K.; Li, Q. Angew. Chem., Int. Ed. 2021, 60, 11247. |
| [14] | Ma, X. X.; Chi, W. J.; Han, X.; Wang, C.; Liu, S. H.; Liu, X. G.; Yin, J. Chin. Chem. Lett. 2021, 32, 1790. |
| [15] | Yang, J.; Qin, J. W.; Ren, Z. C.; Peng, Q.; Xie, G. H.; Li, Z. Molecules 2017, 22, 2144. |
| [16] | Feng, X.; Qi, C. X.; Feng, H. T.; Zhao, Z.; Sung, H. H. Y.; Williams, I. D.; Kwok, R. T. K.; Lam, J. W. Y.; Qin, A. J.; Tang, B. Z. Chem. Sci. 2018, 9, 5679. |
| [17] | Feng, X.; Xu, Z.; Hu, Z.; Qi, C. X.; Luo, D. X.; Zhao, X. Y.; Mu, Z. F.; Redshaw, C.; Lam, J. W. Y.; Ma, D. G.; Tang, B. Z. J. Mater. Chem. C 2019, 7, 2283. |
| [18] | Yang, X. L.; Zhao, Z.; Ran, H. J.; Zhang, J. L.; Chen, L. J.; Han, R. J.; Duan, X. W.; Sun, H. M.; Hu, J.-Y. Dyes Pigm. 2020, 173, 107881. |
| [19] | Xie, F. L.; Ran, H. J.; Duan, X. W.; Han, R. J.; Sun, H. M.; Hu, J.-Y. J. Mater. Chem. C 2020, 8, 17450. |
| [20] | Chen, S.-H.; Jiang, K.; Xiao, Y.; Cao, X.-Y.; Arulkumar, M.; Wang, Z.-Y. Dyes Pigm. 2020, 175,108157. |
| [21] | Chen, S.-H.; Luo, S.-H.; Xing, L.-J.; Jiang, K.; Huo, Y.-P.; Chen, Q.; Wang, Z.-Y. Chem.-Eur. J. 2022, 28, e202103478. |
| [22] | Tao, T.; Zhao, J. G.; Fan, B.; Chen, Z. L.; Sun, J. W. Dyes Pigm. 2020, 177, 108277. |
| [23] | Zhang, J. S.; Bai, Y. Q.; Wei, Q.; Cao, L.; Wang, T.; Ge, Z. Y. J. Mater. Chem. C 2020, 8. 11771. |
| [24] | Wang, Z. B.; Peng, Z. X.; Huang, K.; Lu, P.; Wang, Y. G. J. Mater. Chem. C 2019, 7, 6706. |
| [25] | Liang, A. H.; Wang, H.; Chen, Y.; Zheng, X. Y.; Cao, T.; Yang, X. L.; Cai, P.; Wang, Z. P.; Zhang, X. W.; Huang, F. Dyes Pigm. 2018, 149, 399. |
| [26] | Yan, Y. H.; Laine, R. M.; Liu, H. Z. Chem. Sci. 2018, 9, 6118. |
| [27] | Qin, W.; Li, K.; Feng, G.; Li, M.; Yang, Z.; Liu, B.; Tang, B. Z. Adv. Funct. Mater. 2014, 24, 635. |
| [28] | Ying, F. P.; Lu, H. S.; Yi, X. Q.; Xu, Y. Q.; Lv, Y. Y. Sens. Actuators, B 2021, 340, 129997. |
| [29] | Zhang, Y. P.; Zhao, Y. Q.; Han, Z. G.; Zhang, R. Z.; Du, P. Y.; Wu, Y. X.; Lu, X. Q. Angew. Chem., Int. Ed. 2020, 59, 23261. |
| [30] | Qi, Y. P.; Wang, Y. T.; Ge, G. X.; Liu, Z. Y.; Yu, Y. J.; Xue, M. J. Mater. Chem. C 2017, 5, 11030. |
| [31] | Liu, W. W.; Yu, H. K.; Hu, R. R.; Xu, T.; Lun, Y. P.; Gan, J. L.; Xu, S. H.; Yang, Z. M.; Tang, B. Z. Small 2020, 16, 1907074. |
