Citation: Huo Bochao, Li Bin, Su Hang, Zeng Xianqiang, Xu Kaidi, Cui Lei. Linear and Cross-Linked Supramolecular Polymers Based on a Dibenzo-24-crown-8 Bridged Pillar[5]arene Dimer[J]. Chinese Journal of Organic Chemistry, ;2019, 39(7): 1990-1995. doi: 10.6023/cjoc201811003 shu

Linear and Cross-Linked Supramolecular Polymers Based on a Dibenzo-24-crown-8 Bridged Pillar[5]arene Dimer

Department of Chemistry, Shanghai University, Shanghai 200444

Corresponding author: Cui Lei, cuilei@shu.edu.cn
Received Date: 1 November 2018
Revised Date: 22 January 2019
Available Online: 29 July 2019
Fund Project: the National Natural Science Foundation of China 21472122the National Natural Science Foundation of China 21772118Project supported by the National Natural Science Foundation of China (Nos. 21772118, 21472122)

Figures(5)

One hybrid host molecule of dibenzo-24-crown-8 bridged pillar[5]arene dimer (1) was designed and synthesized. The combination of host 1 and ditopic guest 2 containing two 5-(1H-1, 2, 3-triazol-1-yl)pentanenitrile (TAPN) binding sites could afford linear AA/BB-type supramolecular polymers based on TAPN•pillar[5]arene recognition motif. Further introduction of ditopic guest 3 containing two secondary ammonium parts yields cross-linked supramolecular polymers through the host-guest inclusion between dibenzo-24-crown-8 and secondary ammonium salt. The supramolecular polymers were characterized by various techniques such as ¹H NMR, viscosity, DOSY and SEM, indicating that the formation of these supramolecular polymer was concentration-dependent. The critical polymerization concentration (CPC) of the formation of linear supramolecular polymers in chloroform/acetone (V:V=4:1) solutions is 28 mmol/L. This work provides a new strategy for the fabrication of novel supramolecular aggregates based on orthogonal host-guest interactions of hybrid macrocycles.
- supramolecular polymer,
- crown ether,
- pillararene,
- hybrid host
1. [1]
  Fouquey, C.; Lehn, J. M.; Levelut, A. M. Adv. Mater. 1990, 2, 254. doi: 10.1002/adma.19900020506
2. [2]
  Wijnands, S. P. W.; Engelen, W.; Lafleur, R. P. M.; Meijer, E. W.; Merkx, M. Nat. Commun. 2018, 9, 65. doi: 10.1038/s41467-017-02559-0
3. [3]
  Zhou, Z.; Yan, X.; Cook, T. R.; Saha, M. L.; Stang, P. J. J. Am. Chem. Soc. 2016, 13, 806.
4. [4]
  Hu, X.; Zhang, P.; Wu, X.; Xia, W.; Xiao, T.; Jiang, J.; Lin, C.; Wang, L. Polym. Chem. 2012, 3, 3060. doi: 10.1039/c2py20285a
5. [5]
