超分子手性组装体的构建与应用

doi:10.6023/cjoc202008011

摘要/Abstract

超分子手性组装体通常由多种非共价相互作用协同驱动形成, 是一类具有独特手性限域微环境的软物质, 对材料工程、生命科学、光学器件、催化合成等领域的发展具有重要作用. 其主要构建方法分为三种: 手性基元组装、手性因素诱导非手性基元组装、非手性基元对称性破缺组装. 通过分析近年来的研究成果, 归纳了利用这三种方法构建超分子手性组装体的一般策略, 并简要综述了超分子手性组装体在手性模板、手性识别、圆偏振发光及不对称催化领域中的应用进展与亟需弥补的缺陷. 随着研究的深入, 手性传递机制将得到进一步解释, 未来将有助于人们理解生命体内的手性现象, 有望最终解答自然界中的手性起源问题.

关键词: 超分子手性组装体, 手性模板, 手性识别, 圆偏振发光, 不对称催化

As a kind of soft materials promoted by multiple noncovalent interactions, supramolecular chiral assemblies own the distinctive confined chiral microenvironment and play an important role in material engineering, life science, optical devices and catalytic synthesis. In general, supramolecular chiral assembles can be fabricated through the assembly of chiral molecules, or a combination of achiral molecules and chiral inducements, or mere achiral molecules in symmetry breaking manner. In this paper, the general fabrication strategies of supramolecular chiral assemblies in recent years are summarized, and their improvements in chiral template, chiral recognition, circularly polarized luminescence and asymmetric catalysis are briefly reviewed, as well as the shortcomings in these fields. With the development of supramolecular chiral assemblies, the mechanism of chirality transfer will be explained in depth in future, which may help us understand the chirality phenomenon in organism and give a clue to answer to the origin of homochirality in nature.

Key words: supramolecular chiral assembly, chiral template, chiral recognition, circularly polarized luminescence, asymmetric catalysis

引用此文

刘金果, 殷凤, 胡君, 巨勇. 超分子手性组装体的构建与应用[J]. 有机化学, 2021, 41(3): 1031-1052.

Jinguo Liu, Feng Yin, Jun Hu, Yong Ju. Fabrication and Applications of Supramolecular Chiral Assemblies[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1031-1052.

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

分享此文

图/表 40

图1. (a) D-葡萄糖衍生物1的化学结构式和组装体的透射电镜图[19], 以及(b) Fmoc-D-葡萄糖胺2及Fmoc-D-半乳糖胺3的化学结构式[20]

Figure 1. (a) Chemical structures of D-glucose-based amphiphile 1 and TEM image of its assembly[19], and (b) chemical structures of Fmoc-D-glucosamine 2 and Fmoc-D-glucosamine 3[20]

图2. 化合物4形成左手螺旋与片层两种组装体的示意图[22]

Figure 2. Illustration of the self-assembly for twisted ribbons and microplates of 4[22]

图3. 二糖偶氮苯衍生物5~7以及组装体(a) 5和(b) 6的原位低压扫描电镜图(标尺: 1 μm) [25]

Figure 3. Disaccharide-azobenzene compounds 5~7, and in situ LVSEM images of their assemblies (a) 5 and (b) 6 (scale bar: 1 μm) [25]

图4. D-苯丙氨酸衍生物8~9以及其组装体(a) 8和(b) 9的扫描电镜图[28]

Figure 4. Chemical structures of D-phenylalanine derivatives 8~9 and SEM images of assemblies of (a) 8 and (b) 9[28]

图5. Bola型两亲性缬氨酸衍生物DD-10和LL-10[29]

Figure 5. Chemical structures of Bola-type valine-based amphiphiles DD-10 and LL-10[29]

图6. (a) D/L-11、12、13的化学结构式和它们形成棱形和六边形金属环的示意图, 以及(b) D-14, (c) L-14, (d) D-15, (e) L-15凝胶的扫描电镜图(插图为对应的透射电镜图)[30]

Figure 6. (a) Chemical structures of D/L-11, 12, 13 and illustration of the formation of metallacycles rhomboids and hexagons, SEM images of gels of (b) D-14, (c) L-14, (d) D-15, (e) L-15 (Inset: corresponding TEM images)[30]

