Citation: Lin Zu-Jin, Cao Rong. Porous Hydrogen-bonded Organic Frameworks (HOFs): Status and Challenges[J]. Acta Chimica Sinica, ;2020, 78(12): 1309-1335. doi: 10.6023/A20080359 shu

Porous Hydrogen-bonded Organic Frameworks (HOFs): Status and Challenges

Lin Zu-Jin ^a,b,, ,
Cao Rong ^b,,

a.
Department of Applied Chemistry, College of Life Science, Fujian Agriculture and Forestry University, Fuzhou 350002, China
b.
State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, China

Corresponding author: Lin Zu-Jin, linzujin@fafu.edu.cn Cao Rong, rcao@fjirsm.ac.cn
Received Date: 12 August 2020
Available Online: 3 September 2020
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21520102001), Natural Science Foundation of Fujian Province of China (No. 2020J01549), and Fujian Agriculture and Forestry University (Nos. 118360020, XJQ201616)Natural Science Foundation of Fujian Province of China 2020J01549Fujian Agriculture and Forestry University 118360020Fujian Agriculture and Forestry University XJQ201616the National Natural Science Foundation of China 21520102001

Figures(31)

Hydrogen-bonded organic frameworks (HOFs), usually self-assembled by organic or metal-organic building blocks via intermolecular H-bonding interactions, have become a unique type of crystalline porous material. Although the weak and flexible nature of hydrogen bonds makes most HOFs fragile, the high stability and permanent porosity could be realized by the judicious selection of rigid building blocks with special spatial configuration as well as the introduction of framework interpenetration and/or other intermolecular interactions like π-π stacking and electrostatic interactions, etc. Compared with other crystalline porous materials like metal-organic frameworks (MOFs) and covalent-organic frameworks (COFs), HOFs feature mild preparation condition, high crystallinity, permissible solution processability, easy healing and regeneration, etc. These distinguishing merits make HOFs capable to be used as unique multifunctional porous materials. Herein, we first review the basic rules to design and synthesize stable and porous HOFs, and then systematically summarize the representative supramolecular synthons and backbones that have been used to build stable and porous HOFs. Emphasis is put on the potential applications of HOFs in gas adsorption and separation, proton conduction, heterogeneous catalysis, luminescence and sensing, biological applications, enantiomeric resolution and aromatic compounds separation, pollutants removal, and structure determination, etc.
- hydrogen-bonded organic framework (HOF),
- supramolecular synthon,
- hydrogen bond,
- structural design,
- permanent porosity
1. [1]
  Yaghi, O. M.; Li, G.; Li, H. Nature 1995, 378, 703.
2. [2]
  Zhang, X.; Wang, X.; Fan, W.; Sun, D. Chin. J. Chem. 2020, 38, 509.
3. [3]
  Kitagawa, S.; Kitaura, R.; Noro, S.-i. Angew. Chem. Int. Ed. 2004, 43, 2334.
4. [4]
  Côté, A. P.; Benin, A. I.; Ockwig, N. W.; O'Keeffe, M.; Matzger, A. J.; Yaghi, O. M. Science 2005, 310, 1166.
5. [5]
  Lv, H.; Sa, R.; Li, P.; Yuan, D.; Wang, X.; Wang, R. Sci. China Chem. 2020, 63, 1289.
6. [6]
  He, Y.; Xiang, S.; Chen, B. J. Am. Chem. Soc. 2011, 133, 14570.
7. [7]
  Lin, Z.-J.; Lü, J.; Hong, M.; Cao, R. Chem. Soc. Rev. 2014, 43, 5867.
8. [8]
  Hoskins, B. F.; Robson, R. J. Am. Chem. Soc. 1989, 111, 5962.
9. [9]
  Hoskins, B. F.; Robson, R. J. Am. Chem. Soc. 1990, 112, 1546.
10. [10]
  Li, H.; Eddaoudi, M.; Groy, T. L.; Yaghi, O. M. J. Am. Chem. Soc. 1998, 120, 8571.
11. [11]
  Kondo, M.; Yoshitomi, T.; Matsuzaka, H.; Kitagawa, S.; Seki, K. Angew. Chem. Int. Ed. 1997, 36, 1725.
12. [12]
  Kim, J.; Chen, B.; Reineke, T. M.; Li, H.; Eddaoudi, M.; Moler, D. B.; O'Keeffe, M.; Yaghi, O. M. J. Am. Chem. Soc. 2001, 123, 8239.
