Citation: Wanqian Lv, Yunyi Song, Xinyuan Lv, Jun Yuan, Kelong Zhu. Synthesis, structure, and host-guest chemistry of a pair of isomeric selenanthrene-bridged molecular cages[J]. Chinese Chemical Letters, ;2023, 34(11): 108179. doi: 10.1016/j.cclet.2023.108179 shu

Synthesis, structure, and host-guest chemistry of a pair of isomeric selenanthrene-bridged molecular cages

Wanqian Lv ^a ,
Yunyi Song ^a ,
Xinyuan Lv ^a ,
Jun Yuan ^{b, *,} ,
Kelong Zhu ^{a, *,}

a.
School of Chemistry, Sun Yat-sen University, Guangzhou 510275, China
b.
School of Innovation and Entrepreneurship, Shaoguan University, Shaoguan 512005, China

^☆

yuanj9@mail2.sysu.edu.cn

zhukelong@mail.sysu.edu.cn

Received Date: 26 November 2022
Revised Date: 15 January 2023
Accepted Date: 29 January 2023
Available Online: 1 February 2023

Figures(8)

A pair of selenanthrene-bridged molecular cages have been constructed through a one-step cyclization reaction of a tetrakis(iodo) crown ether with selenium powder. The tubular belt-shaped cage has an intrinsic cavity which can adaptively transform to accommodate electron-deficient guests forming [2]pseudorotaxane complexes. The other product was determined to be an isomeric cage featuring a Möbius strip structure, which exhibits slower twist-migration dynamics than its thianthrene counterpart. The success of using selenanthrene as joints enables an alternative way to structural design and property regulation of molecular cages.
- Selenanthrene,
- Crown ether,
- Molecular cage,
- Möbius strip,
- Host-guest chemistry
1. [1]
  Q.H. Guo, Y. Qiu, M.X. Wang, et al., Nat. Chem. 13 (2021) 402–419. doi: 10.1038/s41557-021-00671-9
2. [2]
  S. Lei, H. Cong, Chin. Chem. Lett. 33 (2022) 1493–1496. doi: 10.1016/j.cclet.2021.08.068
3. [3]
  H. Feng, Y. Chen, R. Wang, et al., Chin. Chem. Lett. 34 (2023) 108038. doi: 10.1016/j.cclet.2022.108038
4. [4]
  D. Eisenberg, R. Shenhar, M. Rabinovitz, Chem. Soc. Rev. 39 (2010) 2879–2890. doi: 10.1039/b904087k
5. [5]
  L. Zhu, W. Zeng, M. Li, et al., Chin. Chem. Lett. 33 (2022) 229–233. doi: 10.1016/j.cclet.2021.06.003
6. [6]
  G. Huang, W. Liu, A. Valkonen, et al., Chin. Chem. Lett. 29 (2018) 91–94. doi: 10.1016/j.cclet.2017.07.005
7. [7]
  Y. Han, Z. Meng, Y.X. Ma, et al., Acc. Chem. Res. 47 (2014) 2026–2040. doi: 10.1021/ar5000677
8. [8]
  T. Feng, X. Li, J. Wu, et al., Chin. Chem. Lett. 31 (2022) 95–98. doi: 10.1117/12.2660054
9. [9]
  J. Pan, W. Lin, F. Bao, et al., Chin. Chem. Lett. 34 (2023) 107519. doi: 10.1016/j.cclet.2022.05.033
10. [10]
  T.H. Shi, M.X. Wang, CCS Chem. 3 (2020) 916–931.
11. [11]
  Y. He, X. Yang, M. Qi, et al., Chin. Chem. Lett. 32 (2021) 2043–2046. doi: 10.1016/j.cclet.2020.11.009
12. [12]
  Y. Xiong, C. Huang, H. Liu, et al., Chin. Chem. Lett. 32 (2021) 3522–3525. doi: 10.1016/j.cclet.2021.04.060
