Citation: Fang-Yuan Chen, Wen-Chao Geng, Kang Cai, Dong-Sheng Guo. Molecular recognition of cyclophanes in water[J]. Chinese Chemical Letters, ;2024, 35(5): 109161. doi: 10.1016/j.cclet.2023.109161 shu

Molecular recognition of cyclophanes in water

Fang-Yuan Chen ^a ,
Wen-Chao Geng ^a ,
Kang Cai ^{b, *,} ,
Dong-Sheng Guo ^{a, *,}

a.
College of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Key Laboratory of Functional Polymer Materials (Ministry of Education), Frontiers Science Center for New Organic Matter, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, China
b.
College of Chemistry, Nankai University, Tianjin 300071, China

^☆

kangcai@nankai.edu.cn

dshguo@nankai.edu.cn

Received Date: 4 July 2023
Revised Date: 15 September 2023
Accepted Date: 26 September 2023
Available Online: 28 September 2023

Figures(14)

Molecular recognition in water, the biological solvent, always receives significant research focus in supramolecular chemistry. The mechanisms of molecular recognition in water is key to comprehending biological processes at the molecular level. Over the past five decades, supramolecular chemists have developed a vast array of synthetic receptors with highly diverse structures and recognition properties. Among them, cyclophanes represent an important family of macrocyclic receptors that have been extensively explored. The aromatic moieties in cyclophanes not only facilitate chemical modifications to impart water solubility but also enable forming hydrophobic cavities for guest inclusion in aqueous environments. Pioneered by Koga et al., who reported the first inclusion complex of cyclophanes in water and solid state, numerous water-soluble cyclophanes, including derivatives of blue box, calixarenes, resorcinarenes, pillararenes, octopusarenes, biphenarenes, coronarenes, and naphthotubes, etc., have been synthesized and subjected to investigation of the recognition capabilities in aqueous solutions. This review provides an overview of cyclophane receptors designed to bind organic guests in water. We categorize them into two classes based on the modifications made to their hydrophobic cavities: those with "exo-functionalized hydrophobic cavities" and those with "endo-functionalized hydrophobic cavities". We introduce their distinctive features and discuss strategies to enhance recognition affinity and selectivity. This review aims to inspire the development of novel synthetic receptors with intriguing properties and foster practical applications of cyclophanes.
- Biomimetic receptor,
- Cyclophane,
- Molecular recognition,
- Hydrophobic effect,
- High-affinity,
- Macrocycles
1. [1]
  C.L. Schreiber, B.D. Smith, Nat. Rev. Chem. 3 (2019) 393–400. doi: 10.1038/s41570-019-0095-1
2. [2]
  X. Wang, F. Jia, L.P. Yang, H. Zhou, W. Jiang, Chem. Soc. Rev. 49 (2020) 4176–4188. doi: 10.1039/D0CS00341G
3. [3]
  H.P. Ferguson Johns, E.E. Harrison, K.J. Stingley, M.L. Waters, Chem. Eur. J. 27 (2021) 6620–6644. doi: 10.1002/chem.202003759
4. [4]
  E. Persch, O. Dumele, F. Diederich, Angew. Chem. Int. Ed. 54 (2015) 3290–3327. doi: 10.1002/anie.201408487
5. [5]