图7. D/L-16的化学结构及其共组装体形貌随ee值变化的扫描电镜图(标尺: 5 μm) [31]

Figure 7. Chemical structures of D/L-16 and SEM images of their co-assemblies with various ee values (scale bar: 5 μm) [31]

图8. D/L-17的化学结构及其与Ag+组装成线性超分子结构的示意图[32]

Figure 8. Chemical structures of D/L-17 and illustration of the linear supramolecular structure assembled form D/L-17 and Ag+[32]

图9. 胆固醇-偶氮吡啶分子18及紫外光、金属离子对组装体维度和超分子手性的调控[38]

Figure 9. Chemical structure of cholesterol-azopyridine conjugate 18, and control on dimensions and supramolecular chirality of it sassemblies through UV and metal ions[38]

图10. 胆甾酸衍生物19~21的化学结构式及组装体19 (a)和20 (b)的扫描电镜图[39]

Figure 10. Chemical structures of bile acid derivatives 19~21, and SEM images of assemblies of 19 (a) and 20 (b)[39]

图11. 甘草酸22在水中自组装形成右手螺旋纤维的示意图[43]

Figure 11. Illustration of right-handed fibrils assembled from 22 in water[43]

图12. 23诱导甲酚红产生超分子手性信号[44]

Figure 12. CD spectra signal of cresol red induced by 23[44]

图13. 三萜-吡啶盐分子24~27形成的螺旋组装体[45]

Figure 13. Helical assemblies constructed by triterpenoid-pyridinium 24~27[45]

图14. C3对称性分子28和29的化学结构和螺旋组装示意图[51]

Figure 14. Chemical structures of C3-symmetrical 28 and 29, and illustration of their helical assemblies[51]

图15. 30, 31的化学结构式与共组装体CD信号随31比例在(a)正庚烷和(b)甲苯中的变化[53]

Figure 15. Chemical structures of 30, 31 and CD spectra of co-assemblies at different ratio of 31 in (a) n-heptane and (b) toluene[53]

图16. (a) D/L-32,33,34及D/L-32与34形成手性复合物的化学结构、(b) CD信号随D/L-32与33混合物中D/L-32比例的变化(■ D-32, ▲ L-32)、(c) CD信号随D/L-32混合物ee值的变化(■ L-32/▲ D-32的ee值)[54]

Figure 16. (a) Chemical structures of D/L-32, 33, 34 and the chiral complexes of D-32+34 and L-32+34, (b) CD spectra versus different molar fractions of D/L-32 in the mixtures of D/L-32 and 34 (■ D-32, ▲ L-32), and (c) plot of CD intensity at 315 nm versus different ee values of mixed D/L-32 (■ ee of L-32, ▲ ee of D-32)[54]

图17. 类胡萝卜素35~37的化学结构[55]

Figure 17. Chemical structures of carotenoids 35~37[55]

图18. 圆偏振光调控38的超分子手性组装[61]

Figure 18. Manipulation of supramolecular chiral assembly of 38 by circularly polarized light[61]

图19. 39的化学结构式及其组装体在两种波长圆偏振光诱导下产生的CD信号(a) 365 nm (b)313 nm[62]

Figure 19. Chemical structure of 39 and CD spectra of chiral assemblies of 39 induced by CPL at (a) 365 nm (b) 313 nm[62]

图20. 40的化学结构式及涡流和有效重力对40组装体的手性诱导[64]

Figure 20. Chemical structure of 40 and supramolecular chirality of assembled 40 induced by vortex and efficient gravity[64]

图21. 41的化学结构式及其与Ag(I)的手性组装模型[70]

Figure 21. Chemical structure of 41 and the proposed chiral model of 41-Ag(I)[70]

图22. (a) 42, 43及其六聚体的化学结构以及(b) 40份独立测试中组装体的CD信号[73]

Figure 22. (a) Chemical structures of 42, 43 and their hexamer, and (b) CD spectra of 40 independent assemblies[73]

图23. 44的化学结构及其凝胶对称性破缺、手性诱导与手性记忆的示意图[74]

Figure 23. Chemical structure of 44 and illustration of symmetry breaking, chiral induction and chiral memory of 44 gel[74]

图24. (a) 45和46的化学结构及其手性组装示意图, 以及(b, c)组装体中相反手性(明暗)的结构域[75]

