Citation: Zhang Runmiao, Wang Chenwei, Sun Jing, Yan Chaoguo, Yao Yong. Design and Construction of Pillar[5]arene-Based Bis-[1]rotaxane[J]. Chinese Journal of Organic Chemistry, ;2019, 39(12): 3483-3489. doi: 10.6023/cjoc201906006 shu

Design and Construction of Pillar[5]arene-Based Bis-[1]rotaxane

Zhang Runmiao ^a,b ,
Wang Chenwei ^b ,
Sun Jing ^a ,
Yan Chaoguo ^a,, ,
Yao Yong ^b,,

a.
College of Chemistry and Chemistry Engineering, Yangzhou University, Yangzhou, Jiangsu 225000
b.
College of Chemistry and Chemistry Engineering, Nantong University, Nantong, Jiangsu 226019

Corresponding author: Yan Chaoguo, cgyan@yzu.edu.cn Yao Yong, yaoyong1986@ntu.edu.cn
Received Date: 6 June 2019
Revised Date: 30 July 2019
Available Online: 7 December 2019
Fund Project: the National Natural Science Foundation of China 21871227the Natural Science Foundation of Jiangsu Province BK20180942the Natural Science Foundation of Nantong University for High-Level Talent 03083004the National Natural Science Foundation of China 21801139the Large Instruments Open Foudation of Nantong University KFJN1814Project supported by the National Natural Science Foundation of China (Nos. 21801139, 21871227), the Natural Science Foundation of Jiangsu Province (No. BK20180942), the Natural Science Foundation of Nantong University for High-Level Talent (No. 03083004), and the Large Instruments Open Foudation of Nantong University (No. KFJN1814)

Figures(5)

