Research Advances of Host-Guest Supramolecular Self-Assemblies with Aggregration-Induced Emission Effect and Their Applications in Biomedical Field

doi:10.6023/cjoc202003066

Abstract

Host-guest interaction, as one of the most important behaviors in supramolecular self-assemblies, is often used to construct functional supramolecular materials. Based on host-guest interaction, it has become a hotspot in supramolecular chemistry by utilizing macrocyclic hosts and guests with aggregation-induced emission (AIE) properties as building blocks to construct supramolecular system, which can be widely used in drug delivery, cellular imaging, biosensing and so on. According to the origination of fluorescence effects of supramolecular assemblies, either from the host or guest molecules, the recent 5-year advances of AIE supramolecular self-assemblies based on host-guest interaction by utilizing macrocycles such as cyclodextrin, calixarene, cucurbituril, pillararene and other water-soluble host molecules are summarized, and their applications in the biomedical field are discussed.

Key words: host-guest interaction, self-assembly, aggregation-induced emission, cell imaging, drug delivery

Cite this article

Tian Xueqi, Zuo Minzan, Niu Pengbo, Wang Kaiya, Hu Xiaoyu. Research Advances of Host-Guest Supramolecular Self-Assemblies with Aggregration-Induced Emission Effect and Their Applications in Biomedical Field[J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 1823-1834.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Lehn, J.-M. Angew. Chem., Int. Ed. 1988, 27, 89.
[2] Shao, W.; Liu, X.; Wang, T.; Hu, X. Chin. J. Org. Chem. 2018, 38, 1107(in Chinese). (邵为, 刘昕, 王婷婷, 胡晓玉, 有机化学, 2018, 38, 1107.)
[3] Aida, T.; Meijer, E. W.; Stupp, S. I. Science 2012, 335, 813.
[4] Blanazs, A.; Armes, S. P.; Ryan, A. J. Macromol. Rapid Comm. 2009, 30, 267.
[5] Xu, Z.-Y.; Zhang, Y.-C.; Lin, J.-L.; Wang, H.; Zhang, D.-W.; Li, Z.-T. Prog. Chem. 2019, 31, 1540(in Chinese). (徐子悦, 张运昌, 林佳乐, 王辉, 张丹维, 黎占亭, 化学进展, 2019, 31, 1540.)
[6] Bae, Y.; Fukushima, S.; Harada, A.; Kataoka, K. Angew. Chem., Int. Ed. 2003, 42, 4640.
[7] Lammers, T.; Kiessling, F.; Hennink, W. E.; Storm, G. Mol. Pharm. 2010, 7, 1899.
[8] Mura, S.; Nicolas, J.; Couvreur, P. Nat. Mater. 2013, 12, 991.
[9] Gao, T.; Li, L.; Wang, B.; Zhi, J.; Xiang, Y.; Li, G. Anal. Chem. 2016, 88, 9996.
[10] Ma, X.; Zhao, Y. Chem. Rev. 2015, 115, 7794.