| [32] | Ma, L. W.; Li, C. P.; Yan, Q.; Wang, S.; Miao, W. G.; Cao, D. R. Chin. Chem. Lett. 2020, 31, 361. |
| [33] | Wang, N.; Zhang, J.; Xu, X. D.; Feng, S. Y. Dalton Trans. 2020, 49, 1883. |
| [34] | Zheng, X. J.; Zhu, W. C.; Zhang, C.; Zhang, Y.; Zhong, C.; Li, H.; Xie, G. H.; Wang, X. J.; Yang, C. L. J. Am. Chem. Soc. 2019, 141, 4704. |
| [35] | 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. |
| [36] | Li, X. Q.; Gu, J. P.; Zhou, Z.; Liu, W. Q.; Gao, J. W.; Wang, Q. M. Dyes Pigm. 2020, 172, 107844. |
| [37] | Guan, Q. H.; Li, N.; Shi, L. L.; Yu, C. Y.; Gao, X. H.; Yang, J. P.; Guo, Y. Y.; Li, P. Y.; Zhu, X. ACS Biomater. Sci. Eng. 2019, 5, 3618. |
| [38] | Huang, R. R.; Liu, H. J.; Liu, K.; Wang, G.; Liu, Q.; Wang, Z. L.; Liu, T. H.; Miao, R.; Peng, H. N.; Fang, Y. Anal. Chem. 2019, 91, 14451. |
| [39] | Wang, X. X.; Ding, Z. Y.; Ma, Y.; Zhang, Y. P.; Shang, H. X.; Jiang, S. M. Soft Matter 2019, 15, 1658. |
| [40] | Li, Y.; Liu, Y. F.; Li, Q. Q.; Zeng, X. D.; Tian, T.; Zhou, W. Y.; Cui, Y.; Wang, X. K.; Cheng, X. D.; Ding, Q. H.; Wang, X. F.; Wu, J. Z.; Deng, H.; Li, Y. Q.; Meng, X. L.; Deng, Z. X.; Hong, X. C.; Xiao, Y. L. Chem. Sci. 2020, 11, 2621. |
| [41] | Peng, Z. X.; Huang, K.; Tao, Y. H.; Li, X. H.; Zhang, L. P.; Lu, P.; Wang, Y. G. Mater. Chem. Front. 2017, 1, 1858. |
| [42] | Roy, B.; Mengji, R.; Roy, S.; Pal, B.; Jana, A.; Singh, N. D. P. ACS Appl. Mater. Interfaces 2022, 14, 4862. |
| [43] | Song, F. Y.; Zhang, C. H.; Dong, H. Y.; Fan, Y. Q.; Wu, M. Y.; Shan, G. G.; Lai, P. X.; Gao, H.; Zhao, Y. S.; Chen, S. J. J. Mater. Chem. C 2021, 9, 11180. |
| [44] | Wu, M. Y.; Leung, J. K.; Kam, C.; Chou, T. Y.; Wang, D.; Feng, S.; Chen, S. J. Mater. Chem. Front. 2021, 5, 3043. |
| [45] | Zhang, S. S.; Mei, J. New J. Chem. 2021, 45, 19118. |
| [46] | Caruso, U.; Panunzi, B.; Diana, R.; Concilio, S.; Sessa, L.; Shikler, R.; Nabha, S.; Tuzi, A.; Piotto, S. Molecules 2018, 23, 1947. |
| [47] | Zhang, X. Y.; Qin, W. W.; Cheng, B. F.; Guo, H. Y.; Yang, F. F. J. Mol. Liq. 2020, 298, 112074. |
| [48] | Nie, H. L.; Liang, Y. H.; Han, C.; Zhang, R. B.; Zhang, X. L.; Yan, H. Y. Dyes Pigm. 2019, 168, 42. |
| [49] | Ren, F.; Liu, Z. Q.; Lei, Y. X.; Dai, W. B.; Shi, J. B.; Cai, Z. X.; Tong, B.; Dong, Y. P. Dyes Pigm. 2021, 188, 109222. |
