Research Progress of Aggregation-Caused Quenching (ACQ) to Aggregation-Induced Emission (AIE) Transformation Based on Organic Small Molecules

doi:10.6023/cjoc202201007

Abstract

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.

Key words: aggregation-caused quenching (ACQ), aggregation-induced emission (AIE), restriction of intramolecular motion (RIM), molecular design, synthesis, optical application

Cite this article

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.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 27

Figure 1. Molecular structures of starting material for TPE derivatives

Figure 2. Molecular structures of AIE compounds 2 and 3

Scheme 1. Synthetic route of AIE compounds 5~7

Figure 3. Molecular structures of AIE compounds 8~10

Figure 4. Molecular structures of AIE compounds 12 and 13

Scheme 2. Synthetic route of AIE compound 14

Scheme 3. Synthetic route of AIE compound 15

Figure 5. Molecular structures of ACQ compound 16 and AIE compound 17

Scheme 4. Synthesis routes of AIE compounds 18 and 19

Figure 6. Molecular structures of AIE compounds 21 and 22

Scheme 5. Synthesis routes of ACQ compound 23 and AIE compound 24

Scheme 6. Synthesis routes of AIE compounds 25 and 26

Scheme 7. Synthesis route of AIE compound 27

Figure 7. Molecular structures of ACQ compound 30 and AIE compounds 31~34

Figure 8. Molecular structure of AIE compounds 35~38

Scheme 8. Synthesis routes of AIE compounds 39~41

Scheme 9. Synthesis route to target compound 42

Scheme 10. Synthesis routes of ACQ compound 43 and AIE compound 44

Scheme 11. Synthesis routes of ACQ compound 45 and AIE compound 46

Scheme 12. Synthesis routes of ACQ compound 47 and AIE compound 48

Scheme 13. Synthesis routes of ACQ compound 49 and AIE compound 50

Scheme 14. Synthesis routes of ACQ compound 51 and AIE compound 52

Scheme 15. Synthesis routes of ACQ compound 53 and AIE compounds 54 & 55

Figure 9. Molecular structures of ACQ compounds 56 & 57 and AIE compound 58

Figure 10. Molecular structures of AIE compounds 59 and 60 and their corresponding probes

