A Strategy for Preparing Star Polymers Containing Metal–Metal Bonds Along the Polymeric Arms Using Click Chemistry

Article

Abstract

The [(η5-C5H4(CH2)3N3)Mo(CO)3]2 dimer (3) was prepared and used to determine if the Huisgen cycloaddition reaction could be used to synthesize high molecular weight star polymers with metal–metal bonds in the arms. Several different click catalysts were examined. Cp*Ru(PPh3)2Cl (Cp* = η5-C5(CH3)5) was previously shown to catalyze the formation of metal–metal bond-containing polymers using click chemistry; however, this catalyst underwent a Staudinger reaction with dimer 3 when a model coupling reaction was attempted with phenylacetylene. In order to avoid the Staudinger reaction, Cp*Ru(COD)Cl was used as the catalyst in the reaction of 3 with phenylacetylene, and coupling was observed after 14 h. Synthesis of a star polymer was attempted with 3 and 1,3,5-triethynylbenzene. Instead of coupling, Cp*Ru(COD)Cl reacted with the 1,3,5-triethynylbenzene. A third catalyst, Cu(IMes)Cl (IMes = 1,3-dimesityl-imidazol-2-ylidene) was used to couple 3 with 1,3,5-triethynylbenzene in 48 h. Both a high molecular weight polymer (Mn = 77,000 g mol−1) and a tripodal star core (Mn = 1,800 g mol−1) were successfully prepared with this catalyst.

Keywords

Click chemistry Huisgen cycloaddition reaction Metal–metal bond-containing polymers Star polymers Click chemistry catalysts 