  H.J. Schneider, Angew. Chem. Int. Ed. 48 (2009) 3924–3977. doi: 10.1002/anie.200802947
6. [6]
  E.A. Meyer, R.K. Castellano, F. Diederich, Angew. Chem. Int. Ed. 42 (2003) 1210–1250. doi: 10.1002/anie.200390319
7. [7]
  J.M. Lehn, Angew. Chem. Int. Ed. 27 (1988) 89–112. doi: 10.1002/anie.198800891
8. [8]
  F. Diederich, J. Chem. Educ. 67 (1990) 813. doi: 10.1021/ed067p813
9. [9]
  F. Biedermann, W.M. Nau, H.J. Schneider, Angew. Chem. Int. Ed. 53 (2014) 11158–11171. doi: 10.1002/anie.201310958
10. [10]
  L. You, D. Zha, E.V. Anslyn, Chem. Rev. 115 (2015) 7840–7892. doi: 10.1021/cr5005524
11. [11]
  Y. Li, X. Lou, C. Wang, et al., Chin. Chem. Lett. 34 (2023) 107877. doi: 10.1016/j.cclet.2022.107877
12. [12]
  L. Tian, S. Zhou, J. Zhao, et al., J. Hazard. Mater. 441 (2023) 129873. doi: 10.1016/j.jhazmat.2022.129873
13. [13]
  Q. Shi, M.P. Mower, D.G. Blackmond, J. Rebek Jr., Proc. Natl. Acad. Sci. U. S. A. 113 (2016) 9199–9203. doi: 10.1073/pnas.1610006113
14. [14]
  K. Wang, X. Tian, J.H. Jordan, et al., Chin. Chem. Lett. 33 (2022) 89–96. doi: 10.1016/j.cclet.2021.06.026
15. [15]
  H. Ke, L.P. Yang, M. Xie, Nat. Chem. 11 (2019) 470–477. doi: 10.1038/s41557-019-0235-8
16. [16]
  Y.C. Pan, H.W. Tian, S. Peng, X.Y. Hu, D.S. Guo, Chin. Chem. Lett. 28 (2017) 787–792. doi: 10.1016/j.cclet.2016.12.027
17. [17]
  K. Wang, M. Zuo, T. Zhang, H. Yue, X.Y. Hu, Chin. Chem. Lett. 34 (2023) 107848. doi: 10.1016/j.cclet.2022.107848
18. [18]
  Y.C. Pan, X.Y. Hu, D.S. Guo, Angew. Chem. Int. Ed. 60 (2021) 2768–2794. doi: 10.1002/anie.201916380
19. [19]
  J.J. Wu, F.Y. Chen, B.B. Han, et al., CCS Chem. 5 (2023) 885–901. doi: 10.31635/ccschem.022.202201859
20. [20]
  B. Hazarika, V.P. Singh, Chin. Chem. Lett. (2023) 108220.
21. [21]
  W.C. Geng, Z. Zheng, D.S. Guo, VIEW (2020) 20200059.
22. [22]
  Y.L. Ma, S. Yan, X.J. Xu, H. Cao, R. Wang, Chin. Chem. Lett. (2023) 108645.
23. [23]
  Y.L. Ma, C. Sun, Z. Li, et al., CCS Chem. 4 (2022) 1977–1989. doi: 10.31635/ccschem.021.202101178
24. [24]
  F. Diederich, Angew. Chem. Int. Ed. 27 (1988) 362–386. doi: 10.1002/anie.198803621
25. [25]
  S. Sarkar, P. Ballester, M. Spektor, E.A. Kataev, Angew. Chem. Int. Ed. (2022) e202214705.
26. [26]
  H. Han, R. Fu, R. Wang, et al., J. Am. Chem. Soc. 144 (2022) 20351–20362. doi: 10.1021/jacs.2c08144
27. [27]
  X.N. Han, Q.S. Zong, Y. Han, C.F. Chen, CCS Chem. 4 (2022) 318–330. doi: 10.31635/ccschem.021.202100870
28. [28]
  H. Stetter, E.E. Roos, Chem. Ber. 88 (1955) 1390–1395. doi: 10.1002/cber.19550880909
29. [29]
  R. Hilgenfeld, W. Saenger, Angew. Chem. Int. Ed. 21 (1982) 787–788. doi: 10.1002/anie.198207871
30. [30]
  K. Odashima, A. Itai, Y. Iitaka, K. Koga, J. Am. Chem. Soc. 102 (1980) 2504–2505. doi: 10.1021/ja00527a083
31. [31]
  F. Diederich, K. Dick, J. Am. Chem. Soc. 106 (1984) 8024–8036. doi: 10.1021/ja00338a005
32. [32]
  X.Y. Chen, H. Chen, J. Fraser Stoddart, Angew. Chem. Int. Ed. 62 (2023) e202211387. doi: 10.1002/anie.202211387
33. [33]
  D.S. Guo, Y. Liu, Acc. Chem. Res. 47 (2014) 1925–1934. doi: 10.1021/ar500009g
34. [34]
  S.M. Biros, J. Rebek Jr., Chem. Soc. Rev. 36 (2007) 93–104. doi: 10.1039/B508530F
35. [35]
  D.S. Kim, J.L. Sessler, Chem. Soc. Rev. 44 (2015) 532–546. doi: 10.1039/C4CS00157E