| [50] | Zhang, Y. B.; Yan, Y. N.; Xia, S.; Wan, S. L.; Steenwinkel, T. E.; Medford, J.; Durocher, E.; Luck, R. L.; Werner, T.; Liu, H. Y. ACS Appl. Mater. Interfaces 2020, 12, 20172. |
| [51] | Kong, X. Q.; Li, M.; Zhang, Y. Y.; Yin, Y. G.; Lin, W. Y. Sens. Actuators, B 2021, 329, 129232. |
| [52] | Zhu, M. G.; Chen, Y. X.; Zhang, X. Y.; Chen, M. H.; Guo, H. Y.; Yang, F. F. Soft Matter 2018, 1, 6737. |
| [53] | Han, C. Y.; Jiang, S. J.; Qiu, J. B.; Guo, H. Y.; Yang, F. F. New J. Chem. 2019, 43, 3317. |
| [54] | Niu, G. L.; Zheng, X. L.; Zhao, Z.; Zhang, H. K.; Wang, J. G.; He, X. W.; Chen, Y. C.; Shi, X. J.; Ma, C.; Kwok, R. T. K.; Lam, J. W. Y.; Sung, H. H. Y.; Williams, I. D.; Wong, K. S.; Wang, P. F.; Tang, B. Z. J. Am. Chem. Soc. 2019, 141, 15111. |
| [55] | Tarai, A.; Huang, M. N.; Das, P.; Pan, W. H.; Zhang, J. G.; Gu, Z. Y.; Yan, W.; Qu, J. L.; Yang, Z. G. Molecules 2020, 25, 585. |
| [56] | Peng, L.; Xu, S. D.; Zheng, X. K.; Cheng, X. M.; Zhang, R. Y.; Liu, J.; Liu, B.; Tong, A. J. Anal. Chem. 2017, 89, 3162. |
| [57] | Wang, K.; Su, H.; Wang, P. F.; Wang, W. J.; Li, H. RSC Adv. 2019, 9, 14268. |
| [58] | Qin, W.; Alifu, N.; Lam, J. W. Y.; Cui, Y. H.; Su, H. F.; Liang, G. D.; Qian, J.; Tang, B. Z. Adv. Mater. 2020, 32, 2000364. |
| [59] | Lv, Z.; Man, Z. W.; Cui, H. T.; Xu, Z. Z.; Cao, H. H.; Li, S.; Liao, Q.; He, Q. H.; Zheng, L. M.; Fu, H. B. Adv. Funct. Mater. 2021, 31, 2009329. |
| [60] | Yan, Y. H.; Laine, R. M.; Liu, H. Z. ChemPlusChem 2019, 84, 1630. |
| [61] | Yan, L. Q.; Xie, Y.; Li, J. P.; Zhu, W. Y. Spectrochim. Acta A 2020, 228, 117794. |
| [62] | Qiu, J. B.; Chen, Y. X.; Jiang, S. J.; Guo, H. Y.; Yang, F. F. Analyst 2018, 143, 4298. |
| [63] | Xiao, F. M.; Wang, M. Z.; Lei, Y. X.; Xie, Y. F.; Liu, M. C.; Zhou, Y. B.; Gao, W. X.; Huang, X. B.; Wu, H. Y. Chem.-Asian J. 2020, 15, 3437. |
| [64] | Fu, W.; Yan, C. X.; Zhang, Y. T.; Ma, Y. Y.; Guo, Z. Q.; Zhu, W. H. Front. Chem. 2019, 7, 291. |
| [65] | Guo, Z. Q.; Yan, C. X.; Zhu, W.-H. Angew. Chem., Int. Ed. 2020, 59, 9812. |
| [66] | Han, X. J.; Yang, X. P.; Zhang, Y. R.; Li, Z. P.; Cao, W. B.; Zhang, D.; Ye, Y. Sens. Actuators, B 2020, 32, 128510. |
| [67] | Nishino, K.; Uemura, K.; Gon, M.; Tanaka, K.; Chujo, Y. Molecules 2017, 22, 2009. |
