Skip to main content
SpringerLink
Log in

Reversible Addition-Fragmentation Chain Transfer Polymerization of 2-Chloroethyl Methacrylate and Post-Polymerization Modification

  • Article
  • Published:
Macromolecular Research Aims and scope Submit manuscript

Abstract

An alkyl halide containing monomer, 2-chloroethyl methacrylate (CEMA) was synthesized via the chorination of 2-hydroethyl methacryalte and polymerized by reversible addition-fragmentation chain transfer (RAFT) polymerization. The kinetics of the controlled/living radical polyemrization (CRP) was systematically investigated. The chain end livingness of poly(2-chloroethyl methacrylate) (PCEMA) was confirmed by the chain extension with methyl methacrylate (MMA) under RAFT polymerization conditions. PCEMA with dangling alkyl chloride groups was directly azidated through a nucleophilic substitution with sodium azide, affording a polymer with an azido group at each repeating unit. The resulting polymer was readily available for post-polymerization modifications by various click reactions. These strategies may open new perspectives toward more effective and milder conditions for azide involving reactions.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. J. F. Lutz, Angew. Chem. Int. Ed., 46, 1018 (2017).

    Article  CAS  Google Scholar 

  2. M. Meldal and C. W. Tornøe, Chem. Rev., 108, 2952 (2018).

    Article  CAS  Google Scholar 

  3. P. L. Golas, and K. Matyjaszewski, Chem. Soc. Rev., 39, 1338 (2010).

    Article  CAS  PubMed  Google Scholar 

  4. H. C. Kolb, M. G. Finn, and K. B. Sharpless, Angew. Chem. Int. Ed., 40, 2004 (2001).

    Article  CAS  Google Scholar 

  5. W. Xi, T. F. Scott, C. J. Kloxin, and C. N. Bowman, Adv. Funct. Mater., 24, 2572 (2014).

    Article  CAS  Google Scholar 

  6. X. Du, X. Li, H. Tang, W. Wang, D. Ramella, and Y. Luan, New J. Chem., 42, 12722 (2018).

    Article  CAS  Google Scholar 

  7. Z. Miao, Z. Zhou, H. Tang, M. Yu, D. Ramella, X. Du, and Y. Luan, Catal. Sci. Technol., 8, 3406 (2018).

    Article  CAS  Google Scholar 

  8. H. Tang, and N. V. Tsarevsky, Polym. Chem., 6, 6936 (2015).

    Article  CAS  Google Scholar 

  9. K. L. Killops, L. M. Campos, and C. J. Hawker, J. Am. Chem. Soc., 130, 5062 (2008).

    Article  CAS  PubMed  Google Scholar 

  10. C. J. Hawker, V. V. Fokin, M. G. Finn, and K. B. Sharpless, Aust. J. Chem., 60, 381 (2007).

    Article  CAS  Google Scholar 

  11. B. Liu, H. Zhou, S. Zhou, H. Zhang, A. Feng, C. Jian, J. Hu, W. Gao, and J. Yuan, Macromolecules, 9, 2938 (2014).

    Article  CAS  Google Scholar 

  12. B. S. Sumerlin and A. P. Vogt, Macromolecules, 43, 1 (2010).

    Article  CAS  Google Scholar 

  13. H. Tang and N. V. Tsarevsky, J. Polym. Sci. Part A: Polym. Chem., 54, 3683 (2016).

    Article  CAS  Google Scholar 

  14. H. Cheradame, J. De la Croix Habimana, E. Rousset, and F. Chen, Makromol. Chem., 192, 2777 (1991).

    Article  CAS  Google Scholar 

  15. B. S. Sumerlin, N. V. Tsarevsky, G. Louche, R. Y. Lee, and K. Matyjaszewski, Macromolecules, 38, 7540 (2005).

    Article  CAS  Google Scholar 

  16. Y. Li, J. Yang, and B. C. Benicewicz, J. Polym. Sci. Part A: Polym. Chem., 45, 4300 (2007).

    Article  CAS  Google Scholar 

  17. S. Braese, C. Gil, K. Knepper, and V. Zimmermann, Angew. Chem. Int. Ed., 44, 5188 (2005).

    Article  CAS  Google Scholar 

  18. M. Takeishi and M. Okawara, J. Polym. Sci. Polym. Lett. Ed., 7, 201 (1969).

    Article  CAS  Google Scholar 

  19. T. Iizawa, T. Nishikubo, Y. Masuda, and M. Okawara, Macromolecules, 17, 992 (1984).

    Article  CAS  Google Scholar 

  20. W. R. Roush, D. Feitler, and J. Rebek, Tetrahedron Lett., 15, 1391 (1974).

    Article  Google Scholar 

  21. K. Schuh, O. Prucker, and J. Ruehe, Macromolecules, 41, 9284 (2008).

    Article  CAS  Google Scholar 

  22. T. Nishikubo, T. Iizawa, N. Numazaki, and M. Okawara, Makromol. Chem. Rapid Commun., 4, 187 (1983).

    Article  CAS  Google Scholar 

  23. R. K. O’Reilly, M. J. Joralemon, K. L. Wooley, and C. J. Hawker, Chem. Mater., 17, 5976 (2005).

    Article  CAS  Google Scholar 

  24. N. V. Tsarevsky, S. A. Bencherif, and K. Matyaszewski, Macromolecules, 40, 4439 (2007).

    Article  CAS  Google Scholar 

  25. P. D. Topham, N. Sandon, E. S. Read, J. Madsen, A. J. Ryan, and S. P. Armes, Macromolecules, 41, 9542 (2008).

