Citation: Yongwei Qian, Shengyang Huang, Yaoyi Su, Songna Zhang, Yang Liu, Ming Liu, Bin Sun, Hao Li. A conformationally adaptive cage with multiple guest recognition modes[J]. Chinese Chemical Letters, ;2026, 37(4): 111354. doi: 10.1016/j.cclet.2025.111354 shu

A conformationally adaptive cage with multiple guest recognition modes

Yongwei Qian ^{a, 1} ,
Shengyang Huang ^{a, 1} ,
Yaoyi Su ^b ,
Songna Zhang ^b ,
Yang Liu ^a ,
Ming Liu ^{a, b, *,} ,
Bin Sun ^{c, *,} ,
Hao Li ^{a, b, *,}

a.
Department of Chemistry, Zhejiang University, Hangzhou 310058, China
b.
ZJU-Hangzhou Global Scientific and Technological Innovation Center, Zhejiang University, Hangzhou 311200, China
c.
Homogeneous, Supramolecular and Bio-Inspired Catalysis, Van't Hoff Institute for Molecular Sciences, University of Amsterdam, Amsterdam 1098XH, The Netherlands

mingliu@zju.edu.cn

sunbinnmg@gmail.com

lihao2015@zju.edu.cn

Received Date: 22 March 2025
Revised Date: 9 May 2025
Accepted Date: 19 May 2025
Available Online: 20 May 2025

Figures(3)