Figure 24. (a) Chemical structures of 45, 46 and illustration of their chiral assemblies, and (b, c) chiral domains with opposite handedness (bright/dark) in assemblies[75]

图25. 47的组装过程以及手性从螺旋组装体到无机二氧化硅的印迹过程示意图[79]

Figure 25. Schematic of self-assembly process of 47 and chirality imprinting from helical-assembled 47 to inorganic silica[79]

图26. D/L-48, 49的化学结构及D-48与49形成螺旋带和双螺旋金纳米线的结构[80]

Figure 26. Chemical structures of D/L-48, 49 and supramolecular structures of twisted nanoribbons and double-helical Au nanowires fabricated by D-48 and 49[80]

图27. 两亲性分子50的自组装及其诱导纳米金颗粒/棒的手性排列[81]

Figure 27. Self-assembly of amphiphile 50 and DNA-directed chiral organization of AuNPs and AuNRs[81]

图28. D/L-51超分子组装体作为模板构建螺旋纳米结构的MOF[82]

Figure 28. Fabrication of helical MOF nanostructures by supramolecular assembly templates of D/L-51[82]

图29. 52的化学结构及其囊泡对D/L-酒石酸阴离子响应的DLS检测结果[85]

Figure 29. Chemical structure of 52 and response of vesicles self-assembled from 52 to D/L-tartrate monitored by DLS[85]

图30. 53的组装体结构模型及其对R/S-TBSA的响应[86]

Figure 30. Structure model of assemblies 53 and its responses to R/S-TBSA[86]

图31. 54的化学结构及其组装体识别RR/SS-环己烷二羧酸后的荧光变化[87]

Figure 31. Chemical structure of 54 and fluorescent change of assembled 54 in the presence of RR/SS-CHDA[87]

图32. 55, R-56的化学结构及其共组装、手性识别过程示意图[88]

Figure 32. Chemical structures of 56, R-56 and schematic representation of their co-assembly and enantioselective recognition[88]

图33. 57的化学结构[91]

Figure 33. Chemical structure of 57[91]

图34. 具有AIE活性的手性分子58及其组装体的透射电镜图[93]

Figure 34. Chiral AIE-active molecule 58 and TEM image of its assembly[93]

图35. 59的化学结构及其与荧光染料共组装得到的CPL光谱[94]

Figure 35. Chemical structure of 59 and CPL spectra of fluorescent dye co-assembled with 59[94]

图36. 60和量子点的化学结构及它们共组装体的全彩CPL光谱[95]

Figure 36. Chemical structures of 60, QDs and the full-color CPL spectra of their co-assemblies[95]

图37. 61~63的分子结构[100-101]

Figure 37. Chemical structures of 61~63[100-101]

图38. 64组装形成的纳米管与它催化的不对称Aldol反应[102]

Figure 38. Nanotubes self-assembled from 64 and the asymmetric aldol reaction catalyzed by these nanotubes[102]

图39. 65, 66的化学结构与纳米棒催化的不对称氢化反应[103]

Figure 39. Chemical structures of 65, 66 and the asymmetric hydrogenation catalyzed by nanorods of 65[103]

图40. (a) L-67和(b) D-67的化学结构与原子力显微镜下的螺旋组装体[104], 以及(c)螺旋纳米管不催化Dies-Alder反应的机理[105]

Figure 40. Chemical structures and AFM images of the helical assemblies of (a) L-67 and (b) D-67[104], and (c) proposed mechanism of asymmetric Diels-Alder reaction catalyzed by helical nanotubes[105]