| [68] | Liu, X.; Li, M. W.; Liu, M. F.; Yang, Q. H.; Chen, Y. L. Chem.-Eur. J. 2018, 24, 13197. |
| [69] | Zuo, B.; Liu, L.; Feng, X. C.; Li, D. H.; Li, W. F.; Huang, M. X.; Deng, Q. Y. Dyes Pigm. 2021, 193, 109534. |
| [70] | Wang, L. F.; Qian, Y. Dyes Pigm. 2021, 198, 110018. |
| [71] | Chen, S.-H.; Chen, Q.; Luo, S.-H.; Cao, X.-Y.; Yang, G.-X.; Zeng, X.-Q.; Wang, Z.-Y. Chin. J. Org. Chem. 2021, 41, 919. (in Chinese) |
| [71] | ( 陈思鸿, 陈淇, 罗时荷, 曹西颖, 杨国贤, 曾晓晴, 汪朝阳, 有机化学, 2021, 41, 919.) |
| [72] | Nirmalananthan-Budau, N.; Budau, J. H.; Moldenhauer, D.; Hermann, G.; Kraus, W.; Hoffmann, K.; Paulus, B.; Resch-Genger, U. Phys. Chem. Chem. Phys. 2020, 22, 14142. |
| [73] | Wang, D.-H.; Chen, L.-J.; Zhao, X.; Yan, X.-P. Talanta 2021, 225, 122046. |
| [74] | Zhang, F.; Li, Z.; Liu, Y. M.; Yang, B. S.; Qiao, H.; Chai, J.; Wen, G. M.; Liu, B. J. Mater. Chem. B 2020, 8, 9533. |
| [75] | Liu, C. C.; Wang, X. X.; Liu, J. K.; Yue, Q.; Chen, S. J.; Lam, J. W. Y.; Luo, L.; Tang, B. Z. Adv. Mater. 2020, 32, 2004685. |
| [76] | Peng, C.; Ma, X. Y.; Lin, D.; Feng, X. W.; Yu, H.; Li, Y. H. Anal. Chim. Acta 2021, 1187, 339146. |
| [77] | Liang, A. H.; Wang, H.; Chen, Y.; Zheng, X. Y.; Cao, T.; Yang, X. L.; Cai, P.; Wang, Z. P.; Zhang, X. W.; Huang, F. Dyes Pigm. 2018, 149, 399. |
| [78] | Wan, Q.; Zhang, R. Y.; Zhuang, Z. Y.; Li, Y. X.; Huang, Y. H.; Wang, Z. M.; Zhang, W. J.; Hou, J. Q.; Tang, B. Z. Adv. Funct. Mater. 2020, 30, 2002057. |
| [79] | Jiang, M. J.; Gu, X. G.; Lam, J. W. Y.; Zhang, Y. L.; Kwok, R. T. K.; Wong, K. S.; Tang, B. Z. Chem. Sci. 2017, 8, 5440. |
| [80] | Hwang, T. G.; Kim, G. Y.; Han, J. I.; Kim, S.; Kim, J. P. ACS Sustainable Chem. Eng. 2020, 8,15888. |
| [81] | Zhang, K. M.; Shu, J.; Chu, W. D.; Liu, X. Q.; Xu, B.; Jiang, W. D. Dyes Pigm. 2021, 185, 108898. |
| [82] | Luo, Q. F.; Cao, F.; Xiong, C. C.; Dou, Q. Y.; Qu, D. H. J. Org. Chem. 2017, 82, 10960. |
| [83] | Adil, L. R.; Iyer, P. K. Chem. Commun. 2020, 56, 7633. |
| [84] | Monika, Verma, A.; Verma, S.; Pandey, N.; Tilak, R.; Saha, S. New J. Chem. 2020, 44, 14116. |
| [85] | Li, Y. Y.; Liu, S. J.; Ni, H. W.; Zhang, H.; Zhang, H. Q.; Chuah, C.; Ma, C.; Wong, K. S.; Lam, J. W. Y., Kwok, R. T. K.; Qian, J.; Lu, X. F.; Tang, B. Z. Angew. Chem., Int. Ed. 2020, 59, 12822. |
