Citation: Nianqiang Jiang, Yiqiang Ou, Yanpeng Zhu, Dingyong Zhong, Jiaobing Wang. Assembly of fullerenes using a highly preorganized janusarene[J]. Chinese Chemical Letters, ;2025, 36(4): 110004. doi: 10.1016/j.cclet.2024.110004 shu

Assembly of fullerenes using a highly preorganized janusarene

Nianqiang Jiang ^{a, 1} ,
Yiqiang Ou ^{a, 1} ,
Yanpeng Zhu ^{a, *,} ,
Dingyong Zhong ^b ,
Jiaobing Wang ^{a, *,}

a.
School of Chemistry, Sun Yat-sen University, Guangzhou 510006, China
b.
School of Physics and State Key Laboratory of Optoelectronic Materials and Technologies, Sun Yat-sen University, Guangzhou 510275, China

zhuyp23@mail.sysu.edu.cn

wangjb5@mail.sysu.edu.cn

Received Date: 14 March 2024
Revised Date: 8 May 2024
Accepted Date: 11 May 2024
Available Online: 12 May 2024

Figures(5)

Molecular recognition of fullerene using various host compounds is well-known in literature. But most studies focus on host-guest complexation in solution using host compounds with a single binding cavity. Herein, we report a series of highly preorganized janusarene derivatives with homoditopic binding sites. These novel janusarenes can bind and align various fullerenes such as C₆₀, C₇₀, C₈₄, and Gd@C₈₂ in a highly efficient manner. Robust shape complementary association and assembly are observed in solution, in the bulk solid state, in the liquid crystalline state, or on surface, and the assembled structures are characterized by nuclear magnetic resonance (NMR) titration, X-ray diffraction, polarized optical microscopy, and scanning tunneling microscopy.
- Janusarene,
- Conformation,
- Fullerene,
- Host,
- Assembly
1. [1]
  T. Kawase, H. Kurata, Chem. Rev. 106 (2006) 5250–5273. doi: 10.1021/cr0509657
2. [2]
  E.M. Pérez, N. Martín, Chem. Soc. Rev. 37 (2008) 1512–1519. doi: 10.1039/b802589b
3. [3]
  X. Hou, Y. Sun, L. Liu, et al., Chin. Chem. Lett. 27 (2016) 1166–1174. doi: 10.1016/j.cclet.2016.06.028
4. [4]
  R. Chen, R. Lu, P. Shi, et al., Chin. Chem. Lett. 27 (2016) 1175–1183. doi: 10.1016/j.cclet.2016.06.033
5. [5]
  X. Chang, Y. Xu, M. von Delius, Chem. Soc. Rev. 53 (2024) 47–83. doi: 10.1039/D2CS00937D
6. [6]
  M. Yanney, F.R. Fronczek, Angew. Chem. Int. Ed. 54 (2015) 11153–11156. doi: 10.1002/anie.201505327
7. [7]
  Y.M. Liu, D. Xia, B.W. Li, et al., Angew. Chem. Int. Ed. 55 (2016) 13047–13051. doi: 10.1002/anie.201606383
8. [8]
  X.S. Ke, T. Kim, V.M. Lynch, et al., J. Am. Chem. Soc. 139 (2017) 13950–13956. doi: 10.1021/jacs.7b08611
9. [9]
  Y. Yang, K. Cheng, Y. Lu, et al., Org. Lett. 20 (2018) 2138–2142. doi: 10.1021/acs.orglett.8b00306
10. [10]
  Z. Qiu, Y. Cheng, Q. Zeng, et al., J. Am. Chem. Soc. 145 (2023) 3289–3293. doi: 10.1021/jacs.2c12401
11. [11]
  M. Sawamura, K. Kawai, Y. Matsuo, et al., Nature 419 (2002) 702–705. doi: 10.1038/nature01110
