Precise Synthesis of Novel Ferrocene-Based Star-Branched Polymers by Using Specially Designed 1,1-Diphenylethylene Derivatives in Conjunction with Living Anionic Polymerization

  • Tomoyuki Hirano
  • Hee-Soo Yoo
  • Yohko Ozama
  • Ahmed Abou El-Magd
  • Kenji Sugiyama
  • Akira Hirao
Article

Abstract

The precise synthesis of novel ferrocene-based regular and asymmetric star-branched polymers by a methodology using specially designed 1,1-diphenylethylene derivatives in conjunction with living anionic polymerization of ferrocenylmethyl methacrylate (FMMA) is described. The methodology involves three reaction steps, i.e., (1) introduction of 3-(tert-butyldimethylsilyloxymethyl)phenyl (SMOP) group(s) at the polymer chain end or in-chain, (2) conversion of the SMOP group(s) to α-phenyl acrylate function(s), and (3) a linking reaction of the α-phenyl acrylate function(s) with the living anionic polymer of FMMA or methyl methacrylate. By developing this methodology, a variety of 3-arm \( {\text{AA}^{\prime}_{2}} \), A2B, AB2, ABC and 4-arm A4, A3B, A2B2, A2BC, and ABC2 star-branched polymers with well-defined structures have been successfully synthesized. The A, B, and C segments are poly(FMMA), polystyrene, and poly(methyl methacrylate), respectively.

Keywords

Poly(ferrocenylmethyl methacrylate) Ferrocene-based star-branched polymer Miktoarm star-branched polymer Living anionic polymerization 