  Xu, J.; Zhang, X. Acta Polym. Sin. 2017, 1, 37(in Chinese). doi: 10.11777/j.issn1000-3304.2017.16262
6. [6]
7. [7]
  Yang, L.; Tan, X.; Wang, Z.; Zhang, X. Chem. Rev. 2015, 115, 7196. doi: 10.1021/cr500633b
8. [8]
  Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 2495. doi: 10.1021/ja00986a052
9. [9]
  Yan, X.; Xu, D.; Chen, J.; Zhang, M.; Hu, B.; Yu, Y.; Huang, F. Polym. Chem. 2013, 4, 3312. doi: 10.1039/c3py00283g
10. [10]
  Cheng, S.-C.; Chen, K.-J.; Suzaki, Y.; Tsuchido, Y.; Kuo, T.-S.; Osakada, K.; Horie, M. J. Am. Chem. Soc. 2017, 140, 90.
11. [11]
  Chen, K.-J.; Tsai, Y.-C.; Suzaki, Y.; Osakada, K.; Miura, A.; Horie, M. Nat. Commun. 2016, 7, 13321. doi: 10.1038/ncomms13321
12. [12]
  Miyauchi, M.; Harada, A. J. Am. Chem. Soc. 2004, 126, 11418. doi: 10.1021/ja046562q
13. [13]
  Liu, Y.; Song, S.-H.; Chen, Y.; Zhao, Y.-L.; Yang, Y.-W. Chem. Commun. 2005, 13, 1702.
14. [14]
  Zhang, Q.; Qu, D.-H.; Ma, X.; Tian, H. Chem. Commun. 2013, 49, 9800. doi: 10.1039/c3cc46297h
15. [15]
  Zhang, Q.; Qu, D.-H.; Wu, J.; Ma, X.; Wang, Q.; Tian, H. Langmuir 2013, 29, 5345. doi: 10.1021/la4012444
16. [16]
  Guo, Q.-H.; Fu, Z.-D.; Zhao, L.; Wang, M.-X. Angew. Chem., Int. Ed. 2014, 53, 13548. doi: 10.1002/anie.201407670
17. [17]
  Qian, H.; Guo, D.-S.; Liu, Y. Asian J. Org. Chem. 2012, 1, 155. doi: 10.1002/ajoc.201200050
18. [18]
  Yao, X.; Ma, X.; Tian, H. J. Mater. Chem. C 2014, 2, 5155. doi: 10.1039/c4tc00503a
19. [19]
  Guo, D.; Zhang, T.; Wang, Y.; Liu, Y. Chem. Commun. 2013, 49, 6779. doi: 10.1039/c3cc41918e
20. [20]
  Villari, V.; Gattuso, G.; Notti, A.; Pappalardo, A.; Micali, N. J. Phys. Chem. B 2012, 116, 5537. doi: 10.1021/jp300848n
21. [21]
  Liu, Y.; Liu, K.; Wang, Z.; Zhang, X. Chem. Eur. J. 2011, 17, 9930. doi: 10.1002/chem.201101611
22. [22]
  Harada, A.; Takashima, Y.; Yamaguchi, H. Chem. Soc. Rev. 2009, 38, 875. doi: 10.1039/b705458k
23. [23]
  Ogoshi, T.; Kayama, H.; Yamafuji, D.; Aoki, T.; Yamagishi, T. A. Chem. Sci. 2012, 3, 3221. doi: 10.1039/c2sc20982a
24. [24]
  Li, C.; Han, K.; Li, J.; Zhang, Y.; Chen, W.; Yu, Y.; Jia, X. Chem. Eur. J. 2013, 19, 11892. doi: 10.1002/chem.201301022
25. [25]
  Nan, S.; Takahiro, K.; Tada-Aki, Y.; Yang, Y.-W.; Tomoki, O. Chem 2018, 4, 2029. doi: 10.1016/j.chempr.2018.05.015
26. [26]
  Yan, X.; Wang, F.; Zheng, B.; Huang, F. Chem. Soc. Rev. 2012, 41, 6042. doi: 10.1039/c2cs35091b
27. [27]
  Wei, P.; Yan, X.; Huang, F. Chem. Soc. Rev. 2012, 44, 815.
28. [28]