参考文献 108

[1]	Cahn, R. S.; Ingold, S. C.; Prelog, V. Angew. Chem. Int. 1966, 5, 385.
[2]	Smith, D. K. Chem. Soc. Rev. 2009, 38, 684. pmid: 19322462
[3]	Brizard, A.; Oda, R.; Huc, I. Top. Curr. Chem. 2005, 256, 167. pmid: 22160339
[4]	Simonyi, M.; Bikádi, Z.; Zsila, F.; Deli, J. Chirality 2003, 15, 680. pmid: 12923806
[5]	Duan, P. F.; Zhu, X. F.; Liu, M. H. Chem. Commun. 2011, 47, 5569. doi: 10.1039/C1CC10813A
[6]	Cu, J. X.; Zheng, Y. J.; Shen, Z. H.; Wan, X. H. Langmuir 2010, 26, 15508. pmid: 20809603
[7]	Huang, Y. W.; Hu, J. C.; Kuang, W. F.; Wei, Z. X.; Faul, C. F. J. Chem. Commun. 2011, 47, 5554.
[8]	Xie, Y. Y.; Wang, Y. F.; Qi, W.; Huang, R. L.; Su, R. X.; He, Z. M. Small 2017, 13, 17009.
[9]	Cui, J. X.; Liu, A. H.; Guan, Y.; Zheng, J.; Shen, Z. H.; Wan, X. H. Langmuir 2010, 26, 3615. pmid: 19921782
[10]	Xie, F.; Qin, L.; Liu, M. H. Chem. Commun. 2016, 52, 930.
[11]	Shin, S.; Lim, S.; Kim, Y.; Kim, T.; Choi, T. L.; Lee, M. J. Am. Chem. Soc. 2013, 135, 2156. pmid: 23356458
[12]	Duan, P. F.; Cao, H.; Zhang, L.; Liu, M. H. Soft Matter 2014, 10, 5428. doi: 10.1039/c4sm00507d pmid: 24975350
[13]	Barclay, T. G.; Constantopoulos, K.; Matisons, J. Chem. Rev. 2014, 114, 10217. pmid: 25290622
[14]	Du, X. W.; Zhou, J.; Shi, J. F.; Xu, B. Chem. Rev. 2015, 115, 13165. pmid: 26646318
[15]	Zhang, L.; Wang, T. Y.; Shen, Z. C.; Liu, M. H. Adv. Mater. 2016, 28, 1044. pmid: 26385875
[16]	Gao, Y. X.; Liang, Y.; Hu, J.; Ju, Y. Prog. Chem. 2018, 30, 737. (in Chinese)
	(高玉霞, 梁云, 胡君, 巨勇, 化学进展, 2018, 30, 737.)
[17]	Delbianco, M.; Bharate, P.; Varela-Aramburu, S.; Seeberger, P. H. Chem. Rev. 2016, 116, 1693. pmid: 26702928
[18]	Chabre, Y. M.; Roy, R. Chem. Soc. Rev. 2013, 42, 4657. pmid: 23400414
[19]	Jung, J. H.; John, G.; Masuda, M.; Yoshida, K.; Shinkai, S.; Shimizu, T. Langmuir 2001, 17, 7229.
[20]	Birchall, L. S.; Roy, S.; Jayawarna, V.; Hughes, M.; Irvine, E.; Okorogheye, G. T.; Saudi, N.; De Santis, E.; Tuttle, T.; Edwards, A. A.; Ulijn, R. V. Chem. Sci. 2011, 2, 1349.
[21]	Wang, K. R. Prog. Chem. 2015, 27, 775. (in Chinese)
	(王克让, 化学进展, 2015, 57, 775.)
[22]	Sun, K.; Xiao, C. Y.; Liu, C. M.; Fu, W. X.; Wang, Z. H.; Li, Z. B. Langmuir 2014, 30, 11040. pmid: 25166855
[23]	Kobayashi, H.; Friggeri, A.; Koumoto, K.; Amaike, M.; Shinkai, S.; Reinhoudt, D. N. Org. Lett. 2002, 4, 1423. doi: 10.1021/ol025519+ pmid: 11975594
[24]	Rajaganesh, R.; Gopal, A.; Das, T. M.; Ajayaghosh, A. Org. Lett. 2012, 14, 748. doi: 10.1021/ol203294v pmid: 22251145