Here, Friedel–Crafts (FC) reaction is used to synthesize a purely organic cage in a one-pot manner. The trigonal prismatic cage is composed of two trisfuran platforms, bridged by three phenanthrene pillars each bearing two methoxy (OMe) units. The organic cage exhibited good kinetic inertness, allowing for a synthetic post-functionalization. During this transforming process, the electron-donating methoxy (OMe) groups were converted into electron-withdrawing carbonyl groups without any degradation on the cage framework. The cage exhibits multiple guest recognition modes. The oxygen atoms as the Lewis base present in either methoxy or carbonyl before and after post-functionalization, endow the cage with the ability to recognize Lewis acidic guests such as alkali cations. The OMe and carbonyl units grated on the phenanthrene pillars endow the cage with an π-electron-rich and π-electron-deficient cavity, respectively, where π-electron-deficient and π-electron-rich guests can be accommodated.
- Friedel–crafts reaction,
- Post-functionalization,
- Host-guest recognition,
- Conformationally adaptive
1. [1]
  J.M. Lehn, Science 260 (1993) 1762-1763. doi: 10.1126/science.8511582
2. [2]
  D. J. Cram, T. K. Roger, C. Helgeson, G. M. Lein, J. Am. Chem. Soc. 101(1979) 6752-6754. doi: 10.1021/ja00516a048
3. [3]
  D. J. Cram, T, Kaneda, R. C. Helgeson, G.M. Lein, J. Am. Chem. Soc. 89 (1967) 2495–2496. doi: 10.1021/ja00986a052
4. [4]
  Y. H. Ko, H. Kim, Y. Kim, K. Kim, Angew. Chem. Int. Ed. 47 (2008) 4106-4109. doi: 10.1002/anie.200800581
5. [5]
  K. Ariga, H. Ito, J. P. Hill, Chem. Soc. Rev. 41 (2012) 5800-5835. doi: 10.1039/c2cs35162e
6. [6]
  J. Rebek, Jr, J. Am. Chem. Soc. 136 (2014) 5264-5266. doi: 10.1021/ja501685z
7. [7]
  F. U. Rahman, et al, Proc. Natl. Acad. Sci. U. S. A. 116 (2019) 17648-17653. doi: 10.1073/pnas.1909154116
8. [8]
  E.G. Percástegui, T. K. Ronson, J. R. Nitschke, Chem. Rev. 120 (2020) 13480-13544. doi: 10.1021/acs.chemrev.0c00672
9. [9]
  M. Yamanaka, A. Shivanyuk, J. Rebek. Jr, J. Am. Chem. Soc. 126 (2004) 2939-2943. doi: 10.1021/ja037035u
10. [10]
  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
11. [11]
  Q. Zhang, L. Catti, Tiefenbacher, Acc. Chem. Res. 51 (2018) 2107-2114. doi: 10.1021/acs.accounts.8b00320
12. [12]
  J. Rebek. Jr, Y. Yu, Chem. Commun. 55 (2019) 3573-3577. doi: 10.1039/C9CC01611B
13. [13]
  T. A. Young, V. M. Centelles, J. Z Wang, F. Duarte, J. Am. Chem. Soc. 142 (2020) 1300-1310. doi: 10.1021/jacs.9b10302
14. [14]
  J. M. Yang, Y. Yu, J. Rebek. Jr, J. Am. Chem. Soc. 143 (2021) 2190-2193. doi: 10.1021/jacs.0c12302
15. [15]
  P. S. Mukherjee, Angew. Chem. Int. Ed. 62. (2023) e202305338. doi: 10.1002/anie.202305338
16. [16]
  W. M Xuan, M. N. Zhang, Y. Liu, Z. Chen, Y. Cui, J. Am. Chem. Soc. 134. (2012) 6904-6907. doi: 10.1021/ja212132r
17. [17]
  N. Ahmad, H. A. Younus, A. H. Chughtai, Chem. Soc. Rev. 44 (2015) 9-25. doi: 10.1039/C4CS00222A
18. [18]
  C. Lu, X. Yan, X. Li, F. Huang, S. Yin, J. Am. Chem. Soc. 139 (2017) 5067-5074. doi: 10.1021/jacs.6b12536
19. [19]
  Z. Zhang, X. Wang, J. Am. Chem. Soc. 142 (2020) 2592-2600. doi: 10.1021/jacs.9b12689
20. [20]
  T. Tozawa, S. I. Swamy, S. Jiang, A. Steiner, A. I. Cooper, Nat. Mater. 8 (2009) 973-978. doi: 10.1038/nmat2545
21. [21]
  K. Z. Su, W. J. Wang, S. F. Du, C. Q. Ji, D. Q. Yuan, J. Am. Chem. Soc. 142 (2020) 18060-18072. doi: 10.1021/jacs.0c07367
22. [22]
  G. Wu, H. Li, J. Am. Chem. Soc. 140 (2018) 5955-5961. doi: 10.1021/jacs.8b01651
23. [23]
  Y. Zhang, H. Li, CCS Chem. 7 (2025) 50-58. doi: 10.31635/ccschem.024.202404345
24. [24]
  Y.J. Zhou, K.C. Jie, R. Zhao, E. Li, F. H. Huang, J. Am. Chem. Soc. 142 (2020) 6957-6961. doi: 10.1021/jacs.0c02684
25. [25]
  J. Zhou, G. C Yu, Q. Li, M. B Wang, F. H. Huang, J. Am. Chem. Soc. 142 (2020) 2228-2232. doi: 10.1021/jacs.9b13548
26. [26]
  Y.T. Wu, J. Zhou, E. Li, et al., J. Am. Chem. Soc. 142 (2020) 19722-19730. doi: 10.1021/jacs.0c09757
27. [27]