Scheme 16. Interaction mechanism of compounds 63~65 added with H+ or OH–

Figure 11. Molecular structures of AIE compounds 67~69

References 119

[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. doi: 10.1021/acs.chemrev.5b00263 pmid: 26492387
[3]	Kenry; Tang, B.; Liu, B. Chem 2020, 6, 1195. doi: 10.1016/j.chempr.2020.05.018
[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. doi: 10.1002/anie.201914333
[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. doi: 10.1021/acs.chemrev.9b00814
[6]	Mei, J.; Hong, Y. N.; Lam, J. W. Y.; Qin, A. J.; Tang, Y. H.; Tang, B. Z. Adv. Mater. 2014, 26, 5429 doi: 10.1002/adma.201401356
[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. doi: 10.1002/anie.202108326
[8]	Oshchepkov, A. S.; Oshchepkov, M. S.; Oshchepkova, M. V.; Al-Hamry, A.; Kanoun, O.; Kataev, E. A. Adv. Opt. Mater. 2021, 9, 2001913. doi: 10.1002/adom.202001913
[9]	Singh, V. D.; Dwivedi, B. K.; Kumar, Y.; Pandey, D. S. Dyes Pigm. 2021, 184, 108812. doi: 10.1016/j.dyepig.2020.108812
[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. doi: 10.1039/d1sc00270h pmid: 34163770
[11]	Li, Z. Z.; Huo, Y. P.; Yang, X. H.; Ji, S. M. Chin. J. Org. Chem. 2016, 36, 2317. (in Chinese) doi: 10.6023/cjoc201604023
	( 李宗植, 霍延平, 阳香华, 籍少敏, 有机化学, 2016, 36, 2317.) doi: 10.6023/cjoc201604023
[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. doi: 10.1016/j.bios.2018.04.011
[13]	Huang, Y. L.; Bisoyi, H. K.; Li, Q. Angew. Chem., Int. Ed. 2021, 60, 11247. doi: 10.1002/anie.202101881
[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. doi: 10.1016/j.cclet.2020.12.031
[15]	Yang, J.; Qin, J. W.; Ren, Z. C.; Peng, Q.; Xie, G. H.; Li, Z. Molecules 2017, 22, 2144. doi: 10.3390/molecules22122144
[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. doi: 10.1039/C8SC01709C
[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. doi: 10.1039/C8TC05547E
[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. doi: 10.1016/j.dyepig.2019.107881
[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. doi: 10.1039/D0TC04557H
[20]	Chen, S.-H.; Jiang, K.; Xiao, Y.; Cao, X.-Y.; Arulkumar, M.; Wang, Z.-Y. Dyes Pigm. 2020, 175,108157. doi: 10.1016/j.dyepig.2019.108157
[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. doi: 10.1016/j.dyepig.2020.108277
[23]	Zhang, J. S.; Bai, Y. Q.; Wei, Q.; Cao, L.; Wang, T.; Ge, Z. Y. J. Mater. Chem. C 2020, 8. 11771. doi: 10.1039/D0TC02566F
[24]	Wang, Z. B.; Peng, Z. X.; Huang, K.; Lu, P.; Wang, Y. G. J. Mater. Chem. C 2019, 7, 6706. doi: 10.1039/C9TC01059A
[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. doi: 10.1016/j.dyepig.2017.10.020
[26]	Yan, Y. H.; Laine, R. M.; Liu, H. Z. Chem. Sci. 2018, 9, 6118. doi: 10.1039/C8SC01377B
[27]	Qin, W.; Li, K.; Feng, G.; Li, M.; Yang, Z.; Liu, B.; Tang, B. Z. Adv. Funct. Mater. 2014, 24, 635. doi: 10.1002/adfm.201302114
[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. doi: 10.1002/anie.202010216
[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. doi: 10.1039/C7TC02115A
[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. doi: 10.1002/smll.201907074
[32]	Ma, L. W.; Li, C. P.; Yan, Q.; Wang, S.; Miao, W. G.; Cao, D. R. Chin. Chem. Lett. 2020, 31, 361. doi: 10.1016/j.cclet.2019.07.040
[33]	Wang, N.; Zhang, J.; Xu, X. D.; Feng, S. Y. Dalton Trans. 2020, 49, 1883. doi: 10.1039/C9DT03985F
[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. doi: 10.1021/jacs.8b13724
[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. doi: 10.1039/C6TC03791G
[36]	Li, X. Q.; Gu, J. P.; Zhou, Z.; Liu, W. Q.; Gao, J. W.; Wang, Q. M. Dyes Pigm. 2020, 172, 107844. doi: 10.1016/j.dyepig.2019.107844
[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. doi: 10.1021/acsbiomaterials.9b00627
[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. doi: 10.1021/acs.analchem.9b03096
[39]	Wang, X. X.; Ding, Z. Y.; Ma, Y.; Zhang, Y. P.; Shang, H. X.; Jiang, S. M. Soft Matter 2019, 15, 1658. doi: 10.1039/C8SM02434K
