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.
1. [1]
  Shicheng Yan . Experimental Teaching Design for the Integration of Scientific Research and Teaching: A Case Study on Organic Electrooxidation. University Chemistry, 2024, 39(11): 350-358. doi: 10.12461/PKU.DXHX202408036
2. [2]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
3. [3]
  Feng Sha , Xinyan Wu , Ping Hu , Wenqing Zhang , Xiaoyang Luan , Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082
4. [4]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
5. [5]
  Yinglian LI , Chengcheng ZHANG , Xinyu ZHANG , Xinyi WANG . Spin crossover in [Co(pytpy)₂]²⁺ complexes modified by organosulfonate anions. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1162-1172. doi: 10.11862/CJIC.20240087
6. [6]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
7. [7]
  Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
8. [8]
  Yuan Zheng , Quan Lan , Zhenggen Zha , Lingling Li , Jun Jiang , Pingping Zhu . Teaching Reform of Organic Synthesis Experiments by Introducing Reverse Thinking and Design Concepts: Taking the Synthesis of Cinnamic Acid Based on Retrosynthetic Analysis as an Example. University Chemistry, 2024, 39(6): 207-213. doi: 10.3866/PKU.DXHX202310065
9. [9]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
10. [10]
  Xinyu Zhu , Meili Pang . Application of Functional Group Addition Strategy in Organic Synthesis. University Chemistry, 2024, 39(3): 218-230. doi: 10.3866/PKU.DXHX202308106
11. [11]
  Wenxiu Yang , Jinfeng Zhang , Quanlong Xu , Yun Yang , Lijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-. doi: 10.3866/PKU.WHXB202312014
12. [12]
  Liang TANG , Jingfei NI , Kang XIAO , Xiangmei LIU . Synthesis and X-ray imaging application of lanthanide-organic complex-based scintillators. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1892-1902. doi: 10.11862/CJIC.20240139
13. [13]
  Jia Yao , Xiaogang Peng . Theory of Macroscopic Molecular Systems: Theoretical Framework of the Physical Chemistry Course in the Chemistry “101 Plan”. University Chemistry, 2024, 39(10): 27-37. doi: 10.12461/PKU.DXHX202408117
14. [14]
  Yinwu Su , Xuanwen Zheng , Jianghui Du , Boda Li , Tao Wang , Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092
15. [15]
  Yaofeng Yuan , Keyin Ye , Chunfa Xu , Hong Yan , Yuanming Li . Fostering an International Perspective in Postgraduate Student Teaching: A Case Study of the Organic Structure Analysis Course. University Chemistry, 2024, 39(6): 145-150. doi: 10.3866/PKU.DXHX202402024
16. [16]
  Yukun Chang , Haoqin Huang , Baolei Wang . Preparation of Trans-Cinnamic Acid via “One-Pot” Protocol of Aldol Condensation-Hydrolysis Reaction: Recommending an Improved Organic Synthesis Experiment. University Chemistry, 2024, 39(4): 322-328. doi: 10.3866/PKU.DXHX202309095
17. [17]
  Ling Zhang , Jing Kang . Turn Waste into Valuable: Preparation of High-Strength Water-Based Adhesives from Polymethylmethacrylate Wastes: a Comprehensive Chemical Experiments. University Chemistry, 2024, 39(2): 221-226. doi: 10.3866/PKU.DXHX202306075
18. [18]
  Fan Wu , Wenchang Tian , Jin Liu , Qiuting Zhang , YanHui Zhong , Zian Lin . Core-Shell Structured Covalent Organic Framework-Coated Silica Microspheres as Mixed-Mode Stationary Phase for High Performance Liquid Chromatography. University Chemistry, 2024, 39(11): 319-326. doi: 10.12461/PKU.DXHX202403031
19. [19]
  Yufang GAO , Nan HOU , Yaning LIANG , Ning LI , Yanting ZHANG , Zelong LI , Xiaofeng LI . Nano-thin layer MCM-22 zeolite: Synthesis and catalytic properties of trimethylbenzene isomerization reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1079-1087. doi: 10.11862/CJIC.20240036
20. [20]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063

Get Citation

PDF

XML

Metrics

PDF Downloads(574)
Abstract views(10811)
HTML views(3851)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142