Citation: Jia Qiong, Du Xusheng, Wang Chunyu, Meguellati Kamel. A one-pot synthesis of a self-included bisester-functionalized copillar[5]arene[J]. Chinese Chemical Letters, ;2019, 30(3): 721-724. doi: 10.1016/j.cclet.2018.12.015 shu

A one-pot synthesis of a self-included bisester-functionalized copillar[5]arene

a.
International Joint Research Laboratory of Nano-Micro Architecture Chemistry (NMAC), College of Chemistry, Jilin University, Changchun 130012, China
b.
State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, China

kamel_m@jlu.edu.cn

Received Date: 19 October 2018
Revised Date: 4 December 2018
Accepted Date: 12 December 2018
Available Online: 13 March 2018

Figures(4)

We report here a one-pot synthetic method for the synthesis of a bisester-functionalized copillar[5]arene (BECP5A) with yield up to 20%. The properties of BECP5A in solution and in solid state were deeply investigated with the aid of 1D and 2D NMR spectra and X-ray diffraction, showing that this molecule has a fully self-included conformation in chloroform and partial self-inclusion in DMSO, and the compound has an asymmetrical structure with only one self-included side in the cavity of pillar[5]arene in the solid state. This compound will be used as the precursor of complex systems such as polymers and mechanically interlocked molecules.
- Pillar[5]arene,
- One-pot reaction,
- Ester group,
- Supramolecular chemistry,
- X-ray crystal structure
1. [1]
  T. Ogoshi, S. Kanai, S. Fujinami, T.-a. Yamagishi, Y. Nakamoto, J. Am. Chem. Soc. 130(2008) 5022-5023. doi: 10.1021/ja711260m
2. [2]
  P.J. Cragg, K. Sharma, Chem. Soc. Rev. 41(2012) 597-607. doi: 10.1039/C1CS15164A
3. [3]
  T. Ogoshi, T.-a. Yamagishi, Y. Nakamoto, Chem. Rev. 116(2016) 7937-8002. doi: 10.1021/acs.chemrev.5b00765
4. [4]
  M. Xue, Y. Yang, X. Chi, Z. Zhang, F. Huang, Acc. Chem. Res. 45(2012) 1294-1308. doi: 10.1021/ar2003418
5. [5]
  T. Kakuta, T.-a. Yamagishi, T. Ogoshi, Acc. Chem. Res. 51(2018) 1656-1666. doi: 10.1021/acs.accounts.8b00157
6. [6]
  X.B. Hu, Z. Chen, G. Tang, J.L. Hou, Z.T. Li, J. Am. Chem. Soc. 134(2012) 8384-8387. doi: 10.1021/ja302292c
7. [7]
  D.R. Cao, Y.H. Kou, J.Q. Liang, et al., Angew. Chem. 121(2009) 9901-9903. doi: 10.1002/ange.200904765
8. [8]
  J.F. Stoddart, N.L. Strutt, R.S. Forgan, J.M. Spruell, Y.Y. Botros, J. Am. Chem. Soc. 133(2011) 5668-5671. doi: 10.1021/ja111418j
9. [9]
  Z.B. Zhang, B.Y. Xia, C.Y. Han, Y.H. Yu, F.H. Huang, Org. Lett. 12(2010) 3285-3287. doi: 10.1021/ol100883k
10. [10]
  C.J. Li, K. Han, J. Li, et al., Org. Lett. 14(2012) 42-45. doi: 10.1021/ol2027834
11. [11]
  J.R. Wu, C.Y. Wang, Y.C. Tao, et al., Eur. J. Org. Chem. 2018(2018) 1321-1325. doi: 10.1002/ejoc.v2018.11
12. [12]
  J.R. Wu, A.U. Mu, B. Li, et al., Angew. Chem. Int. Ed. 57(2018) 9853-9858. doi: 10.1002/anie.201805980
13. [13]
  X.B. Hu, L. Chen, W. Si, Y. Yu, J.L. Hou, Chem. Commun. 47(2011) 4694-4696. doi: 10.1039/c1cc10633c
14. [14]
  Y.J. Ma, X.F. Ji, F. Xiang, et al., Chem. Commun. 47(2011) 12340-12342. doi: 10.1039/c1cc15660h
15. [15]
  T. Ogoshi, J. Incl. Phenom. Macrocycl. Chem. 72(2012) 247-262. doi: 10.1007/s10847-011-0027-2
16. [16]
  F.H. Huang, Z.B. Zhang, Y. Luo, et al., Angew. Chem. 123(2011) 1433-1437. doi: 10.1002/ange.v123.6
17. [17]
  Z.B. Zhang, G.C. Yu, C.Y. Han, et al., Org. Lett. 13(2011) 4818-4821. doi: 10.1021/ol2018938
18. [18]
  X.Y. Shu, S.H. Chen, J. Li, et al., Chem. Commun. 48(2012) 2967-2969. doi: 10.1039/c2cc00153e