[25]	Ogawa, Y.; Yoshiyama, C.; Kitaoka, T. Langmuir 2012, 28, 4404. pmid: 22339091
[26]	Fu, I. W.; Markegard, C. B.; Nguyen, H. D. Langmuir 2015, 31, 315. pmid: 25488898
[27]	Kurouski, D.; Lu, X. F.; Popova, L.; Wan, W.; Shanmugasundaram, M.; Stubbs, G.; Dukor, R. K.; Lednev, I. K.; Nafie, L. A. J. Am. Chem. Soc. 2014, 136, 2302. pmid: 24484302
[28]	Liu, G. F.; Li, X.; Sheng, J. S.; Li, P. Z.; Ong, W. K.; Phua, S. Z. F.; Ågren, H.; Zhu, L. L.; Zhao, Y. L. ACS Nano 2017, 11, 11880. doi: 10.1021/acsnano.7b06097 pmid: 29140680
[29]	Wu, X. J.; Ji, S. J.; Li, Y.; Li, B.Z; Zhu, X. L.; Hanabusa, K.; Yang, Y. G. J. Am. Chem. Soc. 2009, 131, 5986. doi: 10.1021/ja9001376 pmid: 19348460
[30]	Sun, Y.; Li, S.; Zhou, Z. X.; Saha, M. L.; Datta, S.; Zhang, M. M.; Yan, X. Z.; Tian, D. M.; Wang, H.; Wang, L.; Li, X. P.; Liu, M. H.; Li, H. B.; Stang, P. J. J. Am. Chem. Soc. 2018, 140, 3257. doi: 10.1021/jacs.7b10769
[31]	Cao, H.; Zhu, X. F.; Liu, M. H. Angew. Chem. Int. Ed. 2013, 52, 4122.
[32]	Yuan, Y.; Xiao, Y. W.; Yan, X. S.; Wu, S. X.; Luo, H.; Lin, J. B.; Li, Z.; Jiang, Y. B. Chem. Commun. 2019, 55, 12849.
[33]	Nonappaa; Maitra, U. Org. Biomol. Chem. 2008, 6, 657. doi: 10.1039/b714475j pmid: 18354842
[34]	Qiao, Y.; Lin, Y. Y.; Wang, Y. J.; Yang, Z. Y.; Liu, J.; Zhou, J.; Yan, Y.; Huang, J. B. Nano Lett. 2009, 9, 4500. doi: 10.1021/nl9028335 pmid: 19908861
[35]	Konikoff, F. M.; Chung, D. S.; Donovan, J. M.; Small, D. M.; Carey, M. C. J. Clin. Invest. 1992; 90, 1155. doi: 10.1172/JCI115935 pmid: 1522223
[36]	Abraham, S.; Vijayaraghavan, R. K.; Das, S. Langmuir 2009, 25, 8507. pmid: 19405484
[37]	Travaglini, L.; D’Annibale, A.; Schillén, K.; Olsson, U.; Sennato, S.; Pavela, N. V.; Galantini, L. Chem. Commun. 2012, 48, 12011.
[38]	Liu, G. F.; Sheng, J. H.; Teo, W. L.; Yang, G. B.; Wu, H. W.; Li, Y. X.; Zhao, Y. L. J. Am. Chem. Soc. 2018, 140, 16275. pmid: 30403348
[39]	Li, Y.; Li, G. T.; Wang, X. Y.; Li, W. N.; Su, Z. X.; Zhang, Y. H.; Ju, Y. Chem. Eur. J. 2009, 15, 6399. pmid: 19472246
[40]	Lu, J. R.; Ju, Y. Prog. Chem. 2016, 28, 260. (in Chinese)
	(卢金荣, 巨勇, 化学进展, 2016, 28, 260.)
[41]	Bag, B. G.; Dash, S. S. Nanoscale 2011, 3, 4564. pmid: 21947431
[42]	Bag, B. G.; Dash, S. S. Langmuir 2015, 31, 13664. doi: 10.1021/acs.langmuir.5b03730 pmid: 26671722
[43]	Saha, A.; Adamcik, J.; Bolisetty, S.; Handschin, S.; Mezzenga, R. Angew. Chem. Int. Ed. 2015, 54, 5408.
[44]	Hu, J.; Zhang, M.; Ju, Y. Soft Matter 2009, 5, 4971.
[45]	Gao, Y. X.; Hao, J.; Wu, J. D.; Zhang, X.; Hu, J.; Ju, Y. Nanoscale 2015, 7, 13568. pmid: 26204430