36. [36]
  J.M. Dempsey, Q.W. Zhang, A.G. Oliver, B.D. Smith, Org. Biomol. Chem. 16 (2018) 8976–8983. doi: 10.1039/C8OB02596G
37. [37]
  T. Ogoshi, T.A. Yamagishi, Y. Nakamoto, Chem. Rev. 116 (2016) 7937–8002. doi: 10.1021/acs.chemrev.5b00765
38. [38]
  X.N. Han, P.F. Li, Y. Han, C.F. Chen, Angew. Chem. Int. Ed. 61 (2022) e202202527. doi: 10.1002/anie.202202527
39. [39]
  J. Zhou, G. Yu, L. Shao, B. Hua, F. Huang, Chem. Commun. 51 (2015) 4188–4191. doi: 10.1039/C5CC00225G
40. [40]
  Q.H. Guo, L. Zhao, M.X. Wang, Angew. Chem. Int. Ed. 54 (2015) 8386–8389. doi: 10.1002/anie.201503179
41. [41]
  L.P. Yang, X. Wang, H. Yao, W. Jiang, Acc. Chem. Res. 53 (2020) 198–208. doi: 10.1021/acs.accounts.9b00415
42. [42]
  L. Escobar, P. Ballester, Chem. Rev. 121 (2021) 2445–2514. doi: 10.1021/acs.chemrev.0c00522
43. [43]
  C.A. Hunter, Angew. Chem. Int. Ed. 43 (2004) 5310–5324. doi: 10.1002/anie.200301739
44. [44]
  W. Liu, S.K. Samanta, B.D. Smith, L. Isaacs, Chem. Soc. Rev. 46 (2017) 2391–2403. doi: 10.1039/C7CS00011A
45. [45]
  F. Biedermann, V.D. Uzunova, O.A. Scherman, W.M. Nau, A. De Simone, J. Am. Chem. Soc. 134 (2012) 15318–15323. doi: 10.1021/ja303309e
46. [46]
  F. Biedermann, M. Vendruscolo, O.A. Scherman, A. De Simone, W.M. Nau, J. Am. Chem. Soc. 135 (2013) 14879–14888. doi: 10.1021/ja407951x
47. [47]
  Q. Sun, Chem. Phys. Lett. 672 (2017) 21–25. doi: 10.1016/j.cplett.2017.01.057
48. [48]
  B. Kronberg, Curr. Opin. Colloid Interface Sci. 22 (2016) 14–22. doi: 10.1016/j.cocis.2016.02.001
49. [49]
  S.T. Ryan, J. Del Barrio, I. Ghosh, et al., J. Am. Chem. Soc. 136 (2014) 9053–9060. doi: 10.1021/ja5032437
50. [50]
  M. Petroselli, Y.Q. Chen, J.J. Rebek, Y. Yu, Green Synth. Catal. 2 (2021) 123–130. doi: 10.1016/j.gresc.2021.03.004
51. [51]
  K.N. Houk, A.G. Leach, S.P. Kim, X. Zhang, Angew. Chem. Int. Ed. 42 (2003) 4872–4897. doi: 10.1002/anie.200200565
52. [52]
  J.W. Barnett, M.R. Sullivan, J.A. Long, et al., Nat. Chem. 12 (2020) 589–594. doi: 10.1038/s41557-020-0458-8
53. [53]
  J. Dong, A.P. Davis, Angew. Chem. Int. Ed. 60 (2021) 8035–8048. doi: 10.1002/anie.202012315
54. [54]
  H. Yao, H. Ke, X. Zhang, et al., J. Am. Chem. Soc. 140 (2018) 13466–13477. doi: 10.1021/jacs.8b09157
55. [55]
  D. Li, M. Wu, Signal Transduction Targeted Ther. 6 (2021) 291. doi: 10.1038/s41392-021-00687-0
56. [56]
  T.C. Bruice, S.J. Benkovic, Biochemistry 39 (2000) 6267–6274. doi: 10.1021/bi0003689
57. [57]
  H. Zhang, F. Li, B. Dever, et al., Angew. Chem. Int. Ed. 52 (2013) 10698–10705. doi: 10.1002/anie.201210022
58. [58]
  C.D. Raposo, A.B. Canelas, M.T. Barros, Biomolecules 11 (2021) 188. doi: 10.3390/biom11020188
59. [59]
  O.H. Laitinen, H.R. Nordlund, V.P. Hytonen, M.S. Kulomaa, Trends Biotechnol. 25 (2007) 269–277. doi: 10.1016/j.tibtech.2007.04.001
60. [60]
  B. Odell, M.V. Reddington, A.M.Z. Slawin, et al., Angew. Chem. Int. Ed. 27 (1988) 1547–1550. doi: 10.1002/anie.198815471
61. [61]
  S.A. Staley, B.D. Smith, Tetrahedron Lett. 37 (1996) 283–286. doi: 10.1016/0040-4039(95)02150-7
62. [62]
  A.R. Bernardo, J.F. Stoddart, A.E. Kaifer, J. Am. Chem. Soc. 114 (2002) 10624–10631.
