Citation: Xue Zhang, Xiaoyang Wang, Bin Wang, Zhi-Jun Ding, Chunju Li. Carbon-carbon double bond in pillar[5]arene cavity: Selective binding of cis/trans-olefin isomers[J]. Chinese Chemical Letters, ;2020, 31(12): 3230-3232. doi: 10.1016/j.cclet.2020.02.037 shu

Carbon-carbon double bond in pillar[5]arene cavity: Selective binding of cis/trans-olefin isomers

Xue Zhang ^{a, 1} ,
Xiaoyang Wang ^{b, 1} ,
Bin Wang ^a ,
Zhi-Jun Ding ^{c, *,} ,
Chunju Li ^{a, b, *,}

a.
Key Laboratory of Inorganic-Organic Hybrid Functional Material Chemistry, Ministry of Education, Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, China
b.
Center for Supramolecular Chemistry and Catalysis and Department of Chemistry, Shanghai University, Shanghai 200444, China
c.
State Key Laboratory of NBC Protection for Civilian, Beijing 102205, China

^**

zhijunding01@gmail.com

cjli@shu.edu.cn

Received Date: 6 January 2020
Revised Date: 11 February 2020
Accepted Date: 20 February 2020
Available Online: 20 February 2020

Figures(4)

The binding behavior of pillar[5]arenes (P5As) towards a series of olefin guests ((E)-1, 4-dichlorobut-2-ene (1E), (Z)-1, 4-dichlorobut-2-ene (1Z), (E)-but-2-ene-1, 4-diol (2E), and (Z)-but-2-ene-1, 4-diol (2Z), as well as an alkyne derivative 1, 4-dichlorobut-2-yne (3)) have been studied in organic solution. P5As exhibit considerable selectivities for the trans-olefin isomers (1E and 2E) over their cis-isomers (1Z and 2Z). The cis/trans-selective interactions hold the potential of utilizing P5As to separate olefin isomers.
- Pillararenes,
- Molecular recognition,
- Supramolecular chemistry,
- Olefin,
- Isomers
1. [1]
  T. Ogoshi, S. Kanai, S. Fujinami, T. Yamagishi, Y. Nakamoto, J. Am. Chem. Soc.130(2008) 5022-5023. doi: 10.1021/ja711260m
2. [2]
  M. Zhang, P.P. Zhu, P. Xin, et al., Angew. Chemie. 129(2017) 3045-3049. doi: 10.1002/ange.201612093
3. [3]
  K. Yang, Y. Pei, J. Wen, Z. Pei, Chem. Commun. (2016) 9316-9326.
4. [4]
  M. Ni, N. Zhang, W. Xia, et al., J. Am. Chem. Soc. 138(2016) 6643-6649. doi: 10.1021/jacs.6b03296
5. [5]
  N. Song, T. Kakuta, T. Yamagishi, Y.W. Yang, T. Ogoshi, Chem 4(2018) 2029-2053. doi: 10.1016/j.chempr.2018.05.015
6. [6]
  H. Zhang, Z. Liu, Y. Zhao, Chem. Soc. Rev. 47(2018) 5491-5528. doi: 10.1039/C8CS00037A
7. [7]
  T. Xiao, L. Zhou, X.Q. Sun, et al., Chin. Chem. Lett. 31(2020) 1-9. doi: 10.1016/j.cclet.2019.05.011
8. [8]
  Y. Han, C.Y. Nie, S. Jiang, J. Sun, C.G. Yan, Chin. Chem. Lett. 31(2020) 725-728. doi: 10.1016/j.cclet.2019.09.014
9. [9]
  Z. Liu, J. Wu, C. Wang, et al., Chin. Chem. Lett. 30(2019) 2299-2303. doi: 10.1016/j.cclet.2019.10.023
10. [10]
  K. Jie, Y. Zhou, E. Li, F. Huang, Acc. Chem. Res. 51(2018) 2064-2072. doi: 10.1021/acs.accounts.8b00255