| [86] | Dong, L. C.; Shang, G. J.; Shi, J. B.; Zhi, J. G.; Tong, B.; Dong, Y. P. J. Phys. Chem. C 2017, 121, 11658. |
| [87] | Zhang, H. Y.; Zhang, H.; Huang, G. X.; Li, B. S. Dyes Pigm. 2021, 185, 108947. |
| [88] | Pratihar, S.; Bhattacharyya, A.; Prasad, E. J. Photochem. Photobiol. A 2020, 396, 112458. |
| [89] | Padalkar, V. S.; Seki, S. Chem. Soc. Rev. 2016, 45, 169. |
| [90] | Sedgwick, A. C.; Wu, L. L.; Han, H.-H.; Bull, S. D.; He, X.-P.; James, T. D.; Sessler, J. L.; Tang, B. Z.; Tian, H.; Yoon, J. Chem. Soc. Rev. 2018, 47, 8842. |
| [91] | Huang, X. Y.; Lei, Q.; Huang, S.; Zeng, H. L.; Feng, B.; Zeng, Q. H.; Hu, Y. B.; Zeng, W. B. Chem. Commun. 2021, 57, 6608. |
| [92] | Bhosle, A. A.; Hiremath, S. D.; Bhasikuttan, A. C.; Banerjee, M.; Chatterjee, A. J. Photochem. Photobiol. A 2021, 413, 113265. |
| [93] | Huang, L.; Cao, X. Z.; Gao, T.; Feng, B.; Huang, X. Y.; Song, R.; Du, T.; Wen, S. J.; Feng, X. P.; Zeng, W. B. Talanta 2021, 225, 121950. |
| [94] | Zhang, K. X.; Hu, R.; Wang, Z. M.; Tang, B. Z. Mater. Chem. Front. 2021, 5, 2724. |
| [95] | Wang, Q.; Chen, Q. Q.; Li, C. B.; Lai, Q. F.; Zou, F. L.; Liang, F.; Jiang, G. Y.; Wang, J. G. Microchem. J. 2020, 153, 104503. |
| [96] | Jiang, J.; Sun, H. F.; Hu, Y. L.; Lu, G.; Cui, J. W.; Hao, J. C. Chem. Commun. 2021, 57, 7685. |
| [97] | Li, S. W.; Ling, X.; Lin, Y. H.; Qin, A. J.; Gao, M.; Tang, B. Z. Chem. Sci. 2018, 9, 5730. |
| [98] | Niu, Y. H.; Wang, R.; Pu, L.; Zhang, Y. R. Dyes Pigm. 2019, 170, 107594. |
| [99] | Wu, H. R.; Wang, S. W.; Ding, J.; Wang, R.; Zhang, Y. R. Dyes Pigm. 2020, 170, 107556. |
| [100] | Cheng, X.; Huang, S.; Lei, Q.; Chen, F.; Zheng, F.; Zhong, S.; Huang, X. Y.; Feng, B.; Feng, X. P.; Zeng, W. B. Chin. Chem. Lett. 2022, DOI: 10.1016/j.cclet.2021.10.024. |
| [101] | Liu, M.; Xiao, R. S.; Feng, B.; Fan, D. Y.; Huang, S.; Bi, A. Y.; Zhong, S. B.; Feng, X. P.; Liu, S.; Zeng, W. B. Sens. Actuators, B 2021, 342, 130038. |
| [102] | Li, S. W.; Gao, M.; Wang, S. X.; Hu, R. R.; Zhao, Z. J.; Qin, A. J.; Tang, B. Z. Chem. Commun. 2017, 53, 4795. |
| [103] | Petdee, S.; Chaiwai, C.; Benchaphanthawee, W.; Nalaoh, P.; Kungwan, N.; Namuangruk, S.; Sudyoadsuk, T.; Promarak, V. Dyes Pigm. 2021, 193,109488. |