  Y. Liu, F. H. Huang, J. Am. Chem. Soc. 143 (2021) 3081-3085. doi: 10.1021/jacs.1c01204
28. [28]
  M. Wang, F.H. Huang, Mater. Today Chem. 24 (2022) 2-8.
29. [29]
  C. J. Pedersen, J. Am. Chem. Soc. 89 (1967) 7017. doi: 10.1021/ja01002a035
30. [30]
  M. Fujita, Nature 378 (1996) 469-471.
31. [31]
  M. Fujita, O. Katsuyuki, Nature 400 (1999) 53-55.
32. [32]
  M. Fujita, Nature 398 (1999) 794-796. doi: 10.1038/19734
33. [33]
  D. J. Cram, J. Am. Chem. Soc. 113 (1991) 2754-2755. doi: 10.1021/ja00007a060
34. [34]
  M. Mastalerz, Chem. Commun. (2008) 4756-4758. doi: 10.1039/b808990f
35. [35]
  Y. Liu, G. Li, X. Liu, R. Warmuth, Angew. Chem. Int. Ed. 45 (2006) 901-904. doi: 10.1002/anie.200504049
36. [36]
  Y. Chen, H. Tang, H. L. Chen, H. Li, Acc. Chem. Res. 56 (2023) 2838-2850. doi: 10.1021/acs.accounts.3c00475
37. [37]
  S. J. Rowan, P. A. Brady, M. Sanders, Angew. Chem. Int. Ed. 35 (1996) 2143-2145. doi: 10.1002/anie.199621431
38. [38]
  S. Otto, M Sanders, Science 297 (2002) 590-593. doi: 10.1126/science.1072361
39. [39]
  M Sanders, Angew. Chem. Int. Ed. 108 (2006) 2283-2285.
40. [40]
  L. Y. Wang, V. BÖhmer, Science 304 (2004) 1312-1314. doi: 10.1126/science.1096688
41. [41]
  P. H. Kirchner, F. Beuerle, J. Am. Chem. Soc. 146(2024) 5305-5315. doi: 10.1021/jacs.3c12002
42. [42]
  G. Zhang, O. M. M. A Mastalerz, Angew. Chem. Int. Ed. 53 (2014) 1516-1520. doi: 10.1002/anie.201308924
43. [43]
  M.S. Avinash, S. Bhat, S. M. Elbert, et al., Angew. Chem. Int. Ed. 58 (2019) 8819-8823. doi: 10.1002/anie.201903631
44. [44]
  K. Xu, Z. Y. Zhang, C.G. Yu, et al., Angew. Chem. Int. Ed. 59 (2020) 7214-7218. doi: 10.1002/anie.202000909
45. [45]
  K. D. Xu, B. Li, S. B. Yao, et al., Angew. Chem. Int. Ed. 61 (2022) e202203016. doi: 10.1002/anie.202203016
46. [46]
  X. N. Han, Y. Han, C. F. Chen, Chem. Soc. Rev. 52 (2023) 3265-3298. doi: 10.1039/d3cs00002h
47. [47]
  X. Zhao, H.Y. Cui, L.L. Guo, et al., Angew. Chem. Int. Ed. 63 (2024) e202411613. doi: 10.1002/anie.202411613
48. [48]
  D.S. Zhu, F. Shuai, L. Tong, H. Li, Chem. Commun. 57 (2021) 4440-4443. doi: 10.1039/d1cc00498k
49. [49]
  D. Zhu, B. Sun, L. Tong, H. Li, Org. Lett. 24 (2022) 8980-8985. doi: 10.1021/acs.orglett.2c03560
50. [50]
  C. Denis, M. A. J. Dubois, A. S. Voisin-Chiret, et al., Org. Lett. 21 (2019) 300-304. doi: 10.1021/acs.orglett.8b03745
1. [1]
  Zhen Dai , Linzhi Tan , Yeyu Su , Kerui Zhao , Yushun Tian , Yu Liu , Tao Liu . Site-specific incorporation of reduction-controlled guest amino acids into proteins for cucurbituril recognition. Chinese Chemical Letters, 2024, 35(5): 109121-. doi: 10.1016/j.cclet.2023.109121
2. [2]
  Qiang Fang , Yingbo Lu , Jianying Huang , Cheng Zhang , Jing Wu , Shijun Li . An electrochemical immunosensor based on an antibody-ferrocene-functionalized covalent organic framework. Chinese Chemical Letters, 2026, 37(2): 111218-. doi: 10.1016/j.cclet.2025.111218
3. [3]
  Yu Xia , Yangming Jiang , Xin-Long Ni , Qiaochun Wang , Daoping Wang . A macrocycle-based "Russian doll": The smallest cucurbit[4]uril in cucurbit[10]uril. Chinese Chemical Letters, 2024, 35(12): 109782-. doi: 10.1016/j.cclet.2024.109782
4. [4]
  Yi Zhou , Wei Zhang , Rong Fu , Jiaxin Dong , Yuxuan Liu , Zihang Song , Han Han , Kang Cai . Self-assembly of two pairs of homochiral M₂L₄ coordination capsules with varied confined space using Tröger's base ligands. Chinese Chemical Letters, 2025, 36(2): 109865-. doi: 10.1016/j.cclet.2024.109865
5. [5]
  Yan Fan , Jiao Tan , Cuijuan Zou , Xuliang Hu , Xing Feng , Xin-Long Ni . Unprecedented stepwise electron transfer and photocatalysis in supramolecular assembly derived hybrid single-layer two-dimensional nanosheets in water. Chinese Chemical Letters, 2025, 36(4): 110101-. doi: 10.1016/j.cclet.2024.110101
6. [6]
  Yujuan Zhou , Kecheng Jie . Conformationally adaptive metal–organic cages for dynamic guest encapsulation. Chinese Chemical Letters, 2025, 36(6): 111007-. doi: 10.1016/j.cclet.2025.111007
7. [7]