[46]	George, S. J.; de Bruijn, R.; Tomovića, Z.; Van Averbeke, B.; Beljonne, D.; Lazzaroni, R.; Schenning, A. P. H. J.; Meijer, E. W. J. Am. Chem. Soc. 2012, 134, 17789. doi: 10.1021/ja3086005 pmid: 23030496
[47]	Xing, P.; Zhao, Y. L. Acc. Chem. Res. 2018, 51, 2324. pmid: 30179457
[48]	Kaiser, T. R.; Stepanenko, V.; Würthner, F. J. Am. Chem. Soc. 2009, 131, 6719. doi: 10.1021/ja900684h pmid: 19388696
[49]	Minoia, A.; Destoop, I.; Ghijsens, E.; Feyter, S. D.; Tahara, K.; Tobec, Y.; Lazzaronia, R. RSC Adv. 2015, 5, 6642. doi: 10.1039/C4RA11269E
[50]	Green, M. M.; Reidy, M. P. J. Am. Chem. Soc. 1989, 111, 6452. doi: 10.1021/ja00198a084
[51]	van, Gorp, J. J.; Vekemans,, J. A. J. M.; Meijer,, E. W. J. Am. Chem. Soc. 2002, 124, 14759. pmid: 12465989
[52]	Palmans, A. R. A.; Vekemans, J. A. J. M.; Havinga, E. E.; Meijer, E. W. Angew. Chem. Int. Ed., 1997, 36, 2648. doi: 10.1002/(ISSN)1521-3773
[53]	Veling, N.; van Hameren, R.; van Buul, A. M.; Rowan, A. E.; Nolte, R. J. M.; Elemans, J. A. W. Chem. Commun. 2012, 48, 4371.
[54]	Nie, B.; Zhan, T. G.; Zhou, T. Y.; Xiao, Z. Y.; Jiang, G. f.; Zhao, X. Chem. Asian. J. 2014, 9, 754. pmid: 24458482
[55]	Dudek, M.; Machalska, E.; Oleszkiewicz, T.; Grzebelus, E.; Baranski, R.; Szcześniak, P.; Mlynarski, J.; Zajac, G.; Kaczor, A.; Baranska, M. Angew. Chem. Int. Ed., 2019, 58, 8383.
[56]	Avalos, M.; Babiano, R.; Cintas, P.; Jiméne, J. L.; Palacios, J. C. Chem. Rev. 1998, 98, 2391. pmid: 11848967
[57]	Kim, M. J.; Shin, B. G.; Kim, J. J.; Kim, D. Y. J. Am. Chem. Soc. 2002, 124, 3504. pmid: 11929229
[58]	Xu, Y. Y.; Yang, G.; Xia, H. Y.; Zou, G.; Zhang, Q. J.; Gao, J. G. Nat. Commun. 2014, 5, 5050. pmid: 25247276
[59]	Chen, P. L.; Ma, X. G.; Hu, K. M.; Rong, Y. L.; Liu, M. H. Chem. Eur. J. 2011, 17, 12108. pmid: 21905133
[60]	Bailey, J.; Chrysostomou, A.; Hough, J. H.; Cledhill, T. M.; McCall, A.; Clark, S.; Menard, F.; Tamura, M. Science 1998, 281, 672. pmid: 9714676
[61]	Kim, J.; Lee, J.; Kim, W. Y.; Kim, H.; Lee, S.; Lee, H. C.; Lee, Y. S.; Seo, M.; Kim, S. Y. Nat. Commun. 2015, 6, 6959. pmid: 25903970
[62]	Wang, L. B.; Yin, L.; Zhang, W.; Zhu, X. L.; Fujiki, M. J. Am. Chem. Soc. 2017, 139, 13218. pmid: 28846842
[63]	Ribó, J. M.; Crusats, J.; Sagués, F.; Claret, J.; Rubires, R. Science 2001, 292, 2063. pmid: 11408653
[64]	Micali, N.; Engelkamp, H.; van Rhee, P. G.; Christianen, P. C. M.; Monsù Scolaro, L.; Maan, J. C. Nat. Chem. 2012, 4, 201. pmid: 22354434
