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Synthesis of Metal-containing Polymers via Ring Opening Metathesis Polymerization (ROMP). Part I. Polymers Containing Main Group Metals

  • Valerian Dragutan
  • Ileana Dragutan
  • Helmut Fischer
Review Paper

Abstract

Synthesis of a broad range of diverse polymers containing main group metals by the new ROMP approach starting from metal-functionalized cyclic monomers and taking advantage of both classical and well-defined W-, Mo- and Ru-based metathesis catalytic systems is critically surveyed. Emphasis is laid upon Si-containing ring-opening metathesis polymers, popular due to the easy accessibility of the corresponding monomers and the valuable properties of the obtained polymers. Also highlighted is the production of modern advanced materials based on metal-containing polymers as well as some of their multifarious applications. Future opportunities for this field are finally outlined.

Keywords

Polymers ROMP Metathesis Main group metals W-, Mo-, Ru-catalysis 

Notes

Acknowledgements

V.D. gratefully acknowledges support from DAAD, Bonn, for a short-term research stage at the University of Konstanz, Germany, hosted by Prof. Dr. H. Fischer.

References

  1. 1.
    (a) R.H. Grubbs (ed.), Handbook of Metathesis, vol. 1–3, (VCH-Wiley, Weinheim, 2003)Google Scholar
  2. 2.
    (a) R.R. Schrock, A.H. Hoveyda, Angew. Chem. Int. Ed., 42, 4592 (2003); (b) R.H. Grubbs, R.R. Schrock, A. Furstner (eds.), Adv. Synth. Catal. 349 (12), 1–268 (2007)Google Scholar
  3. 3.
    D. Astruc, New J. Chem. 29, 42–56 (2005)CrossRefGoogle Scholar
  4. 4.
    Y. Imamoglu, V. Dragutan (eds.), Metathesis Chemistry: from Nanostructure Design to Synthesis of Advanced Materials, NATO ASI Series, vol. 243, (Springer, Dordrecht, 2007)Google Scholar
  5. 5.
    (a) I. Dragutan, V. Dragutan, A. Demonceau, Platinum Metals Rev. 49, 123 (2005); (b) I. Dragutan, V. Dragutan, L. Delaude, A. Demonceau, Coord. Chem. Rev. 251, 765 (2007)Google Scholar
  6. 6.
    (a) V. Martinez, J.-C. Blais, D. Astruc, Angew. Chem. Int. Ed. 42, 4366 (2003); (b) V. Martinez, J.-C. Blais, D. Astruc, Organometallics 23, 861–874 (2005)Google Scholar
  7. 7.
    A.S. Abd-El-Aziz, L.J. May, J.A. Hurd, R.M. Okasha, J. Polym. Sci., Part A: Polym. Chem. 39, 2716–2722 (2001)CrossRefGoogle Scholar
  8. 8.
    (a) A.S. Abd-El-Aziz, R.M. Okasha, L.J. May, J. Hurd, J. Polym. Sci., Part A: Polym. Chem. 44, 3053–3070 (2006); (b) A.S. Abd-El-Aziz, P.O. Shipman, ACS Symp. Series 928, 401 (2006)Google Scholar
  9. 9.
    (a) P.S. Wolfe, F.J. Gomez, K.B. Wagener, Polym. Mater. Sci. Eng. 76, 250–251(1997); (b) D. Shultz, V. Ginger, R. Tyler, R. David, Polym. Prepr. 48, 650–651(2007)Google Scholar
  10. 10.
    (a) S. Karabulut, C. Aydogdu, B. Duez, Y. Imamoglu, J. Inorg. Organomet. Polym. Mater. 16, 115–122 (2006); (b) S. Karabulut, C. Aydogdu, B. Düz, Y. İmamoglu, J. Inorg. Organomet. Polym. Mater. 17, 517–523 (2007)Google Scholar
  11. 11.
    W. Steffen, U.H.F. Bunz, 219th ACS National Meeting, San Francisco, CA, March 26–30, 2000 Book of Abstracts, POLY-473, (2000)Google Scholar
  12. 12.
