Citation: Wang Jiao, Yao Hong, Zhou Qi, Kan Xiaotong, Fan Yanqing, Guan Xiaowen, Zhang Youming, Lin Qi, Wei Taibao. Molecule-Responsive Supramolecular Hydrogel Constructed from Pillar[5]arene Based on Host-Guest System[J]. Chinese Journal of Organic Chemistry, ;2020, 40(1): 175-180. doi: 10.6023/cjoc201907042 shu

Molecule-Responsive Supramolecular Hydrogel Constructed from Pillar[5]arene Based on Host-Guest System

Key Laboratory of Eco-environmental Polymer Materials of Gansu Province, Key Laboratory of Eco-functional Polymer Materials of the Ministry of Education, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070

Corresponding author: Yao Hong, yhxbz@126.com Wei Taibao, weitaibao@126.com
Received Date: 27 July 2019
Revised Date: 7 September 2019
Available Online: 18 January 2019
Fund Project: the National Natural Science Foundation of China 21574104the National Natural Science Foundation of China 21662031Project supported by the National Natural Science Foundation of China (Nos. 21662031, 21661028, 21574104)the National Natural Science Foundation of China 21661028

Figures(6)

The host-guest interaction was qualified as an ideal drive force to form stable inclusion complexes with macrocyclic host molecules in aqueous solution. Herein, a multi-responsive supramolecular hydrogel was constructed based on a functionalized benzimidazole derivative guest (M) with soluble pillar[5]arene as a host group. The mechanism of hydrogel formation was explored by the ¹H NMR, 2D NOESY and scanning electron microscope (SEM) in depth study. Interestingly, host-guest inclusion, the ordered "exo-wall" π-π interaction and hierarchical stacking of pillar[5]arene was indispensable to obtain the supramolecular hydrogel, which endowed the gel system with response to temperature change/chemical stimuli. Upon addition of competitive guests adiponitrile (ADN)/paraquat (PQ), pillar[5]arene-based hydrogel could be converted into sol. Herein, the organic molecules could be selectively recognized by the hydrogel.
- supramolecular hydrogel,
- soluble pillar[5]arene,
- competitive inclusion,
- molecular recognition,
- self assembly
1. [1]
  邵为, 刘昕, 王婷婷, 胡晓玉, 有机化学, 2018, 36, 1107.
2. [2]
  Sun, C. L.; Teng, K. X.; Niu, L. Y.; Chen, Y. Z.; Yang, Q. Z. J. Org. Chem. 2018, 10, 779.
3. [3]
  Yan, X.; Wang, F.; Zheng, B. Z.; Huang, F. H. Chem. Soc. Rev. 2012, 41, 6042. doi: 10.1039/c2cs35091b
4. [4]
  Peters, G. M.; Skala, L. P.; Plank, T. N.; Oh, H.; Reddy, G. N. M.; Marsh, A.; Brown, S. P.; Raghavan, S. R.; Davis, J. T. J. Am. Chem. Soc. 2015, 137, 5819. doi: 10.1021/jacs.5b02753
5. [5]
  Yan, C.; Kramer, P. L.; Yuan, R. F.; Fayer, M. D. J. Am. Chem. Soc. 2018, 140, 9466. doi: 10.1021/jacs.8b03547
6. [6]
  Peters, G. M.; Skala, L. P.; Davis, J. T. J. Am. Chem. Soc. 2016, 138, 134. doi: 10.1021/jacs.5b08769
