多硫芳烃化合物的合成及聚集诱导磷光性质研究进展

doi:10.6023/cjoc202204063

摘要/Abstract

聚集诱导发光(AIE)自被发现以来就受到了研究者们的广泛关注, 其中具有高效、长寿命的有机磷光材料表现出优异的发光性质和丰富的可调控性, 是未来有机发光材料的重要发展方向. 多硫芳烃化合物是一类典型的聚集诱导磷光(AIP)材料, 具有高度可扭曲的分子结构和丰富的修饰位点, 目前已发展出多个以此类化合物为基础的发光体系, 在溶液态、薄膜态、晶体态中表现出独特的光物理性质. 同时, 多硫芳烃化合物在激发态表现出特有的分子构象转变, 这一属性为原位光控下的分子自组装形态和发光性质调控提供了结构基础, 也为开发出多功能发光体系提供了条件. 旨在总结不同系列的多硫芳烃化合物在多种调控方式下的聚集诱导磷光性质, 结合本课题组在这方面的研究实践, 综述了近年来多硫芳烃体系的AIP性质研究, 并对其目前研究中可能存在的问题提出简要展望, 希望能为AIP材料的未来发展方向提供一些借鉴和思考.

关键词: 聚集诱导发光, 多硫芳烃化合物, 磷光, 光控, 刺激响应性

Aggregation-induced emission (AIE) has received extensive attention in the field of optical materials since its discovery. Organic phosphorescence with high efficiency and long lifetime exhibits excellent luminescent properties and high flexibility of modification, which is an important development direction of organic light-emitting materials in the future. Persulfurated arenes as a typical class of aggregation-induced phosphorescence (AIP) materials possess highly twistable molecular structures and abundant modification sites. Therefore, a number of luminescent systems (such as solution state, thin film state, crystalline state, etc.) based on these compounds have been developed. At the same time, persulfurated arene exhibit a unique molecular conformation transition in the excited state, which not only provides a theoretical basis for the regulation of molecular self-assembly morphology and luminescence properties under in situ photocontrol, but also builds a fabulous platform for developing abundant luminescence systems. This paper aims to summarize the aggregation induced phosphorescence properties of different series of persulfurated arenes under various regulation modes. Combined with the research practice of our research group in this field, the AIP properties of persulfurated arenes in recent years are reviewed. The possible problems in the current research are briefly prospected, hoping to provide some reference and thinking for the future development direction of AIP materials.

Key words: aggregation induced emission, persulfurated arenes, phosphorescence, light control, stimulus responsiveness

引用此文

路云乐, 王彦杰, 朱亮亮, 岳兵兵. 多硫芳烃化合物的合成及聚集诱导磷光性质研究进展[J]. 有机化学, 2022, 42(11): 3549-3561.

Yunle Lu, Yanjie Wang, Liangliang Zhu, Bingbing Yue. Progress in Synthesis and Aggregation-Induced Phosphorescence of Persulfurated Arene Compounds[J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3549-3561.

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图/表 17

图1. 不同取代度多硫芳烃化合物的化学结构

Figure 1. Chemical structure of multi-substitued (persulfurated) arenes

图2. 二硫苯和四硫苯类芳香化合物的合成和结构

Figure 2. Synthesis and structure of Two-sulfurated and four- sulfurated aromatic compounds

图3. 首次合成全取代六硫苯反应式[30]

Figure 3. First synthesis of hexakis(phenylthio)benzene

图4. 全硫苯类化合物的亲核取代的反应条件

Figure 4. Reaction conditions of nucleophilic substitution for persulfurated benzene molecules

图5. 羧基取代多硫芳烃化合物(Ast_6COOH, Ast_4COOH, Ast_2COOH)的合成[43]

Figure 5. Synthesis of carboxyl-substitued persulfurated arenes(Ast_6COOH, Ast_4COOH and Ast_2COOH).

