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Facile synthesis of block copolymers from a cinnamate derivative by combination of AGET ATRP and click chemistry

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Abstract

An azido- and bromo-containing compound derived from naturally occurring ethyl cinnamate was used successfully to prepare block copolymers by a combination of ‘activator generated by electron transfer atom transfer radical polymerization’ (AGET ATRP) and Huisgen “click” reactions in emulsion. First, azido-end poly(methyl methacrylate) and alkyne-end polystyrene were prepared under AGET ATRP conditions, then, poly(methyl methacrylate) block polystyrene (PMMA-b-PS) diblock copolymer was formed by Huisgen 1,3-dipolar cycloaddition. Finally, polystyrene block poly(methyl methacrylate) block polystyrene (PS-b-PMMA-b-PS) triblock copolymer was synthesized via simultaneous AGET ATRP and click reactions, catalyzed by the same copper-based catalyst. The polymers were characterized by 1H nuclear magnetic resonance (NMR) spectroscopy and gel permeation chromatography (GPC), which confirmed the successful synthesis of the corresponding polymers.

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References

  1. T. Yamamotoam and Y. Tezuka, Polym. Chem., 2, 1930 (2011).

    Article  Google Scholar 

  2. J. Hu, J. L. He, M. Z. Zhang, and P. H. Ni, Acta Polymerica Sinica, 3, 300 (2013).

    Google Scholar 

  3. Y. Bai, X. D. Fan, C. G. Mu, Z. Yang, D. Wang, and H. T. Zhang, Prog. Chem., 25, 363 (2013).

    CAS  Google Scholar 

  4. H. Sai, K. W. Tan, K. Hur, E. Asenath-Smith, R. Hovden, Y. Jiang, M. Riccio, D. A. Muller, V. Elser, L. A. Estroff, S. M. Gruner, and U. Wiesner, Science, 341, 530 (2013).

    Article  CAS  Google Scholar 

  5. M. S. Onses, C. Song, L. Williamson, E. Sutanto, P. M. Ferreira, A. G. Alleyne, P. F. Nealey, H. Ahn, and J. A. Rogers, Nat. Nanotechnol., 8, 667 (2013).

    Article  CAS  Google Scholar 

  6. S. Kumar, J. S. Lee, and C. N. Murthy, Macromol. Res., 19, 1022 (2011).

    Article  CAS  Google Scholar 

  7. C. J. Cheng, Q. L. Fu, Z. B. Liu, L. Shen, Y. L. Qiao, and C. Q. Fu, Macromol. Res., 19, 1048 (2011).

    Article  CAS  Google Scholar 

  8. B. S. Kim, H. K. Lee, S. Jeong, J. O. Lee, and H. J. Paik, Macromol. Res., 19, 1257 (2011).

    Article  CAS  Google Scholar 

  9. I. Y. Song, Y. S. Kwon, J. Lim, and T. Park, ACS Nano, 8, 6893 (2014).

    Article  CAS  Google Scholar 

  10. M. Jeong Im, B. J. Moon, G. Y. Lee, S. Y. Son, and T. Park, J. Polym. Sci. Part A: Polym. Chem., 52, 1068 (2014).

    Article  CAS  Google Scholar 

  11. F. H. Schacher, P. A. Rupar, and I. Manners, Angew. Chem. Int. Ed., 51, 7898 (2012).

    Article  CAS  Google Scholar 

  12. Y. Y. Mai and A. Eisenberg, Chem. Soc. Rev., 41, 5969 (2012).

    Article  CAS  Google Scholar 

  13. M. Luo and T. H. Epps, Macromolecules, 46, 7567 (2013).

    Article  CAS  Google Scholar 

  14. A. Tavakkoli K. G., K. W. Gotrik, A. F. Hannon, A. Alexander-Katz, C. A. Ross, and K. K. Berggren, Science, 336, 1294 (2012).

    Article  CAS  Google Scholar 

  15. N. Hadjichristidis, M. Pitsikalis, and H. Iatrou, Adv. Polym. Sci., 189, 1 (2005).

    Article  CAS  Google Scholar 

  16. Y. Y. Gu and T. P. Lodge, Macromolecules, 44, 1732 (2011).

    Article  CAS  Google Scholar 

  17. A. G. O. de Freitas, S. G. Trindade, P. I. R. Muraro, V. Schmidt, A. J. Satti, M. A. Villar, A. E. Ciolino, and C. Giacomelli, Macromol. Chem. Phys., 214, 2336 (2013).

