Citation: Pan-Pan Hua, Hui-Jun Feng, Shu-Ning Lan, Francisco Aznarez, Li-Fang Zhang. Post-modification-induced supramolecular transformation of Hopf link to macrocycle[J]. Chinese Chemical Letters, ;2025, 36(6): 110684. doi: 10.1016/j.cclet.2024.110684 shu

Post-modification-induced supramolecular transformation of Hopf link to macrocycle

a.
Key Laboratory of Magnetic Molecules and Magnetic Information Materials of the Ministry of Education, School of Chemistry and Material Science, Shanxi Normal University, Taiyuan 030031, China
b.
Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, State Key Laboratory of Molecular Engineering of Polymers, Department of Chemistry, Fudan University, Shanghai 200438, China

17110220045@fudan.edu.cn

zhanglf705@163.com

Received Date: 14 October 2024
Revised Date: 15 November 2024
Accepted Date: 26 November 2024
Available Online: 27 November 2024

Figures(7)

Although supramolecular transformations have been emerged as a potent strategy for transitioning between various topologies, post-modification induced topological transformations have never been explored in the context of [2]catenane topologies. In this study, we present a novel supramolecular transformation between a Hopf link and a macrocycle, induced by the Diels–Alder click reaction. By strategically selecting the half-sandwich ruthenium binuclear fragment B as a rigid capping agent, we successfully integrated tetrazine moieties into the metalla[2]catenane structure. We demonstrated that the introduction of 2,5-norbornadiene (NBD) as an external stimulus allows for the transformation of the novel metalla[2]catenane, featuring reactive tetrazine sites, into the corresponding monomeric ring through post-modification for the first time. The synthetic results are corroborated by single-crystal X-ray diffraction analysis, ESI-TOF/MS, elemental analysis, and detailed solution-state NMR techniques.
- Diels–Alder reaction,
- Half-sandwich ruthenium acceptor,
- Hopf link,
- Post-modification,
- Supramolecular transformation
1. [1]
  C. Shi, H. Li, W. Xie, Org. Lett. 26 (2024) 6910–6914. doi: 10.1021/acs.orglett.4c02572
2. [2]
  Y.S. Wang, S. Bai, Y.Y. Wang, et al., Chem. Commun. 55 (2019) 13689–13692. doi: 10.1039/c9cc07113j
3. [3]
  Q.F. Sun, S. Sato, M. Fujita, Angew. Chem. 126 (2014) 13728–13731. doi: 10.1002/ange.201408652
4. [4]
  S.J. Chen, D.K. Su, C.C. Jia, et al., Chem 8 (2022) 243–252. doi: 10.1016/j.chempr.2021.11.012
5. [5]
  Yu. Mao, J. Ma, J. Ji, et al., Chin. Chem. Lett. 35 (2024) 109927. doi: 10.1016/j.cclet.2024.109927
6. [6]
  Q. Chai, L. Duan, Y. Ma, Sci. China Chem. 67 (2024) 1510–1523. doi: 10.1007/s11426-023-1919-2
7. [7]
  H.H. Duan, F. Cao, H.X. Hao, et al., ACS Appl. Mater. Interfaces 13 (2021) 16837–16845. doi: 10.1021/acsami.1c01867
8. [8]
  Y. Liu, Z. Guo, Y. Guo, et al., Chin. Chem. Lett. 34 (2023) 108531. doi: 10.1016/j.cclet.2023.108531
9. [9]