图6. 六羧酸根六硫苯(Ast_6COO－)与铅离子自组装形成强绿色磷光[35]

Figure 6. Strong green phosphorescence formed by self-assembly of Ast_6COO－ in water with Pb2＋

图7. Ca2＋与AS(CN)T_4COO－配位引发聚集诱导发光[44]

Figure 7. AIP of AS(CN)T_4COO－ triggered by coordination with Ca2＋

图8. 六羧基六硫苯(Ast_6COO－)的光激发聚集诱导磷光过程[50]

Figure 8. Photo-induced AIP process of Ast_6COO－

图9. 光诱导有机相AIE示意图[51]

Figure 9. Illustration of photoinduced organic-phase AIE

图10. 六乙酰胺六硫苯(Ast_6NHCOCH3)的可调节磷光荧光双发射[54]

Figure 10. Tunable fluorescence-phosphorescence complex emission of Ast_6NHCOCH3

图11. 螺旋自组装诱导的超分子手性磷光-荧光开关[55]

Figure 11. Supramoleular chiral switch between fluorescence and phosphorescence induced by helical self-assemble

图12. HTB-D/LG凝胶剂搭建的兼具AIE、RTP、CPL性质的平台[74]

Figure 12. Sol-gel platform with a combination of AIE, RTP, CPL properties constructed by HTB-D/LG gelator

图13. Ceroni团队合成的多硫芳烃化合物[75]

Figure 13. Persulfurated arene compounds syntheised by Ceroni group

图14. 具有离子传感性能的多硫芳烃化合物[32]

Figure 14. Persulfurated arenes exhibiting properties of ion sensing

图15. AST_6BN[34]和AST_6OH[82]在不同刺激下的多色发光性质

Figure 15. Multi-color luminescence properties of AST_6BN and AST_6OH under different stimuli

图16. 光激发分子重组实现晶体的光物理调控[83]

Figure 16. Manipulating crystals through photophysical method realized by photoexcitation-induced molecular realignment

图17. 八硫苯取代萘(Na_8)和八对甲基硫苯取代萘(Na_8CH3)的化学结构以及CH-π自组装诱导发光示意图[84]

Figure 17. Chemical structure of Na_8 and Na_8CH3 and schematic illustration of emission induced by CH-π interaction