  Lou, X.-Y.; Yang, Y.-W. Adv. Opt. Mater. 2018, 6, 1800668. doi: 10.1002/adom.201800668
29. [29]
  Wu, X.; Duan, Q.; Ni, M.; Hu, X.; Wang, L. Chin. J. Org. Chem. 2014, 34, 437(in Chinese).
30. [30]
  Li, M.; Han, K.; Li, J.; Jia, X.; Li, C. Acta Polym. Sin. 2017, 129(in Chinese). doi: 10.11777/j.issn1000-3304.2017.16276
31. [31]
  Liu, Y.; Yang, Y.-W.; Li, L.; Chen, Y. Org. Biomol. Chem. 2004, 2, 1542. doi: 10.1039/B402841D
32. [32]
  Li, S.-L.; Xiao, T.; Hu, B.; Zhang, Y.; Zhao, F.; Ji, Y.; Yu, Y.; Lin, C.; Wang, L. Chem. Commun. 2011, 47, 10755. doi: 10.1039/c1cc14559b
33. [33]
  Wang, K.; Guo, D.; Zhao, H.; Liu, Y. Chem. Eur. J. 2014, 20, 4023. doi: 10.1002/chem.201303344
34. [34]
  Guo, D.-S.; Chen, K.; Zhang, H.-Q.; Liu, Y. Chem. Asian J. 2009, 4, 436. doi: 10.1002/asia.200800410
35. [35]
  Zhao, H.; Guo, D.; Wang, L.; Qian, H.; Liu, Y. Chem. Commun. 2012, 48, 11319. doi: 10.1039/c2cc34834a
36. [36]
  Li, H.; Wang, J.; Ni, Y.; Zhou, Y.; Yan, D. Acta Chim. Sinica 2016, 74, 415(in Chinese).
37. [37]
  Ogoshi, T.; Kanai, S.; Fujinami, S.; Yamagishi, T. A.; Nakamoto, Y. J. Am. Chem. Soc. 2008, 130, 5022. doi: 10.1021/ja711260m
38. [38]
  Ogoshi, T.; Takashima, S.; Yamagishi, T. J. Am. Chem. Soc. 2015, 137, 10962. doi: 10.1021/jacs.5b07415
39. [39]
  Li, C. Chem. Commun. 2014, 50, 12420. doi: 10.1039/C4CC03170A
40. [40]
  Kakuta, T.; Yamagishi, T.; Ogoshi, T. Acc. Chem. Res. 2018, 51, 1656. doi: 10.1021/acs.accounts.8b00157
41. [41]
  Mirzaei, S.; Wang, D.; Lindeman, S. V.; Sem, C. M.; Rathore, R. Org. Lett. 2018, 20, 6583. doi: 10.1021/acs.orglett.8b02937
42. [42]
  Trinh, T. M.; Nierengarten, I.; Holler, M. Chem. Eur. J. 2015, 21, 8019. doi: 10.1002/chem.201501124
43. [43]
  Hu, W.-B.; Yang, H.-M.; Hu, W.-J.; Ma, M.-L.; Zhao, X.-L.; Mi, X.-Q.; Liu, Y.; Li, J.-S.; Jiang, B.; Wen, K. Chem. Commun. 2014, 50, 10460. doi: 10.1039/C4CC01810A
44. [44]
  Li, C.; Zhao, L.; Li, J; Ding, X.; Chen, S.; Zhang, Q.; Yu, Y.; Jia, X. Chem. Commun. 2010, 46, 9016. doi: 10.1039/c0cc03575k
45. [45]
  Li, Z.-Y.; Zhang, Y.; Zhang, C.-W.; Chen, L.-J.; Wang, C.; Tan, H.; Yu, Y.; Li, X.; Yang, H.-B. J. Am. Chem. Soc. 2014, 136, 8577. doi: 10.1021/ja413047r
46. [46]
  Li, C.; Xu, Q.; Li, J.; Yao, F.; Jia, X. Org. Biomol. Chem. 2010, 8, 1568. doi: 10.1039/b920146g
47. [47]
  Sun, Y.; Guo, F.; Zuo, T.; Hua, J.; Diao, G. Nat. Commun. 2016, 7, 12042. doi: 10.1038/ncomms12042
48. [48]
  Wang, Y.; Ping, G.; Li, C. Chem. Commun. 2016, 52, 9858. doi: 10.1039/C6CC03999E
49. [49]