A series of pillar[5]arene monoamide derivatives with different lengths of alkylenediamine unites as the side chains on the pillar[5]arene's rim can form pseudo[1]rotaxanes. Thus, based on the construction of this intermediate of pseudo[1]rotaxane, eight pillar[5]arene-baed mechanically interlocked molecules (MIMs) of bis-[1]rotaxane were successful constructed through condensation reaction of pillar[5]arene monoamide derivative and salicylaldehyde. The newly synthesized bis-[1]rotaxane was investigated in detail by various methods, including ¹H NMR, ¹³C NMR, 2D NOESY NMR and MS analysis. It was found that this kind of MIMs has a strong recognition effect with Cu²⁺, which complexed by 1:2.
- pillar[5]arene,
- bis-[1]rotaxane,
- pseudo[1]rotaxane,
- mechanically interlocked molecules
1. [1]
  Krakowiak, K. E.; Bradshaw, J.; Zamecka-Krakowiak, D. J. Chem. Rev. 1989, 89, 929. doi: 10.1021/cr00094a008
2. [2]
  (a) Lehn, J. M. Science 1993, 260, 1762.
  (b) Chen, Y.; Sun, S.; Lu, D.; Shi, Y.; Yao, Y. Chin. Chem. Lett. 2019, 30, 27.
  (c) He, M.; Chen, L.; Jiang, B.; Tan, H.; Yang, H. Chin. Chem. Lett., 2019, 30, 131.
3. [3]
  Leininger, S.; Olenyuk, B.; Stang, P. J. Chem. Rev. 2000, 100, 853. doi: 10.1021/cr9601324
4. [4]
5. [5]
  (a) Amabilino, D. B.; Perez-Garcia, L. Chem. Soc. Rev. 2009, 38, 1562.
  (b) Ma, X.; Tian, H. Chem. Soc. Rev. 2010, 39, 70.
  (c) Forgan, R. S.; Sauvage, J. P.; Stoddart, J. F. Chem. Rev. 2011, 111, 5434.
  (d) Dongen, S. F. M. van; Cantekin, S.; Elemans, J. A. A. W.; Rowan, A. E.; Nolte, R. J. M. Chem. Soc. Rev. 2014, 43, 99.
  (e) Xue, M.; Yang, Y.; Chi, X.; Yan, X.; Huang, F. Chem. Rev. 2015, 115, 7398.
6. [6]
  (a) Cao, J.; Ma, X.; Min, M. Chem. Commun. 2014, 50, 3224.
  (b) Leigh, D. A.; Marcos, V.; Nalbantoglu, T. J. Am. Chem. Soc. 2017, 139, 7104.
  (c) Niu, Z. B.; Gibson, H. W. Chem. Rev. 2009, 109, 6024.
  (d) Raymo, F. M.; Stoddart, J. F. Chem. Rev. 1999, 99, 1643.
  (e) Balzani, V.; Gómez-López, M.; Stoddart, J. F. Acc. Chem. Res. 1998, 31, 405.
  (f) Harada, A.; Takashima, Y.; Yamaguchi, H. Chem. Soc. Rev. 2009, 38, 875.
7. [7]
  Ashton, P. R.; Goodnow, T. T.; Kaifer, A. E. Angew. Chem. Int. Ed. 1989, 28, 1396. doi: 10.1002/anie.198913961
8. [8]
  (a) Silvi, S.; Venturi, M.; Credi, A. J. Mater. Chem. 2009, 19, 2279.
  (b) Crowley, J. D.; Goldup, S. M.; Lee, A. L.; Leigh, D. A.; McBurney, R. T. Chem. Soc. Rev. 2009, 38, 1530.
  (c) Anelli, P. L.; Spencer, N.; Stoddart, J. F. J. Am. Chem. Soc. 1991, 113, 5131.
9. [9]
  Tan, L. L.; Li, H.; Qiu, Y. C. Chem. Sci. 2015, 6, 1640. doi: 10.1039/C4SC03749A
10. [10]
  (a) Mandal, A. K.; Gangopadhyay, M.; Das, A. Chem. Soc. Rev. 2015, 44, 663.
  (b) Qu, D. H.; Wang, Q. C.; Zhang, Q. W.; Ma, X.; Tian, H. Chem. Rev. 2015, 115, 7543.
11. [11]
  Wang, Y.; Tian, Y.; Chen, Y. Z. Chem. Commun. 2018, 54, 7991. doi: 10.1039/C8CC04542A
12. [12]
  Ma, L.; Wang, S.; Li, C. Chem. Commun. 2018, 54, 2405. doi: 10.1039/C8CC00213D
13. [13]
  Wu, D.; Li, Y.; Shen, J. Chem. Commun. 2018, 54, 8198. doi: 10.1039/C8CC04334E
14. [14]
  (a) Liu, Y.; Chipot, C.; Shao, X.; Cai, W. J. Phys. Chem. C 2014, 118, 19380.
