固态荧光光开关分子研究进展

doi:10.6023/cjoc202403056

摘要/Abstract

荧光光开关分子具有良好的快速响应性、可逆性和抗疲劳性, 在防伪、超分辨成像、光学数据存储、传感器件等领域显示出巨大的应用潜能. 荧光光开关分子的荧光切换需要一定的空间自由度, 因此相比于溶液荧光光开关, 实现固态的荧光光开关具有一定的难度. 一个行之有效的方法是将聚集诱导发光(AIE)分子与荧光光开关分子通过共价键或超分子相互作用结合, AIE分子扭曲的构象可以为荧光光开关分子光照后的构型变化提供足够的空间, 从而实现固态的荧光光开关. 主要综述了这一策略在几种典型的光开关分子中的应用, 为新型固态荧光光开关分子体系的设计提供有效的参考, 对理解固态光开关分子刺激响应机制、开发新材料和拓展其应用具有重要意义.

关键词: 光开关, 聚集诱导发光, 荧光

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

引用此文

胡甲松, 李春娟, 徐斌, 田文晶. 固态荧光光开关分子研究进展[J]. 有机化学, 2024, 44(8): 2425-2440.

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.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 15

图1. 几种光开关分子

Figure 1. Several types of optical switch molecules

图2. (a) SPTS光致异构化示意图; (b) SPTS在纳米成像中的示意图; (c) DSA-2SP与DSA-2MC的可逆光致异构示意图; (d) BOSA-SP与BOSA-MC的可逆光致异构示意图[10,57-58]

Figure 2. (a) Schematic diagram of SPTS photoisomerization; (b) schematic diagram of SPTS in nanoimaging; (c) schematic diagram of reversible photoisomerism between DSA-2SP and DSA-2MC; (d) schematic diagram of reversible photoisomerism between BOSA-SP and BOSA-MC[10,57-58] Copyrights 2015 and 2017 American Chemical Society and 2022 Wiley-VCH.

图3. (a) DSA-2SP粉末(上)和薄膜(下)的可见光和荧光图片; (b)传统荧光成像(上)和超分辨率成像(下); (c) DSA-2SP传统成像与超分辨率成像的荧光截面轮廓(上)和傅里叶环相关曲线(下)[57]

Figure 3. (a) Visible light and fluorescence images of DSA-2SP powder (top) and thin film (bottom); (b) conventional fluorescence imaging (top) and super-resolution imaging (bottom); (c) fluorescence cross-sectional profiles of DSA-2SP conventional imaging and super-resolution imaging (top) and fourier ring correlation (FRC) curve (bottom).[57] Copyright 2017 American Chemical Society.

图4. (a)普通螺吡喃荧光光开光分子荧光切换示意图; (b) BOSA-SP三重荧光切换示意图[58]

图5. (a) Rot-A-SP与Rot-B-SP在酸/碱作用下可逆互变; (b) Rot-A-SP光致荧光变色示意图; (c) Rot-B-SP光致荧光变色示意图; (d) TPEA-SP或TPEB-SP光致异构化示意图; (e) TPEA-SP粉末的可见光和荧光图片; (f) TPEA-SP的可见光(上)和荧光(下)图案[61-62]

Figure 5. (a) Reversible mutual transformation between Rot-A-SP and Rot-B-SP under acid/base interaction; (b) schematic diagram of Rot-A-SP photoluminescence color change; (c) schematic diagram of Rot-B-SP photoluminescence color change; (d) schematic diagram of TPEA-SP or TPEB-SP photoisomerization; (e) visible light and fluorescence images of TPEA-SP powder; (f) visible light (upper) and fluorescence (lower) patterns of TPEA-SP[61-62] Copyrights 2020 and 2021American Chemical Society.

图6. (a) CS-FPNPs的制备; (b) CS-FPNPs结构和光致荧光变色示意图[63]

图7. (a) DTE-TPE在溶液和聚集态下的光致异构示意图; (b) TPE-2DTE和OTPE-2DTE的光致异构示意图; (c)小位阻体系BTTE、ABTE与大位阻体系BBTE的结构变化示意图[72?-74]

Figure 7. (a) Schematic diagram of photoisomerism of DTE-TPE in solution and aggregated state; (b) schematic diagram of photoisomerism of TPE-2DTE and OTPE-2DTE; (c) schematic diagram of structural changes in large steric hindrance systems of BBTE[72?-74] Copyrights 2013 Royal Society of Chemistry, 2020 American Chemical Society and 2019 Wiley-VCH

图8. 不对称二噻吩乙烯光开关分子[75]

图9. YL在溶液、聚集态以及PYL的光致荧光变色性能示意图[80]

图10. (a) [1]RPA的分子结构以及酸/碱和光响应示意图; (b) DAE-R1-OF的分子结构以及酸/碱和光响应示意图; (c)光控超分子光捕捉系统示意图[81?-83]

Figure 10. (a) Molecular structure of [1]RPA and schematic diagram of acid/base and light response; (b) molecular structure of DAE-R1-OF and schematic diagram of acid/base and light response; (c) schematic diagram of photo controlled supramolecular light-harvesting system[81?-83] Copyrights 2022 Wiley-YCH, 2023 American Chemical Society and 2020 Wiley-YCH

图11. (a) 4-氨基偶氮苯钴配合物的光响应结构和颜色变化; (b) 四(偶氮苯)甲烷的结构; (c) 四(偶氮苯)甲烷光响应结构变化[87-88]