13. [13]
  Eddaoudi, M.; Moler, D. B.; Li, H.; Chen, B.; Reineke, T. M.; O'Keeffe, M.; Yaghi, O. M. Acc. Chem. Res. 2001, 34, 319.
14. [14]
  Ockwig, N. W.; Delgado-Friedrichs, O.; O'Keeffe, M.; Yaghi, O. M. Acc. Chem. Res. 2005, 38, 176.
15. [15]
  O’Keeffe, M.; Peskov, M. A.; Ramsden, S. J.; Yaghi, O. M. Acc. Chem. Res. 2008, 41, 1782.
16. [16]
  O’Keeffe, M. Chem. Soc. Rev. 2009, 38, 1215.
17. [17]
  Zeng, Y.-N.; Zheng, H.-Q.; Gu, J.-F.; Cao, G.-J.; Zhuang, W.-E.; Lin, J.-D.; Cao, R.; Lin, Z.-J. Inorg. Chem. 2019, 58, 13360.
18. [18]
  Zeng, Y.-N.; Zheng, H.-Q.; He, X.-H.; Cao, G.-J.; Wang, B.; Wu, K.; Lin, Z.-J. Dalton Trans. 2020, 49, 9680.
19. [19]
  Zheng, H.-Q.; Liu, C.-Y.; Zeng, X.-Y.; Chen, J.; Lü, J.; Lin, R.-G.; Cao, R.; Lin, Z.-J.; Su, J.-W. Inorg. Chem. 2018, 57, 9096.
20. [20]
  Wang, Z.; Zhang, S.; Chen, Y.; Zhang, Z.; Ma, S. Chem. Soc. Rev. 2020, 49, 708.
21. [21]
  Liu, J. G.; Zhang, M. Y.; Wang, N.; Wang, C. G.; Ma, L. L. Acta Chim. Sinica 2020, 78, 311 (in Chinese).
22. [22]
  Peng, Z. K.; Ding, H. M.; Chen, R. F.; Gao, C.; Wang, C. Acta Chim. Sinica 2019, 77, 681 (in Chinese).
23. [23]
  Luo, J.; Wang, J.-W.; Zhang, J.-H.; Lai, S.; Zhong, D.-C. CrystEngComm 2018, 20, 5884.
24. [24]
  Hisaki, I.; Xin, C.; Takahashi, K.; Nakamura, T. Angew. Chem. Int. Ed. 2019, 58, 11160.
25. [25]
  Lin, R.-B.; He, Y.; Li, P.; Wang, H.; Zhou, W.; Chen, B. Chem. Soc. Rev. 2019, 48, 1362.
26. [26]
  Yang, J.; Wang, J.; Hou, B.; Huang, X.; Wang, T.; Bao, Y.; Hao, H. Chem. Eng. J. 2020, 399, 125873.
27. [27]
  Wang, B.; Lin, R.-B.; Zhang, Z.; Xiang, S.; Chen, B. J. Am. Chem. Soc. 2020, 14399.
28. [28]
  Lü, J.; Cao, R. Angew. Chem. Int. Ed. 2016, 55, 9474.
29. [29]
  Duchamp, D. J.; Marsh, R. E. Acta Crystallogr. B 1969, 25, 5.
30. [30]
  Simard, M.; Su, D.; Wuest, J. D. J. Am. Chem. Soc. 1991, 113, 4696.
31. [31]
  Wang, X.; Simard, M.; Wuest, J. D. J. Am. Chem. Soc. 1994, 116, 12119.
32. [32]
  Yang, W.; Greenaway, A.; Lin, X.; Matsuda, R.; Blake, A. J.; Wilson, C.; Lewis, W.; Hubberstey, P.; Kitagawa, S.; Champness, N. R.; Schrder, M. J. Am. Chem. Soc. 2010, 132, 14457.
33. [33]
  Hu, Y.-X.; Li, W.-J.; Jia, P.-P.; Wang, X.-Q.; Xu, L.; Yang, H.-B. Adv. Opt. Mater. 2020, 8, 2000265.
34. [34]
  Hu, F.; Liu, C.; Wu, M.; Pang, J.; Jiang, F.; Yuan, D.; Hong, M. Angew. Chem. Int. Ed. 2017, 56, 2101.
35. [35]
  Huang, Q.; Li, W.; Mao, Z.; Qu, L.; Li, Y.; Zhang, H.; Yu, T.; Yang, Z.; Zhao, J.; Zhang, Y.; Aldred, M. P.; Chi, Z. Nat. Commun. 2019, 10, 3074.