13. [13]
  H. Kim, Y. Kim, M. Yoon, et al., J. Am. Chem. Soc. 132 (2010) 12200–12202. doi: 10.1021/ja105211w
14. [14]
  D.W. Zhang, W.K. Wang, Z.T. Li, Chem. Rec. 15 (2015) 233–251. doi: 10.1002/tcr.201402046
15. [15]
  M.A. Majewski, Y. Hong, T. Lis, et al., Angew. Chem. Int. Ed. 55 (2016) 14072–14076. doi: 10.1002/anie.201608384
16. [16]
  R. Ning, H. Zhou, S.X. Nie, et al., Angew. Chem. Int. Ed. 59 (2020) 10894–10898. doi: 10.1002/anie.202003673
17. [17]
  D. Kauerhof, J. Niemeyer, ChemPlusChem 85 (2020) 889–899. doi: 10.1002/cplu.202000152
18. [18]
  F.E. Golling, M. Quernheim, M. Wagner, et al., Angew. Chem. Int. Ed. 53 (2014) 1525–1528. doi: 10.1002/anie.201309104
19. [19]
  S. Hitosugi, T. Yamasaki, H. Isobe, J. Am. Chem. Soc. 134 (2012) 12442–12445. doi: 10.1021/ja305723j
20. [20]
  R. Herges, Chem. Rev. 106 (2006) 4820–4842. doi: 10.1021/cr0505425
21. [21]
  S. Nishigaki, Y. Shibata, A. Nakajima, et al., J. Am. Chem. Soc. 141 (2019) 14955–14960. doi: 10.1021/jacs.9b06197
22. [22]
  Y. Segawa, T. Watanabe, K. Yamanoue, et al., Nat. Synth. 1 (2022) 535–541. doi: 10.1038/s44160-022-00075-8
23. [23]
  B. Yao, X. Liu, T. Guo, et al., Org. Chem. Front. 9 (2022) 4171–4177. doi: 10.1039/d2qo00829g
24. [24]
  D.M. Walba, R.M. Richards, R.C. Haltiwanger, J. Am. Chem. Soc. 104 (1982) 3219–3221. doi: 10.1021/ja00375a051
25. [25]
  J.F. Ayme, J.E. Beves, C.J. Campbell, et al., Chem. Soc. Rev. 42 (2013) 1700–1712. doi: 10.1039/C2CS35229J
26. [26]
  S. Wang, J. Yuan, J. Xie, et al., Angew. Chem. Int. Ed. 60 (2021) 18443–18447. doi: 10.1002/anie.202104054
27. [27]
  J. Xie, X. Li, S. Wang, et al., Nat. Commun. 11 (2020) 3348. doi: 10.1038/s41467-020-17134-3
28. [28]
  J. Xie, X. Li, Z. Du, et al., CCS Chem. 5 (2023) 958–970. doi: 10.31635/ccschem.022.202202019
29. [29]
  J. Yuan, W. Lv, A. Li, et al., Chem. Commun. 57 (2021) 12848–12851. doi: 10.1039/d1cc05581j
30. [30]
  J. Yuan, Y. Song, X. Li, et al., Org. Lett. 23 (2021) 9554–9558. doi: 10.1021/acs.orglett.1c03781
31. [31]
  S. Kim, Y. Kwon, J.P. Lee, et al., J. Mol. Struct. 655 (2003) 451–458. doi: 10.1016/S0022-2860(03)00326-0
32. [32]
  M.F. Peintinger, J. Beck, T. Bredow, Phys. Chem. Chem. Phys. 15 (2013) 18702–18709. doi: 10.1039/c3cp53410c
33. [33]
  A. Panda, S.C. Menon, H.B. Singh, et al., Eur. J. Inorg. Chem. (2005) 1114–1126. doi: 10.1002/ejic.200400757
34. [34]
  S. Ji, H.E. Mard, M. Smet, et al., Sci. China Chem. 60 (2017) 1191–1196. doi: 10.1007/s11426-017-9059-4
35. [35]
  J. Shang, B. Li, X. Shen, et al., J. Org. Chem. 86 (2021) 1430–1436. doi: 10.1021/acs.joc.0c02083
36. [36]
  H. Bock, A. Rauschenbach, C. Nather, et al., Phosphorus Sulfur 115 (1996) 51–83. doi: 10.1080/10426509608037954
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