Figure 11. (a) Photoresponsive structure and color changes of (4-aminoazobenzene)(β-cyanoethyl)cobaloxime; (b) the structure of tetra(azobenzene)methane; (c) light-responsive structural changes of tetra(azobenzene)methane[87-88] Copyrights 2012 Oxford University Press and 2015 Springer Nature

图12. (a)偶氮-BF2 1所有可能的反应途径; (b)偶氮-BF2 1的光热响应性质[89]

图13. (a) TPE-AZ-CN的合成路线; (b) trans-Cn-Chol的分子结构和光响应结构变化; (c)非发光偶氮苯转化为发光发色团的设计策略[90?-92]

Figure 13. (a) Synthetic route of TPE-AZ-CN; (b) molecular structure and photoresponsive structural changes in trans-Cn-Chol; (c) design strategy of turning non-emissive azobenzene into luminescent chromophores[91-92] Copyrights 2018 Elsevier, 2018 Royal Society of Chemistry and 2023 Elsevier

图14. (a)紫外线照射前后TPE-FUL的结构、颜色、荧光变化; (b) TPE-FUL在信息加密领域的应用[93]

Figure 14. (a) Structure, color, and fluorescence changes of TPE-FUL before and after UV irradiation; (b) application of TPE-FUL in the field of message encryption[93] Copyright 2021 Chinese Chemical Society

图15. (a) 1E, 2E和3E化学结构式; (b) 1E, 2E和3E在紫外光照射前后的图片; (c) MIX-1E和MIX-2E晶体的紫外光照射射前后以及两种不同光再照射后的图片[94]

Figure 15. (a) Chemical structural formulas of 1E, 2E, and 3E; (b) images of 1E, 2E, and 3E before and after UV irradiation; (c) images of MIX-1E and MIX-2E crystals before and after UV irradiation, as well as after reirradiation with two different types of light[94] Copyright 2017 American Chemical Society

参考文献 94

[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. doi: 10.1021/ja302395f pmid: 22548499
[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).
	(韩鹏博, 秦安军, 有机化学, 2023, 43, 2254.) doi: 10.6023/cjoc202300032
[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. doi: 10.1021/jacs.7b10697 pmid: 29112401
[14]	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
[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).
	(徐赫, 韩鹏博, 秦安军, 唐本忠, 化学学报, 2023, 81, 1420.) doi: 10.6023/A23050232
[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).
	(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
[21]	Zhao, Y.-Q.; Zhang, X.; Yang, Y. R.; Zhu, L. P.; Zhou, Y. Acta Chim. Sinic. 2024, 82, 265 (in Chinese).
	(赵玉强, 张霞, 杨芸如, 朱立平, 周莹, 化学学报, 2024, 82, 265.) doi: 10.6023/A23100457
[22]	Zhao, Y.; Chen, P.; Li, G.; Niu, Z.; Wang, E. Chin. J. Org. Chem. 2023, 43, 2156 (in Chinese).
	(赵洋, 陈盼盼, 李高楠, 钮智刚, 王恩举, 有机化学, 2023, 43, 2156.) doi: 10.6023/cjoc202210002
[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).
	(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.) doi: 10.6023/cjoc202303022
[24]	Zeng, C.; Hu, P.; Wang, B.; Fang, W.; Zhao, K.; Donnio, B. Acta Chim. Sinic. 2023, 81, 469 (in Chinese).
	(曾崇洋, 胡平, 汪必琴, 方文彦, 赵可清, Donnio Bertrand, 化学学报, 2023, 81, 469.) doi: 10.6023/A23010006
[25]	Liu, B.; Chen, P. Acta Chim. Sinic. 2022, 80, 929 (in Chinese).
	(刘斌, 陈磅宽, 化学学报, 2022, 80, 929.) doi: 10.6023/A22030122
[26]	Lu, H.; Ma, L.; Ma, H. Chin. J. Org. Chem. 2023, 43, 4075 (in Chinese).
	(鲁会名, 马拉毛草, 马恒昌, 有机化学, 2023, 43, 4075.) doi: 10.6023/cjoc202305010
[27]	Zhao, Y.; Chen, P.; Han, L.; Wang, E. Chin. J. Org. Chem. 2023, 43, 2454 (in Chinese).
	(赵洋, 陈盼盼, 韩立志, 王恩举, 有机化学, 2023, 43, 2454.) doi: 10.6023/cjoc202212004
[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).
	(曾崇洋, 胡平, 汪必琴, 方文彦, 赵可清, 有机化学, 2023, 43, 3287.) doi: 10.6023/cjoc202302025
[32]	Feng, X.; Zhu, L.; Yue, B. Acta Chim. Sinic. 2022, 80, 647 (in Chinese).
	(冯锡成, 朱亮亮, 岳兵兵, 化学学报, 2022, 80, 647.) doi: 10.6023/A22010015
[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. doi: 10.1021/acsami.9b21970 pmid: 32026696
[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. doi: 10.1016/j.cbpa.2008.08.008 pmid: 18809508
[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. doi: 10.1021/ja500496n pmid: 24521350
[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. doi: 10.1021/jacs.7b00274 pmid: 28437075
[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).
	(刘铃, 浩涛涛, 伍晚花, 杨成, 有机化学, 2023, 43, 2189.) doi: 10.6023/cjoc202210020
[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. doi: 10.1021/jacs.9b02836 pmid: 31117648
[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. doi: 10.1038/nchem.2304 pmid: 26201739
[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.