7. [7]
  Du, X.; Zhou, J.; Shi, J.; Xu, B. Chem. Rev. 2015, 115, 13165. doi: 10.1021/acs.chemrev.5b00299
8. [8]
  Yu Chan, B. Q.; Kenny Low, Z. W.; Wen Heng, S. J.; Chan, S. Y.; Owh, C.; Loh, X. J. ACS Appl. Mater. Interfaces 2016, 8, 10070. doi: 10.1021/acsami.6b01295
9. [9]
  Busschaert, N.; Caltagirone, C.; Rossom, W. V.; Gale, P. A. Chem. Rev. 2015, 115, 8038. doi: 10.1021/acs.chemrev.5b00099
10. [10]
  Wu, X.; Yu, Y.; Gao, L.; Hu, X. Y.; Wang, L. Org. Chem. Front. 2016, 3, 966. doi: 10.1039/C6QO00197A
11. [11]
  Hajebi, S.; Rabiee, N.; Bagherzadeh, M.; Ahmadi, S.; Rabiee, M.; Mamaqani, H. R.; Tahriri, M.; Tayebi, L.; Hamblin, M. R. Acta Biomater. 2019, 92, 1. doi: 10.1016/j.actbio.2019.05.018
12. [12]
  Wang, Y. Q.; Yu, X. D.; Li, Y. J.; Zhang, Y. J.; Geng, L. J.; Shen, F. J.; Ren, J. J. ACS Appl. Mater. Interfaces 2019, 11, 19605. doi: 10.1021/acsami.9b02592
13. [13]
  Xu, Y.; Cui, M. Y.; Patsis, P. A.; Günther, M.; Yang, X. G.; Eckert, K.; Zhang, Y. X. ACS Appl. Mater. Interfaces 2019, 11, 7715. doi: 10.1021/acsami.8b19482
14. [14]
  Zeng, X. J.; Yang, K. Q.; Huang, C. Y.; Yang, K.; Xu, S. P.; Wang, L.; Pi, P. H.; Wen, X. F. ACS Sustainable Chem. Eng. 2019, 7, 1368.
15. [15]
  Zeng, M. Y.; Tan, J. Y.; Chen. K, ; Zang, D. J.; Yang, Y.; Zhang, J.; Wei, Y. G. ACS Appl. Mater. Interfaces 2019, 118, 8537.
16. [16]
  Li, Z. Y.; Hou, N. N.; Shao, W.; Xiao, S. J.; Lin, C.; Wang, L. Y. Chin. J. Org. Chem. 2018, 8, 2002.
17. [17]
  Li, Z. T.; Yang, J.; Huang, F. H. Chin. J. Chem. 2018, 38, 59.
18. [18]
  Li, C.; Shen, C. S.; Nie, J. C.; Qiu, H. B. Chem.-Asian J. 2018, 13, 1678. doi: 10.1002/asia.201800572
19. [19]
  Wang, J. Z.; Liu, L.; Chen, J.; Deng, M. X.; Feng, X.; Chen, L. Eur. Polym. J. 2019, 118, 222. doi: 10.1016/j.eurpolymj.2019.04.051
20. [20]
  Xiao, T. X.; Zhong, W. W.; Xu, L. X.; Sun, X. Q.; Hu, X. Y.; Wang, L. Y. Org. Biomol. Chem. 2019, 17, 1336. doi: 10.1039/C8OB03095B
21. [21]
  Liu, Y. M.; Shi, K. J.; Ma, D. Chem.-Asian J. 2019, 14, 307.
22. [22]
  Li, B.; Meng, Z.; Li, Q.; Huang, X.; Kang, Z.; Dong, H.; Chen, J.; Sun, J.; Dong, Y.; Li, J.; Jia, X.; Sessler, J. L.; Meng, Q.; Li, C. Chem. Sci. 2017, 8, 4458. doi: 10.1039/C7SC01438D
23. [23]
  Li, P. Y.; Chen, Y.; Liu, Y. Chin. Chem. Lett. 2019, 30, 1190. doi: 10.1016/j.cclet.2019.03.035
24. [24]
  Ogoshi, T.; Kanai, S.; Fujinami, S.; Yamagishi, T.; Nakamoto, Y. J. Am. Chem. Soc. 2008, 130, 5022. doi: 10.1021/ja711260m
25. [25]
  Zeng, M. Y.; Tan, J. Y.; Chen, K.; Zang, D. J.; Yang, Y.; Zhang, J.; Wei, Y. G. ACS Appl. Mater. Interfaces 2019, 118, 8537.
26. [26]
  Jiang, B.; Wang, W.; Zhang, Y.; Lu, Y.; Zhang, C. W.; Yin, G. Q.; Zhao, X. L.; Xu, L.; Tan, H. W.; Li, X. P.; Jin, G. X.; Yang, H. B. Angew. Chem., Int. Ed. 2017, 56, 14438. doi: 10.1002/anie.201707209
27. [27]