References

  1. 1.
    B.J. Bauer, L.J. Fetters, Rubber Chem. Technol. 51, 406 (1978)Google Scholar
  2. 2.
    S. Bywater, Adv. Polym. Sci. 30, 89 (1979)CrossRefGoogle Scholar
  3. 3.
    J. Roovers, in Encyclopedia of Polymer Science and Engineering, 2nd edn. Suppl. vol., ed. by J.I. Kroschwitz (Wiley-Interscience, New York, 1985), p. 478Google Scholar
  4. 4.
    P. Rempp, J.E. Herz, in Encyclopedia of Polymer Science and Engineering, 2nd edn. Suppl. vol., ed. by J.I. Kroschwitz (Wiley-Interscience, New York, 1989), p. 493Google Scholar
  5. 5.
    L.J. Fetters, E.L. Thomas, Material Science and Technology, vol. 12 (VCH Verlangesellschaft, Weinheim, 1993), p. 1Google Scholar
  6. 6.
    H.L. Hsieh, R.P. Quirk, Anionic Polymerization: Principles and Applications (Marcel Dekker, New York, 1996), p. 333Google Scholar
  7. 7.
    G.S. Grest, L.J. Fetters, J.S. Huang, D. Richter, Adv. Chem. Phys. 94, 67 (1996)CrossRefGoogle Scholar
  8. 8.
    P.J. Lutz, D. Rein, in Star and Hyperbranched Polymers, ed. by M.K. Mishra, S. Kobayashi (Marcel Dekker, New York, 1999)Google Scholar
  9. 9.
    M. Pitsikalis, S. Pispas, J.W. Mays, N. Hadjichristidis, Adv. Polym. Sci. 135, 1 (1998)CrossRefGoogle Scholar
  10. 10.
    N. Hadjichristidis, H. Iatrou, S. Pispas, M. Pitsikalis, J. Polym. Sci. A 37, 857 (1999)CrossRefGoogle Scholar
  11. 11.
    N. Hadjichristidis, S. Pispas, M. Pitsikalis, H. Iatrou, C. Vlahos, Adv. Polym. Sci. 142, 71 (1999)CrossRefGoogle Scholar
  12. 12.
    N. Hadjichristidis, M. Pitsikalis, S. Pispas, H. Iatrou, Chem. Rev. 101, 3747 (2001)CrossRefGoogle Scholar
  13. 13.
    A. Hirao, M. Hayashi, Y. Tokuda, N. Haraguchi, T. Higashihara, S.-W. Ryu, Polym. J. 34, 633 (2002)CrossRefGoogle Scholar
  14. 14.
    N. Hadjichristidis, H. Iatrou, M. Pitsikalis, S. Pispas, A. Avgeropoulos, Prog. Polym. Sci. 30, 725 (2005)CrossRefGoogle Scholar
  15. 15.
    A. Hirao, M. Hayashi, S. Loykulnant, K. Sugiyama, S.-W. Ryu, N. Haraguchi, A. Matsuo, T. Higashihara, Prog. Polym. Sci. 30, 111 (2005)CrossRefGoogle Scholar
  16. 16.
    N. Hadjichristidis, H. Iatrou, M. Pitsikalis, J.W. Mays, Prog. Polym. Sci. 31, 1068 (2006)CrossRefGoogle Scholar
  17. 17.
    A. Hirao, K. Inoue, T. Higashihara, M. Hayashi, Polym. J. 40, 923 (2008)CrossRefGoogle Scholar
  18. 18.
    T. Higashihara, K. Sugiyama, H.-S. Yoo, M. Hayashi, A. Hirao, Macromol. Rapid Commun. 31, early view (2010)Google Scholar
  19. 19.
    D.J. Lohse, N. Hadjichristidis, Curr. Opin. Colloid Interface Sci. 2, 171 (1997)CrossRefGoogle Scholar
  20. 20.
    H. Huckstadt, A. Gopfert, V. Abetz, Macromol. Chem. Phys. 201, 296 (2000)CrossRefGoogle Scholar
  21. 21.
    T.M. Birshtein, A.A. Polotsky, V. Abetz, Macromol. Theory Simul. 13, 512 (2004)CrossRefGoogle Scholar
  22. 22.
    K. Yamauchi, K. Takahashi, H. Hasegawa, H. Iatrou, N. Hadjichristidis, T. Kaneko, Y. Nishikawa, H. Jinnai, T. Matsui, H. Nishioka, M. Shimizu, H. Furukawa, Macromolecules 36, 6962 (2003)CrossRefGoogle Scholar
  23. 23.
    A. Takano, S. Wada, S. Sato, T. Araki, K. Hirahara, T. Kazama, S. Kawahara, Y. Isono, A. Ohno, N. Tanaka, Y. Matsushita, Macromolecules 37, 9941 (2004)CrossRefGoogle Scholar
  24. 24.
    K. Hayashida, A. Takano, S. Arai, Y. Shinohara, Y. Amemiya, Y. Matsushita, Macromolecules 39, 9402 (2006)CrossRefGoogle Scholar
  25. 25.
    K. Hayashida, N. Saito, S. Arai, A. Takano, N. Tanaka, Y. Matsushita, Macromolecules 40, 3695 (2007)CrossRefGoogle Scholar
  26. 26.
    Y. Matsushita, Polym. J. 40, 177 (2008)CrossRefGoogle Scholar