11. [11]
  T. Xiao, L. Qi, W. Zhong, et al., Mater. Chem. Front. 3(2019) 1973-1993. doi: 10.1039/C9QM00428A
12. [12]
  T. Xiao, W. Zhong, L. Xu, et al., Org. Biomol. Chem. 17(2019) 1336-1350. doi: 10.1039/C8OB03095B
13. [13]
  T. Xiao, L. Zhou, L. Xu, et al., Chin. Chem. Lett. 30(2019) 271-276. doi: 10.1016/j.cclet.2018.05.039
14. [14]
  C. Ke, N.L. Strutt, H. Li, et al., J. Am. Chem. Soc. 135(2013) 17019-17030. doi: 10.1021/ja407229h
15. [15]
  Z. Zhang, Y. Luo, J. Chen, et al., Angew. Chem. Int. Ed. 50(2011) 1397-1401. doi: 10.1002/anie.201006693
16. [16]
  T. Ogoshi, T. Yamagishi, Y. Nakamoto, Chem. Rev. 116(2016) 7937-8002. doi: 10.1021/acs.chemrev.5b00765
17. [17]
  B. Li, Z. Meng, Q. Li, et al., Chem. Sci. 8(2017) 4458-4464. doi: 10.1039/C7SC01438D
18. [18]
  K. Jie, Y. Zhou, E. Li, et al., J. Am. Chem. Soc. 140(2018) 3190-3193. doi: 10.1021/jacs.7b13156
19. [19]
  J. Chen, H. Ni, Z. Meng, et al., Nat. Commun. 10(2019) 3546. doi: 10.1038/s41467-019-11553-7
20. [20]
  X.Q. Wang, W. Wang, W.J. Li, et al., Nat. Commun. 9(2018) 3190. doi: 10.1038/s41467-018-05670-y
21. [21]
  D. Cao, Y. Kou, J. Liang, et al., Angew. Chem. Int. Ed. 48(2009) 9721-9723. doi: 10.1002/anie.200904765
22. [22]
  Q. Hao, Y. Chen, Z. Huang, et al., ACS Appl. Mater. Interfaces 10(2018) 5365-5372. doi: 10.1021/acsami.7b19784
23. [23]
  X. Shu, J. Fan, J. Li, et al., Org. Biomol. Chem. 10(2012) 3393-3397. doi: 10.1039/c2ob25251a
24. [24]
  Y. Wang, G. Ping, C. Li, Chem. Commun. 52(2016) 9858-9872. doi: 10.1039/C6CC03999E
25. [25]
  C. Li, L. Zhao, J. Li, et al., Chem. Commun. 46(2010) 9016-9018. doi: 10.1039/c0cc03575k
26. [26]
  C. Li, S. Chen, J. Li, et al., Chem. Commun. 47(2011) 11294-11296. doi: 10.1039/c1cc14829j
27. [27]
  X. Shu, S. Chen, J. Li, et al., Chem. Commun. 48(2012) 2967-2969. doi: 10.1039/c2cc00153e
28. [28]
  C. Li, K. Han, J. Li, et al., Org. Lett. 14(2012) 42-45. doi: 10.1021/ol2027834
29. [29]
  C. Li, K. Han, J. Li, et al., Chem. Eur. J. 19(2013) 11892-11897. doi: 10.1002/chem.201301022
30. [30]
  X. Wang, K. Han, J. Li, X. Jia, C. Li, Polym. Chem. 4(2013) 3998-4003. doi: 10.1039/c3py00462g
31. [31]
  Y. Wang, K. Xu, B. Li, et al., Angew. Chem. Int. Ed. 58(2019) 10281-10284. doi: 10.1002/anie.201905563
32. [32]
  Y. Zhou, K. Jie, R. Zhao, F. Huang, J. Am. Chem. Soc. 141(2019) 11847-11851. doi: 10.1021/jacs.9b06188
33. [33]
  H. Chen, J. Fan, X. Hu, et al., Chem. Sci. 6(2015) 197-202. doi: 10.1039/C4SC02422B
34. [34]
  B. Li, B. Wang, X. Huang, et al., Angew. Chem. Int. Ed. 58(2019) 3885-3889. doi: 10.1002/anie.201813972
35. [35]
  K. Xu, Z.Y. Zhang, C. Yu, et al., Angew. Chem. Int. Ed. 59(2020) 7214-7218. doi: 10.1002/anie.202000909
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