Advertisement

Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

New tridentate ligands with mixed donor atoms for Cu-based atom transfer radical polymerization

Abstract

2-Furancarboxaldehyde-2-pyridinylhydrazone (FPH) and 5-methyl-2-furancarboxaldehyde-2-pyridinylhydrazone (MFPH) were synthesized and used as tridentate ligands of copper (I) bromide for the atom transfer radical polymerization of methyl methacrylate (MMA) and styrene. The polymerization of methyl methacrylate achieved high conversion and yielded polymers with a good control of molecular weight and low polydispersity (PDI=1.33). Higher PDI were observed in the polymerization of styrene. Using 1-phenyl ethylbromide (PEBr) and ethyl 2-bromoisobutyrate (EBiB) as model compounds for the polymeric chain ends, the activation rate constants of the new catalytic systems were measured. These results were correlated with the polymerization results and compared with another catalytic system previously reported.

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

References

  1. (1)

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

  2. (2)

    M. Kamigaito, T. Ando, and M. Sawamoto,Chem. Rev.,101, 3689 (2001).

  3. (3)

    H. Fischer,Chem. Rev.,101, 3581 (2001).

  4. (4)

    Y. A. Kabachii, S. Y. Kochev, L. M. Bronstein, I. B. Blagodatskikh, and P. M. Valetsky,Polym. Bull.,50, 271 (2003).

  5. (5)

    J. A. M. Brandts, P. van de Geijn, E. E. van Faassen, J. Boersma, and G. Van Koten,J. Organomet. Chem.,584, 246 (1999).

  6. (6)

    E. Le Grognec, J. Claverie, and R. Poli,J. Am. Chem. Soc.,123, 9513 (2001).

  7. (7)

    M. Kato, M. Kamigaito, M. Sawamoto, and T. Higashimura,Macromolecules,28, 1721 (1995).

  8. (8)

    C. Granel, P. Dubois, R. Jerome, and P. Teyssie,Macromolecules,29, 8576 (1996).

  9. (9)

    J. Xia and K. Matyjaszewski,Macromolecules,30, 7697 (1997).

  10. (10)

    M. Teodorescu, S. G. Gaynor, and K. Matyjaszewski,Macromolecules,33, 2335 (2000).

  11. (11)

    V. C. Gibson, R. K. O’Reilly, W. Reed, D. F. Wass, A. J. P. White, and D. J. Williams,Chem. Comm., 1850 (2002).

  12. (12)

    V. C. Gibson, R. K. O’Reilly, D. F. Wass, A. J. P. White, and D. J. Williams,Macromolecules,36, 2591 (2003).

  13. (13)

    K. Matyjaszewski, T. E. Patten, and J. Xia,J. Am. Chem. Soc.,119, 674 (1997).

  14. (14)

    D. M. Haddleton, C. B. Jasieczek, M. J. Hannon, and A. J. Shooter,Macromolecules,30, 2190 (1997).

  15. (15)

    B. Göbelt and K. Matyjaszewski,Macromol. Chem. Phys.,201, 1619 (2000).

  16. (16)

    S. C. Hong and K. Matyjaszewski,Macromolecules,35, 7592 (2002).

  17. (17)

    P. Kubisa,Prog. Polym. Sci.,29, 3 (2004).

  18. (18)

    T. Sarbu and K. Matyjaszewski,Macromol. Chem. Phys.,202, 3379 (2001).

  19. (19)

    J. Xia, T. Johnson, S. G. Gaynor, K. Matyjaszewski, and J. DeSimone,Macromolecules,32, 4802 (1999).

  20. (20)

    J. Xia and K. Matyjaszewski,Macromolecules,32, 2434 (1999).

  21. (21)

    J. Xia, X. Zhang, and K. Matyjaszewski,Macromolecules,32, 3531 (1999).

  22. (22)

    K. Matyjaszewski, B. Göbelt, H.-j. Paik, and C. P. Horwitz,Macromolecules,34, 430 (2001).

  23. (23)

    G. H. Li and C. G. Cho,Macromol. Res.,10, 339 (2002).

  24. (24)

    W. Xu, X. Zhu, Z. Cheng, J. Chen, and J. Lu,Macromol. Res.,12, 32 (2004).

  25. (25)

    Y.-W. Lee, S. M. Kang, K. R. Yoon, Y. S. Chi, I. S. Choi, S.-P. Hong, B.-C. Yu, H.-j. Paik, and W. S. Yun,Macromol. Res.,13, 356 (2005).

  26. (26)

    T. Pintauer and K. Matyjaszewski,Coord. Chem. Rev.,249, 1155 (2005).

  27. (27)

    S. Perrier, S. P. Armes, X. S. Wang, F. Malet, and D. M. Haddleton,J. Polym. Sci. Polym. Chem.,39, 1696 (2001).

  28. (28)

    T. E. Patten, J. Xia, T. Abernathy, and K. Matyjaszewski,Science,272, 866 (1996).

  29. (29)

    G. Kickelbick and K. Matyjaszewski,Macromol. Rapid Comm.,20, 341 (1999).

  30. (30)

    J. M. Goodwin, M. M. Olmstead, and T. E. Patten,J. Am. Chem. Soc.,126, 14352 (2004).

  31. (31)

    J. Xia, S. G. Gaynor, and K. Matyjaszewski,Macromolecules,31, 5958 (1998).

  32. (32)

    K. Matyjaszewski, H.-j. Paik, P. Zhou, and S. J. Diamanti,Macromolecules,34, 5125 (2001).

Download references

Author information

Correspondence to Hyun-jong Paik.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Cho, H.Y., Han, B.H., Kim, I. et al. New tridentate ligands with mixed donor atoms for Cu-based atom transfer radical polymerization. Macromol. Res. 14, 539–544 (2006). https://doi.org/10.1007/BF03218721

Download citation

Keywords

  • atom transfer radical polymerization
  • copper complex
  • styrene
  • methyl methacrylate
  • activation rate constant
  • tridentate ligand
  • mixed donor atoms