36. [36]
  Li, Y.-L.; Alexandrov, E. V.; Yin, Q.; Li, L.; Fang, Z.-B.; Yuan, W.; Proserpio, D. M.; Liu, T.-F. J. Am. Chem. Soc. 2020, 142, 7218.
37. [37]
  Pulido, A.; Chen, L.; Kaczorowski, T.; Holden, D.; Little, M. A.; Chong, S. Y.; Slater, B. J.; McMahon, D. P.; Bonillo, B.; Stackhouse, C. J.; Stephenson, A.; Kane, C. M.; Clowes, R.; Hasell, T.; Cooper, A. I.; Day, G. M. Nature 2017, 543, 657.
38. [38]
  Cui, P.; McMahon, D. P.; Spackman, P. R.; Alston, B. M.; Little, M. A.; Day, G. M.; Cooper, A. I. Chem. Sci. 2019, 10, 9988.
39. [39]
  Cui, P.; Svensson Grape, E.; Spackman, P. R.; Wu, Y.; Clowes, R.; Day, G. M.; Inge, A. K.; Little, M. A.; Cooper, A. I. J. Am. Chem. Soc. 2020, 12743.
40. [40]
  Desiraju, G. R. Angew. Chem. Int. Ed. 1995, 34, 2311.
41. [41]
  Herbstein, F. H.; Kapon, M.; Reisner, G. M. J. Incl. Phenom. 1987, 5, 211.
42. [42]
  Zentner, C. A.; Lai, H. W. H.; Greenfield, J. T.; Wiscons, R. A.; Zeller, M.; Campana, C. F.; Talu, O.; FitzGerald, S. A.; Rowsell, J. L. C. Chem. Commun. 2015, 51, 11642.
43. [43]
  Nandi, S.; Chakraborty, D.; Vaidhyanathan, R. Chem. Commun. 2016, 52, 7249.
44. [44]
  Yang, W.; Wang, J.; Wang, H.; Bao, Z.; Zhao, J. C.-G.; Chen, B. Cryst. Growth Des. 2017, 17, 6132.
45. [45]
  Lai, H. W. H.; Wiscons, R. A.; Zentner, C. A.; Zeller, M.; Rowsell, J. L. C. Cryst. Growth Des. 2016, 16, 821.
46. [46]
  Yang, W.; Zhou, W.; Chen, B. Cryst. Growth Des. 2019, 19, 5184.
47. [47]
  Yin, Q.; Zhao, P.; Sa, R. J.; Chen, G. C.; Lu, J.; Liu, T. F.; Cao, R. Angew. Chem. Int. Ed. 2018, 57, 7691.
48. [48]
  Wang, B.; Lv, X.-L.; Lv, J.; Ma, L.; Lin, R.-B.; Cui, H.; Zhang, J.; Zhang, Z.; Xiang, S.; Chen, B. Chem. Commun. 2020, 56, 66.
49. [49]
  Ma, K.; Li, P.; Xin, J. H.; Chen, Y.; Chen, Z.; Goswami, S.; Liu, X.; Kato, S.; Chen, H.; Zhang, X.; Bai, J.; Wasson, M. C.; Maldonado, R. R.; Snurr, R. Q.; Farha, O. K. Cell Reports Physical Science 2020, 1, 100024.
50. [50]
  Hisaki, I.; Nakagawa, S.; Tohnai, N.; Miyata, M. Angew. Chem. Int. Ed. 2015, 54, 3008.
51. [51]
  Hisaki, I.; Ikenaka, N.; Tohnai, N.; Miyata, M. Chem. Commun. 2016, 52, 300.
52. [52]
  Hisaki, I.; Nakagawa, S.; Ikenaka, N.; Imamura, Y.; Katouda, M.; Tashiro, M.; Tsuchida, H.; Ogoshi, T.; Sato, H.; Tohnai, N.; Miyata, M. J. Am. Chem. Soc. 2016, 138, 6617.
53. [53]
  Hisaki, I.; Nakagawa, S.; Sato, H.; Tohnai, N. Chem. Commun. 2016, 52, 9781.
54. [54]
  Hisaki, I.; Ikenaka, N.; Gomez, E.; Cohen, B.; Tohnai, N.; Douhal, A. Chem. Eur. J. 2017, 23, 11611.