  Li, Z. T.; Xing, H.; Shi, B. B. Polym. Chem. 2017, 8, 2747. doi: 10.1039/C7PY00280G
28. [28]
  师海雄, 程晓斌, 林奇, 姚虹, 张有明, 魏太保, 有机化学, 2018, 36, 1718.
29. [29]
  Zhang, Z. B.; Sun, K. C.; Li, S. J.; Yu, G. C. Chin. Chem. Lett. 2019, 30, 957. doi: 10.1016/j.cclet.2019.01.018
30. [30]
  Wang, M. J.; Du, X. S.; Tian, H. S.; Jia, Q.; Deng, R.; Cui, Y. H.; Wang, C. Y.; Meguellati, K, Chin. Chem. Lett. 2019, 30, 345. doi: 10.1016/j.cclet.2018.10.014
31. [31]
  Lin, Q.; Zhong, K. P.; Zhu, J. H.; Ding, L.; Su, J. X.; Yao, H.; Wei, T. B.; Zhang, Y. M. Macromolecules 2017, 50, 7863. doi: 10.1021/acs.macromol.7b01835
32. [32]
  Chen, Y.; Huang, F. H.; Li, Z. T.; Liu, Y. Sci. China, Chem. 2018, 8, 979.
33. [33]
  Gao, L. Y.; Li, M. J.; Ehrmann, S.; Tu, Z. X.; Haag, R. Angew. Chem., Int. Ed. 2019, 58, 3645. doi: 10.1002/anie.201810314
34. [34]
  Holler, M.; Stoerkler, T.; Louis, A.; Fischer, F.; Nierengarten, J. F. Eur. J. Org. Chem. 2019, 50, 401.
35. [35]
  Brun, A. M.; Harriman, A. J. Am. Chem. Soc. 1991, 113, 8153. doi: 10.1021/ja00021a047
36. [36]
  Tan, X. P.; Wu, Y.; Yu, S.; Zhang, T. Y.; Tian, H. X.; He, S. H.; Zhao, A. N.; Chen, Y. W.; Gou, Q. Talanta 2019, 195, 472. doi: 10.1016/j.talanta.2018.11.099
37. [37]
  Zhang, Y. M.; Zhu, W.; Qu, W. J.; Zhong, K. P.; Chen, X. P.; Yao, H.; Wei, T. B.; Lin, Q. Chem. Commun. 2018, 54, 4549. doi: 10.1039/C8CC00814K
38. [38]
  Zhang, Y. M.; He, J. X.; Zhu, W.; Li, Y. F.; Fang, H.; Yao, H.; Wei, T. B.; Lin, Q. Mater. Sci. Eng. C. 2019, 100, 62. doi: 10.1016/j.msec.2019.02.094
39. [39]
  Zhang, Y. M.; Li, Y. F.; Zhong, K. P.; Qu, W. J.; Chen, X. P.; Yao, H.; Wei, T. B.; Lin, Q. Soft Matter 2018, 14, 3624. doi: 10.1039/C8SM00426A
40. [40]
  Yao, H.; Wang, J.; Fan, Y. Q.; Zhou, Q.; Guan, W. X.; Kan, X. T.; Zhang, Y. M.; Lin, Q.; Wei, T. B. Dyes Pigm. 2019, 167, 16. doi: 10.1016/j.dyepig.2019.04.011
41. [41]
  Mei, J.; Leung, N. L. C.; Kwok, R. T. K.; Lam, J. W. Y.; Tang, B. Z. Chem. Rev. 2015, 115, 11718. doi: 10.1021/acs.chemrev.5b00263
42. [42]
  Zhang, Y. M.; Zhu, W.; Huang, X. J.; Qu, W. J.; He, J. X.; Fang, H.; Yao, H.; Wei, T. B.; Lin, Q. ACS Sustainable Chem. Eng. 2018, 612, 16597.
43. [43]
  Yao, H.; Wang, J.; Song, S. S.; Fan, Y. Q.; Guan, W. X.; Zhou, Q.; Wei, T. B.; Lin, Q.; Zhang, Y. M. New J. Chem. 2018, 42, 18059. doi: 10.1039/C8NJ04160A
44. [44]
  Zhang, Y. M.; Zhu, W.; Qu, W. J.; Zhong, K. P.; Chen, X. P.; Yao, H.; Wei, T. B.; Lin, Q. Chem. Commun. 2018, 54, 4549. doi: 10.1039/C8CC00814K
45. [45]
  Lin, Q.; Lu Liu, Zheng, F.; Mao, P. P.; Liu, J.; Zhang, Y. M.; Yao, H.; Wei, T. B. Tetrahedron 2017, 73, 5307. doi: 10.1016/j.tet.2017.07.028
46. [46]
  Lin, Q.; Lu Liu, Zheng, F.; Mao, P. P.; Liu, J.; Zhang, Y. M.; Yao, H.; Wei, T. B. RSC Adv. 2017, 7, 34411 doi: 10.1039/C7RA05750D
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