[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. doi: 10.1039/C9SC06567A
[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. doi: 10.1039/C7QM00145B
[42]	Roy, B.; Mengji, R.; Roy, S.; Pal, B.; Jana, A.; Singh, N. D. P. ACS Appl. Mater. Interfaces 2022, 14, 4862. doi: 10.1021/acsami.1c19022
[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. doi: 10.1039/D1TC00604E
[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. doi: 10.1039/D0QM00914H
[45]	Zhang, S. S.; Mei, J. New J. Chem. 2021, 45, 19118. doi: 10.1039/D1NJ03747A
[46]	Caruso, U.; Panunzi, B.; Diana, R.; Concilio, S.; Sessa, L.; Shikler, R.; Nabha, S.; Tuzi, A.; Piotto, S. Molecules 2018, 23, 1947. doi: 10.3390/molecules23081947
[47]	Zhang, X. Y.; Qin, W. W.; Cheng, B. F.; Guo, H. Y.; Yang, F. F. J. Mol. Liq. 2020, 298, 112074. doi: 10.1016/j.molliq.2019.112074
[48]	Nie, H. L.; Liang, Y. H.; Han, C.; Zhang, R. B.; Zhang, X. L.; Yan, H. Y. Dyes Pigm. 2019, 168, 42. doi: 10.1016/j.dyepig.2019.04.034
[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. doi: 10.1016/j.dyepig.2021.109222
[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. doi: 10.1021/acsami.0c00903
[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. doi: 10.1039/C8NJ05785K
[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. doi: 10.1021/jacs.9b06196
[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. doi: 10.3390/molecules25030585
[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. doi: 10.1021/acs.analchem.6b04974 pmid: 28192960
[57]	Wang, K.; Su, H.; Wang, P. F.; Wang, W. J.; Li, H. RSC Adv. 2019, 9, 14268. doi: 10.1039/c9ra00977a
[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. doi: 10.1002/adma.202000364
[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. doi: 10.1002/adfm.202009329
[60]	Yan, Y. H.; Laine, R. M.; Liu, H. Z. ChemPlusChem 2019, 84, 1630. doi: 10.1002/cplu.201900568
[61]	Yan, L. Q.; Xie, Y.; Li, J. P.; Zhu, W. Y. Spectrochim. Acta A 2020, 228, 117794. doi: 10.1016/j.saa.2019.117794
[62]	Qiu, J. B.; Chen, Y. X.; Jiang, S. J.; Guo, H. Y.; Yang, F. F. Analyst 2018, 143, 4298. doi: 10.1039/C8AN00863A
[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. doi: 10.1002/asia.202000884
[64]	Fu, W.; Yan, C. X.; Zhang, Y. T.; Ma, Y. Y.; Guo, Z. Q.; Zhu, W. H. Front. Chem. 2019, 7, 291. doi: 10.3389/fchem.2019.00291
[65]	Guo, Z. Q.; Yan, C. X.; Zhu, W.-H. Angew. Chem., Int. Ed. 2020, 59, 9812. doi: 10.1002/anie.201913249
[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. doi: 10.3390/molecules22112009
[68]	Liu, X.; Li, M. W.; Liu, M. F.; Yang, Q. H.; Chen, Y. L. Chem.-Eur. J. 2018, 24, 13197. doi: 10.1002/chem.201801507
[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. doi: 10.1016/j.dyepig.2021.109534
[70]	Wang, L. F.; Qian, Y. Dyes Pigm. 2021, 198, 110018. doi: 10.1016/j.dyepig.2021.110018
[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) doi: 10.6023/cjoc202009012
	( 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.) doi: 10.6023/cjoc202009012
[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. doi: 10.1039/d0cp00413h pmid: 32555804
[73]	Wang, D.-H.; Chen, L.-J.; Zhao, X.; Yan, X.-P. Talanta 2021, 225, 122046. doi: 10.1016/j.talanta.2020.122046
[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. doi: 10.1039/D0TB01806F
[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. doi: 10.1002/adma.202004685
[76]	Peng, C.; Ma, X. Y.; Lin, D.; Feng, X. W.; Yu, H.; Li, Y. H. Anal. Chim. Acta 2021, 1187, 339146. doi: 10.1016/j.aca.2021.339146
[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. doi: 10.1016/j.dyepig.2017.10.020
[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. doi: 10.1002/adfm.202002057
[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. doi: 10.1039/C7SC01400G
[80]	Hwang, T. G.; Kim, G. Y.; Han, J. I.; Kim, S.; Kim, J. P. ACS Sustainable Chem. Eng. 2020, 8,15888. doi: 10.1021/acssuschemeng.0c04456