55. [55]
  Hisaki, I.; Toda, H.; Sato, H.; Tohnai, N.; Sakurai, H. Angew. Chem. Int. Ed. 2017, 56, 15294.
56. [56]
  Hisaki, I.; Ikenaka, N.; Tsuzuki, S.; Tohnai, N. Mater. Chem. Front. 2018, 2, 338.
57. [57]
  Hisaki, I.; Nakagawa, S.; Suzuki, Y.; Tohnai, N. Chem. Lett. 2018, 47, 1143.
58. [58]
  Hisaki, I.; Suzuki, Y.; Gomez, E.; Cohen, B.; Tohnai, N.; Douhal, A. Angew. Chem. Int. Ed. 2018, 57, 12650.
59. [59]
  Gomez, E.; Suzuki, Y.; Hisaki, I.; Moreno, M.; Douhal, A. J. Mater. Chem. C 2019, 7, 10818.
60. [60]
  Hisaki, I.; Suzuki, Y.; Gomez, E.; Ji, Q.; Tohnai, N.; Nakamura, T.; Douhal, A. J. Am. Chem. Soc. 2019, 141, 2111.
61. [61]
  Gomez, E.; di Nunzio, M. R.; Moreno, M.; Hisaki, I.; Douhal, A. J. Phys. Chem. C 2020, 124, 6938.
62. [62]
  Hisaki, I.; Ji, Q.; Takahashi, K.; Tohnai, N.; Nakamura, T. Cryst. Growth Des. 2020, 20, 3190.
63. [63]
  Hisaki, I. J. Incl. Phenom. Macro. 2020, 96, 215.
64. [64]
  Yin, Q.; Lü, J.; Li, H.-F.; Liu, T.-F.; Cao, R. Cryst. Growth Des. 2019, 19, 4157.
65. [65]
  Li, P.; Chen, Z.; Ryder, M. R.; Stern, C. L.; Guo, Q.-H.; Wang, X.; Farha, O. K.; Stoddart, J. F. J. Am. Chem. Soc. 2019, 141, 12998.
66. [66]
  Li, P.; Li, P.; Ryder, M. R.; Liu, Z.; Stern, C. L.; Farha, O. K.; Stoddart, J. F. Angew. Chem. Int. Ed. 2019, 58, 1664.
67. [67]
  Zhou, Y.; Liu, B.; Sun, X.; Li, J.; Li, G.; Huo, Q.; Liu, Y. Cryst. Growth Des. 2017, 17, 6653.
68. [68]
  Bassanetti, I.; Bracco, S.; Comotti, A.; Negroni, M.; Bezuidenhout, C.; Canossa, S.; Mazzeo, P. P.; Marchió, L.; Sozzani, P. J. Mater. Chem. A 2018, 6, 14231.
69. [69]
  Zhang, X.; Li, L.; Wang, J.-X.; Wen, H.-M.; Krishna, R.; Wu, H.; Zhou, W.; Chen, Z.-N.; Li, B.; Qian, G.; Chen, B. J. Am. Chem. Soc. 2020, 142, 633.
70. [70]
  Gong, W.; Chu, D.; Jiang, H.; Chen, X.; Cui, Y.; Liu, Y. Nat. Commun. 2019, 10, 600.
71. [71]
  Wang, L.; Yang, L.; Gong, L.; Krishna, R.; Gao, Z.; Tao, Y.; Yin, W.; Xu, Z.; Luo, F. Chem. Eng. J. 2020, 383, 123117.
72. [72]
  Liu, T.; Wang, B.; He, R.; Arman, H.; Schanze, K. S.; Xiang, S.; Li, D.; Chen, B. Can. J. Chem. 2020, 98, 352.
73. [73]
  Takeda, T.; Ozawa, M.; Akutagawa, T. Angew. Chem. Int. Ed. 2019, 58, 10345.
74. [74]
  Wang, B.; He, R.; Xie, L.-H.; Lin, Z.-J.; Zhang, X.; Wang, J.; Huang, H.; Zhang, Z.; Schanze, K. S.; Zhang, J.; Xiang, S.; Chen, B. J. Am. Chem. Soc. 2020, 142, 12478.
75. [75]
  Brunet, P.; Simard, M.; Wuest, J. D. J. Am. Chem. Soc. 1997, 119, 2737.
76. [76]
  Fournier, J.-H.; Maris, T.; Wuest, J. D. J. Org. Chem. 2004, 69, 1762.