References

  1. 1.
    G. Geuskens, Compr. Chem. Kinet. 14, 333 (1975)CrossRefGoogle Scholar
  2. 2.
    D.R. Tyler, Coord. Chem. Rev. 246, 291 (2003)CrossRefGoogle Scholar
  3. 3.
    G.V. Shultz, J.M. Zemke, D.R. Tyler, Macromolecules 42, 7644 (2009)CrossRefGoogle Scholar
  4. 4.
    S.E. Brady, G.V. Shultz, D.R. Tyler, J. Inorg. Organomet. Polym. 20, 511 (2010)CrossRefGoogle Scholar
  5. 5.
    S.C. Tenhaeff, D.R. Tyler, Organometallics 10, 1116 (1991)CrossRefGoogle Scholar
  6. 6.
    S.C. Tenhaeff, D.R. Tyler, Organometallics 10, 473 (1991)CrossRefGoogle Scholar
  7. 7.
    S.C. Tenhaeff, D.R. Tyler, Organometallics 11, 1466 (1992)CrossRefGoogle Scholar
  8. 8.
    G.V. Shultz, D.R. Tyler, J. Inorg. Organomet. Polym. 19, 423 (2009)CrossRefGoogle Scholar
  9. 9.
    A.E. Stiegman, M. Stieglitz, D.R. Tyler, J. Am. Chem. Soc. 105, 6032 (1983)CrossRefGoogle Scholar
  10. 10.
    R. Chen, D.R. Tyler, Macromolecules 37, 5430 (2004)CrossRefGoogle Scholar
  11. 11.
    B.C. Daglen, D.R. Tyler, J. Inorg. Organomet. Polym. Mater. 19, 91 (2009)CrossRefGoogle Scholar
  12. 12.
    B.C. Daglen, J.D. Harris, D.R. Tyler, J. Inorg. Organomet. Polym. Mater. 17, 267 (2007)CrossRefGoogle Scholar
  13. 13.
    I. Manners, Science 294, 1664 (2001)CrossRefGoogle Scholar
  14. 14.
    I. Manners, Synthetic Metal-containing Polymers (Wiley-VCH, Wienheim, 2004)Google Scholar
  15. 15.
    P. Nguyen, P. Gomez-Elipe, I. Manners, Chem. Rev. 99, 1515 (1999)CrossRefGoogle Scholar
  16. 16.
    A.S. Abd-El-Aziz, I. Manners, Frontiers in Metal-containing Polymers (Wiley-Interscience, New Jersey, 2007)CrossRefGoogle Scholar
  17. 17.
    A.E. Steigman, D.R. Tyler, Coord. Chem. Rev. 63, 217 (1985)CrossRefGoogle Scholar
  18. 18.
    M. Meldel, Macromol. Rapid Commun. 29, 1016 (2008)CrossRefGoogle Scholar
  19. 19.
    J.A. Opsteen, J.C.M. van Hest, Chem. Commun. 57 (2004)Google Scholar
  20. 20.
    N.V. Tsarevsky, B.S. Sumerlin, K. Matyjaszewski, Macromolecules 38, 3558 (2005)CrossRefGoogle Scholar
  21. 21.
    V.V. Rostovtsev, L.G. Green, V.V. Fokin, K.B. Sharpless, Angew. Chem. Int. Ed. 41, 2596 (2002)CrossRefGoogle Scholar
  22. 22.
    H. Nandivada, X. Jiang, J. Lahann, Adv. Mater. 19, 2197 (2007)CrossRefGoogle Scholar
  23. 23.
    X. Wang, A. Kimyonok, M. Weck, Chem. Commun. 3933 (2006)Google Scholar
  24. 24.
    L. Liang, D. Astruc, Coord. Chem. Rev. 255, 2933 (2011)CrossRefGoogle Scholar
  25. 25.
    R. Chen, M. Yoon, A. Smalley, D.C. Johnson, D.R. Tyler, J. Am. Chem. Soc. 126, 3054 (2004)CrossRefGoogle Scholar
  26. 26.
    L. Liu, W. Wong, C. Ho, Aust. J. Chem. 59, 434 (2006)CrossRefGoogle Scholar
  27. 27.
    M.S. Chinn, D.M. Heinekey, J. Am. Chem. Soc. 112, 5166 (1990)CrossRefGoogle Scholar
  28. 28.
    S.G. Alvarez, M.T. Alvarez, Synthesis 413 (1997)Google Scholar
  29. 29.
    K. Matyjaszewski, Y. Nakagawa, S.G. Gaynor, Macromol. Rapid Commun. 18, 1057 (1997)CrossRefGoogle Scholar
  30. 30.
    L. Zhang, X. Chen, P. Xue, H.H.Y. Sun, I.D. Williams, K.B. Sharpless, V.V. Fokin, G. Jia, J. Am. Chem. Soc. 127, 15998 (2005)CrossRefGoogle Scholar
  31. 31.
    S. Diez-Gonzalez, S.P. Nolan, Angew. Chem. Int. Ed. 47, 8881 (2008)CrossRefGoogle Scholar
  32. 32.
    T. Nakamura, T. Terashima, K. Ogata, S. Fukuzawa, Org. Lett. 13, 620 (2011)CrossRefGoogle Scholar
  33. 33.
    D. Fournier, F. Du Prez, Macromolecules 41, 4622 (2008)CrossRefGoogle Scholar
  34. 34.
    P.L. Golas, N.V. Tsarevsky, K. Matyjaszewski, Macromol. Rapid. Commun. 29, 1167 (2008)CrossRefGoogle Scholar
  35. 35.
    B. Iskin, G. Yilmaz, Y. Yagci, J. Polym. Sci. A Polym. Chem. 49, 2417 (2011)CrossRefGoogle Scholar
  36. 36.
    D.J.V.C. van Steenis, O.R.P. David, G.P.F. van Strijdonck, J.H. van Maarseveen, J.N.H. Reek Chem. Commun. 4333 (2005)Google Scholar
  37. 37.
    P. Wu, A.K. Feldman, A.K. Nugent, C.J. Hawker, A. Scheel, B. Voit, J. Pyun, J.M.J. Fréchet, K.B. Sharpless, V.V. Fokin, Angew. Chem. Int. Ed. 43, 3928 (2004)CrossRefGoogle Scholar
  38. 38.
    S. Bräse, C. Gil, K. Knepper, V. Zimmerman, Angew. Chem. Int. Ed. 44, 5188 (2005)CrossRefGoogle Scholar
  39. 39.
    J.A. Reisz, E.B. Klorig, M.W. Wright, S.B. King, Org. Lett. 11, 2719 (2009)CrossRefGoogle Scholar
  40. 40.
    T. Saplinova, L. Jäger, A. Kolbe, C. Wagner, J. Mol. Struct. 690, 25 (2004)CrossRefGoogle Scholar
  41. 41.
    V. Maraval, R. Laurent, B. Donnadieu, M. Mauzac, A.-M. Caminade, J.-P. Majoral, J. Am. Chem. Soc. 122, 2499 (2000)CrossRefGoogle Scholar
  42. 42.
    B.C. Boren, S. Narayan, L.K. Rasmussen, L. Zhang, H. Zhao, Z. Lin, G. Jia, V.V. Fokin, J. Am. Chem. Soc. 130, 8923 (2008)CrossRefGoogle Scholar
  43. 43.
    V. Cadierno, S.E. García-Garrido, J. Gimeno, J. Am. Chem. Soc. 128, 15094 (2006)CrossRefGoogle Scholar
  44. 44.
    B. Dutta, B.F.E. Curchod, P. Campomanes, E. Solari, R. Scopelliti, U. Rothlisberger, K. Severin, Chem. Eur. J. 16, 8400 (2010)CrossRefGoogle Scholar
  45. 45.
    Y. Yamamoto, H. Takagishi, K. Itoh, J. Am. Chem. Soc. 124, 28 (2002)CrossRefGoogle Scholar
  46. 46.
    R.-X. Yao, L. Kong, Z.-S. Yin, F.-L. Qing, J. Fluor. Chem. 129, 1003 (2008)CrossRefGoogle Scholar
  47. 47.
    M.-H. Ryu, J.-W. Choi, B.-K. Cho, J. Mat. Chem. 20, 1806 (2010)CrossRefGoogle Scholar
  48. 48.
    R. Hourani, A. Sharma, A. Kakkar, Tetrahedron Lett. 51, 3792 (2010)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2012

Authors and Affiliations

  1. 1.1253 Department of ChemistryUniversity of OregonEugeneUSA

Personalised recommendations