Citation: Shu Niu, Hongyan Xiao, Xiao-Di Yang, Huan Cong. Chloride anion-induced dimer capsule based on a polyfluorinated macrocycle meta-WreathArene[J]. Chinese Chemical Letters, ;2023, 34(7): 108042. doi: 10.1016/j.cclet.2022.108042 shu

Chloride anion-induced dimer capsule based on a polyfluorinated macrocycle meta-WreathArene

Shu Niu ^a ,
Hongyan Xiao ^b ,
Xiao-Di Yang ^c ,
Huan Cong ^{a, *,}

a.
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry; School of Future Technology, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Beijing 100190, China
b.
Key Laboratory of Bio-inspired Materials and Interfacial Science, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, China
c.
Research Center of Chiral Drugs, Innovation Research Institute of Traditional Chinese Medicine, Shanghai University of Traditional Chinese Medicine, Shanghai 200438, China

cong@mail.ipc.ac.cn

Received Date: 6 October 2022
Revised Date: 1 December 2022
Accepted Date: 5 December 2022
Available Online: 10 December 2022

Figures(5)

[1_n]metacyclophanes are a class of important building blocks for supramolecular assembly of artificial capsules. Herein we present the preparation and properties of a novel polyfluorinated macrocycle meta-WreathArene, a C₂-symmetrical [1₄]metacyclophane. Adopting a cone conformation in acetone solution, the macrocycle can form dimer capsules through hydrogen bonds induced by chloride anions. Each dimer capsule consists of two meta-WreathArene and two chloride anions, and has been unambiguously characterized both in solution and in solid state.
- Macrocycle,
- Metacyclophane,
- Anion,
- Assembly,
- Capsule
1. [1]
  J. Rebek Jr., Angew. Chem. Int. Ed. 44 (2005) 2068–2078. doi: 10.1002/anie.200462839
2. [2]
  S. Zarra, D.M. Wood, D.A. Roberts, J.R. Nitschke, Chem. Soc. Rev. 44 (2015) 419–432. doi: 10.1039/C4CS00165F
3. [3]
  J. Gaitzsch, X. Huang, B. Voit, Chem. Rev. 116 (2016) 1053–1093. doi: 10.1021/acs.chemrev.5b00241
4. [4]
  Y. Ferrand, I. Huc, Acc. Chem. Res. 51 (2018) 970–977. doi: 10.1021/acs.accounts.8b00075
5. [5]
  M. Yokoya, S. Kimura, M. Yamanaka, Chem. Eur. J. 27 (2021) 5601–5614. doi: 10.1002/chem.202004367
6. [6]
  J. Rebek Jr., Chem. Commun. 8 (2000) 637–643.
7. [7]
  F. Hof, S.L. Craig, C. Nuckolls, J. Rebek Jr., Angew. Chem. Int. Ed. 41 (2002) 1488–1508. doi: 10.1002/1521-3773(20020503)41:9<1488::AID-ANIE1488>3.0.CO;2-G
8. [8]
  K. Wang, E.C. Yang, X.J. Zhao, H.X. Dou, Y. Liu, Cryst. Growth Des. 14 (2014) 4631–4639. doi: 10.1021/cg500730m
9. [9]
  V. Böhmer, Angew. Chem. Int. Ed. 34 (1995) 713–745. doi: 10.1002/anie.199507131
10. [10]
  Z. Asfari, V. Böhmer, J. Harrowfield, J. Vicens, Calixarenes, Kluwer Academic Publishers, Dordrecht, 2001.