63. [63]
  M. Bria, G. Cooke, A. Cooper, et al., Tetrahedron Lett. 48 (2007) 301–304. doi: 10.1016/j.tetlet.2006.11.003
64. [64]
  E.J. Dale, N.A. Vermeulen, M. Juricek, et al., Acc. Chem. Res. 49 (2016) 262–273. doi: 10.1021/acs.accounts.5b00495
65. [65]
  J.C. Barnes, M. Juricek, N.L. Strutt, et al., J. Am. Chem. Soc. 135 (2013) 183–192. doi: 10.1021/ja307360n
66. [66]
  E.J. Dale, N.A. Vermeulen, A.A. Thomas, et al., J. Am. Chem. Soc. 136 (2014) 10669–10682. doi: 10.1021/ja5041557
67. [67]
  W. Liu, S. Bobbala, C.L. Stern, et al., J. Am. Chem. Soc. 142 (2020) 3165–3173. doi: 10.1021/jacs.9b12982
68. [68]
  Y. Shi, K. Cai, H. Xiao, et al., J. Am. Chem. Soc. 140 (2018) 13835–13842. doi: 10.1021/jacs.8b08555
69. [69]
  W. Liu, C. Lin, J.A. Weber, et al., J. Am. Chem. Soc. 142 (2020) 8938–8945. doi: 10.1021/jacs.0c02311
70. [70]
  H. Duan, Y. Li, Q. Li, et al., Angew. Chem. Int. Ed. 59 (2020) 10101–10110. doi: 10.1002/anie.201912730
71. [71]
  L. Cheng, K. Liu, Y. Duan, et al., CCS Chem. 3 (2021) 2749–2763. doi: 10.31635/ccschem.020.202000509
72. [72]
  K. Wang, S.Y. Xing, X.G. Wang, H.X. Dou, Org. Biomol. Chem. 13 (2015) 5432–5443. doi: 10.1039/C5OB00053J
73. [73]
  N. Douteau-Guével, F. Perret, A.W. Coleman, J.P. Morel, N. Morel-Desrosiers, J. Chem. Soc., Perkin Trans. 2 (2002) 524–532.
74. [74]
  T.X. Zhang, Z.Z. Zhang, Y.X. Yue, et al., Adv. Mater. 32 (2020) 1908435. doi: 10.1002/adma.201908435
75. [75]
  S. Li, R. Ma, X.Y. Hu, et al., Adv. Mater. 34 (2022) 2203765. doi: 10.1002/adma.202203765
76. [76]
  Y.X. Yue, Z. Zhang, Z.H. Wang, et al., Small Struct. 3 (2022) 2200067. doi: 10.1002/sstr.202200067
77. [77]
  Data source: https://suprabank.org/.
78. [78]
  T. Ogoshi, S. Kanai, S. Fujinami, T.A. Yamagishi, Y. Nakamoto, J. Am. Chem. Soc. 130 (2008) 5022–5023. doi: 10.1021/ja711260m
79. [79]
  T. Ogoshi, M. Hashizume, T.A. Yamagishi, Y. Nakamoto, Chem. Commun. 46 (2010) 3708–3710. doi: 10.1039/c0cc00348d
80. [80]
  X. Shu, K. Xu, D. Hou, C. Li, Isr. J. Chem. 58 (2018) 1230–1240. doi: 10.1002/ijch.201800115
81. [81]
  W. Xue, P.Y. Zavalij, L. Isaacs, Angew. Chem. Int. Ed. 59 (2020) 13313–13319. doi: 10.1002/anie.202005902
82. [82]
  Y. Ma, X. Ji, F. Xiang, et al., Chem. Commun. 47 (2011) 12340–12342. doi: 10.1039/c1cc15660h
83. [83]
  W. Chen, Y. Zhang, J. Li, et al., Chem. Commun. 49 (2013) 7956–7958. doi: 10.1039/c3cc44328k
84. [84]
  B. Gomez-Gonzalez, V. Francisco, R. Montecinos, L. Garcia-Rio, Org. Biomol. Chem. 15 (2017) 911–919. doi: 10.1039/C6OB02573K
85. [85]
  T. Ogoshi, R. Shiga, T.A. Yamagishi, J. Am. Chem. Soc. 134 (2012) 4577–4580. doi: 10.1021/ja300989n
86. [86]
  Y. Zhang, J. Chen, L. Chen, et al., Chin. Chem. Lett. 34 (2023) 107697. doi: 10.1016/j.cclet.2022.07.040
87. [87]
  Y. Tanaka, Y. Aoyama, Bull. Chem. Soc. Jpn. 63 (1990) 3343–3344. doi: 10.1246/bcsj.63.3343
88. [88]