  F. Cui, Q. Zhang, T. Xiao, et al., Chin. Chem. Lett. 35 (2024) 110061. doi: 10.1016/j.cclet.2024.110061
10. [10]
  T. Feng, X. Li, Y.Y. An, et al., Angew. Chem., Int. Ed. 59 (2020) 13516–13520. doi: 10.1002/anie.202004112
11. [11]
  Y.S. Wang, H. Li, S. Bai, Sci. China Chem. 66 (2023) 778–782.
12. [12]
  R. Huang, X. Wei, P. Wang, et al., Org. Lett. 26 (2024) 1405–1409. doi: 10.1021/acs.orglett.3c04367
13. [13]
  S.N. Lei, H. Cong, Chin. Chem. Lett. 33 (2022) 1493–1496. doi: 10.1016/j.cclet.2021.08.068
14. [14]
  Y. Liu, S.H. Liao, W.T. Dai, et al., Angew. Chem. Int. Ed. 62 (2023) e202217215. doi: 10.1002/anie.202217215
15. [15]
  P.P. Hua, H.J. Feng, X. Gao, et al., Inorg. Chem. Front. 11 (2024) 5026–5033. doi: 10.1039/d4qi01288g
16. [16]
  T. Chen, Y. Zhao, L.L. Dang, et al., J. Am. Chem. Soc. 145 (2023) 18036–18047. doi: 10.1021/jacs.3c05720
17. [17]
  W.B. Yu, F.Y. Qiu, S.T. Luo, et al., Inorg. Chem. Front. 8 (2021) 2356–2364. doi: 10.1039/d1qi00174d
18. [18]
  Q.S. Mu, X. Gao, Z. Cui, et al., Sci. China Chem. 66 (2023) 2885–2891. doi: 10.1007/s11426-023-1675-0
19. [19]
  M.M. Gan, J.Q. Liu, L. Zhang, et al., Chem. Rev. 118 (2018) 9587–9641. doi: 10.1021/acs.chemrev.8b00119
20. [20]
  Y. Zhou, H.-N. Zhang, Q.S. Mu, et al., Chin. J. Chem. 41 (2023) 3229–3237. doi: 10.1002/cjoc.202300359
21. [21]
  Y.R. Shen, X. Gao, Z. Cui, et al., Chin. J. Chem. 39 (2021) 3303–3308. doi: 10.1002/cjoc.202100546
22. [22]
  W.L. Shan, Y.J. Lin, F.E. Hahn, et al., Angew. Chem. Int. Ed. 58 (2019) 5882–5886. doi: 10.1002/anie.201900556
23. [23]
  Y. Li, G.F. Jin, Y.Y. An, et al., Chin. J. Chem. 37 (2019) 1147–1152. doi: 10.1002/cjoc.201900348
24. [24]
  Y.H. Song, N. Singh, J. Jung, Angew. Chem. 128 (2016) 2047–2051. doi: 10.1002/ange.201508257
25. [25]
  Y.Y. Zhang, F.Y. Qiu, H.T. Shi, et al., Chem. Commun. 57 (2021) 3010–3013. doi: 10.1039/d0cc08052g
26. [26]
  M. Koizumi, C. Dietrich-Buchecker, J.P. Sauvage, Eur. J. Org. Chem. 2004 (2004) 770–775. doi: 10.1002/ejoc.200300572
27. [27]
  Y.W. Zhang, Y. Lu, L.Y. Sun, et al., Angew. Chem. Int. Ed. 62 (2023) e202312323. doi: 10.1002/anie.202312323
28. [28]
  C.C. Yee, A.W.H. Ng, H.Y. Au-Yeung, Chem. Commun. 55 (2019) 6169–6172. doi: 10.1039/c9cc02263e
29. [29]
  H. Lee, P. Elumalai, N. Singh, et al., J. Am. Chem. Soc. 137 (2015) 4674–4677. doi: 10.1021/jacs.5b02573
30. [30]
  P.P. Hua, J.H. Bai, H.J. Feng, et al., J. Am. Chem. Soc. 146 (2024) 26427–26434. doi: 10.1021/jacs.4c09385
31. [31]
  Y. Zou, S.J. Bao, H. Tang, et al., Angew. Chem. Int. Ed. 63 (2024) e202410722. doi: 10.1002/anie.202410722
32. [32]
  L.L. Dang, Z.B. Sun, W.L. Shan, et al., Nat. Commun. 10 (2019) 2057. doi: 10.1038/s41467-019-10075-6
33. [33]
  S.C. Li, L.X. Cai, L.P. Zhou, et al., Sci. China Chem. 62 (2019) 713–718. doi: 10.1007/s11426-018-9427-4
34. [34]
  B.H. Northrop, Y.R. Zheng, K.W. Chi, Acc. Chem. Res. 42 (2009) 1554–1563. doi: 10.1021/ar900077c
35. [35]