77. [77]
  Demers, E.; Maris, T.; Wuest, J. D. Cryst. Growth Des. 2005, 5, 1227.
78. [78]
  Malek, N.; Maris, T.; Simard, M.; Wuest, J. D. J. Am. Chem. Soc. 2005, 127, 5910.
79. [79]
  Maly, K. E.; Gagnon, E.; Maris, T.; Wuest, J. D. J. Am. Chem. Soc. 2007, 129, 4306.
80. [80]
  Helzy, F.; Maris, T.; Wuest, J. D. Cryst. Growth Des. 2008, 8, 1547.
81. [81]
  Helzy, F.; Maris, T.; Wuest, J. D. J. Org. Chem. 2016, 81, 3076.
82. [82]
  Beaudoin, D.; Blair-Pereira, J.-N.; Langis-Barsetti, S.; Maris, T.; Wuest, J. D. J. Org. Chem. 2017, 82, 8536.
83. [83]
  Duong, A.; Rajak, S.; Tremblay, A. A.; Maris, T.; Wuest, J. D. Cryst. Growth Des. 2019, 19, 1299.
84. [84]
  Li, P.; He, Y.; Guang, J.; Weng, L.; Zhao, J. C.-G.; Xiang, S.; Chen, B. J. Am. Chem. Soc. 2014, 136, 547.
85. [85]
  Li, P.; He, Y.; Zhao, Y.; Weng, L.; Wang, H.; Krishna, R.; Wu, H.; Zhou, W.; O'Keeffe, M.; Han, Y.; Chen, B. Angew. Chem. Int. Ed. 2015, 54, 574.
86. [86]
  Li, P.; He, Y.; Arman, H. D.; Krishna, R.; Wang, H.; Weng, L.; Chen, B. Chem. Commun. 2014, 50, 13081.
87. [87]
  Wang, H.; Li, B.; Wu, H.; Hu, T.-L.; Yao, Z.; Zhou, W.; Xiang, S.; Chen, B. J. Am. Chem. Soc. 2015, 137, 9963.
88. [88]
  Yang, W.; Yang, F.; Hu, T.-L.; King, S. C.; Wang, H.; Wu, H.; Zhou, W.; Li, J.-R.; Arman, H. D.; Chen, B. Cryst. Growth Des. 2016, 16, 5831.
89. [89]
  Yang, W.; Li, B.; Wang, H.; Alduhaish, O.; Alfooty, K.; Zayed, M. A.; Li, P.; Arman, H. D.; Chen, B. Cryst. Growth Des. 2015, 15, 2000.
90. [90]
  Wang, H.; Wu, H.; Kan, J.; Chang, G.; Yao, Z.; Li, B.; Zhou, W.; Xiang, S.; Cong-Gui Zhao, J.; Chen, B. J. Mater. Chem. A 2017, 5, 8292.
91. [91]
  Wang, H.; Bao, Z.; Wu, H.; Lin, R.-B.; Zhou, W.; Hu, T.-L.; Li, B.; Zhao, J. C.-G.; Chen, B. Chem. Commun. 2017, 53, 11150.
92. [92]
  Wang, Y.; Liu, D.; Yin, J.; Shang, Y.; Du, J.; Kang, Z.; Wang, R.; Chen, Y.; Sun, D.; Jiang, J. Chem. Commun. 2020, 56, 703.
93. [93]
  Feng, S.; Shang, Y.; Wang, Z.; Kang, Z.; Wang, R.; Jiang, J.; Fan, L.; Fan, W.; Liu, Z.; Kong, G.; Feng, Y.; Hu, S.; Guo, H.; Sun, D. Angew. Chem. Int. Ed. 2020, 59, 3840.
94. [94]
  Chen, T.-H.; Popov, I.; Kaveevivitchai, W.; Chuang, Y.-C.; Chen, Y.-S.; Daugulis, O.; Jacobson, A. J.; Miljanić, O. Š. Nat. Commun. 2014, 5, 5131.
95. [95]
  Hashim, M. I.; Le, H. T. M.; Chen, T.-H.; Chen, Y.-S.; Daugulis, O.; Hsu, C.-W.; Jacobson, A. J.; Kaveevivitchai, W.; Liang, X.; Makarenko, T.; Miljanić, O. Š.; Popovs, I.; Tran, H. V.; Wang, X.; Wu, C.-H.; Wu, J. I. J. Am. Chem. Soc. 2018, 140, 6014.