[11] Zhao, J.-Y.; Yang, Y.; Han, X.; Liang, C.; Liu, J.-J.; Song, X.-J.; Ge, Z.-L.; Liu, Z. ACS Appl. Mater. Interfaces 2017, 9, 23555.
[12] Duan, Q.-P.; Cao, Y.; Li, Y.; Hu, X.-Y.; Xiao, T.-X.; Lin, C.; Pan, Y.; Wang, L.-Y. J. Am. Chem. Soc. 2013, 135, 10542.
[13] Chen, P.-P.; Shi, B.-B. Prog. Chem. 2017, 29, 720(in Chinese). (陈盼盼, 史兵兵, 化学进展, 2017, 29, 720.)
[14] Birks, J. B. Photophysics of Aromatic Molecules, Wiley Interscience, London, 1970.
[15] An, B. K.; Kwon, S. K.; Jung, S. D.; Park, S. Y. J. Am. Chem. Soc. 2002, 124, 14410.
[16] Luo, J.-D.; Xie, Z.-L.; Lam, J. W. Y.; Cheng, L.; Tang, B.-Z.; Chen, H.-Y.; Qiu, C.-F.; Kwok, H. S.; Zhan, X.-W.; Liu, Y.-Q.; Zhu, D.-B. Chem. Commun. 2001, 1740.
[17] Jiang, B.-P.; Guo, D.-S.; Liu, Y.-C.; Wang, K.-P.; Liu, Y. ACS Nano 2014, 8, 1609.
[18] Zhang, S.; Qin, A.-J.; Sun, J.-Z.; Tang, B.-Z. Prog. Chem. 2011, 23, 623(in Chinese). (张双, 秦安军, 孙景志, 唐本忠, 化学进展, 2011, 23, 623).
[19] Qian, Y.; Jie, L.-H.; Wang, S.-Q.; Yang, G.-Q. J. Nanjing Univ. Posts Telecommun. (Nat. Sci.) 2008, 28, 1(in Chinese). (钱妍, 解令海, 王双清, 杨国强, 南京邮电大学学报(自然科学版), 2008, 28, 1.)
[20] Tang, B.-Z.; Zhan, X.-W.; Yu, G.; Lee, P.; Liu, Y.-Q.; Zhu, D.-B. J. Mater. Chem. 2001, 11, 2974.
[21] Zhou, J.; Hua, B.; Shao, L.; Feng, H.; Yu, G.-C. Chem. Commun. 2016, 52, 5749.
[22] Wang, P.; Yan, X.-Z.; Huang, F.-H. Chem. Commun. 2014, 50, 5017.
[23] Cram, D. J.; Cram, J. M. Science 1974, 183, 803.
[24] Zhang, L.-X.; Chen, Q. Synth. Mater. Aging Appl. 2018, 47, 108(in Chinese). (张来新, 陈琦, 合成材料老化与应用, 2018, 47, 108.)
[25] Liang, G.; Lam, J. W. Y.; Qin, W.; Li, J.; Xie, N.; Tang, B.-Z. Chem. Commun. 2014, 50, 1725.
[26] Xu, L.-X. Ph.D. Dissertation, South China University of Technology, Guangzhou, 2019 (in Chinese). (许林贤, 博士论文, 华南理工大学, 广州, 2019.)
[27] Wang, Y.; Yang, N.; Wang, D.-D.; He, Y.; Chen, L.; Zhao, Y.-P. Polym. Degrad. Stab. 2018, 147, 123.
[28] Zhang, P.; Qian, X.-P.; Zhang, Z.-K.; Li, C.; Xie, C.; Wu, W.; Jiang, X.-Q. ACS Appl. Mater. Interfaces 2017, 9, 5768.
[29] Bortolus, P.; Grabner, G.; Kohler, G.; Monti, S. Coord. Chem. Rev. 1993, 125, 261.
[30] Zhang, L.; Hu, W.; Yu, L.; Wang, Y. Chem. Commun. 2015, 51, 4298.
[31] Zhao, Q.; Chen, Y.; Sun, M.; Wu, X.-J.; Liu, Y. RSC Adv. 2016, 6, 50673.
[32] Li, Q.-L.; Wang, D.; Cui, Y.-Z.; Fan, Z.-Y.; Ren, L.; Li, D.-D.; Yu, J.-H. ACS Appl. Mater. Interfaces 2018, 10, 12155.
[33] Guo, Y.-M.; Cao, F.-P.; Lei, X.-L.; Mang, L.-H.; Cheng, S.-J.; Song, J.-T. Nanoscale 2016, 8, 4852.
