Citation: Wu Jiacheng, Liu Zhenghui, Yao Yuan, Lin Shaoliang. Synthesis and Self-Assembly of Alternating Amphiphilic Copolymer with Azobenzene Pendants[J]. Chinese Journal of Organic Chemistry, ;2019, 39(10): 2952-2957. doi: 10.6023/cjoc201905019 shu

Synthesis and Self-Assembly of Alternating Amphiphilic Copolymer with Azobenzene Pendants

Shanghai Key Laboratory of Advanced Polymeric Materials, School of Materials Science and Engineering, East China University of Science and Technology, Shanghai 200237

Corresponding author: Lin Shaoliang, slin@ecust.edu.cn
Received Date: 10 May 2019
Revised Date: 26 May 2019
Available Online: 28 October 2019
Fund Project: the National Natural Science Foundation of China 51873061the National Natural Science Foundation of China 51622301Project supported by the National Natural Science Foundation of China (Nos. 51622301, 51573088, 51873061, 91834301)the National Natural Science Foundation of China 51573088the National Natural Science Foundation of China 91834301

Figures(4)

A novel alternating amphiphilic copolymer poly(tetra glycol-a-N, N-bis[2-(1H-1, 2, 3-triazol-1-yl)ethyl]-4-phenyl-diazenyl-aniline)[P(EG₄-a-NAzo)] with azobenzene pendants was synthesized through the azide-alkyne click reaction, in which the hydrophilic unit was tetra glycol (EG₄) and N, N-bis[2-(1H-1, 2, 3-triazol-1-yl)ethyl]-4-phenyldiazenyl-aniline (NAzo) performed the hydrophobic unit. P(EG₄-a-NAzo) could self-assemble into worm-like aggregate in aqueous solution with initially low concentration. Because of its unique alternating topologies, the azobenzene moiety of P(EG₄-a-NAzo) micelle could not pile up orderly. This novel azobenzene copolymer has arisen new thoughts and approaches for the molecular design of photo-functional polymers.
- click reaction,
- alternating copolymer,
- azobenzene,
- self-assembly
1. [1]
  (a) Thorkelsson, K.; Bai, P.; Xu, T. Nano Today 2015, 10, 48.
  (b) Mai, Y.; Eisenberg, A. Chem. Soc. Rev. 2012, 41, 18.
2. [2]
  (a) Howe, D. H.; Hart, J. L.; McDaniel, R. M.; Taheri, M. L.; Magenau, A. J. ACS Macro Lett. 2018, 7, 1503.
  (b) Zhang, L.; Eisenberg, A. Science 1995, 268, 1728.
  (c) Shen, H.; Eisenberg, A. Angew. Chem., Int. Ed. 2000, 39, 3310.
  (d) Zhang, L.; Eisenberg, A. J. Am. Chem. Soc. 1996, 118, 3168.
3. [3]
  (a) Gao, F.; Xing, Y.; Yao, Y.; Sun, L.; Sun, Y.; He, X.; Lin, S. Polym. Chem. 2017, 8, 7529.
  (b) Sun, L.; Gao, F.; Shen, D.; Liu, Z.; Yao, Y.; Lin, S. Polym. Chem. 2018, 9, 2977.
4. [4]
  (a) Dong, R.; Zhu, B.; Zhou, Y.; Yan, D.; Zhu, X. Angew. Chem., Int. Ed. 2012, 51, 11633.
  (b) Ren, H.; Chen, D.; Shi, Y.; Yu, H.; Fu, Z. Polym. Chem. 2015, 6, 270.
  (c) Ren, H.; Chen, D.; Shi, Y.; Yu, H.; Fu, Z. Polymer 2016, 97, 533.
5. [5]
  Yu, S.; Azzam, T.; Rouiller, I.; Eisenberg, A. J. Am. Chem. Soc. 2009, 131, 10557. doi: 10.1021/ja902869q
6. [6]
  Lv, J. A.; Liu, Y.; Wei, J.; Chen, E.; Qin, L.; Yu, Y. Nature 2016, 537, 179. doi: 10.1038/nature19344
7. [7]
  (a) Takeshima, T.; Liao, W. Y.; Nagashima, Y.; Beppu, K.; Hara, M.; Nagano, S.; Seki, T. Macromolecules 2015, 48, 6378.
  (b) Gao, F.; Wang, W.; Li, X.; Li, L.; Lin, J.; Lin, S. J. Colloid Interface Sci. 2016, 468, 70.
  (c) Kong, X.; Wang, X.; Luo, T.; Yao, Y.; Li, L.; Lin, S. ACS Appl. Mater. Interfaces 2017, 9, 19345.
  (d) Lee, S.; Kang, H. S.; Park, J. K. Adv. Mater. 2012, 24, 2069.
  (e) Wang, W.; Shen, D.; Li, X.; Yao, Y.; Lin, J.; Wang, A.; Yu, J.; Wang, Z. L.; Hong, S. W.; Lin, Z; Lin, S. Angew. Chem., Int. Ed. 2018, 130, 2161.
  (f) Wang, W.; Du, C.; Wang, X.; He, X.; Lin, J.; Li, L.; Lin, S. Angew. Chem., Int. Ed. 2014, 126, 12312.
  (g) Fu, S.; Zhao, Y. Macromolecules 2015, 48, 5088.
8. [8]
  Moses, J. E.; Moorhouse, A. D. Chem. Soc. Rev. 2007, 36, 1249. doi: 10.1039/B613014N
9. [9]
  Chen, J.; Yu, C.; Shi, Z.; Yu, S.; Lu, Z.; Jiang, W.; Zhang, M.; He, W.; Zhou, Y.; Yan, D. Angew. Chem., Int. Ed. 2015, 54, 3621. doi: 10.1002/anie.201408290
10. [10]
  Xu, Q.; Huang, T.; Li, S.; Li, K.; Li, C.; Liu, Y.; Wang, Y.; Yu, C.; Zhou, Y. Angew. Chem., Int. Ed. 2018, 57, 8043. doi: 10.1002/anie.201802833
11. [11]
  (a) Lee, L. V.; Mitchell, M. L.; Huang, S.-J.; Fokin, V. V.; Sharpless, K. B.; Wong, C.-H. J. Am. Chem. Soc. 2003, 125, 9588.
  (b) Li, Z. a.; Yu, G.; Hu, P.; Ye, C.; Liu, Y.; Qin, J.; Li, Z. Macromolecules 2009, 42, 1589.
12. [12]
  (a) Hii, K. K.; Thornton-Pett, M.; Jutand, A.; Tooze, R. P. Organometallics 1999, 18, 1887.
  (b) Lee, S. J.; Lee, S. S.; Lee, J. Y.; Jung, J. H. Chem. Mater. 2006, 18, 4713.
13. [13]
  Wu, S.; Yu, X.; Huang, J.; Shen, J.; Yan, Q.; Wang, X.; Wu, W.; Luo, Y.; Wang, K.; Zhang, Q. J. Mater. Chem. 2008, 18, 3223. doi: 10.1039/b802198h
14. [14]
  (a) Weis, P.; Wu, S. Macromol. Rapid Commun. 2018, 39, 1700220.
  (b) Weis, P.; Tian, W.; Wu, S. Chem.-Eur. J. 2018, 24, 6494.
15. [15]
  (a) Wu, S.; Wang, L.; Kroeger A.; Wu, Y.; Zhang, Q.; Bubeck, C. Soft Mater. 2011, 7, 11535.
  (b) Li, Y.; Deng, Y.; Tong, X.; Wang, X. Macromolecules 2006, 39, 1108.
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