96. [96]
  Yan, W.; Yu, X.; Yan, T.; Wu, D.; Ning, E.; Qi, Y.; Han, Y.-F.; Li, Q. Chem. Commun. 2017, 53, 3677.
97. [97]
  Yamagishi, H.; Sato, H.; Hori, A.; Sato, Y.; Matsuda, R.; Kato, K.; Aida, T. Science 2018, 361, 1242.
98. [98]
  Luo, X.-Z.; Jia, X.-J.; Deng, J.-H.; Zhong, J.-L.; Liu, H.-J.; Wang, K.-J.; Zhong, D.-C. J. Am. Chem. Soc. 2013, 135, 11684.
99. [99]
  Smith, A. Acta Crystallographica 1952, 5, 224.
100. [100]
  Harris, K. D. M. Chem. Soc. Rev. 1997, 26, 279.
101. [101]
  Mastalerz, M.; Oppel, I. M. Angew. Chem. Int. Ed. 2012, 51, 5252.
102. [102]
  Adachi, T.; Ward, M. D. Acc. Chem. Res. 2016, 49, 2669.
103. [103]
  Karmakar, A.; Illathvalappil, R.; Anothumakkool, B.; Sen, A.; Samanta, P.; Desai, A. V.; Kurungot, S.; Ghosh, S. K. Angew. Chem. Int. Ed. 2016, 55, 10667.
104. [104]
  Kang, D. W.; Kang, M.; Kim, H.; Choe, J. H.; Kim, D. W.; Park, J. R.; Lee, W. R.; Moon, D.; Hong, C. S. Angew. Chem. Int. Ed. 2019, 58, 16152.
105. [105]
  Brekalo, I.; Deliz, D. E.; Barbour, L. J.; Ward, M. D.; Friščić, T.; Holman, K. T. Angew. Chem. Int. Ed. 2020, 59, 1997.
106. [106]
  Yamamoto, A.; Hirukawa, T.; Hisaki, I.; Miyata, M.; Tohnai, N. Tetrahedron Lett. 2013, 54, 1268.
107. [107]
  Comotti, A.; Bracco, S.; Yamamoto, A.; Beretta, M.; Hirukawa, T.; Tohnai, N.; Miyata, M.; Sozzani, P. J. Am. Chem. Soc. 2014, 136, 618.
108. [108]
  Xing, G.; Yan, T.; Das, S.; Ben, T.; Qiu, S. Angew. Chem. Int. Ed. 2018, 57, 5345.
109. [109]
  Morshedi, M.; Ward, J. S.; Kruger, P. E.; White, N. G. Dalton Trans. 2018, 47, 783.
110. [110]
  Boer, S. A.; Morshedi, M.; Tarzia, A.; Doonan, C. J.; White, N. G. Chem. Eur. J. 2019, 25, 10006.
111. [111]
  Boer, S. A.; Wang, P.-X.; MacLachlan, M. J.; White, N. G. Cryst. Growth Des. 2019, 19, 4829.
112. [112]
  Cullen, D. A.; Gardiner, M. G.; White, N. G. Chem. Commun. 2019, 55, 12020.
113. [113]
  Liang, W.; Carraro, F.; Solomon, M. B.; Bell, S. G.; Amenitsch, H.; Sumby, C. J.; White, N. G.; Falcaro, P.; Doonan, C. J. J. Am. Chem. Soc. 2019, 141, 14298.
114. [114]
  Morshedi, M.; Thomas, M.; Tarzia, A.; Doonan, C. J.; White, N. G. Chem. Sci. 2017, 8, 3019.
115. [115]
  Morshedi, M.; White, N. G. CrystEngComm 2017, 19, 2367.
116. [116]
  Huang, Y.-G.; Shiota, Y.; Wu, M.-Y.; Su, S.-Q.; Yao, Z.-S.; Kang, S.; Kanegawa, S.; Li, G.-L.; Wu, S.-Q.; Kamachi, T.; Yoshizawa, K.; Ariga, K.; Hong, M.-C.; Sato, O. Nat.Commun. 2016, 7, 11564.
117. [117]
  Luo, Y.-H.; He, X.-T.; Hong, D.-L.; Chen, C.; Chen, F.-H.; Jiao, J.; Zhai, L.-H.; Guo, L.-H.; Sun, B.-W. Adv. Funct. Mater. 2018, 28, 1804822.
118. [118]
  Zheng, X.; Xiao, N.; Long, Z.; Wang, L.; Ye, F.; Fang, J.; Shen, L.; Xiao, X. Synth. Met. 2020, 263, 116365.
