Citation: Wei Zhang, Yang Luo, Jie Zhao, Chao Zhang, Xin-Long Ni, Zhu Tao, Xin Xiao. Controllable fabrication of a supramolecular polymer incorporating twisted cucurbit[14]uril and cucurbit[8]uril via self-sorting[J]. Chinese Chemical Letters, ;2022, 33(5): 2455-2458. doi: 10.1016/j.cclet.2021.11.053 shu

Controllable fabrication of a supramolecular polymer incorporating twisted cucurbit[14]uril and cucurbit[8]uril via self-sorting

Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025, China

gyhxxiaoxin@163.com

Received Date: 8 July 2021
Revised Date: 13 November 2021
Accepted Date: 14 November 2021
Available Online: 19 November 2021

Figures(7)

A linear supramolecular polymer with controllable features based on twisted cucurbit[14]uril (tQ[14]) and cucurbit[8]uril (Q[8]) was firstly fabricated via an effective self-sorting strategy. Herein we designed a monomer, 1-butyl-1′-(naphthalen- 2-ylmethyl)-4, 4′-bipyridinium bromide (BNB), that contains bipyridyl, aliphatic butyl and aromatic naphthyl groups, simultaneously. Two host molecules, tQ[14] and Q[8] were employed to develop an effective strategy for constructing a linear supramolecular polymer with controllable features. The alkyl groups on both sides of BNB could insert into the two cavities of tQ[14], the naphthyl part of BNB via π-π stacking in Q[8] cavity, serving as the driving force for supramolecular polymerization. Through self-sorting of the monomer, tQ[14] and Q[8], led to the formation of the linear supramolecular polymer. Depolymerization could be achieved by addition of adamantane hydrochloride (AH) which driven two BNB guest molecules out of the Q[8] cavity. This self-sorting strategy has great potential, not only for designing supramolecular polymer materials with different controllable structures through introduction of multiple functional groups, but also for broadening the application of twisted cucurbit[14]uril in supramolecular chemistry.
- Cucurbit[n]urils,
- Twisted cucurbit[14]uril,
- Supramolecular polymer,
- Self-sorting,
- Host-guest interaction
1. [1]
  R. Zhao, Y.J. Zhou, F.H. Huang, et al., Chin. J. Polym. Sci. 38 (2020) 1-8. doi: 10.1007/s10118-019-2305-1
2. [2]
  X.F. Ji, F. Wang, F.H. Huang, et al., Chin. J. Chem. 38 (2020) 1473-1479. doi: 10.1002/cjoc.202000314
3. [3]
  A.R. Palmans, E.W. Meijer, Angew. Chem. Int. Ed. 46 (2007) 8948-8968. doi: 10.1002/anie.200701285
4. [4]
  C.B. Winiger, S. Li, R. Haner, et al., Angew. Chem. Int. Ed. 53 (2014) 13609-13613. doi: 10.1002/anie.201407968
5. [5]
  C.C. Lee, C. Grenier, E.W. Meijer, et al., Chem. Soc. Rev. 38 (2009) 671. doi: 10.1039/B800407M
6. [6]
  J.R. Kumpfer, S.J. Rowan, J. Am. Chem. Soc. 133 (2011) 12866-128743. doi: 10.1021/ja205332w
7. [7]
  W. Weng, J.B. Beck, S.J. Rowan, et al., J. Am. Chem. Soc. 128 (2006) 11663-11672. doi: 10.1021/ja063408q
8. [8]
  X. Xiao, J.S. Sun, J.Z. Jiang, Chem. Eur. J. 19 (2013) 16891-16896. doi: 10.1002/chem.201303530
9. [9]
  Z.Y. Zhang, Y. Chen, Y. Liu, Angew. Chem. Int. Ed. 58 (2019) 6028-6032. doi: 10.1002/anie.201901882
10. [10]
  T.K. Ellis, M. Galerne, J.J. Armao, et al., Angew. Chem. Int. Ed. 57 (2018) 15749-15753. doi: 10.1002/anie.201809756
11. [11]
  B. Qin, S. Zhang, X. Zhang, et al., Angew. Chem. Int. Ed. 58 (2017) 7639-7643.
12. [12]
  Q. Li, K.C. Jie, F.H. Huang, et al., Angew. Chem. Int. Ed. 59 (2020) 5355-5358. doi: 10.1002/anie.201916041
13. [13]
  E. Krieg, M.M.C. Bastings, P. Besenius, et al., Chem. Rev. 116 (2016) 2414-2477. doi: 10.1021/acs.chemrev.5b00369
