Chinese Journal of Organic Chemistry >
Fabrication and Applications of Supramolecular Chiral Assemblies
Received date: 2020-08-10
Revised date: 2020-09-10
Online published: 2020-09-30
Supported by
National Natural Science Foundation of China(21772112); National Natural Science Foundation of China(21604085)
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.
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 . DOI: 10.6023/cjoc202008011
| [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. |
| [3] | Brizard, A.; Oda, R.; Huc, I. Top. Curr. Chem. 2005, 256, 167. |
| [4] | Simonyi, M.; Bikádi, Z.; Zsila, F.; Deli, J. Chirality 2003, 15, 680. |
| [5] | Duan, P. F.; Zhu, X. F.; Liu, M. H. Chem. Commun. 2011, 47, 5569. |
| [6] | Cu, J. X.; Zheng, Y. J.; Shen, Z. H.; Wan, X. H. Langmuir 2010, 26, 15508. |
| [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. |
| [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. |
| [12] | Duan, P. F.; Cao, H.; Zhang, L.; Liu, M. H. Soft Matter 2014, 10, 5428. |
| [13] | Barclay, T. G.; Constantopoulos, K.; Matisons, J. Chem. Rev. 2014, 114, 10217. |
| [14] | Du, X. W.; Zhou, J.; Shi, J. F.; Xu, B. Chem. Rev. 2015, 115, 13165. |
| [15] | Zhang, L.; Wang, T. Y.; Shen, Z. C.; Liu, M. H. Adv. Mater. 2016, 28, 1044. |
| [16] | Gao, Y. X.; Liang, Y.; Hu, J.; Ju, Y. Prog. Chem. 2018, 30, 737. (in Chinese) |
| [16] | (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. |
| [18] | Chabre, Y. M.; Roy, R. Chem. Soc. Rev. 2013, 42, 4657. |
| [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) |
| [21] | (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. |
| [23] | Kobayashi, H.; Friggeri, A.; Koumoto, K.; Amaike, M.; Shinkai, S.; Reinhoudt, D. N. Org. Lett. 2002, 4, 1423. |
| [24] | Rajaganesh, R.; Gopal, A.; Das, T. M.; Ajayaghosh, A. Org. Lett. 2012, 14, 748. |
| [25] | Ogawa, Y.; Yoshiyama, C.; Kitaoka, T. Langmuir 2012, 28, 4404. |
| [26] | Fu, I. W.; Markegard, C. B.; Nguyen, H. D. Langmuir 2015, 31, 315. |
| [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. |
| [28] | Liu, G. F.; Li, X.; Sheng, J. S.; Li, P. Z.; Ong, W. K.; Phua, S. Z. F.; ?gren, H.; Zhu, L. L.; Zhao, Y. L. ACS Nano 2017, 11, 11880. |
| [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. |
| [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. |
| [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. |
| [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. |
| [35] | Konikoff, F. M.; Chung, D. S.; Donovan, J. M.; Small, D. M.; Carey, M. C. J. Clin. Invest. 1992; 90, 1155. |
| [36] | Abraham, S.; Vijayaraghavan, R. K.; Das, S. Langmuir 2009, 25, 8507. |
| [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. |
| [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. |
| [40] | Lu, J. R.; Ju, Y. Prog. Chem. 2016, 28, 260. (in Chinese) |
| [40] | (卢金荣, 巨勇, 化学进展, 2016, 28, 260.) |
| [41] | Bag, B. G.; Dash, S. S. Nanoscale 2011, 3, 4564. |
| [42] | Bag, B. G.; Dash, S. S. Langmuir 2015, 31, 13664. |
| [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. |
| [46] | George, S. J.; de Bruijn, R.; Tomovic?a, Z.; Van Averbeke, B.; Beljonne, D.; Lazzaroni, R.; Schenning, A. P. H. J.; Meijer, E. W. J. Am. Chem. Soc. 2012, 134, 17789. |
| [47] | Xing, P.; Zhao, Y. L. Acc. Chem. Res. 2018, 51, 2324. |
| [48] | Kaiser, T. R.; Stepanenko, V.; Würthner, F. J. Am. Chem. Soc. 2009, 131, 6719. |
| [49] | Minoia, A.; Destoop, I.; Ghijsens, E.; Feyter, S. D.; Tahara, K.; Tobec, Y.; Lazzaronia, R. RSC Adv. 2015, 5, 6642. |
| [50] | Green, M. M.; Reidy, M. P. J. Am. Chem. Soc. 1989, 111, 6452. |
| [51] | van, Gorp, J. J.; Vekemans,, J. A. J. M.; Meijer,, E. W. J. Am. Chem. Soc. 2002, 124, 14759. |