  27. 27.
    C. Park, J. Yoon, E.L. Thomas, Polymer 44, 6724 (2003)Google Scholar
  28. 28.
    R. Adhikari, G.M. Michler, Prog. Polym. Sci. 29, 949 (2004)CrossRefGoogle Scholar
  29. 29.
    F.J.M. Hoeben, P. Jonkheijm, E.W. Meijer, A.P.H.J. Schenning, Chem. Rev. 105, 1491 (2005)CrossRefGoogle Scholar
  30. 30.
    A.S. Abd-El-Aziz, I. Manners, Frontiers in Transition Metal-Containing Polymers (Wiley-Interscience, Hoboken, 2007)Google Scholar
  31. 31.
    D.A. Rulkens, A.J. Lough, I. Manners, J. Am. Chem. Soc. 116, 797 (1994)CrossRefGoogle Scholar
  32. 32.
    N. Yizeng, R. Rulkens, I. Manners, J. Am. Chem. Soc. 118, 4102 (1996)CrossRefGoogle Scholar
  33. 33.
    K.N. Power-Billard, R.J. Spontak, I. Manners, Angew. Chem. Int. Ed. 43, 1260 (2004)CrossRefGoogle Scholar
  34. 34.
    D.A. Rider, K.A. Cavicchi, L. Vanderark, T.P. Russell, I. Manners, Macromolecules 40, 3790 (2007)CrossRefGoogle Scholar
  35. 35.
    O. Neyken, V. Burkhardt, C. Hübsch, Macromol. Chem. Phys. 198, 3353 (1997)CrossRefGoogle Scholar
  36. 36.
    T. Higashihara, R. Faust, Macromolecules 40, 7453 (2007)CrossRefGoogle Scholar
  37. 37.
    C.U. Pittman Jr., A. Hirao, J. Polym. Sci. A 15, 1677 (1977)Google Scholar
  38. 38.
    M. Gallei, B.V.K.J. Schmidt, R. Klein, M. Rehahn, Macromol. Rapid Commun. 30, 1463 (2009)CrossRefGoogle Scholar
  39. 39.
    T. Ishizone, K. Sugiyama, Y. Sakano, H. Mori, A. Hirao, S. Nakahama, Polym. J. 31, 983 (1999)CrossRefGoogle Scholar
  40. 40.
    A. Matsuo, A. Hirao, Macromolecules 36, 9742 (2003)CrossRefGoogle Scholar
  41. 41.
    K. Sugiyama, T. Oie, A.E.-M. Ahmed, A. Hirao, Macromolecules 43, 1403 (2010)CrossRefGoogle Scholar
  42. 42.
    T. Higashihara, M. Nagura, K. Inoue, N. Haraguchi, A. Hirao, Macromolecules 38, 4577 (2005)CrossRefGoogle Scholar
  43. 43.
    A. Matsuo, T. Watanabe, A. Hirao, Macromolecules 37, 6283 (2004)CrossRefGoogle Scholar
  44. 44.
    A. Hirao, A. Matsuo, T. Watanabe, Macromolecules 38, 8701 (2005)CrossRefGoogle Scholar
  45. 45.
    J.C. Lai, T.D. Rounsefell, C.U. Pittman Jr, Macromolecules 4, 155 (1971)CrossRefGoogle Scholar
  46. 46.
    D. Xie, S. Tomczak, T.E. Hogen-Esch, J. Polym. Sci. A 39, 1403 (2001)CrossRefGoogle Scholar
  47. 47.
    H.L. Hsieh, R.P. Quirk, Anionic Polymerization: Principles and Applications (Marcel Dekker, New York, 1996)Google Scholar
  48. 48.
    S. Nakahama, A. Hirao, Prog. Polym. Sci. 15, 299 (1990)CrossRefGoogle Scholar
  49. 49.
    A. Hirao, S. Nakahama, Prog. Polym. Sci. 17, 283 (1992)CrossRefGoogle Scholar
  50. 50.
    A. Hirao, S. Loykulnant, T. Ishizone, Prog. Polym. Sci. 27, 1399 (2002)CrossRefGoogle Scholar
  51. 51.
    A. Hirao, K. Sugiyama, H. Yokoyama, Prog. Polym. Sci. 32, 1393 (2007)CrossRefGoogle Scholar
  52. 52.
    A. Hirao, T. Higashihara, M. Nagura, T. Sakurai, Macromolecules 39, 6081 (2006)CrossRefGoogle Scholar
  53. 53.
    A. Hirao, T. Higashihara, K. Inoue, Macromolecules 41, 3579 (2008)CrossRefGoogle Scholar
  54. 54.
    T. Higashihara, T. Sakurai, A. Hirao, Macromolecules 42, 6006 (2009)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2010

Authors and Affiliations

  • Tomoyuki Hirano
    • 1
  • Hee-Soo Yoo
    • 1
  • Yohko Ozama
    • 1
  • Ahmed Abou El-Magd
    • 1
  • Kenji Sugiyama
    • 1
  • Akira Hirao
    • 1
  1. 1.Division of Soft Materials Chemistry, Polymeric and Organic Materials Department, Graduate School of Science and EngineeringTokyo Institute of TechnologyTokyoJapan

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