    Article  Google Scholar 

  18. M. Y. Khan, X. X. Chen, and S. K. Noh, Macromol. Res., 21, 442 (2013).

    Article  CAS  Google Scholar 

  19. D. Quémener, T. P. Davis, C. Barner-Kowollik, and M. H. Stenzel, Chem. Commun., 5051 (2006).

    Google Scholar 

  20. X. B. Jiang, L. Hu, and Y. M. Chen, Polym. Int., 62, 1777 (2013).

    Article  CAS  Google Scholar 

  21. G. Yilmaz, B. Iskin, and Y. Yagci, Macromol. Chem. Phys., 215, 662 (2014).

    Article  CAS  Google Scholar 

  22. M. A. Tasdelen and Y. Yagci, Angew. Chem. Int. Ed., 52, 5930 (2013).

    Article  CAS  Google Scholar 

  23. M. Uygun, M. A. Tasdelen, and Y. Yagci, Macromol. Chem. Phys., 211, 103 (2010).

    Article  CAS  Google Scholar 

  24. Q. Zhang, X. Y. Wang, C. J. Cheng, R. Zhu, N. Liu, and Y. F. Hu, Org. Biomol. Chem., 10, 2847 (2012).

    Article  CAS  Google Scholar 

  25. J. C. Chen, M. Z. Liu, H. H. Gong, G. J. Cui, S. Y. Lü, C. M. Gao, F. Huang, T. T. Chen, X. Y. Zhang, and Z. Liu, Polym. Chem., 4, 1815 (2013).

    Article  CAS  Google Scholar 

  26. C. Huang, K. G. Neoh, and E. T. Kang, Langmuir, 28, 563 (2012).

    Article  CAS  Google Scholar 

  27. H. Liu, S. Li, M. Zhang, W. Shao, and Y. Zhao, J. Polym. Sci. Part A: Polym. Chem., 50, 4705 (2012).

    Article  CAS  Google Scholar 

  28. C. J. Cheng, X. X. Bai, S. J. Liu, Q. H. Huang, Y. M. Tu, H. W. Wu, and X. J. Wang, J. Polym. Res., 20, 197 (2013).

    Article  Google Scholar 

  29. G. Lligadas, Macromol. Chem. Phys., 214, 415 (2013).

    Article  CAS  Google Scholar 

  30. S. Todros, A. N. Natali, G. Pace, and V. Di Noto, Macromol. Chem. Phys., 214, 2061 (2013).

    Article  CAS  Google Scholar 

  31. S. Saengthong, T. Piroonpan, T. Tangthong, and W. Pasanphan, Macromol. Res., 22, 717 (2014).

    Article  CAS  Google Scholar 

  32. W. D. N. Ayutthaya and S. Poompradub, Macromol. Res., 22, 686 (2014).

    Article  Google Scholar 

  33. Q. H. Huang, M. Chen, X. X. Bai, L. L. Gu, Y. M. Tu, and C. J. Cheng, Chemical Research and Application, 26, 277 (2014).

    CAS  Google Scholar 

  34. I. Saikia and P. Phukan, C. R. Chim., 15, 688 (2012).

    Article  CAS  Google Scholar 

  35. J. L. Pan, J. Miao, L. F. Zhang, Z. Y. Si, C. W. Zhang, Z. P. Cheng, and X. L. Zhu, Polym. Chem., 4, 5664 (2013).

    Article  CAS  Google Scholar 

  36. H. Y. Zhang, Y. M. Zhang, W. W. Liu, and H. P. Wang, J. Appl. Polym. Sci., 110, 244 (2008).

    Article  CAS  Google Scholar 

  37. L. Q. Xu, F. Yao, G. D. Fu, and E. T. Kang, Biomacromolecules, 11, 1810 (2010).

    Article  CAS  Google Scholar 

  38. Y. F. Zhang, C. H. Li, and S. Y. Liu, J. Polym. Sci. Part A: Polym. Chem., 47, 3066 (2009).

    Article  CAS  Google Scholar 

  39. F. Yao, L. Q. Xu, G. D. Fu, and B. P. Lin, Macromolecules, 43, 9761 (2010).

    Article  CAS  Google Scholar 

  40. W. Li, Y. H. Xu, Y. Zhou, W. H. Ma, S. X. Wang, and Y. N. Dai, Nanoscale Res. Lett., 7, 485 (2012).

    Article  Google Scholar 

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Authors and Affiliations

  1. Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Fenglin Street, Nanchang, Jiangxi, 330013, P. R. China

    Chuanjie Cheng, Xiongxiong Bai, Xu Zhang, Ming Chen, Qinghua Huang, Zhongyu Hu & Yuanming Tu

Authors
  1. Chuanjie Cheng
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  2. Xiongxiong Bai
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  3. Xu Zhang
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  4. Ming Chen
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  5. Qinghua Huang
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  6. Zhongyu Hu
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  7. Yuanming Tu
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Correspondence to Chuanjie Cheng.

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Cheng, C., Bai, X., Zhang, X. et al. Facile synthesis of block copolymers from a cinnamate derivative by combination of AGET ATRP and click chemistry. Macromol. Res. 22, 1306–1311 (2014). https://doi.org/10.1007/s13233-014-2180-0

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  • DOI: https://doi.org/10.1007/s13233-014-2180-0

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