119. [119]
  Lü, J.; Perez-Krap, C.; Suyetin, M.; Alsmail, N. H.; Yan, Y.; Yang, S.; Lewis, W.; Bichoutskaia, E.; Tang, C. C.; Blake, A. J.; Cao, R.; Schröder, M. J. Am. Chem. Soc. 2014, 136, 12828.
120. [120]
  Lü, J.; Perez-Krap, C.; Trousselet, F.; Yan, Y.; Alsmail, N. H.; Karadeniz, B.; Jacques, N. M.; Lewis, W.; Blake, A. J.; Coudert, F.-X.; Cao, R.; Schrder, M. Cryst. Growth Des. 2018, 18, 2555.
121. [121]
  He, X.-T.; Luo, Y.-H.; Hong, D.-L.; Chen, F.-H.; Zheng, Z.-Y.; Wang, C.; Wang, J.-Y.; Chen, C.; Sun, B.-W. ACS Appl. Nano Mater. 2019, 2, 2437.
122. [122]
  Suh, M. P.; Park, H. J.; Prasad, T. K.; Lim, D.-W. Chem. Rev. 2012, 112, 782.
123. [123]
  Wang, B.; Zhang, X.; Huang, H.; Zhang, Z.; Yildirim, T.; Zhou, W.; Xiang, S.; Chen, B. Nano Res. 2020, doi: 10.1007/s12274-020- 2713-0. doi: 10.1007/s12274-020-2713-0
124. [124]
  Sumida, K.; Brown, C. M.; Herm, Z. R.; Chavan, S.; Bordiga, S.; Long, J. R. Chem. Commun. 2011, 47, 1157.
125. [125]
  Farha, O. K.; Spokoyny, A. M.; Mulfort, K. L.; Galli, S.; Hupp, J. T.; Mirkin, C. A. Small 2009, 5, 1727.
126. [126]
  Nugent, P. S.; Rhodus, V. L.; Pham, T.; Forrest, K.; Wojtas, L.; Space, B.; Zaworotko, M. J. J. Am. Chem. Soc. 2013, 135, 10950.
127. [127]
  Yoon, T.-U.; Baek, S. B.; Kim, D.; Kim, E.-J.; Lee, W.-G.; Singh, B. K.; Lah, M. S.; Bae, Y.-S.; Kim, K. S. Chem. Commun. 2018, 54, 9360.
128. [128]
  Zhang, Z.; Li, J.; Yao, Y.; Sun, S. Cryst. Growth Des. 2015, 15, 5028.
129. [129]
  Stackhouse, C.; Ren, J.; Shan, C.; Nafady, A.; Al-Enizi, A. M.; Ubaidullah, M.; Niu, Z.; Ma, S. Cryst. Growth Des. 2019, 19, 6377.
130. [130]
  Khadivjam, T.; Che-Quang, H.; Maris, T.; Ajoyan, Z.; Howarth, A. J.; Wuest, J. D. Chem. Eur. J. 2020, 26, 7026.
131. [131]
  Han, B.; Wang, H.; Wang, C.; Wu, H.; Zhou, W.; Chen, B.; Jiang, J. J. Am. Chem. Soc. 2019, 141, 8737.
132. [132]
  Bao, Z.; Xie, D.; Chang, G.; Wu, H.; Li, L.; Zhou, W.; Wang, H.; Zhang, Z.; Xing, H.; Yang, Q.; Zaworotko, M. J.; Ren, Q.; Chen, B. J. Am. Chem. Soc. 2018, 140, 4596.
133. [133]
  Zhou, M.; Liu, G.; Ju, Z.; Su, K.; Du, S.; Tan, Y.; Yuan, D. Cryst. Growth Des. 2020, 20, 4127.
134. [134]
  Chen, B. Sci.China Chem. 2017, 60, 683.
135. [135]
  Yin, Q.; Li, Y.-L.; Li, L.; Lü, J.; Liu, T.-F.; Cao, R. ACS Appl. Mater. Inter. 2019, 11, 17823.
136. [136]
  Shi, Z.-Q.; Ji, N.-N.; Guo, K.-M.; Li, G. Appl. Surf. Sci. 2020, 504, 144484.
137. [137]
  Yang, Q.; Wang, Y.; Shang, Y.; Du, J.; Yin, J.; Liu, D.; Kang, Z.; Wang, R.; Sun, D.; Jiang, J. Cryst. Growth Des. 2020, 20, 3456.