参考文献 84

[1]	Sagara, Y.; Kato, T. Nat. Chem. 2009, 1, 605. doi: 10.1038/nchem.411
[2]	Hsu, C.-W.; Lin, C.-C.; Chung, M.-W.; Chi, Y.; Lee, G.-H.; Chou, P.-T.; Chang, C.-H.; Chen, P.-Y. J. Am. Chem. Soc. 2011, 133, 12085. doi: 10.1021/ja2026568
[3]	Xu, S.; Chen, R.; Zheng, C.; Huang, W. Adv. Mater. 2016, 28, 9920. doi: 10.1002/adma.201602604
[4]	Hong, Y.; Lam, J. W. Y.; Tang, B. Z. Chem. Soc. Rev. 2011, 40, 5361. doi: 10.1039/c1cs15113d
[5]	Luo, J.; Xie, Z.; Lam, J. W. Y.; Cheng, L.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhan, X.; Liu, Y.; Zhu, D.; Tang, B. Z. Chem. Commun. 2001, 1740.
[6]	Liu, J.; Lam, J. W. Y.; Tang, B. Z. J. Inorg. Organomet. Polym. 2009, 19, 249. doi: 10.1007/s10904-009-9282-8
[7]	Hong, Y.; Lam, J. W. Y.; Tang, B. Z. Chem. Commun. 2009, 4332.
[8]	Lu, H.; Zheng, Y.; Zhao, X.; Wang, L.; Ma, S.; Han, X.; Xu, B.; Tian, W.; Gao, H. Angew. Chem., Int. Ed. Engl, 2016, 55, 155.
[9]	Cai, X.; Liu, B. Angew. Chem., Int. Ed. 2020, 59, 9868. doi: 10.1002/anie.202000845
[10]	Hu, R.; Yang, X.; Qin, A.; Tang, B. Z. Mater. Chem. Front. 2021, 5, 4073. doi: 10.1039/D1QM00078K
[11]	Feng, X. C.; Zhu, L. L.; Yue, B. B. Acta Chim. Sinica 2022, 80, 647. (in Chinese) doi: 10.6023/A22010015
	( 冯锡成, 朱亮亮, 岳兵兵, 化学学报 2022, 80, 647.) doi: 10.6023/A22010015
[12]	Han, P. B.; Xu, H.; An, Z. F.; Cai, Z. Y.; Cai, Z. X.; Chao, H.; Chen, B.; Chen, M.; Chen, Y.; Chi, Z. G,.; Dai, S. D.; Ding, D.; Dong, Y. P.; Gao, Z. Y.; Guan, W. J.; He, Z. K.; Hu, J. J.; Hu, R.; Hu, Y. X.; Huang, Q. Y.; Kang, M. M.; Li, D. X.; Li, J. S.; Li, S. Z.; Li, W. L.; Li, Z.; Lin, X. L.; Liu, H. Y.; Liu, P. Y.; Lou, X. D.; Lu, C.; Ma, D. G.; Ou, H. L.; Ouyang, J.; Peng, Q.; Qian, J.; Qin, A. J.; Qu, J. M.; Shi, J. B.; Shuai, Z. G.; Sun, L. H.; Tian, R.; Tian, W. J.; Tong, B.; Wang, H. L.; Wang, D.; Wang, H.; Wang, T.; Wang, X.; Wang, Y. C.; Wu, S. Z.; Xia, F.; Xie, Y. J.; Xiong, K.; Xu, B.; Yan, D. P.; Yang, H. B.; Yang, Q. Z.; Yang, Z. Y.; Yuan, L. Z.; Yuan, W. Z.; Zang, S. Q.; Zeng, F.; Zeng, J. J.; Zeng, Z.; Zhang, G. Q.; Zhang, X. Y.; Zhang, X. P.; Zhang, Y.; Zhang, Y. F.; Zhang, Z. J.; Zhao, J.; Zhao, Z.; Zhao, Z. H.; Zhao, Z. J.; Tang, B. Z. Prog. Chem. 2022, 34, 1. (in Chinese)
	( 韩鹏博, 徐赫, 安众福, 蔡哲毅, 蔡政旭, 巢晖, 陈彪, 陈明, 陈禹, 池振国, 代淑婷, 丁丹, 董宇平, 高志远, 管伟江, 何自开, 胡晶晶, 胡蓉, 胡毅雄, 黄秋忆, 康苗苗, 李丹霞, 李济森, 李树珍, 李文朗, 李振, 林新霖, 刘骅莹, 刘佩颖, 娄筱叮, 吕超, 马东阁, 欧翰林, 欧阳娟, 彭谦, 钱骏, 秦安军, 屈佳敏, 石建兵, 帅志刚, 孙立和, 田锐, 田文晶, 佟斌, 汪辉亮, 王东, 王鹤, 王涛, 王晓, 王誉澄, 吴水珠, 夏帆, 谢育俊, 熊凯, 徐斌, 闫东鹏, 杨海波, 杨清正, 杨志涌, 袁丽珍, 袁望章, 臧双全, 曾钫, 曾嘉杰, 曾卓, 张国庆, 张晓燕, 张学鹏, 张艺, 张宇凡, 张志军, 赵娟, 赵征, 赵子豪, 赵祖金, 唐本忠, 化学进展 2022, 34, 1.) doi: 10.7536/PC211037