[34] Huang, Y.-Y.; Ji, J.-H.; Zhang, J.; Wang, F.; Lei, J.-P. Chem. Commun. 2020, 56, 313.
[35] Barrow, S. J.; Kasera, S.; Rowland, M. J.; Del Barrio, J.; Scherman, O. A. Chem. Rev. 2015, 115, 12320.
[36] Lagona, J.; Mukhopadhyay, P.; Chakrabarti, S.; Isaacs, L. Angew. Chem., Int. Ed. 2005, 44, 4844.
[37] Masson, E.; Ling, X.-X.; Roymon, J.; Lawrence, K. M.; Lu, X.-Y. RSC Adv. 2012, 2, 1213.
[38] Chen, J.-F.; Liu, Y.-M.; Mao, D.-K.; Ma, D. Chem. Commun. 2017, 53, 8739.
[39] Ogoshi, T.; Kanai, S.; Fujinami, S.; Yamagishi, T.; Nakamoto, Y. J. Am. Chem. Soc. 2008, 130, 5022.
[40] Ogoshi, T.; Yamagishi, T. A.; Nakamoto, Y. Chem. Rev. 2016, 116, 7937.
[41] Xue, M.; Yang, Y.; Chi, X.-D.; Zhang, Z.-B.; Huang, F.-H. Acc. Chem. Res. 2012, 45, 1294.
[42] Cao, D.-R.; Meier, H. Chin. Chem. Lett. 2019, 30, 1758.
[43] Zhang, H.-C.; Liu, Z.-N.; Xin, F.-F.; Hao, A.-Y. Chin. J. Org. Chem. 2012, 32, 219(in Chinese). (张华承, 刘召娜, 辛飞飞, 郝爱友, 有机化学, 2012, 32, 219.)
[44] Sun, J.-F.; Shao, L.; Zhou, J.; Hua, B.; Zhang, Z.-H.; Li, Q.; Yang, J. Tetrahedron Lett. 2018, 59, 147.
[45] Zhang, C.-W.; Ou, B.; Jiang, S.-T.; Yin, G.-Q.; Chen, L.-J.; Xu, L.; Li, X.-P.; Yang, H.-B. Polym. Chem.-UK 2018, 9, 2021.
[46] Wang, P.; Liang, B.-C.; Xia, Y.-D. Inorg. Chem. 2019, 58, 2252.
[47] Wu, Y.-H.; Chen, Q.-X.; Li, Q.-Y.; Lu, H.-G.; Wu, X.-S.; Ma, J.-B.; Gao, H. J. Mater. Chem. B 2016, 4, 6350.
[48] Dong, R.-J.; Ravinathan, S. P.; Xue, L.-Z.; Li, N.; Zhang, Y.-J.; Zhou, L.-Z.; Cao, C.-X.; Zhu, X.-Y. Chem. Commun. 2016, 52, 7950.
[49] Hui, X.; Xu, D.-Z.; Wang, K.; Yu, W.-J.; Yuang, H.-Y.; Liu, M.-Y.; Shen, Z.-Y.; Zhang, X.-Y.; Wei, Y. RSC Adv. 2015, 5, 107355.
[50] Huang, H.; Xu, D.; Liu, M.; Jiang, R.; Mao, L.; Huang, Q.; Wan, Q.; Wen, Y.; Zhang, X.-Y.; Wei, Y. Mater. Sci. Eng., C 2017, 78, 862.
[51] Xu, D.-Z.; Liu, M.-Y.; Zou, H.; Huang, Q.; Huang, H.-Y.; Tian, J.-W.; Jiang, R.-M.; Wen, Y.-Q.; Zhang, X.-Y.; Wei, Y. J. Taiwan Inst. Chem. Eng. 2017, 78, 455.
[52] Guo, L.-L.; Xu, D.-Z.; Huang, L.; Liu, M.-Y.; Huang, H.-Y.; Tian, J.-W.; Jiang, R.-M.; Wen, Y.-Q.; Zhang, X.-Y.; Wei, Y. Mater. Sci. Eng., C 2018, 85, 233.
[53] Liow, S.-S.; Zhou, H.; Sugiarto, S.; Guo, S.-F.; Chalasani, M. L. S.; Verma, N. K.; Xu, J.-W.; Loh, X.-J. Biomacromolecules 2017, 18, 886.
[54] Perret, F.; Coleman, A. W. Chem. Commun. 2011, 47, 7303.
[55] Tian, H.-W.; Liu, Y.-C.; Guo, D.-S. Mater. Chem. Front. 2020, 4, 46.
[56] Guo, D.-S.; Liu, Y. Acc. Chem. Res. 2014, 47, 1925.