  Wheate, N. J.; Dickson, K. A.; Kim, R. R.; Nematollahi, A.; Macquart, R. B.; Kayser, V.; Yu, G. C.; Bret Church, W.; Marsh, D. J. J. Pharm. Sci. 2016, 105, 3615. doi: 10.1016/j.xphs.2016.09.008
50. [50]
  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
51. [51]
  Huerta, E.; Metselaar, G. A.; Fragoso, A.; Santos, E.; Bo, C.; De, M. J. Angew. Chem., Int. Ed. 2007, 46, 202. doi: 10.1002/anie.200603223
52. [52]
  Zhang, Z.; Luo, Y.; Chen, J.; Dong, S.; Yu, Y.; Ma, Z.; Huang, F. Angew. Chem., Int. Ed. 2011, 50, 1397. doi: 10.1002/anie.201006693
53. [53]
  Wang, C.; Lv, M.-Z.; Song, N.; Liu, Z.-J.; Wang, C.; Yang, Y.-W. Macromolecules 2017, 50, 5759. doi: 10.1021/acs.macromol.7b01010
54. [54]
  Song, N.; Chen, D.; Xia, M.-C.; Qiu, X.-L.; Ma, K.; Xu, B.; Tian, W.; Yang, Y.-W. Chem. Commun. 2015, 51, 5526. doi: 10.1039/C4CC08205B
55. [55]
  Wang, K.; Wang, C.-Y.; Wang, Y.; Li, H.; Bao, C.-Y.; Liu, J.; Zhang, S. X.-A.; Yang, Y.-W. Chem. Commun. 2013, 49, 10528. doi: 10.1039/c3cc46477f
56. [56]
  Shao, L.; Sun, J.; Hua, B.; Huang, F. Chem. Commun. 2018, 54, 4866. doi: 10.1039/C8CC02077A
57. [57]
  Khairou, K.; Hassan, R. Eur. Polym. J. 2000, 36, 2021. doi: 10.1016/S0014-3057(99)00040-3
58. [58]
  Song, N.; Chen, D.-X.; Qiu, Y.-C.; Yang, X.-Y.; Xu, B.; Tian, W.; Yang, Y.-W. Chem. Commun. 2014, 50, 8231. doi: 10.1039/c4cc03105a
59. [59]
  Li, C.; Chen, S.; Li, J.; Han, K.; Xu, M.; Hu, B.; Yu, Y.; Jia, X. Chem. Commun. 2011, 47, 11294. doi: 10.1039/c1cc14829j
60. [60]
  Han, K.; Zhang, Y.; Li, J.; Yu, Y.; Jia, X.; Li, C. Eur. J. Org. Chem. 2013, 11, 2057.
61. [61]
  Li, C.; Han, K.; Li, J.; Zhang, H.; Ma, J.; Shu, X.; Chen, Z.; Weng, L.; Jia, X. Org. Lett. 2012, 14, 42. doi: 10.1021/ol2027834
62. [62]
  Shu, X.; Chen, W.; Hou, D.; Meng, Q.; Zheng, R.; Li, C. Chem. Commun. 2014, 50, 4820. doi: 10.1039/C4CC00800F
63. [63]
  Wang, X.; Han, K.; Li, J.; Jia, X.; Li, C. Polym. Chem. 2013, 4, 3998. doi: 10.1039/c3py00462g
64. [64]
  S ntjens, S. H. M.; Sijbesma, R. P.; van Genderen, M. H. P.; Meijer, E. W. Macromolecules 2001, 34, 3815. doi: 10.1021/ma002010q
65. [65]
  Xu, H.; Rudkevich, D. M. Chem. Eur. J. 2010, 10, 5432.
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沈阳化工大学材料科学与工程学院沈阳 110142

Linear and Cross-Linked Supramolecular Polymers Based on a Dibenzo-24-crown-8 Bridged Pillar[5]arene Dimer

南开大学师唯/华北电力大学（保定）刘景维：二维配位聚合物中有序的亲锂冠醚位点用于无枝晶锂沉积

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通讯作者: 陈斌, bchen63@163.com