    Article  CAS  Google Scholar 

  26. H. Han and N. V. Tsarevsky, Chem. Sci., 5, 4599 (2014).

    Article  CAS  Google Scholar 

  27. W. A. Braunecker, and K. Matyjaszewski, Prog. Polym. Sci., 32, 93 (2007).

    Article  CAS  Google Scholar 

  28. Z. Li, H. Tang, A. Feng, S. H. Thang, Prog. Chem., 30, 1097 (2018).

    Google Scholar 

  29. L. Yang, H. Tang, and H. Sun, Micromachines, 9, 296 (2018).

    Article  PubMed Central  Google Scholar 

  30. C. J. Hawker, A. W. Bosman, and E. Harth, Chem. Rev., 101, 3661 (2001).

    Article  CAS  PubMed  Google Scholar 

  31. K. Matyjaszewski and J. Xia, Chem. Rev., 101, 2921 (2001).

    Article  CAS  PubMed  Google Scholar 

  32. K. Matyjaszewski and N. V. Tsarevsky, Nat. Chem., 1, 276 (2009).

    Article  CAS  PubMed  Google Scholar 

  33. H. Sun, C. P. Kabb, Y. Dai, M. R. Hill, I. Ghiviriga, A. P. Bapat, and B. S. Sumerlin, Nat. Chem., 9, 817 (2017).

    Article  CAS  PubMed  Google Scholar 

  34. H. Sun, C. P. Kabb, and B. S. Sumerlin, Chem. Sci., 5, 4646 (2014).

    Article  CAS  Google Scholar 

  35. G. Moad, E. Rizzardo, and S. H. Thang, Aust. J. Chem., 62, 1402 (2009).

    Article  CAS  Google Scholar 

  36. A. Gregory and M. H. Stenzel, Prog. Polym. Sci., 37, 38 (2012).

    Article  CAS  Google Scholar 

  37. A. Feng, C. Zhan, Q. Yan, B. Liu, and J. Yuan, Chem. Commun., 64, 8958 (2014).

    Article  Google Scholar 

  38. K. A. Cimatu, S. C. Chan, J. H. Jang, and K. Hafer, J. Phys. Chem. C, 119, 25327 (2015).

    Article  CAS  Google Scholar 

  39. B. M. Blunden, D. S. Thomas, and M. H. Stenzel, Polym. Chem., 3, 2964 (2012).

    Article  CAS  Google Scholar 

  40. Y. Zhang, J. Zhao, P. Yang, S. He, and H. Huang, Polym. Eng. Sci., 52, 768 (2012).

    Article  CAS  Google Scholar 

  41. A. W. Snow, J. Polym. Sci. Part A: Polym. Chem., 55, 93 (2017).

    Article  CAS  Google Scholar 

  42. T. Ishikawa, A. Takenaka, M. Kikuchi, M. Kobayashi, and A. Takahara, Macromolecules, 46, 9189 (2013).

    Article  CAS  Google Scholar 

  43. C. Chen, X. Guo, J. Du, B. Choi, H. Tang, A. Feng, and S. H. Thang, Polym. Chem., 10, 228 (2019).

    Article  CAS  Google Scholar 

  44. A. Thomas, K. Niederer, F. Wurm, and H. Frey, Polym. Chem., 5, 899 (2014).

    Article  CAS  Google Scholar 

  45. R. Appel, Angew. Chem. Int. Ed., 14, 801 (1975).

    Article  Google Scholar 

  46. H. Sun, C. P. Kabb, M. B. Sims, and B. S. Sumerlin, Prog. Polym. Sci.. (2018).

    Google Scholar 

  47. H. Tang, W. Zhao, J. Yu, Y. Li, and C. Zhao, Molecules, 24, 4 (2019).

    Article  CAS  Google Scholar 

  48. H. Tang, Y. Luan, L. Yang, and H. Sun, Molecules, 23, 2870 (2018).

    Article  CAS  PubMed Central  Google Scholar 

  49. S. H. Thang, R. T. Mayadunne, G. Moad, and E. Rizzardo, Tetrahedron Lett., 40, 2435 (1999).

    Article  CAS  Google Scholar 

  50. J. Zhao, W. Wang, H. Tang, D. Ramella, and Y. Luan, Mol. Catal., 456, 57 (2018).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Beijing Advanced Innovation Center for Soft Matter Science and Engineering, College of Materials Science and Engineering, Beijing University of Chemical Technology, Beijing, 100029, P. R. China

    Anchao Feng

  2. Department of Chemistry, Southern Methodist University, Dallas, Texas, 75275, USA

    Houliang Tang

  3. School of Materials Science and Engineering, University of Science and Technology Beijing, Beijing, 100083, P. R. China

    Yi Luan

Authors
  1. Anchao Feng
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Houliang Tang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yi Luan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Anchao Feng or Yi Luan.

Additional information

Acknowledgements: This work was supported by the National Natural Science Foundation of China (21704001), the Fundamental Research Funds for the Central Universities (buctrc201724) and Beijing Advanced Innovation Center for Soft Matter Science and Engineering.

Electronic supplementary material

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Feng, A., Tang, H. & Luan, Y. Reversible Addition-Fragmentation Chain Transfer Polymerization of 2-Chloroethyl Methacrylate and Post-Polymerization Modification. Macromol. Res. 27, 686–692 (2019). https://doi.org/10.1007/s13233-019-7118-0

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13233-019-7118-0

Keywords

Search

Navigation