19. [19]
  J.H. Bi, X.F. Zeng, D.M. Tian, H.B. Li, Org. Lett. 18(2016) 1092-1095. doi: 10.1021/acs.orglett.6b00097
20. [20]
  Y.C. Chang, K. Yang, P. Wei, et al., Angew. Chem. 53(2014) 13126-13130. doi: 10.1002/anie.201407272
21. [21]
  P. Wang, Y. Yao, M. Xue, Chem. Commun. 50(2014) 5064-5067. doi: 10.1039/C4CC01403K
22. [22]
  X. Wu, Y. Li, C. Lin, X.Y. Hu, L.Y. Wang, Chem. Commun. 51(2015) 6832-6835. doi: 10.1039/C5CC01393C
23. [23]
  Q.F. Yao, B.Z. Lv, C.D. Ji, Y. Cai, M.Z. Yin, ACS Appl. Mater. Interfaces 9(2017) 36320-36326. doi: 10.1021/acsami.7b12063
24. [24]
  G.C. Yu, C.Y. Han, Z.B. Zhang, et al., J. Am. Chem. Soc. 134(2012) 8711-8717. doi: 10.1021/ja302998q
25. [25]
  F. Zhang, J.K. Ma, Y. Sun, et al., Chem. Sci. 7(2016) 3227-3233. doi: 10.1039/C5SC04726A
26. [26]
  H.T.Z. Zhu, L.Q. Shangguan, B.B. Shi, G.C. Yu, F.H. Huang, Mater. Chem. Front. 2(2018) 2152-2174. doi: 10.1039/C8QM00314A
27. [27]
  J.F. Chen, Q. Lin, Y.M. Zhang, H. Yao, T.B. Wei, Chem. Commun. 53(2017) 13296-13311. doi: 10.1039/C7CC08365C
28. [28]
  X. Li, Z. Li, Y.W. Yang, Adv. Mater. 30(2018) 1800177. doi: 10.1002/adma.v30.20
29. [29]
  X.Y. Jin, N. Song, X. Wang, et al., Sci. Rep. 8(2018) 4035. doi: 10.1038/s41598-018-22446-y
30. [30]
  T. Ogoshi, D. Yamafuji, T.-a. Yamagishi, A.M. Brouwer, Chem. Commun. 49(2013) 5468-5470. doi: 10.1039/c3cc42612b
31. [31]
  X. Wu, M.F. Ni, W. Xia, X.Y. Hu, L.Y. Wang, Org. Chem. Front. 2(2015) 1013-1017. doi: 10.1039/C5QO00159E
32. [32]
  X.Z. Yan, P.F. Wei, Z.T. Li, et al., Chem. Commun. 49(2013) 2512-2514. doi: 10.1039/c3cc40474a
33. [33]
  X.Z. Yan, B. Zheng, F.H. Huang, Polym. Chem. 4(2013) 2395-2399. doi: 10.1039/c3py00060e
34. [34]
  C.J. Li, X.Y. Shu, J. Li, et al., Org. Lett. 14(2012) 4126-4129. doi: 10.1021/ol301757q
35. [35]
  X. Wu, Y. Yu, L. Gao, X.Y. Hu, L.Y. Wang, Org. Chem. Front. 3(2016) 966-970. doi: 10.1039/C6QO00197A
36. [36]
  H.C. Zhang, Y.L. Zhao, Chem. Eur. J. 19(2013) 16862-16879. doi: 10.1002/chem.v19.50
37. [37]
  L.Y. Gao, B. Zheng, W. Chen, C.A. Schalley, Chem. Commun. 51(2015) 14901-14904. doi: 10.1039/C5CC06207A
38. [38]
  K. Yang, Y.C. Chang, J. Wen, et al., Chem. Mater. 28(2016) 1990-1993. doi: 10.1021/acs.chemmater.6b00696
39. [39]
  Y.J. Zhou, K.C. Jie, F.H. Huang, Chem. Commun. 53(2017) 8364-8367. doi: 10.1039/C7CC04779G
40. [40]
  X.Y. Shu, K.D. Xu, D.B. Hou, C.J. Li, Isr. J. Chem. 58(2018) 1194-1204. doi: 10.1002/ijch.201800013
41. [41]
  J.F. Chen, X. Liu, J.F. Ma, et al., Soft Matter 13(2017) 5214-5218. doi: 10.1039/C7SM01118K
42. [42]
  N. Song, T. Kakuta, T.-a. Yamagishi, Y.W. Yang, T. Ogoshi, Chem 4(2018) 2029-2053. doi: 10.1016/j.chempr.2018.05.015
43. [43]
  T. Ogoshi, M. Hashizume, T.-a. Yamagishi, Y. Nakamoto, Chem. Commun. 46(2010) 3708-3710. doi: 10.1039/c0cc00348d
44. [44]
  W. Si, L. Chen, X.B. Hu, et al., Angew. Chem. 123(2011) 12772-12776. doi: 10.1002/ange.201106857
45. [45]
  H. Li, D.X. Chen, Y.L. Sun, et al., J. Am. Chem. Soc. 135(2013) 1570-1576. doi: 10.1021/ja3115168
46. [46]
  Y. Chen, D. Cao, L. Wang, et al., Chem. Eur. J. 19(2013) 7064-7070. doi: 10.1002/chem.v19.22
47. [47]
  X.S. Du, C.Y. Wang, Q. Jia, et al., Chem. Commun. 53(2017) 5326-5329. doi: 10.1039/C7CC02364B
48. [48]
  Y. Han, G.F. Huo, J. Sun, et al., Sci. Rep. 6(2016) 28748. doi: 10.1038/srep28748
49. [49]
  Z.Y. Li, Y. Zhang, C.W. Zhang, et al., J. Am. Chem. Soc. 136(2014) 8577-8589. doi: 10.1021/ja413047r
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