[65]	Yuan, J.; Zhang, L.; Huang, X.; Jiang, S. G.; Liu, M. H. Prog. Chem. 2005, 17, 780. (in Chinese)
	(袁菁, 张莉, 黄昕, 姜思光, 刘鸣华, 化学进展, 2005, 17, 780.)
[66]	Hegstrom, R. A.; Kondepudi, D. K. Sci. Am. 1990, 262, 108.
[67]	Zhang, J.; Yuan, H.; Cai, J.; Wei, X. H.; Liu, D. S. Sci. Bull. 2016, 61, 630. (in Chinese)
	(张静, 袁鸿, 蔡瑾, 魏学红, 刘滇生, 科学通报, 2016, 61, 630.)
[68]	Sang, Y. T.; Liu, M. H. Symmetry 2019, 11, 950.
[69]	Viswanathan, R.; Zasadzinski, J. A.; Schwartz, D. K. Nature 1994, 368, 440. doi: 10.1038/368440a0
[70]	Yuan, J.; Liu, M. H. J. Am. Chem. Soc. 2003, 125, 5051. doi: 10.1021/ja0288486 pmid: 12708854
[71]	Maity, A.; Gangopadhyay, M.; Basu, A.; Aute, S.; Babu, S. S.; Das, A. J. Am. Chem. Soc. 2016, 138, 11113. pmid: 27517868
[72]	Cantekin, S.; de Greef, T. F. A.; Palmans, A. R. A. Chem. Soc. Rev. 2012, 41, 6125. pmid: 22773107
[73]	Karunakaran, S. C.; Cafferty, B. J.; Weigert-Muñoz, A.; Schuster, G.B., Hud, N. V. Angew. Chem. Int. Ed. 2019, 58, 1453. doi: 10.1002/anie.v58.5
[74]	Shen, Z. C.; Jiang, Y. Q.; Wang, T. Y.; Liu, M. H. J. Am. Chem Soc. 2015, 137, 16109. pmid: 26647220
[75]	Buchs, J.; Vogel, L.; Janietz, D.; Prehm, M.; Tschierske, C. Angew. Chem. Int. Ed. 2017, 56, 280.
[76]	Ariga, K.; Mori, T.; Kitao, T.; Uemura, T. Adv. Mater. 2020,1905657.
[77]	Llusar, M.; Sanchez, C. Chem. Mater. 2008, 20, 782.
[78]	Sone, E. D.; Zubarev, E. R.; Stupp, S. I. Angew. Chem. Int. Ed. 2002, 41, 1705.
[79]	Gao, Y. X.; Hao, J.; Liu, J. G.; Liang, Y.; Du, F. P.; Hu, J.; Ju, Y. Mater. Chem. Front. 2019, 3, 308.
[80]	Nakagawa, M.; Kawai, T. J. Am. Chem. Soc. 2018, 140, 4991. doi: 10.1021/jacs.8b00910 pmid: 29613794
[81]	Golla, M.; Albert, S. K.; Atchimnaidu, S.; Perumal, D.; Krishnan, N.; Varghese, R. Angew. Chem. Int. Ed. 2019, 58, 3865.
[82]	Wang, H.; Zhu, W.; Li, J.; Tian, T.; Lan, Y.; Gao, N.; Wang, C.; Zhang, M.; Faul, C. F. J.; Li, G. T. Chem. Sci. 2015, 6, 1910. doi: 10.1039/c4sc03278k pmid: 28757993
[83]	Savić, S. M.; Vojisavljević, K.; Počuča-Nešić, M.; Živojević, K.; Mladenović, M.; Knežević, N. Ž. Metall. Mater. Eng. 2018, 24, 225.
[84]	Hembury, G. A.; Borovkov, V. V.; Inoue, Y. Chem. Rev. 2008, 108, 1 73. pmid: 18095713
[85]	He, Q.; Tuo, D. T.; Ao, Y. F.; Wang, Q. Q.; Wang, D. X. ACS Appl. Mater. Interfaces 2018, 10, 3181.
[86]	Li, S.; Zhang, L.; Jiang, J.; Meng, Y.; Liu, M. H. ACS Appl. Mater. Interfaces 2017, 9, 37386. doi: 10.1021/acsami.7b10353
[87]	Noguchi, T.; Roy, B.; Yoshihara, D.; Sakamoto, J.; Yamamoto, J.; Shinkai, S. Angew. Chem. Int. Ed. 2017, 56, 12518. doi: 10.1002/anie.v56.41