| [104] | Peng, L.; Xiao, L.; Ding, Y. W.; Xiang, Y.; Tong, A. J. J. Mater. Chem. B 2018, 6, 3922. |
| [105] | Shen, Y. M.; Li, M. Y.; Yang, M.; Zhang, Y. Y.; Li, H. T.; Zhang, X. Y. Spectrochim. Acta A 2019, 222, 117230. |
| [106] | Song, H. H.; Zhou, Y. M.; Qu, H. N.; Xu, C. G.; Wang, X.; Liu, X. Q.; Zhang, Q. Y.; Peng, X. J. Ind. Eng. Chem. Res. 2018, 57, 15216. |
| [107] | Li, K.; Wang, J. M.; Li, Y. Y.; Si, Y.; He, J.; Meng, X. R.; Hou, H. W.; Tang, B. Z. Sens. Actuators, B 2018, 274, 654. |
| [108] | Wang, Z. L.; Yang, J. L.; Yang, Y. Q.; Xu, X.; Li, M. X.; Zhang, Y.; Fang, H.; Xu, H. J.; Wang, S. F. Chin. J. Org. Chem. 2018, 38, 1401. (in Chinese) |
| [108] | ( 王忠龙, 杨金来, 杨益琴, 徐徐, 李明新, 张燕, 方华, 徐海军, 王石发, 有机化学, 2018, 38, 1401.) |
| [109] | Singh, H.; Sharma, R.; Bhargava, G.; Kumar, S.; Singh, P. New J. Chem. 2018, 42, 12900. |
| [110] | Dai, F. F.; Zhao, M.; Yang, F. Z.; Wang, T. T.; Wang, C. Dyes Pigm. 2020, 183, 108627. |
| [111] | Long, R. Q.; Tang, C.; Yang, Z.; Fu, Q. C.; Xu, J. J.; Tong, C. Y.; Shi, S. Y.; Guo, Y.; Wang, D. J. J. Mater. Chem. C 2020, 8, 11860. |
| [112] | Yin, W.; Li, Y.; Li, N.; Yang, W. Y.; An, H.; Gao, J. R.; Bi, Y.; Zhao, N. Adv. Opt. Mater. 2020, 8, 1902027. |
| [113] | Fang, W.; Liu, K.; Wang, G.; Liang, Y. Z.; Huang, R. R.; Liu, T. H.; Ding, L. P.; Peng, J. X.; Peng, H. N.; Fang, Y. Anal. Chem. 2021, 93, 8501. |
| [114] | Choi, S. K.; Rho, J.; Yoon, S. E.; Seok, J. H.; Kim, H.; Min, J.; Yoon, W.; Lee, S.; Yun, H.; Kwon, O. P.; Kim, J. H.; Kim, W.; Kim, E. Bioconjugate Chem. 2020, 31, 2522. |
| [115] | Moreno-Alcantar, G.; Aliprandi, A.; De, Cola, L. Top. Curr. Chem. 2021, 379, 31. |
| [116] | Xing, C.; Liu, J. X.; Chen, F.; Li, Y. Y.; Lv, C. J.; Peng, Q. C.; Hou, H. W.; Li, K. Chem. Commun. 2020, 56, 4220. |
| [117] | Huang, M. M.; Lu, H.; Wang, K.; Liu, B. B.; Wang, M.; Qiao, X. Y.; Yang, J. P. Dyes Pigm. 2021, 186, 108992. |
| [118] | Wang, Y. J.; Nie, J. Y.; Fang, W.; Yang, L.; Hu, Q. L.; Wang, Z. K.; Sun, J. Z.; Tang, B. Z. Chem. Rev. 2020, 120, 4534. |
| [119] | Yang, K.; Chen, Z.-X.; Zhou, Y.-J.; Chen, Q.; Yu, S.-W.; Luo, S.-H.; Wang, Z.-Y. Org. Chem. Front. 2022, 9, 1127. |
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