[57] Guo, D.-S.; Liu, Y. Chem. Soc. Rev. 2012, 41, 5907.
[58] Jiang, B.-P.; Guo, D.-S.; Liu, Y.-C.; Wang, K.-P.; Liu, Y. ACS Nano. 2014, 8, 1609.
[59] Chen, C.; Ni, X.; Tian, H.-W.; Liu, Q.; Guo, D.-S.; Ding, D. Angew. Chem., Int. Ed. 2020, 59, 10008.
[60] Wu, D.; Li, Y.; Yang, J.; Shen, J.; Zhou, J.; Hu, Q.-L.; Yu, G.-C.; Tang, G.-P.; Chen, X.-Y. ACS Appl. Mater. Interfaces 2017, 9, 44392.
[61] Yao, C.; Tian, J.; Wang, H.; Zhang, D.-W.; Liu, Y.; Zhang, F.; Li, Z.-T. Chin. Chem. Lett. 2017, 28, 893.
[62] Tian, J.; Chen, L.; Zhang, D.-W.; Liu, Y.; Li, Z.-T. Chem. Commun. 2016, 52, 6351.
[63] Wang, H.; Zhang, D.-W.; Zhao, X.; Li, Z.-T. Acta Chim. Sinica 2015, 73, 471(in Chinese). (王辉, 张丹维, 赵新, 黎占亭, 化学学报, 2015, 73, 471.)
[64] Li, Y.-W.; Dong, Y.-H.; Miao, X.-R.; Ren, Y.-L.; Zhang, B.-L.; Wang, P.-P.; Yu, Y.; Li, B.; Isaacs, L.; Cao, L.-P. Angew. Chem., Int. Ed. 2018, 57, 729.
[65] Liu, H.; Zhang, Z.-H.; Zhao, Y.-J.; Zhou, Y.-X.; Xue, B.; Han, Y.-C.; Wang, Y.-L.; Mu, X.-L.; Zang, S.-L.; Zhou, X.-F.; Li, Z.-B. J. Mater. Chem. B 2019, 7, 1435.
[66] Yu, G.-C.; Tang, G.-P.; Huang, F.-H. J. Mater. Chem. C 2014, 2, 6609.
[67] Yu, G.-C.; Wu, D.; Li, Y.; Zhang, Z.-H.; Shao, L.; Zhou, J.; Hu, Q.-L.; Tang, G.-P.; Huang, F.-H. Chem. Sci. 2016, 7, 3017.
[68] Yu, G.-C.; Zhao, R.; Wu, D.; Zhang, F.-W.; Shao, L.; Zhou, J.; Yang, J.; Tang, G.-P.; Chen, X.-Y.; Huang, F.-H. Polym. Chem.-UK 2016, 7, 6178.
[69] Wang, Y.; Lv, M.-Z.; Song, N.; Liu, Z.-J.; Wang, C.-Y.; Yang, Y.-W. Macromolecules 2017, 50, 5759.
[70] Zhang, C.-W.; Jiang, S.-T.; Yin, G.-Q.; Li, X.; Zhao, X.-L.; Yang, H.-B. Isr. J. Chem. 2018, 58, 1265.
[71] Li, X.-S.; Han, J.-Y.; Qin, J.-C.; Sun, M.; Wu, J,-R.; Lei, L.-C.; Li, J.; Fang, L.; Yang, Y.-W. Chem. Commun. 2019, 55, 14099.
[72] Chi, X.-D.; Zhang, H.-C.; Vargas-Zúñiga, G. I.; Peters, G. M.; Sessler, J. L. J. Am. Chem. Soc. 2016, 138, 5829.
[73] Gao, J.; Guo, D.-S. Sci. Sin.:Chim. 2019, 49, 811(in Chinese). (高杰, 郭东升, 中国科学:化学, 2019, 49, 811.)
[74] Yang, J.; Li, Z. Chin. J. Org. Chem. 2019, 39, 3304(in Chinese). (杨杰, 李振, 有机化学, 2019, 39, 3304.)
[75] Lou, X.-Y.; Yang, Y.-W. Adv. Opt. Mater. 2018, 6, 1800668.
[76] Li, Y.-W.; Ao, W.-T.; Jin, H.-L.; Cao, L.-P. Prog. Chem. 2019, 31, 121(in Chinese). (李亚雯, 敖宛彤, 金慧琳, 曹利平, 化学进展, 2019, 31, 121.)
[77] Li, B.; He, T.; Shen, X.; Tang, D.-T.; Yin, S.-C. Polym. Chem.-UK 2019, 10, 796.
[78] Chen, H.; Li, M.-H. Chin. J. Polym. Sci. 2019, 37, 352.

基于主客体作用构筑的聚集诱导发光型超分子组装体在生物医用领域的研究进展