  (b) Li, H.; Li, X.; Ågren, H.; Qu, D. H. Org. Lett. 2014, 16, 4940.
  (c) Cao, J.; Ma, X.; Min, M.; Cao, T.; Wu, S.; Tian, H. Chem. Commun. 2014, 50, 3224.
  (d) Li, H.; Zhang, J. N.; Zhou, W.; Zhang, H.; Zhang, Q.; Qu, D. H.; Tian, H. Org. Lett. 2013, 15, 3070.
  (e) Yamauchi, K.; Miyawaki, A.; Takashima, Y.; Yamaguchi, H.; Harada, A. Org. Lett. 2010, 12, 1284.
  (f) Miyawaki, A.; Kuad, P.; Takashima, Y.; Yamaguchi, H.; Harada, A. J. Am. Chem. Soc. 2008, 130, 17062.
  (g) Liu, Y.; Yang, Z. X.; Chen, Y. J. Org. Chem. 2008, 73, 5298.
  (h) Franchi, P.; Fanì, M.; Mezzina, E.; Lucarini, M. Org. Lett. 2008, 10, 190.
  (i) Hiratani, K.; Kaneyama, M.; Nagawa, Y.; Koyama, E.; Kanesato, M. J. Am. Chem. Soc. 2004, 126, 13568.
15. [15]
16. [16]
17. [17]
18. [18]
  (a) Zhang, Z.; Xia, B.; Han, C.; Yu, Y.; Huang, F. Org. Lett. 2010, 12, 3285.
  (b) Li, C.; Zhao, L.; Li, J.; Ding, X.; Chen, S.; Zhang, Q.; Yu, Y.; Jia, X. Chem. Commun. 2010, 46, 9016.
  (c) Zhang, H.; Liu, Z.; Liu, F.; Hao, A. Chin. J. Org. Chem. 2012, 32, 219.
  (d) Zhang, H.; Zhao, Y. Chem. Eur. J. 2013, 19, 16862.
  (e) Wang, Y.; Xu, J. F.; Chen, Y. Z.; Niu, L. Y.; Wu, L. Z.; Tung, C. H.; Yang, Q. Z. Chem. Commun. 2014, 50, 7001.
  (f) Wang, Y.; Ping, G.; Li, C. Chem. Commun. 2016, 52, 9858.
  (g) Jiang, S.; Han Y.; Sun, J.; Yan, C. G. Tetrahedron 2017, 73, 5107.
  (h) Sun, Y.; Fu, W.; Chen, C.; Wang, J.; Yao, Y. Chem. Commun. 2017, 53, 3725.
19. [19]
  Ogoshi, T.; Demachi, K.; Kitajima, K.; Yamagishi, T. A. Chem. Commun. 2011, 47, 7164. doi: 10.1039/c1cc12333e
20. [20]
  Chen, Y.; Cao, D.; Wang, L.; He, M.; Zhou, L.; Schollmeyer, D.; Meier, H. Chem. Eur. J. 2013, 19, 7064. doi: 10.1002/chem.201204628
21. [21]
  Xia, B. Y.; Xue, M. Chem. Commun. 2014, 50, 1021. doi: 10.1039/C3CC48014C
22. [22]
  Cheng, M.; Wang, Q.; Cao, Y. Tetrahedron Lett. 2016, 57, 4133. doi: 10.1016/j.tetlet.2016.07.038
23. [23]
  Sun, C. L.; Xu, J. F.; Chen, Y. Z. Chin. Chem. Lett. 2015, 26, 843. doi: 10.1016/j.cclet.2015.05.030
24. [24]
  Li, S. H.; Zhang, H. Y.; Xu, X.; Liu, Y. Nat. Commun. 2015, 6, 7590. doi: 10.1038/ncomms8590
25. [25]
  (a) Han, Y.; Huo, G. F.; Sun, J.; Xie, Y. J.; Yan, C. G.; Zhao, Y.; Wu, X.; Lin, C.; Wang, L.; Sci. Rep. 2016, 6, 28748.
  (b) Han, Y.; Huo, G. F.; Sun, J.; Yan, C. G.; Lu, Y.; Lin, C.; Wang, L. Supramol. Chem. 2017, 29, 547.
26. [26]
  Cheng, M.; Wang, Q.; Cao, Y.; Pan, Y.; Yang, Z.; Jiang, J.; Wang, L. Tetrahedron Lett. 2016, 57, 4133. doi: 10.1016/j.tetlet.2016.07.038
27. [27]
  Zhao, L-L.; Han, Y.; Yan, C.-G. Chin. Chem. Lett. 2019, doi: 10.1016/j.cclet.2019.04.024.
28. [28]
  Cerrada. L.; Pinol, M.; Serrano, L. J. J. Polym. Sci., Part A:Polym. Chem. 1996, 34, 2603. doi: 10.1002/(SICI)1099-0518(19960930)34:13<2603::AID-POLA6>3.0.CO;2-S
29. [29]
  (a) Huo, G. F.; Han, Y.; Sun, J. J. Incl. Phenom. Macrocycl. Chem. 2016, 86, 231.
  (b) Jiang, S.; Han, Y.; Sun, J. Tetrahedron 2017, 73, 5107.
  (c) Yin, C. B.; Han, Y.; Huo, G. F. Chin. Chem. Lett. 2017, 28, 431.
  (d) Jiang, S.; Han, Y.; Cheng, M. New J. Chem. 2018, 42, 7603.
  (e) Han, Y.; Xu, L. M.; Nie, C. Y. Beilstein J. Org. Chem. 2018, 14, 1660.
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