  K. Wang, Q. Liu, L. Zhou, et al., Chin. Chem. Lett. (2023) 108559.
89. [89]
  K. Kobayashi, Y. Asakawa, Y. Kato, Y. Aoyama, J. Am. Chem. Soc. 114 (1992) 10307–10313. doi: 10.1021/ja00052a030
90. [90]
  C. Gropp, B.L. Quigley, F. Diederich, J. Am. Chem. Soc. 140 (2018) 2705–2717. doi: 10.1021/jacs.7b12894
91. [91]
  C.L. Gibb, B.C. Gibb, J. Am. Chem. Soc. 126 (2004) 11408–11409. doi: 10.1021/ja0475611
92. [92]
  Y.H. Wan, Y.J. Zhu, J. Rebek Jr., Y. Yu, Molecules 26 (2021). doi: 10.3390/molecules26071922
93. [93]
  Q. Shi, D. Masseroni, J. Rebek Jr., J. Am. Chem. Soc. 138 (2016) 10846–10848. doi: 10.1021/jacs.6b06950
94. [94]
  J.M. Yang, Y. Yu, J. Rebek Jr., J. Am. Chem. Soc. 143 (2021) 2190–2193. doi: 10.1021/jacs.0c12302
95. [95]
  G.W. Zhang, P.F. Li, Z. Meng, et al., Angew. Chem. Int. Ed. 55 (2016) 5304–5308. doi: 10.1002/anie.201600911
96. [96]
  G.W. Zhang, Y. Han, Y. Han, Y. Wang, C.F. Chen, Chem. Commun. 53 (2017) 10433–10436. doi: 10.1039/C7CC05489K
97. [97]
  Y. Guo, Y. Han, C.F. Chen, Front. Chem. 7 (2019) 543. doi: 10.3389/fchem.2019.00543
98. [98]
  Z.Y. Zhang, C. Li, Acc. Chem. Res. 55 (2022) 916–929. doi: 10.1021/acs.accounts.2c00043
99. [99]
  X. Du, M. Ma, Y. Zhang, et al., Angew. Chem. Int. Ed. 62 (2023) e202301857. doi: 10.1002/anie.202301857
100. [100]
  C. Zhai, L. Isaacs, Chem. Eur. J. 28 (2022) e202201743. doi: 10.1002/chem.202201743
101. [101]
  J.R. Wu, C.Y. Wang, Y.C. Tao, et al., Eur. J. Org. Chem. 2018 (2018) 1321–1325. doi: 10.1002/ejoc.201800112
102. [102]
  T. Chen, J. Wang, R. Tang, et al., Chin. Chem. Lett. 34 (2023) 108088. doi: 10.1016/j.cclet.2022.108088
103. [103]
  M.X. Wang, Acc. Chem. Res. 45 (2012) 182–195. doi: 10.1021/ar200108c
104. [104]
  M.X. Wang, Sci. China: Chem. 61 (2018) 993–1003.