[88]	Yue, B. B.; Yin, L. Y.; Zhao, W. D.; Jia, X. Y.; Zhu, M. J.; Wu, B.; Wu, S.; Zhu, L. L. ACS Nano 2019, 13, 12438. doi: 10.1021/acsnano.9b06250 pmid: 31560190
[89]	Sang, Y. T.; Han, J. L.; Zhao, T. H.; Duan, P. F.; Liu, M. H. Adv. Mater. 2019,1900110.
[90]	Kumar, J.; Nakashima, T.; Kawai, T. J. Phys. Chem. Lett. 2015, 6, 3445. doi: 10.1021/acs.jpclett.5b01452 pmid: 26269090
[91]	Kumar, J.; Nakashima, T.; Tsumatori, H.; Mori, M.; Naito, M.; Kawai, T. Chem.-Eur. J. 2013, 19, 14090. pmid: 24026812
[92]	Li, H. K.; Li, B. L.; Tang, B. Z. Chem. Asian J. 2019, 14, 674. pmid: 30417570
[93]	Liu, J. Z.; Su, H. M.; Meng, L. M.; Zhao, Y. H.; Deng, C. M.; Ng, J. C. Y.; Lu, P.; Faisal, M.; Lam, J. W. Y.; Huang, X. H.; Wu, H. K.; Wong, K. S.; Tang, B. Z. Chem. Sci. 2012, 3, 2737. doi: 10.1039/c2sc20382k
[94]	Goto, T.; Okazaki, Y.; Ueki, M.; Kuwahara, Y.; Takafuji, M.; Oda, R.; Ihara, H. Angew. Chem. Int. Ed. 2017, 56, 2989.
[95]	Huo, S. W.; Duan, P. F.; Jiao, T. F.; Peng, Q. M.; Liu, M. H. Angew. Chem. Int. Ed. 2017, 56, 12174. doi: 10.1002/anie.201706308
[96]	Nitti, A.; Pasini, D. Adv. Mater. 2020,1908021.
[97]	Jin, Q. X.; Li, J.; Li, X. G.; Zhang, L.; Fang, S. M.; Liu, M. H. Prog. Chem. 2014, 26, 919. (in Chinese)
	(靳清贤, 李晶, 李孝刚, 张莉, 方少明, 刘鸣华, 化学进展, 2014, 26, 919.)
[98]	Fang, W. W.; Zhang, Y.; Wu, J. J.; Liu, C.; Zhu, H. B.; Tu, T. Chem. Asian J. 2018, 13, 712. pmid: 29377536
[99]	Jiang, J.; Ouyang, G. H.; Zhang, L.; Liu, M. H. Chem.-Eur. J. 2017, 23, 9439. doi: 10.1002/chem.201700727 pmid: 28342230
[100]	Mase, N.; Nakai, Y.; Ohara, N.; Yoda, H.; Takabe, K.; Tanaka, T.; Barbas, C. F. J. Am. Chem. Soc. 2006, 128, 734. doi: 10.1021/ja0573312 pmid: 16417359
[101]	Clarke, M. L.; Fuentes, J. A. Angew. Chem. Int. Ed. 2007, 46, 930.
[102]	Lee, K. S.; Parquette, J. R. Chem. Commun. 2015, 51, 15653.
[103]	Raynal, M.; Portier, F.; van Leeuwen, P. W. N. M.; Bouteiller, L. J. Am. Chem. Soc. 2013, 135, 17687. doi: 10.1021/ja408860s pmid: 24152058
[104]	Jiang, J.; Wang, T. Y.; Liu, M. H. Chem. Commun. 2010, 46, 7178.
[105]	Jiang, J.; Meng, Y.; Zhang, L.; Liu, M. H. J. Am. Chem. Soc. 2016, 138, 15629. pmid: 27934018
[106]	Yuan, C. H.; Jiang, J.; Sun, H.; Wang, D. C.; Hu, Y. H.; Liu, M. H. ChemCatChem 2018, 10, 2190. doi: 10.1002/cctc.v10.10
[107]	Sun, H.; Jiang, J.; Sun, Y. M.; Zhang, Q.; Liu, M. H. Chem. Commun. 2019, 55, 3254. doi: 10.1039/C9CC00941H
[108]	Escuder, B.; Rodríguez-Llansola, F.; Miravet, J. F. New J. Chem. 2010, 34, 1044. doi: 10.1039/b9nj00764d