    A.S. Abd-El-Aziz et al. (eds.), Macromolecules Containing Metal and Metal-Like Elements, vol. 1–3 (John Wiley & Sons, Inc., Hoboken, N.J., 2001–2003)Google Scholar
  13. 13.
    A.S. Abd-El-Aziz, I. Manners, (eds.), Frontiers in Transition Metal-Containing Polymers, (John Wiley & Sons, Inc., Hoboken, N.J., 2007), pp. 1–533Google Scholar
  14. 14.
    K.A. Williams, A.J. Boydston, C.W. Bielawski, Chem. Soc. Rev. 36, 729 (2007)CrossRefGoogle Scholar
  15. 15.
    A.S. Abd-El-Aziz et al., (eds.), Macromolecules Containing Metal and Metal-Like Elements, vol. 4, (John Wiley & Sons, Inc., Hoboken, N.J., 2004)Google Scholar
  16. 16.
    (a) M. Majchrzak, B. Marciniec, Y. Itami, Adv. Synth. Catal. 347, 1285 (2005); (b) P. Pawluc, B. Marciniec, I. Kownacki, H. Maciejewski, Appl. Organomet. Chem. 19, 49 (2005)Google Scholar
  17. 17.
    R. Streck, J. Mol. Catal. 15, 3 (1982)CrossRefGoogle Scholar
  18. 18.
    (a) E.S. Finkelshtein, Polym. Sci., Ser. B 17, 185 (1995); (b) E.S. Finkelshtein, Vysokomol. Soedin., Ser. B 37, 718 (1995); (c) E.S. Finkelshtein, E.B. Portnykh, N.V. Ushakov, M.L. Gringolts, Y.P. Yampolsky, Macromol. Chem.Phys. 198, 1085 (1997)Google Scholar
  19. 19.
    K.L. Makovetsky, E.S. Finkelshtein, I.Ya. Ostrovskaya, E.B. Portnykh, L.I. Gorbacheva, A.I. Golberg, N.V. Ushakov, Y.P. Yampolsky, J. Mol. Catal. 76, 107 (1992)CrossRefGoogle Scholar
  20. 20.
    M. Zimmermann, G. Pampus, D. Maertens, Ger. Offen., 2(460), 911 (1974); Chem. Abstr., 85, 95539 (1976)Google Scholar
  21. 21.
    (a) R. Drozdzak, B. Allaert, N. Ledoux, I. Dragutan, V. Dragutan, F. Verpoort, Adv. Synth. Catal. 347, 1721(2005); (b) R. Drozdzak, B. Allaert, N. Ledoux, I. Dragutan, V. Dragutan, F. Verpoort, Coor. Chem. Rev. 249, 3055 (2005); (c) Drozdzak, N. Ledoux, B. Allaert, I. Dragutan, V. Dragutan, F. Verpoort, Central Eur. J. Chem. 3, 404 (2005)Google Scholar
  22. 22.
    E.S. Finkelshtein, K.L. Makovetsky, Yu.P. Yampolskii, E.B. Portnykh, I.Ya. Ostrovskaya, N.E. Kaliuzhny, N.A. Pritula, A.I. Golberg, M.S. Yatsenko, N.A. Plate, Makromol. Chem. 192, 1 (1991)CrossRefGoogle Scholar
  23. 23.
    R.R. Schrock, Acc. Chem. Res. 23, 158 (1990)CrossRefGoogle Scholar
  24. 24.
    E.S. Finkelshtein, E.B. Portnykh, N.V. Ushakov, M.L. Gringolts, K.L. Makovetsky, A.A. Zakharian, G.N. Bondarenko, Paper presented at 10th International symposium on olefin metathesis and polymerisation, Tihany-Veszprem, Hungary, June 27–July 2, 1993Google Scholar
  25. 25.
    E.S. Finkelshtein, E.B. Portnykh, N.V. Ushakov, M.L. Greengolis, G.K. Fedorova, N.A. Plate, Macromol. Chem. Rapid Commun. 15, 155 (1994)CrossRefGoogle Scholar
  26. 26.
    E.S. Finkelshtein, E.B. Portnykh, K.L. Makovetsky, I.Ya.Ostrovskaya, N.B. Bespalova, Yu.P. Yampolskii, Paper presented at NATO ASI ring-opening metathesis polymerization of olefins and polymerization of alkynes, Akcay, Balikesir, Turkey, 3–16 September, 1995Google Scholar
  27. 27.
    Y. Kawakami, H. Toda, M. Higashimo, Y. Yamashita, Polym. J. 20, 285 (1988)CrossRefGoogle Scholar
  28. 28.
    D.L. Stonich, W.P. Weber, Polym. Bull. 26, 493 (1991)CrossRefGoogle Scholar
  29. 29.