[13]	Zhang, L. L.; Wang, Y. Y.; Zhu, G. N.; Dai, W. B.; Zhao, Z. X.; Zhao, Y.; Zhi, J. G.; Dong, Y. P. Acta Chim. Sinica 2022, 80, 282. (in Chinese) doi: 10.6023/A21120556
	( 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.) doi: 10.6023/A21120556
[14]	Tsang, M.-K.; Bai, G.; Hao, J. Chem. Soc. Rev. 2015, 44, 1585. doi: 10.1039/C4CS00171K
[15]	Qi, Y.; Ding, N.; Wang, Z.; Xu, L.; Fang, Y. ACS Appl. Mater. Interfaces 2019, 11, 8676. doi: 10.1021/acsami.8b21617
[16]	Ma, Z.; Wang, Z.; Teng, M.; Xu, Z.; Jia, X. ChemPhysChem 2015, 16, 1811. doi: 10.1002/cphc.201500181
[17]	Huang, L.; Qian, C.; Ma, Z. Chem.-Eur. J. 2020, 26, 11914. doi: 10.1002/chem.202000526
[18]	Xie, Y.; Li, Z. Mater. Chem. Front. 2020, 4, 317. doi: 10.1039/C9QM00580C
[19]	Cai, S.; Shi, H.; Tian, D.; Ma, H.; Cheng, Z.; Wu, Q.; Gu, M.; Huang, L.; An, Z.; Peng, Q. Adv. Funct. Mater. 2018, 28, 1705045 doi: 10.1002/adfm.201705045
[20]	Shi, H.; Song, L.; Ma, H.; Sun, C.; Huang, K.; Lv, A.; Ye, W.; Wang, H.; Cai, S.; Yao, W.; Zhang, Y.; Zheng, R.; An, Z.; Huang, W. J. Phys. Chem. Lett. 2019, 10, 595.
[21]	Shi, H.; An, Z.; Li, P.-Z.; Yin, J.; Xing, G.; He, T.; Chen, H.; Wang, J.; Sun, H.; Huang, W.; Zhao, Y. Cryst. Growth Des. 2016, 16, 808. doi: 10.1021/acs.cgd.5b01400
[22]	Shoji, Y.; Ikabata, Y.; Wang, Q.; Nemoto, D.; Sakamoto, A.; Tanaka, N.; Seino, J.; Nakai, H.; Fukushima, T. J. Am. Chem. Soc. 2017, 139, 2728. doi: 10.1021/jacs.6b11984
[23]	An, Z.; Zheng, C.; Tao, Y.; Chen, R.; Shi, H.; Chen, T.; Wang, Z.; Li, H.; Deng, R.; Liu, X.; Huang, W. Nat. Mater. 2015, 14, 685. doi: 10.1038/nmat4259
[24]	Gong, Y.; Chen, G.; Peng, Q.; Yuan, W. Z.; Xie, Y.; Li, S.; Zhang, Y.; Tang, B. Z. Adv. Mater. 2015, 27, 6195. doi: 10.1002/adma.201502442
[25]	Zhao, W.; He, Z.; Lam, J. W. Y.; Peng, Q.; Ma, H.; Shuai, Z.; Bai, G.; Hao, J.; Tang, B. Z. Chem 2016, 1, 592. doi: 10.1016/j.chempr.2016.08.010
[26]	Reineke, S.; Seidler, N.; Yost, S. R.; Prins, F.; Tisdale, W. A.; Baldo, M. A. Appl. Phys. Lett. 2013, 103, 093302. doi: 10.1063/1.4819444
[27]	Yang, J.; Zhen, X.; Wang, B.; Gao, X.; Ren, Z.; Wang, J.; Xie, Y.; Li, J.; Peng, Q.; Pu, K.; Li, Z. Nat. Commun. 2018, 9, 840. doi: 10.1038/s41467-018-03236-6 pmid: 29483501
[28]	Zhao, Y.; Yang, X. G.; Lu, X. M.; Yang, C. D.; Fan, N. N.; Yang, Z. T.; Wang, L. Y.; Ma, L. F. Inorg. Chem. 2019, 58, 6215. doi: 10.1021/acs.inorgchem.9b00450