  Y. Lu, H.N. Zhang, G.X. Jin, Acc. Chem. Res. 51 (2018) 2148–2158. doi: 10.1021/acs.accounts.8b00220
36. [36]
  X.Z. Li, L.P. Zhou, L.L. Yang, et al., Nat. Commun. 9 (2018) 547. doi: 10.2174/1871527317666180711093538
37. [37]
  S. Wang, Z. Huang, A. Li, et al., Angew. Chem. Int. Ed. 60 (2021) 9573–9579. doi: 10.1002/anie.202100441
38. [38]
  Z. Jiang, H. Zhao, J. Wang, et al., Chin. Chem. Lett. 34 (2023) 108334. doi: 10.1016/j.cclet.2023.108334
39. [39]
  H. Duan, T. Yang, Q. Li, et al., Chin. Chem. Lett. 35 (2024) 108878. doi: 10.1016/j.cclet.2023.108878
40. [40]
  F. Zeng, L.L. Tang, H. Yu, et al., Chin. Chem. Lett. 34 (2023) 108304. doi: 10.1016/j.cclet.2023.108304
41. [41]
  L. Cheng, P. Tian, Q. Li, et al., CCS Chem. 3 (2021) 3608–3614.
42. [42]
  H. Duan, F. Cao, M. Zhang, et al., Chin. Chem. Lett. 33 (2022) 2459–2463. doi: 10.1016/j.cclet.2021.11.010
43. [43]
  D. Chen, T. Xiao, É. Monflier, et al., Commun. Chem. 7 (2024) 88. doi: 10.1038/s42004-024-01175-6
44. [44]
  J. Jiao, H. Li, W. Xie, et al., Chem. Sci. 14 (2023) 11402–11409. doi: 10.1039/d3sc02995f
45. [45]
  X. Gao, Z. Cui, Y.R. Shen, et al., J. Am. Chem. Soc. 143 (2021) 17833–17842. doi: 10.1021/jacs.1c09333
46. [46]
  S.J. Hu, X.Q. Guo, L.P. Zhou, et al., J. Am. Chem. Soc. 144 (2022) 4244–4253. doi: 10.1021/jacs.2c00760
47. [47]
  L.X. Cai, D.N. Yan, P.M. Cheng, et al., J. Am. Chem. Soc. 143 (2021) 2016–2024. doi: 10.1021/jacs.0c12064
48. [48]
  Y.W. Zhang, S. Bai, Y.Y. Wang, et al., J. Am. Chem. Soc. 142 (2020) 13614–13621. doi: 10.1021/jacs.0c06470
49. [49]
  L.L. Dang, T.T. Zhang, T. Chen, et al., Angew. Chem. Int. Ed. 62 (2023) e202301516. doi: 10.1002/anie.202301516
50. [50]
  J.H. Jo, N. Singh, D. Lim, et al., Inorg. Chem. 56 (2017) 8430–8438. doi: 10.1021/acs.inorgchem.7b01101
51. [51]
  T. Feng, X. Li, Y.Y. An, Angew. Chem. Int. Ed. 59 (2020) 13516–13520. doi: 10.1002/anie.202004112
52. [52]
  L.L. Dang, T.T. Zhang, T. Chen, et al., Org. Chem. Front. 9 (2022) 5505–5515. doi: 10.1039/d2qo01107g
53. [53]
  Y. Takezawa, S. Yoneda, J.L. Duprey, et al., Chem. Sci. 7 (2016) 3006–3010. doi: 10.1039/C6SC00383D
54. [54]
  S. Chen, L.J. Chen, H.B. Yang, et al., J. Am. Chem. Soc. 134 (2012) 13596–13599. doi: 10.1021/ja306748k
55. [55]
  Y. Sun, C. Chen, J. Liu, et al., Chem. Soc. Rev. 49 (2020) 3889–3919. doi: 10.1039/d0cs00038h
56. [56]
  H.N. Zhang, W.B. Yu, Y.J. Lin, et al., Angew. Chem., Int. Ed. 60 (2021) 15466–15471. doi: 10.1002/anie.202103264
57. [57]
  H. Tang, H.N. Zhang, X. Gao, et al., J. Am. Chem. Soc. 146 (2024) 16020–16027. doi: 10.1021/jacs.4c03019
58. [58]
  F.G. Zhang, Z. Chen, X. Tang, et al., Chem. Rev. 121 (2021) 14555–14593. doi: 10.1021/acs.chemrev.1c00611
59. [59]
  G.X. Xu, X. Bai, Q. Dang, et al., Acc. Chem. Res. 53 (2020) 773–781. doi: 10.1021/acs.accounts.9b00604
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4. [4]
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