| [52] | Palmans, A. R. A.; Vekemans, J. A. J. M.; Havinga, E. E.; Meijer, E. W. Angew. Chem. Int. Ed., 1997, 36, 2648. |
| [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. |
| [55] | Dudek, M.; Machalska, E.; Oleszkiewicz, T.; Grzebelus, E.; Baranski, R.; Szcze?niak, 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. |
| [57] | Kim, M. J.; Shin, B. G.; Kim, J. J.; Kim, D. Y. J. Am. Chem. Soc. 2002, 124, 3504. |
| [58] | Xu, Y. Y.; Yang, G.; Xia, H. Y.; Zou, G.; Zhang, Q. J.; Gao, J. G. Nat. Commun. 2014, 5, 5050. |
| [59] | Chen, P. L.; Ma, X. G.; Hu, K. M.; Rong, Y. L.; Liu, M. H. Chem. Eur. J. 2011, 17, 12108. |
| [60] | Bailey, J.; Chrysostomou, A.; Hough, J. H.; Cledhill, T. M.; McCall, A.; Clark, S.; Menard, F.; Tamura, M. Science 1998, 281, 672. |
| [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. |
| [62] | Wang, L. B.; Yin, L.; Zhang, W.; Zhu, X. L.; Fujiki, M. J. Am. Chem. Soc. 2017, 139, 13218. |
| [63] | Ribó, J. M.; Crusats, J.; Sagués, F.; Claret, J.; Rubires, R. Science 2001, 292, 2063. |
| [64] | Micali, N.; Engelkamp, H.; van Rhee, P. G.; Christianen, P. C. M.; Monsù Scolaro, L.; Maan, J. C. Nat. Chem. 2012, 4, 201. |
| [65] | Yuan, J.; Zhang, L.; Huang, X.; Jiang, S. G.; Liu, M. H. Prog. Chem. 2005, 17, 780. (in Chinese) |
| [65] | (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) |
| [67] | (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. |
| [70] | Yuan, J.; Liu, M. H. J. Am. Chem. Soc. 2003, 125, 5051. |
| [71] | Maity, A.; Gangopadhyay, M.; Basu, A.; Aute, S.; Babu, S. S.; Das, A. J. Am. Chem. Soc. 2016, 138, 11113. |
| [72] | Cantekin, S.; de Greef, T. F. A.; Palmans, A. R. A. Chem. Soc. Rev. 2012, 41, 6125. |
| [73] | Karunakaran, S. C.; Cafferty, B. J.; Weigert-Mu?oz, A.; Schuster, G.B., Hud, N. V. Angew. Chem. Int. Ed. 2019, 58, 1453. |
| [74] | Shen, Z. C.; Jiang, Y. Q.; Wang, T. Y.; Liu, M. H. J. Am. Chem Soc. 2015, 137, 16109. |
| [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. |
| [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. |
| [83] | Savi?, S. M.; Vojisavljevi?, K.; Po?u?a-Ne?i?, M.; ?ivojevi?, K.; Mladenovi?, M.; Kne?evi?, N. ?. Metall. Mater. Eng. 2018, 24, 225. |
| [84] | Hembury, G. A.; Borovkov, V. V.; Inoue, Y. Chem. Rev. 2008, 108, 1 73. |
| [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. |
| [87] | Noguchi, T.; Roy, B.; Yoshihara, D.; Sakamoto, J.; Yamamoto, J.; Shinkai, S. Angew. Chem. Int. Ed. 2017, 56, 12518. |
| [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. |
| [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. |
| [91] | Kumar, J.; Nakashima, T.; Tsumatori, H.; Mori, M.; Naito, M.; Kawai, T. Chem.-Eur. J. 2013, 19, 14090. |
| [92] | Li, H. K.; Li, B. L.; Tang, B. Z. Chem. Asian J. 2019, 14, 674. |
| [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. |
| [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. |
| [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) |
| [97] | (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. |
| [99] | Jiang, J.; Ouyang, G. H.; Zhang, L.; Liu, M. H. Chem.-Eur. J. 2017, 23, 9439. |
| [100] | Mase, N.; Nakai, Y.; Ohara, N.; Yoda, H.; Takabe, K.; Tanaka, T.; Barbas, C. F. J. Am. Chem. Soc. 2006, 128, 734. |
| [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. |
| [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. |
| [106] | Yuan, C. H.; Jiang, J.; Sun, H.; Wang, D. C.; Hu, Y. H.; Liu, M. H. ChemCatChem 2018, 10, 2190. |
| [107] | Sun, H.; Jiang, J.; Sun, Y. M.; Zhang, Q.; Liu, M. H. Chem. Commun. 2019, 55, 3254. |
| [108] | Escuder, B.; Rodríguez-Llansola, F.; Miravet, J. F. New J. Chem. 2010, 34, 1044. |
/
| 〈 |
|
〉 |