    D.L. Stonich, W.P. Weber, Polym. Bull. 27, 243 (1992)CrossRefGoogle Scholar
  30. 30.
    D. Albagli, G.C. Bazan, R.R. Schrock, M.S. Wrighton, J. Am. Chem. Soc. 115, 7328 (1993)CrossRefGoogle Scholar
  31. 31.
    C.B. Gorman, E.J. Ginsburg, R.H. Grubbs, J. Am. Chem. Soc. 115, 1397 (1993)CrossRefGoogle Scholar
  32. 32.
    R. Streck, J. Mol. Catal. 15, 3 (1981)Google Scholar
  33. 33.
    K.L. Makovetsky, E.S. Finkelshtein, I.Ya. Ostrovskaya, E.B. Portnykh, L.I. Gorbacheva, A.I. Golberg, N.V. Ushakov, Yu.P. Yampolsky, J. Mol. Catal. 76, 107 (1992)CrossRefGoogle Scholar
  34. 34.
    (a) E.S. Finkelshtein, E.B. Portnykh, M.L. Gringoltz, N.V. Ushakov, K.L. Makovetsky, A.A. Zakharian, B. Marcinec, Paper presented at the 10th international symposium on olefin metathesis and polymerization”, Veszprem, Hungary, June 27–July 2, 1993, Abstracts, p. 5; (b) E.S. Finkelshtein, in: Metathesis Chemistry: from Nanostructure Design to Synthesis of Advanced Materials, vol. 243, ed. by Y. Imamoglu, V. Dragutan, (Springer, NATO ASI Series, Dordrecht, 2007)Google Scholar
  35. 35.
    R.S. Saunders, R.E. Cohen, R.R. Schrock, Macromolecules 24, 5599 (1991)CrossRefGoogle Scholar
  36. 36.
    Kanaoka , R.H. Grubbs, Macromolecules 28, 4707 (1995)Google Scholar
  37. 37.
    E.S. Finkelshtein, N.V. Ushakov, E.B. Portnykh, M.L. Gringolts, K.L. Makovetsky, G.N. Bondarenko, I.Ya. Ostrovskaya, M.P. Filatova, E.A. Andreev, A.I. Goldberg, J. Polym. Sci. 35, 291 (1993)Google Scholar
  38. 38.
    E.S. Finkelshtein, K.L. Makovetsky, Yu.P. Yamploskii, E.B. Portnykh, I.Ya. Ostrovskaya, N.E. Kaliuzhny, N.A. Pritula, A.I. Golberg, M.S. Yatsenko, N.A. Plate, Makromol. Chem. 192, 1 (1991)CrossRefGoogle Scholar
  39. 39.
    C.C. Cummins, M.D. Beachy, R.R. Schrock, M.G. Vale, V. Sankaran, R.E. Cohen, Chem. Mater. 4, 1153 (1992)CrossRefGoogle Scholar
  40. 40.
    V. Sankaran, R.E. Cohen, C.C. Cummins, and R.R. Schrock, Macromolecules. 24, 6664 (1991)CrossRefGoogle Scholar
  41. 41.
    (a)Y. Tanaka, T. Ueshima, S. Kurosawa, Japan. Patent 75,160,400 1975, Chem. Abstr. 84, 151261 (1976); (b)Y. Tanaka, T. Ueshima, S. Kobayashi, Japan. Patent 75,159,598 1975, Chem. Abstr. 84, 165412 (1976)Google Scholar
  42. 42.
    D. Zerpner, R. Streck (to: Chemische Werke Hüls A.G.), Ger. Offen. 2,922,335 (1980)Google Scholar
  43. 43.
    R. Schrock, in Ring-Opening Polymerization: Mechanisms, Catalysis, Structure, Utility, ed. by D.J. Brunelle, (Hanser Publishers, New York, 1993), pp. 129–155Google Scholar
  44. 44.
    V. Sankaran, C.C. Cummins, R.R. Schrock, R.E. Cohen, R.J. Silbey, J. Am. Chem. Soc. 112, 6858 (1990)CrossRefGoogle Scholar
  45. 45.
    R. Tassoni, R.R. Schrock, Chem. Mater. 6, 744 (1994)CrossRefGoogle Scholar
  46. 46.
    J. Yue, V. Sankaran, R.E. Cohen, R.R. Schrock, J. Am. Chem. Soc. 115, 4409 (1993)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2007

Authors and Affiliations

  • Valerian Dragutan
    • 1
  • Ileana Dragutan
    • 1
  • Helmut Fischer
    • 2
  1. 1.Romanian AcademyInstitute of Organic ChemistryBucharestRomania
  2. 2.Fakultät für ChemieUniversität KonstanzKonstanzGermany

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