[29]	Niembro, S.; Vallribera, A.; Moreno-Mañas, M. New J. Chem. 2008, 32, 94. doi: 10.1039/B707776A
[30]	Adams, R.; Ferretti, A. J. Am. Chem. Soc. 1959, 81, 4927. doi: 10.1021/ja01527a042
[31]	Bergamini, G.; Fermi, A.; Botta, C.; Giovanella, U.; Di Motta, S.; Negri, F.; Peresutti, R.; Gingras, M.; Ceroni, P. J. Mater. Chem. C 2013, 1, 2717. doi: 10.1039/c3tc00878a
[32]	Fermi, A.; Bergamini, G.; Roy, M.; Gingras, M.; Ceroni, P. J. Am. Chem. Soc. 2014, 136, 6395. doi: 10.1021/ja501458s
[33]	MacNicol, D. D.; Mallinson, P. R.; Robertson, C. D. J. Chem. Soc., Chem. Commun. 1985, 1649.
[34]	Jia, X.; Yue, B.; Zhou, L.; Niu, X.; Wu, W.; Zhu, L. Chem. Commun. 2020, 56, 4336. doi: 10.1039/D0CC00371A
[35]	Villa, M.; Roy, M.; Bergamini, G.; Gingras, M.; Ceroni, P. Dalton Trans. 2019, 48, 3815. doi: 10.1039/C9DT00251K
[36]	Rocklin, A. L. J. Org. Chem. 1956, 21, 1478. doi: 10.1021/jo01118a040
[37]	Kulka, M. J. Org. Chem. 1959, 24, 235. doi: 10.1021/jo01084a021
[38]	Langille, K. R.; Peach, M. E. J. Fluorine Chem. 1972, 1, 407. doi: 10.1016/S0022-1139(00)82961-9
[39]	MacNicol, D. D.; Mallison, P. R.; Murphy, A.; Sym, G. J. Tetrahedron Lett. 1982, 23, 4131.
[40]	Pastor, S. D.; Hessell, E. T. J. Org. Chem. 1985, 50, 4812. doi: 10.1021/jo00224a032
[41]	Testaferri, L.; Tiecco, M.; Tingoli, M.; Chianelli, D.; Montanucci, M. Synthesis 1983, 751.
[42]	Maiolo, F.; Testaferri, L.; Tiecco, M.; Tingoli, M. J. Org. Chem. 1981, 46, 3070. doi: 10.1021/jo00328a016
[43]	Villa, M.; Del Secco, B.; Ravotto, L.; Roy, M.; Rampazzo, E.; Zaccheroni, N.; Prodi, L.; Gingras, M.; Vinogradov, S. A.; Ceroni, P. J. Phys. Chem. C 2019, 123, 29884. doi: 10.1021/acs.jpcc.9b09206
[44]	Chen, G.; Zhou, Z.; Feng, H.; Zhang, C.; Wang, Y.; Qian, Z.; Pan, J. Chem. Commun. 2019, 55, 4841. doi: 10.1039/C9CC01580A
[45]	Wu, H.; Chen, Z.; Chi, W.; Bindra, A. K.; Gu, L.; Qian, C.; Wu, B.; Yue, B.; Liu, G.; Yang, G.; Zhu, L.; Zhao, Y. Angew. Chem., Int. Ed. 2019, 58, 11419. doi: 10.1002/anie.201906507
[46]	Li, X.; Baryshnikov, G.; Ding, L.; Bao, X.; Li, X.; Lu, J.; Liu, M.; Shen, S.; Luo, M.; Zhang, M.; Ågren, H.; Wang, X.; Zhu, L. Angew. Chem., Int. Ed. 2020, 59, 7548. doi: 10.1002/anie.202000185
[47]	Luo, M.; Li, X.; Ding, L.; Baryshnikov, G.; Shen, S.; Zhu, M.; Zhou, L.; Zhang, M.; Lu, J.; Agren, H.; Wang, X. D.; Zhu, L. Angew. Chem., Int. Ed. 2020, 59, 17018. doi: 10.1002/anie.202009077