105. [105]
  D. Xia, Y. Li, K. Jie, B. Shi, Y. Yao, Org. Lett. 18 (2016) 2910–2913. doi: 10.1021/acs.orglett.6b01264
106. [106]
  C.M. Hong, R.G. Bergman, K.N. Raymond, F.D. Toste, Acc. Chem. Res. 51 (2018) 2447–2455. doi: 10.1021/acs.accounts.8b00328
107. [107]
  Y. Wu, C. Zhang, S. Fang, et al., Angew. Chem. Int. Ed. 61 (2022) e202209078. doi: 10.1002/anie.202209078
108. [108]
  M. Yoshizawa, L. Catti, Acc. Chem. Res. 52 (2019) 2392–2404. doi: 10.1021/acs.accounts.9b00301
109. [109]
  L. Escobar, G. Aragay, P. Ballester, Chem. Eur. J. 22 (2016) 13682–13689. doi: 10.1002/chem.201602987
110. [110]
  L. Escobar, P. Ballester, Org. Chem. Front. 6 (2019) 1738–1748. doi: 10.1039/C9QO00171A
111. [111]
  J.J. Gassensmith, E. Arunkumar, L. Barr, et al., J. Am. Chem. Soc. 129 (2007) 15054–15059. doi: 10.1021/ja075567v
112. [112]
  E.M. Peck, W. Liu, G.T. Spence, et al., J. Am. Chem. Soc. 137 (2015) 8668–8671. doi: 10.1021/jacs.5b03573
113. [113]
  W. Liu, A. Johnson, B.D. Smith, J. Am. Chem. Soc. 140 (2018) 3361–3370. doi: 10.1021/jacs.7b12991
114. [114]
  H. Zhang, L.L. Wang, X.Y. Pang, L.P. Yang, W. Jiang, Chem. Commun. 57 (2021) 13724–13727. doi: 10.1039/D1CC05818E
115. [115]
  N.P. Barwell, M.P. Crump, A.P. Davis, Angew. Chem. Int. Ed. 48 (2009) 7673–7676. doi: 10.1002/anie.200903104
116. [116]
  Y. Ferrand, M.P. Crump, A.P. Davis, Science 318 (2007) 619–622. doi: 10.1126/science.1148735
117. [117]
  P. Rios, T.S. Carter, T.J. Mooibroek, et al., Angew. Chem. Int. Ed. 55 (2016) 3387–3392. doi: 10.1002/anie.201510611
118. [118]
  R.A. Tromans, T.S. Carter, L. Chabanne, et al., Nat. Chem. 11 (2019) 52–56. doi: 10.1038/s41557-018-0155-z
119. [119]
  B.J. Shorthill, C.T. Avetta, T.E. Glass, J. Am. Chem. Soc. 126 (2004) 12732–12733. doi: 10.1021/ja047639d
120. [120]
  H. Chai, Z. Chen, S.H. Wang, et al., CCS Chem. 2 (2020) 440–452. doi: 10.31635/ccschem.020.202000160
121. [121]
  X. Huang, X. Wang, M. Quan, et al., Angew. Chem. Int. Ed. 60 (2021) 1929–1935. doi: 10.1002/anie.202012467
122. [122]
  X. Wang, M. Quan, H. Yao, et al., Nat. Commun. 13 (2022) 2291. doi: 10.1038/s41467-022-30012-4
123. [123]
  Z. Zheng, W.C. Geng, J. Gao, Chem. Sci. 9 (2018) 2087–2091. doi: 10.1039/C7SC04989G
124. [124]
  L.M. Bai, H. Yao, L.P. Yang, W. Zhang, W. Jiang, Chin. Chem. Lett. 30 (2019) 881–884. doi: 10.1016/j.cclet.2018.11.033
125. [125]
  L.L. Wang, Z. Chen, W.E. Liu, et al., J. Am. Chem. Soc. 139 (2017) 8436–8439. doi: 10.1021/jacs.7b05021
126. [126]
  C. Zhai, C.L. Schreiber, S. Padilla-Coley, A.G. Oliver, B.D. Smith, Angew. Chem. Int. Ed. 59 (2020) 23740–23747. doi: 10.1002/anie.202009599
127. [127]
  A.T. Brockett, W. Xue, D. King, et al., Chem 9 (2023) 881–900. doi: 10.1016/j.chempr.2022.11.019
128. [128]
  S. Mosca, Y. Yu, J.V. Gavette, K.D. Zhang, J. Rebek Jr., J. Am. Chem. Soc. 137 (2015) 14582–14585. doi: 10.1021/jacs.5b10028
129. [129]
  L.P. Yang, H. Ke, H. Yao, W. Jiang, Angew. Chem. Int. Ed. 60 (2021) 21404–21411. doi: 10.1002/anie.202106998
130. [130]
  J.N. Jin, X.R. Yang, Y.F. Wang, et al., Angew. Chem. Int. Ed. 62 (2023) e202218313. doi: 10.1002/anie.202218313
131. [131]
  C. Gao, Q. Wang, J. Li, et al., Sci. Adv. 8 (2022) eabn1805. doi: 10.1126/sciadv.abn1805
1. [1]
  Cheng-Da Zhao , Huan Yao , Shi-Yao Li , Fangfang Du , Li-Li Wang , Liu-Pan Yang . Amide naphthotubes: Biomimetic macrocycles for selective molecular recognition. Chinese Chemical Letters, 2024, 35(4): 108879-. doi: 10.1016/j.cclet.2023.108879
2. [2]
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15. [15]
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16. [16]
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17. [17]
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18. [18]
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19. [19]
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20. [20]
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沈阳化工大学材料科学与工程学院沈阳 110142