14. [14]
  L. Wang, L. Cheng, F.H. Huang, et al., J. Am. Chem. Soc. 142 (2020) 2051-2058. doi: 10.1021/jacs.9b12164
15. [15]
  H.L. Sun, H.Y. Zhang, Y. Liu, et al., Chem. Asian J. 12 (2017) 265-270. doi: 10.1002/asia.201601545
16. [16]
  M.Z. Zuo, W.R. Qian, L.Y. Wang, et al., Small 14 (2018) 1801942.
17. [17]
  Y.C. Yang, X.L. Ni, X. Zhang, et al., Chem. Commun. 55 (2019) 13836. doi: 10.1039/C9CC07127J
18. [18]
  D. Yang, M. Liu, C. Redshaw, et al., Coordin. Chem. Rev. 434 (2021) 213733. doi: 10.1016/j.ccr.2020.213733
19. [19]
  Y.C. Yang, H. Hu, X. Zhang, et al., Macromol. Rapid Commun. 41 (2020) 2000080. doi: 10.1002/marc.202000080
20. [20]
  X.Y. Dai, X.Y. Dong, Y. Liu, et al., Biomacromolecules 21 (2020) 5369-5379. doi: 10.1021/acs.biomac.0c01547
21. [21]
  W.R. Qian, M.Z. Zuo, R.B. Wang, et al., Chem. Commun. 56 (2020) 7301. doi: 10.1039/D0CC02962A
22. [22]
  S.W. Guo, Q.X. Huang, R.B. Wang, et al., Angew. Chem. Int. Ed. 60 (2021) 618-623. doi: 10.1002/anie.202013975
23. [23]
  J. Kang, D. Miyajima, T. Aida, et al., Science 347 (2015) 646-651. doi: 10.1126/science.aaa4249
24. [24]
  S. Ogi, V. Stepanenko, K. Sugiyasu, et al., J. Am. Chem. Soc. 137 (2015) 3300-3307. doi: 10.1021/ja511952c
25. [25]
  Z. Huang, L. Yang, X. Zhang, Angew. Chem. Int. Ed. 53 (2014) 5351-5355. doi: 10.1002/anie.201402817
26. [26]
  H.B. Qiu, Z.M. Hudson, I. Manners, et al., Science 347 (2015) 1329-1332. doi: 10.1126/science.1261816
27. [27]
  W. Jiang, A. Schafer, P.C. Mohr, et al., J. Am. Chem. Soc. 132 (2010) 2309-2320. doi: 10.1021/ja9101369
28. [28]
  L. Wang, L. Cheng, X.Z. Yan, et al., J. Am. Chem. Soc. 142 (2020) 2051-2058. doi: 10.1021/jacs.9b12164
29. [29]
  H.L. Sun, H.Y. Zhang, Y. Liu, et al., Chem. Asian J. 12 (2017) 265-270. doi: 10.1002/asia.201601545
30. [30]
  J. Lagona, P. Mukhopadhyay, L. Isaacs, et al., Angew. Chem. Int. Ed. 44 (2005) 4844. doi: 10.1002/anie.200460675
31. [31]
  X.L. Ni, X. Xiao, Z. Tao, et al., Acc. Chem. Res. 47 (2014) 1386-1395. doi: 10.1021/ar5000133
32. [32]
  Y. Huang, R.H. Gao, Z. Tao, et al., Angew. Chem. Int. Ed. 60 (2021) 15166-15191. doi: 10.1002/anie.202002666
33. [33]
  M. Liu, J.L. Kan, Z. Tao, et al., Sensor Actuat. B: Chem. 283 (2019) 290-297. doi: 10.1016/j.snb.2018.12.024
34. [34]
  M. Liu, L.X. Chen, Z. Tao, et al., ACS Appl. Mater. Inter. 13 (2021) 7434-7442. doi: 10.1021/acsami.0c20292
35. [35]
  W.T. Xu, Y. Luo, X. Xiao, et al., J. Agric. Food Chem. 69 (2021) 584-591. doi: 10.1021/acs.jafc.0c05577
36. [36]
  S.J. Barrow, S. Kasera, M.J. Rowland, et al., Chem. Rev. 115 (2015) 12320-12406. doi: 10.1021/acs.chemrev.5b00341
37. [37]
  Y.L. Liu, Z.H. Huang, X. Zhang, et al., Chem. Commun. 49 (2013) 5766-5768. doi: 10.1039/c3cc41864b
38. [38]
  R.L. Lin, J.X. Liu, C. Redshaw, et al., Inorg. Chem. Front. 7 (2020) 3217-3246. doi: 10.1039/D0QI00529K
39. [39]
  K.M. Park, M.Y. Hur, K. Kim, et al., Chem. Commun. 55 (2019) 10654-10664. doi: 10.1039/C9CC05567C
40. [40]
  X.J. Cheng, L.L. Liang, Z. Tao, et al., Angew. Chem. Int. Ed. 52 (2013) 7393-7396.
41. [41]
  Z.Z. Gao, J. Zhang, X. Xiao, et al., Org. Chem. Front. 3 (2016) 1144. doi: 10.1039/C6QO00310A
42. [42]
  Q. Li, S.C. Qiu, G. Wei, et al., Org. Lett. 18 (2016) 4020-4023. doi: 10.1021/acs.orglett.6b01842
43. [43]
  L.H. Chen, Z.H. Huang, X. Zhang, et al., Polym. Chem. 7 (2016) 1397. doi: 10.1039/C5PY01923K
44. [44]
  Y.C. Yang, H. Hu, X. Zhang, et al., Mater. Chem. Front. 3 (2019) 806-811. doi: 10.1039/C9QM00028C
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