11. [11]
  A. Ikeda, S. Shinkai, Chem. Rev. 97 (1997) 1713–1734. doi: 10.1021/cr960385x
12. [12]
  Z. Liu, S.K.M. Nalluri, J.F. Stoddart, Chem. Soc. Rev. 46 (2017) 2459–2478. doi: 10.1039/C7CS00185A
13. [13]
  J.L. Liu, M. Sun, Y.H. Shi, et al., J. Incl. Phenom. Macro. Chem. 102 (2022) 201–233. doi: 10.1007/s10847-021-01119-w
14. [14]
  R.E. Brewster, S.B. Shuker, J. Am. Chem. Soc. 124 (2002) 7902–7903. doi: 10.1021/ja026084o7/s10847-021-01119-w
15. [15]
  L. Adriaenssensa, P. Ballester, Chem. Soc. Rev. 42 (2013) 3261–3277. doi: 10.1039/c2cs35461f
16. [16]
  G. Aragay, P. Ballester, H-Bonding Assembly of Macrocycles, Reference Module in Chemistry, Molecular Sciences and Chemical Engineering, Elsevier, 2016.
17. [17]
  S. Merget, L. Catti, S. Zev, D.T. Major, N. Trapp, Chem. Eur. J. 27 (2021) 4447–4453. doi: 10.1002/chem.202005046
18. [18]
  F. Corbellini, R. Fiammengo, P. Timmerman, et al., J. Am. Chem. Soc. 124 (2002) 6569–6575. doi: 10.1021/ja012058z
19. [19]
  R. Zadmard, T. Schrader, T. Grawe, A. Kraft, Org. Lett. 4 (2002) 1687–1690. doi: 10.1021/ol0257631
20. [20]
  S.M. Birosa, J. Rebek Jr., Chem. Soc. Rev. 36 (2007) 93–104. doi: 10.1039/B508530F
21. [21]
  M.A. Beatty, F. Hof, Chem. Soc. Rev. 50 (2021) 4812–4832. doi: 10.1039/D0CS00495B
22. [22]
  M. Johnston, M.J. Latter, Supramol. Chem. 17 (2005) 595–607. doi: 10.1080/10610270500128400
23. [23]
  S.J. Dalgarno, N.P. Power, J.L. Atwood, Coord. Chem. Rev. 252 (2008) 825–841. doi: 10.1016/j.ccr.2007.10.010
24. [24]
  P.P. Cholewa, S.J. Dalgarno, CrystEngComm 16 (2014) 3655–3666. doi: 10.1039/c3ce42169d
25. [25]
  Y. Voloshin, I. Belaya, R. Krämer, The Encapsulation Phenomenon: Synthesis, Reactivity and Applications of Caged Ions and Molecules, Springer International Publishing, Switzerland, 2016.
26. [26]
  M. Morie, R. Sekiya, T. Haino, Chem. Asian J. 16 (2021) 49–55. doi: 10.1002/asia.202001154
27. [27]
  K. Sikligar, S.P. Kelley, L. Shao, G.A. Baker, J.L. Atwood, Cryst. Growth Des. 21 (2021) 1891–1897. doi: 10.1021/acs.cgd.0c01482
28. [28]
  L. Shao, X. Hu, K. Sikligar, G.A. Baker, J.L. Atwood, Acc. Chem. Res. 54 (2021) 3191–3203. doi: 10.1021/acs.accounts.1c00275
29. [29]
  X. Fan, L. Yuan, J. Zhang, L. Zhang, Chin. Chem. Lett. 32 (2021) 2415–2418. doi: 10.1016/j.cclet.2021.01.010
30. [30]
  H. Mansikkamäki, M. Nissinena, K. Rissanen, Chem. Commun. 17 (2002) 1902–1903.
31. [31]
  J.L. Atwood, A. Szumna, J. Supramol. Chem. 2 (2002) 479–482. doi: 10.1016/S1472-7862(03)00068-6
32. [32]
  H. Mansikkamäki, M. Nissinen, C.A. Schalleyb, K. Rissanen, New J. Chem. 27 (2003) 88–97. doi: 10.1039/b207875a
33. [33]