[48]	Zhang, G.; Palmer, G. M.; Dewhirst, M. W.; Fraser, C. L. Nat. Mater. 2009, 8, 747. doi: 10.1038/nmat2509
[49]	Ding, D.; Li, K.; Liu, B.; Tang, B. Z. Acc. Chem. Res. 2013, 46, 2441. doi: 10.1021/ar3003464
[50]	Jia, X.; Shao, C.; Bai, X.; Zhou, Q.; Wu, B.; Wang, L.; Yue, B.; Zhu, H.; Zhu, L. Proc. Natl. Acad. Sci. U. S. A. 2019, 116, 4816. doi: 10.1073/pnas.1821991116
[51]	Gu, J.; Yue, B.; Baryshnikov, G. V.; Li, Z.; Zhang, M.; Shen, S.; Ågren, H.; Zhu, L. Research 2021, 9862093.
[52]	Zhang, G.; Chen, J.; Payne, S. J.; Kooi, S. E.; Demas, J. N.; Fraser, C. L. J. Am. Chem. Soc. 2007, 129, 8942. doi: 10.1021/ja0720255
[53]	Morris, W. A.; Sabat, M.; Butler, T.; DeRosa, C. A.; Fraser, C. L. J. Phys. Chem. C 2016, 120, 14289. doi: 10.1021/acs.jpcc.6b03239
[54]	Wu, H.; Hang, C.; Li, X.; Yin, L.; Zhu, M.; Zhang, J.; Zhou, Y.; Ågren, H.; Zhang, Q.; Zhu, L. Chem. Commun. 2017, 53, 2661. doi: 10.1039/C6CC04901J
[55]	Wu, H.; Zhou, Y.; Yin, L.; Hang, C.; Li, X.; Ågren, H.; Yi, T.; Zhang, Q.; Zhu, L. J. Am. Chem. Soc. 2017, 139, 785. doi: 10.1021/jacs.6b10550
[56]	Li, M.; Li, S.-H.; Zhang, D.; Cai, M.; Duan, L.; Fung, M.-K.; Chen, C.-F. Angew. Chem., Int. Ed. 2018, 57, 2889. doi: 10.1002/anie.201800198
[57]	Song, F.; Xu, Z.; Zhang, Q.; Zhao, Z.; Zhang, H.; Zhao, W.; Qiu, Z.; Qi, C.; Zhang, H.; Sung, H. H. Y.; Williams, I. D.; Lam, J. W. Y.; Zhao, Z.; Qin, A.; Ma, D.; Tang, B. Z. Adv. Funct. Mater. 2018, 28, 1800051.
[58]	Sun, S.; Wang, J.; Chen, L.; Chen, R.; Jin, J.; Chen, C.; Chen, S.; Xie, G.; Zheng, C.; Huang, W. J. Mater. Chem. C 2019, 7, 14511. doi: 10.1039/C9TC04941J
[59]	Zinna, F.; Giovanella, U.; Bari, L. D. Adv. Mater. 2015, 27, 1791. doi: 10.1002/adma.201404891
[60]	Wang, Y.; Li, Q. Adv. Mater. 2012, 24, 1926. doi: 10.1002/adma.201200241
[61]	Qiu, Y.; Chen, P.; Guo, P.; Li, Y.; Liu, M. Adv. Mater. 2008, 20, 2908. doi: 10.1002/adma.200801165
[62]	Hayasaka, H.; Miyashita, T.; Nakayama, M.; Kuwada, K.; Akagi, K. J. Am. Chem. Soc. 2012, 134, 3758. doi: 10.1021/ja2088053
[63]	Canary, J. W. Chem. Soc. Rev. 2009, 38, 747. doi: 10.1039/b800412a pmid: 19322467
[64]	Zong, Z.; Zhang, P.; Qiao, H.; Hao, A.; Xing, P. J. Mater. Chem. 2020, 8, 16224.
[65]	Malik, A. U.; Gan, F.; Shen, C.; Yu, N.; Wang, R.; Crassous, J.; Shu, M.; Qiu, H. J. Am. Chem. Soc. 2018, 140, 2769. doi: 10.1021/jacs.7b13512
[66]	Tang, X.; Chu, D.; Jiang, H.; Gong, W.; Jiang, C.; Cui, Y.; Liu, Y. Mater. Chem. Front. 2020, 4, 2772. doi: 10.1039/D0QM00416B