12. [12]
  T. Haino, Y. Matsumoto, Y. Fukazawa, J. Am. Chem. Soc. 127 (2005) 8936–8937. doi: 10.1021/ja0524088
13. [13]
  G. Fernández, E.M. Pérez, L. Sánchez, et al., Angew. Chem. Int. Ed. 47 (2008) 1094–1097. doi: 10.1002/anie.200703049
14. [14]
  D.S. Kim, J. Chang, S. Leem, et al., J. Am. Chem. Soc. 137 (2015) 16038–16042. doi: 10.1021/jacs.5b06524
15. [15]
  Z. Sun, X. Guo, Y. Zhao, et al., Chin. Chem. Lett. 35 (2024) 109162. doi: 10.1016/j.cclet.2023.109162
16. [16]
  J.L. Segura, N. Martín, D.M. Guldi, Chem. Soc. Rev. 34 (2005) 31–47. doi: 10.1039/B402417F
17. [17]
  S.S. Babu, H. Möhwald, T. Nakanishi, Chem. Soc. Rev. 39 (2010) 4021–4035. doi: 10.1039/c000680g
18. [18]
  X. Zhang, X. Li, Chin. Chem. Lett. 25 (2014) 912–914. doi: 10.1016/j.cclet.2014.03.041
19. [19]
  T. Li, L. Fan, H. Gong, et al., Angew. Chem. Int. Ed. 56 (2017) 9473–9477. doi: 10.1002/anie.201705451
20. [20]
  Z. Yin, L. Fan, C. Lin, et al., Chin. Chem. Lett. 33 (2022) 280–282. doi: 10.1016/j.cclet.2021.06.057
21. [21]
  B.W. Smith, M. Monthioux, D.E. Luzzi, Nature 396 (1998) 323–324.
22. [22]
  M. Shirakawa, N. Fujita, S. Shinkai, J. Am. Chem. Soc. 125 (2003) 9902–9903. doi: 10.1021/ja035933k
23. [23]
  T. Yamaguchi, N. Ishii, K. Tashiro, et al., J. Am. Chem. Soc. 125 (2003) 13934–13935. doi: 10.1021/ja038178j
24. [24]
  K. Wei, J. Li, W. Zhang, et al., Chin. Chem. Lett. 35 (2024) 109055. doi: 10.1016/j.cclet.2023.109055
25. [25]
  T. Homma, K. Harano, H. Isobe, et al., J. Am. Chem. Soc. 133 (2011) 6364–6370. doi: 10.1021/ja200498g
26. [26]
  H. Isla, E.M. Pérez, N. Martín, Angew. Chem. Int. Ed. 53 (2014) 5629–5633. doi: 10.1002/anie.201402828
27. [27]
  R.C. Huber, A.S. Ferreira, R. Thompson, et al., Science 348 (2015) 1340–1343. doi: 10.1126/science.aaa6850
28. [28]
  D. Gust, J. Am. Chem. Soc. 99 (1977) 6980–6982. doi: 10.1021/ja00463a034
29. [29]
  F. Grein, J. Phys. Chem. A 106 (2002) 3823–3827. doi: 10.1021/jp0122124
30. [30]
  Y.P. Zhu, Z.M. Xia, Z.Y. Cai, et al., J. Am. Chem. Soc. 140 (2018) 4222–4226. doi: 10.1021/jacs.8b01447
31. [31]
  H. Shi, B. Xiong, Y. Chen, et al., Chin. Chem. Lett. 34 (2023) 107520. doi: 10.1016/j.cclet.2022.05.034
32. [32]
  D. Felder, B. Heinrich, D. Guillon, et al., Chem. Eur. J. 6 (2000) 3501–3507. doi: 10.1002/1521-3765(20001002)6:19<3501::AID-CHEM3501>3.0.CO;2-0
33. [33]
  M. Kimura, Y. Saito, K. Ohta, et al., J. Am. Chem. Soc. 124 (2002) 5274–5275. doi: 10.1021/ja012614p
34. [34]
  D. Felder-Flesch, D. Guillon, B. Donnio, Fullerene-containing liquid crystals, in: J.W. Goodby, P.J. Collings, T. Kato, et al. (Eds.), Handbook of Liquid Crystals, Wiley-VCH, Weinheim, 2014.
35. [35]
  M.A. Mezour, I.I. Perepichka, J. Zhu, et al., ACS Nano 8 (2014) 2214–2222. doi: 10.1021/nn405357j
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