  H. Mansikkamäki, M. Nissinen, K. Rissanen, CrystEngComm 7 (2005) 519–526. doi: 10.1039/b508191b
34. [34]
  A. Aman, M. Luostarinen, K. Rissanen, M. Nissinen, New J. Chem. 31 (2007) 169–177. doi: 10.1039/B609117B
35. [35]
  C. Gaeta, C. Talotta, P.D. Sala, et al., J. Org. Chem. 79 (2014) 3704–3708. doi: 10.1021/jo500422u
36. [36]
  M. Chwastek, P. Cmoch, A. Szumna, Angew. Chem. Int. Ed. 60 (2021) 4540–4544. doi: 10.1002/anie.202013105
37. [37]
  M. Chwastek, P. Cmoch, A. Szumna, J. Am. Chem. Soc. 144 (2022) 5350–5358. doi: 10.1021/jacs.1c1179313105
38. [38]
  E.R. Abdurakhmanova, P. Cmoch, A. Szumna, Org. Biomol. Chem. 20 (2022) 5095–5103. doi: 10.1039/D2OB00880G
39. [39]
  S.K. Menon, M. Sewani, Rev. Anal. Chem. 25 (2006) 49–82.
40. [40]
  P. Hu, H. Cui, W. Huang, W. Guo, Chem. Asian J. 15 (2020) 2952–2959. doi: 10.1002/asia.202000791
41. [41]
  S. Niu, L.L. Mao, H. Xiao, et al., Chin. Chem. Lett. 33 (2022) 1970–1974. doi: 10.1016/j.cclet.2021.09.090
42. [42]
  S. Fan, C.Y. He, X. Zhang, Chem. Commun. 46 (2010) 4926–4928. doi: 10.1039/c0cc00598c
43. [43]
  C.D. Gutsche, L.J. Bauer, J. Am. Chem. Soc. 107 (1985) 6052–6059. doi: 10.1021/ja00307a038
44. [44]
  R. Rathore, S.V. Lindeman, K.S. Rao, D. Sun, J.K. Kochi, Angew. Chem. Int. Ed. 39 (2000) 2123–2127. doi: 10.1002/1521-3773(20000616)39:12<2123::AID-ANIE2123>3.0.CO;2-4
45. [45]
  D. Neuhaus, M.P. Williamson, The Nuclear Overhauser Effect in Structural and Conformational Analysis 2nd. ed., Wiley-VCH, New York, 2000.
46. [46]
  P.S. Pregosin, P.G.A. Kumar, I. Fernández, Chem. Rev. 105 (2005) 2977–2998. doi: 10.1021/cr0406716
47. [47]
  A. Macchioni, G. Ciancaleoni, C. Zuccaccia, D. Zuccaccia, Chem. Soc. Rev. 37 (2008) 479–489. doi: 10.1039/B615067P
48. [48]
  V. Balamurugan, J. Mukherjee, M.S. Hundal, R. Mukherjee, Struct. Chem. 18 (2007) 133–144. doi: 10.1007/s11224-006-9113-2
49. [49]
  Y.R. Zhong, M.L. Cao, H.J. Mo, B.H. Ye, Cryst. Growth Des. 8 (2008) 2282–2290. doi: 10.1021/cg700980v
50. [50]
  J. Zhao, D. Yang, X.J. Yang, B. Wu, Coord. Chem. Rev. 378 (2019) 415–444. doi: 10.1016/j.ccr.2018.01.002
51. [51]
  S.A. Boer, E.M. Foyle, C.M. Thomas, N.G. White, Chem. Soc. Rev. 48 (2019) 2596–2614. doi: 10.1039/C8CS00828K
52. [52]
  U. Manna, G. Das, Coord. Chem. Rev. 427 (2021) 213547. doi: 10.1016/j.ccr.2020.213547
53. [53]
  L.M. Salonen, M. Ellermann, F. Diederich, Angew. Chem. Int. Ed. 50 (2011) 4808–4842. doi: 10.1002/anie.201007560
54. [54]
  C.R. Martinez, B.L. Iverson, Chem. Sci. 3 (2012) 2191–2201. doi: 10.1039/c2sc20045g
55. [55]
  W. Caminati, S. Melandri, A. Maris, P. Ottaviani, Angew. Chem. Int. Ed. 45 (2006) 2438–2442. doi: 10.1002/anie.200504486
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