[81]	Zhang, K. M.; Shu, J.; Chu, W. D.; Liu, X. Q.; Xu, B.; Jiang, W. D. Dyes Pigm. 2021, 185, 108898. doi: 10.1016/j.dyepig.2020.108898
[82]	Luo, Q. F.; Cao, F.; Xiong, C. C.; Dou, Q. Y.; Qu, D. H. J. Org. Chem. 2017, 82, 10960. doi: 10.1021/acs.joc.7b01877
[83]	Adil, L. R.; Iyer, P. K. Chem. Commun. 2020, 56, 7633. doi: 10.1039/D0CC02318C
[84]	Monika, Verma, A.; Verma, S.; Pandey, N.; Tilak, R.; Saha, S. New J. Chem. 2020, 44, 14116. doi: 10.1039/D0NJ02891F
[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. doi: 10.1002/anie.202005785
[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. doi: 10.1021/acs.jpcc.7b02125
[87]	Zhang, H. Y.; Zhang, H.; Huang, G. X.; Li, B. S. Dyes Pigm. 2021, 185, 108947. doi: 10.1016/j.dyepig.2020.108947
[88]	Pratihar, S.; Bhattacharyya, A.; Prasad, E. J. Photochem. Photobiol. A 2020, 396, 112458. doi: 10.1016/j.jphotochem.2020.112458
[89]	Padalkar, V. S.; Seki, S. Chem. Soc. Rev. 2016, 45, 169. doi: 10.1039/c5cs00543d pmid: 26506465
[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. doi: 10.1039/c8cs00185e pmid: 30361725
[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. doi: 10.1039/D1CC01940F
[92]	Bhosle, A. A.; Hiremath, S. D.; Bhasikuttan, A. C.; Banerjee, M.; Chatterjee, A. J. Photochem. Photobiol. A 2021, 413, 113265. doi: 10.1016/j.jphotochem.2021.113265
[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. doi: 10.1016/j.talanta.2020.121950
[94]	Zhang, K. X.; Hu, R.; Wang, Z. M.; Tang, B. Z. Mater. Chem. Front. 2021, 5, 2724. doi: 10.1039/D0QM01046D
[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. doi: 10.1039/D1CC02233D
[97]	Li, S. W.; Ling, X.; Lin, Y. H.; Qin, A. J.; Gao, M.; Tang, B. Z. Chem. Sci. 2018, 9, 5730. doi: 10.1039/C8SC01887A
[98]	Niu, Y. H.; Wang, R.; Pu, L.; Zhang, Y. R. Dyes Pigm. 2019, 170, 107594. doi: 10.1016/j.dyepig.2019.107594
[99]	Wu, H. R.; Wang, S. W.; Ding, J.; Wang, R.; Zhang, Y. R. Dyes Pigm. 2020, 170, 107556. doi: 10.1016/j.dyepig.2019.107556
[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. 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. doi: 10.1039/C7CC01602F
[103]	Petdee, S.; Chaiwai, C.; Benchaphanthawee, W.; Nalaoh, P.; Kungwan, N.; Namuangruk, S.; Sudyoadsuk, T.; Promarak, V. Dyes Pigm. 2021, 193,109488. doi: 10.1016/j.dyepig.2021.109488
[104]	Peng, L.; Xiao, L.; Ding, Y. W.; Xiang, Y.; Tong, A. J. J. Mater. Chem. B 2018, 6, 3922. doi: 10.1039/c8tb00414e pmid: 32254320
[105]	Shen, Y. M.; Li, M. Y.; Yang, M.; Zhang, Y. Y.; Li, H. T.; Zhang, X. Y. Spectrochim. Acta A 2019, 222, 117230. doi: 10.1016/j.saa.2019.117230
[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. doi: 10.1021/acs.iecr.8b04643
[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) doi: 10.6023/cjoc201712009
	( 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.) doi: 10.6023/cjoc201712009
[109]	Singh, H.; Sharma, R.; Bhargava, G.; Kumar, S.; Singh, P. New J. Chem. 2018, 42, 12900. doi: 10.1039/C8NJ02646G
[110]	Dai, F. F.; Zhao, M.; Yang, F. Z.; Wang, T. T.; Wang, C. Dyes Pigm. 2020, 183, 108627. doi: 10.1016/j.dyepig.2020.108627
[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. doi: 10.1039/D0TC01981J
[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. doi: 10.1002/adom.201902027
[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. doi: 10.1021/acs.analchem.1c00980 pmid: 34114804
[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. doi: 10.1021/acs.bioconjchem.0c00467
[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. doi: 10.1039/D0CC01031F
[117]	Huang, M. M.; Lu, H.; Wang, K.; Liu, B. B.; Wang, M.; Qiao, X. Y.; Yang, J. P. Dyes Pigm. 2021, 186, 108992. doi: 10.1016/j.dyepig.2020.108992
[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. doi: 10.1021/acs.chemrev.9b00814
[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. doi: 10.1039/D1QO01753E

基于有机小分子的聚集诱导猝灭(ACQ)-聚集诱导发射(AIE)转换研究进展