  Jie Yang , Xin-Yue Lou , Dihua Dai , Jingwei Shi , Ying-Wei Yang . Desymmetrized pillar[8]arenes: High-yield synthesis, functionalization, and host-guest chemistry. Chinese Chemical Letters, 2025, 36(1): 109818-. doi: 10.1016/j.cclet.2024.109818
8. [8]
  Ran Zhu , Pan Zhang , Yitong Xu , Jiutong Ma , Qiong Jia . Design of host-guest interaction based molecularly imprinted polymers: Targeting recognition of the epitope of neuron-specific enolase via a SERS assay. Chinese Chemical Letters, 2025, 36(6): 110259-. doi: 10.1016/j.cclet.2024.110259
9. [9]
  Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024
10. [10]
  Jianmei Guo , Yupeng Zhao , Lei Ma , Yongtao Wang . Ultra-long room temperature phosphorescence, intrinsic mechanisms and application based on host-guest doping systems. Chinese Journal of Structural Chemistry, 2024, 43(9): 100335-100335. doi: 10.1016/j.cjsc.2024.100335
11. [11]
  Cheng He , Renlan Huang , Lingling Wei , Qiuhui He , Jinbo Liu , Jiao Chen , Ge Gao , Cheng Yang , Wanhua Wu . Uncovering the mask of sensitizers to switch on the TTA-UC emission by supramolecular host-guest complexation. Chinese Chemical Letters, 2025, 36(4): 110103-. doi: 10.1016/j.cclet.2024.110103
12. [12]
  Shengyong Liu , Hui Li , Wei Zhang , Yan Zhang , Yan Dong , Wei Tian . Multiple host-guest and metal coordination interactions induce supramolecular assembly and structural transition. Chinese Chemical Letters, 2025, 36(6): 110465-. doi: 10.1016/j.cclet.2024.110465
13. [13]
  Huipeng Li , Xue Yang , Minjie Sun . Self-strengthened cascade-explosive nanogel using host-guest interaction strategy for synergistic tumor treatment. Chinese Chemical Letters, 2025, 36(8): 110651-. doi: 10.1016/j.cclet.2024.110651
14. [14]
  Zeyuan Zhang , Zixuan Li , Chenjing Liu , Yali Hou , Ke Gao , Shijin Jian , Guoping Li , Gang He , Mingming Zhang . Porphyrin metallacage-based host-guest complexation for highly efficient photocatalytic hydrogen production. Chinese Chemical Letters, 2025, 36(12): 111322-. doi: 10.1016/j.cclet.2025.111322
15. [15]
  Zhao Liu , Junjian Xie , Xiaoming Ren , Muhammad Tahir , Shixin Fa , Qiuyu Zhang . Host-guest interaction mediated low-shrinkage photosensitive positioning adhesive. Chinese Chemical Letters, 2026, 37(2): 111949-. doi: 10.1016/j.cclet.2025.111949
16. [16]
  Wenzheng Li , Ke Zhang , Wenjing Liu , Ting Li , Wei Li , Lijuan Wu , Maodong Wang , Hangyun He , Pengfei Tu , Yuelin Song . Multidimensional host-guest molecule screening via 96-well plate assays to facilitate the development of natural product nanomicelles. Chinese Chemical Letters, 2026, 37(3): 111548-. doi: 10.1016/j.cclet.2025.111548
17. [17]
  Haifeng ZHENG , Xingzhe GUO , Yunwei WEI , Xinfang WANG , Huimin QI , Yuting YAN , Jie ZHANG , Bingwen LI . Post-synthetic modification strategy to construct Co-MOF composites for boosting oxygen evolution reaction activity. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 193-202. doi: 10.11862/CJIC.20250029
18. [18]
  Bingbing Shi , Yuchun Wang , Yi Zhou , Xing-Xing Zhao , Yizhou Li , Nuoqian Yan , Wen-Juan Qu , Qi Lin , Tai-Bao Wei . A supramolecular oligo[2]rotaxane constructed by orthogonal platinum(Ⅱ) metallacycle and pillar[5]arene-based host–guest interactions. Chinese Chemical Letters, 2024, 35(10): 109540-. doi: 10.1016/j.cclet.2024.109540
19. [19]
  Xueru Zhao , Aopu Wang , Shimin Wang , Zhijie Song , Li Ma , Li Shao . Adsorption and visual detection of nitro explosives by pillar[n]arenes-based host–guest interactions. Chinese Chemical Letters, 2025, 36(4): 110205-. doi: 10.1016/j.cclet.2024.110205
20. [20]
  Xianchen Hu , Junli Yang , Fang Gao , Zhiyong Zhao , Simin Liu . Highly selective [4+4] cross-photodimerization of (4a-azonia)anthracenes driven by confinement of D-A hetero-guest pair in cucurbit[10]uril host. Chinese Chemical Letters, 2025, 36(3): 109967-. doi: 10.1016/j.cclet.2024.109967

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(95)
HTML views(12)

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