[67]	Zhu, H.; Li, Q.; Shi, B.; Xing, H.; Sun, Y.; Lu, S.; Shangguan, L.; Li, X.; Huang, F.; Stang, P. J. J. Am. Chem. Soc. 2020, 142, 17340. doi: 10.1021/jacs.0c09598
[68]	Jiang, Q.; Xu, X.; Yin, P.-A.; Ma, K.; Zhen, Y.; Duan, P.; Peng, Q.; Chen, W.-Q.; Ding, B. J. Am. Chem. Soc. 2019, 141, 9490. doi: 10.1021/jacs.9b03305 pmid: 31184485
[69]	Górecki, M.; Zinna, F.; Biver, T.; Di Bari, L. J. Pharm. Biomed. Anal. 2017, 144, 6. doi: S0731-7085(17)30296-0 pmid: 28222912
[70]	Sato, I.; Sugie, R.; Matsueda, Y.; Furumura, Y.; Soai, K. Angew. Chem., Int. Ed. 2004, 43, 4490. doi: 10.1002/anie.200454162
[71]	Kawasaki, T.; Sato, M.; Ishiguro, S.; Saito, T.; Morishita, Y.; Sato, I.; Nishino, H.; Inoue, Y.; Soai, K. J. Am. Chem. Soc. 2005, 127, 3274. doi: 10.1021/ja0422108
[72]	Chen, W.; Ma, K.; Duan, P.; Ouyang, G.; Zhu, X.; Zhang, L.; Liu, M. Nanoscale 2020, 12, 19497. doi: 10.1039/D0NR04239K
[73]	Jin, X.; Sang, Y.; Shi, Y.; Li, Y.; Zhu, X.; Duan, P.; Liu, M. ACS Nano 2019, 13, 2804. doi: 10.1021/acsnano.8b08273
[74]	Wu, B.; Wu, H.; Gong, Y.; Li, A.; Jia, X.; Zhu, L. J. Mater. Chem. C 2021, 9, 4275. doi: 10.1039/D1TC00614B
[75]	Fermi, A.; Bergamini, G.; Peresutti, R.; Marchi, E.; Roy, M.; Ceroni, P.; Gingras, M. Dyes Pigm. 2014, 110, 113. doi: 10.1016/j.dyepig.2014.04.036
[76]	Weng, T.; Zou, Q.; Zhang, M.; Wu, B.; Baryshnikov, G. V.; Shen, S.; Chen, X.; Ågren, H.; Jia, X.; Zhu, L. J. Phys. Chem. Lett. 2021, 12, 6182. doi: 10.1021/acs.jpclett.1c01535
[77]	Hu, X.; Zhao, X.; He, B.; Zhao, Z.; Zheng, Z.; Zhang, P.; Shi, X.; Kwok, R. T.; Lam, J. W.; Qin, A. Research 2018, 2018, 3152870.
[78]	Ejaz, A.; Han, J. H.; Dahiya, R. J. Colloid Interface Sci. 2020, 570, 322. doi: 10.1016/j.jcis.2020.02.117
[79]	Ślęczkowski, M. L.; Mabesoone, M. F.; Ślęczkowski, P.; Palmans, A. R.; Meijer, E. Nat. Chem. 2021, 13, 200. doi: 10.1038/s41557-020-00583-0 pmid: 33257888
[80]	Lee, C.; Choi, C. H.; Joo, T. Phys. Chem. Chem. Phys. 2020, 22, 1115. doi: 10.1039/C9CP05090F
[81]	Mayor, M.; Lehn, J.-M. Helv. Chim. Acta 1997, 80, 2277.
[82]	Xu, J.; Feng, H.; Teng, H.; Chen, G.; Pan, S.; Chen, J.; Qian, Z. Chem. Eur. J. 2018, 24, 12773. doi: 10.1002/chem.201801739
[83]	Shen, S.; Baryshnikov, G.; Yue, B.; Wu, B.; Li, X.; Zhang, M.; Ågren, H.; Zhu, L. J. Mater. Chem. C 2021, 9, 11707. doi: 10.1039/D1TC01605A
[84]	Wu, H.; Zhao, P.; Li, X.; Chen, W.; Ågren, H.; Zhang, Q.; Zhu, L. ACS Appl. Mater. Interfaces 2017, 9, 3865. doi: 10.1021/acsami.6b15939