138. [138]
  Chand, S.; Pal, S. C.; Pal, A.; Ye, Y.; Lin, Q.; Zhang, Z.; Xiang, S.; Das, M. C. Chem. Eur. J. 2019, 25, 1691.
139. [139]
  Zheng, H.-Q.; He, X.-H.; Zeng, Y.-N.; Qiu, W.-H.; Chen, J.; Cao, G.-J.; Lin, R.-G.; Lin, Z.-J.; Chen, B. J. Mater. Chem. A 2020, 8, 17219.
140. [140]
  Gong, W.; Liu, Y.; Li, H.; Cui, Y. Coord. Chem. Rev. 2020, 420, 213400.
141. [141]
  Chen, Z. Y.; Liu, J. W.; Cui, H.; Zhang, L.; Su, C. Y. Acta Chim. Sinica 2019, 77, 242 (in Chinese).
142. [142]
  Liu, F. Q.; Liu, J. W.; Gao, Z.; Wang, L.; Fu, X.-Z.; Yang, L. X.; Tao, Y.; Yin, W. H.; Luo, F. Appl. Catal. B: Environ. 2019, 258, 117973.
143. [143]
  Aitchison, C. M.; Kane, C. M.; McMahon, D. P.; Spackman, P. R.; Pulido, A.; Wang, X.; Wilbraham, L.; Chen, L.; Clowes, R.; Zwijnenburg, M. A.; Sprick, R. S.; Little, M. A.; Day, G. M.; Cooper, A. I. J. Mater. Chem. A 2020, 8, 7158.
144. [144]
  He, X.-T.; Luo, Y.-H.; Zheng, Z.-Y.; Wang, C.; Wang, J.-Y.; Hong, D.-L.; Zhai, L.-H.; Guo, L.-H.; Sun, B.-W. ACS Appl. Nano Mater. 2019, 2, 7719.
145. [145]
  Sun, Z.; Li, Y.; Chen, L.; Jing, X.; Xie, Z. Cryst. Growth Des. 2015, 15, 542.
146. [146]
  Feng, J.-F.; Yan, X.-Y.; Ji, Z.-Y.; Liu, T.-F.; Cao, R. ACS Appl. Mater. Inter. 2020, 12, 29854.
147. [147]
  Lin, Z.-J.; Zheng, H.-Q.; Zeng, Y.-N.; Wang, Y.-L.; Chen, J.; Cao, G.-J.; Gu, J.-F.; Chen, B. Chem. Eng. J. 2019, 378, 122196.
148. [148]
  Lin, Z.-J.; Zheng, H.-Q.; Zheng, H.-Y.; Lin, L.-P.; Xin, Q.; Cao, R. Inorg. Chem. 2017, 56, 14178.
149. [149]
  Zeng, C.-H.; Luo, Z.; Yao, J. CrystEngComm 2017, 19, 613.
150. [150]
  Lin, Y.; Jiang, X.; Kim, S. T.; Alahakoon, S. B.; Hou, X.; Zhang, Z.; Thompson, C. M.; Smaldone, R. A.; Ke, C. J. Am. Chem. Soc. 2017, 139, 7172.
151. [151]
  Yao, R.-X.; Cui, X.; Jia, X.-X.; Zhang, F.-Q.; Zhang, X.-M. Inorg. Chem. 2016, 55, 9270.
152. [152]
  Liao, Y.; Weber, J.; Mills, B. M.; Ren, Z.; Faul, C. F. J. Macromolecules 2016, 49, 6322.
153. [153]
  Ren, F.; Zhu, Z.; Qian, X.; Liang, W.; Mu, P.; Sun, H.; Liu, J.; Li, A. Chem. Commun. 2016, 52, 9797.
154. [154]
  Hoshino, M.; Khutia, A.; Xing, H.; Inokuma, Y.; Fujita, M. IUCrJ 2016, 3, 139.
155. [155]
  Lee, S.; Kapustin, E. A.; Yaghi, O. M. Science 2016, 353, 808.
156. [156]
  Pei, X.; Bürgi, H.-B.; Kapustin, E. A.; Liu, Y.; Yaghi, O. M. J. Am. Chem. Soc. 2019, 141, 18862.
157. [157]
  Li, Y.; Tang, S.; Yusov, A.; Rose, J.; Borrfors, A. N.; Hu, C. T.; Ward, M. D. Nat. Commun. 2019, 10, 4477.
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