Skip to main content
Log in

Synthesis and Polymerization of a Four-Arm Star with Pendent Cyclopentadienyliron Moieties

  • Published:
Journal of Inorganic and Organometallic Polymers and Materials Aims and scope Submit manuscript

The synthesis of the title complex was achieved via the reaction of a η6-p-dichlorobenzene-η5-cyclopentadienyliron cation with an organic four-arm core to produce the tetrairon complex. This tetrairon-containing core was subsequently polymerized via nucleophilic aromatic substitution with various dinucelophiles such as 4,4′-thiobenzenethiol, bisphenol-A, 4,4′-(1-phenylethylidene)bisphenol, 4,4′-biphenol, bis(4-hydroxyphenyl)methane, producing five different cross-linked cationic organoiron polymers. Another cross-linked polymer was produced via direct polymerization of the four-arm organic core with the η6-p-dichlorobenzene-η5-cyclopentadienyliron cation. Due to the poor solubility of these cross-linked polymers, solid-state 13C CPMAS NMR was performed in order to verify that polymerization was successful. Thermogravimetric analysis (TGA) revealed that following the decoordination of the cyclopentadienyliron moieties, the polymers were thermally stable. Differential scanning calorimetry (DSC) showed that the polymers exhibited glass transition temperatures (T g’s) ranging from 104 to 146°C.

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

Access this article

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

Instant access to the full article PDF.

Scheme 1
Scheme 2
Scheme 3
Scheme 4
Fig. 1.

Similar content being viewed by others

References

  1. A. S. Abd-El-Aziz, I. Manners, Frontiers in Transition Metal-Containing Polymers,Wiley, NewJersey, (2007)

    Google Scholar 

  2. I. Manners, Synthetic Metal Containing Polymers, Wiley VCH, Weinheim, Germany, (2004)

    Google Scholar 

  3. A. S. Abd-El-Aziz, C. E. Carraher Jr., C. U. Pittman Jr., J. E. Sheats, M. Zeldin, Macromolecules Containing Metal and Metal-Like Elements, volume 1, Wiley, New York (2003)

    Google Scholar 

  4. A. S. Abd-El-Aziz, C. E. Carraher Jr., C. U. Pittman Jr., J. E. Sheats, M. Zeldin, Macromolecules Containing Metal and Metal-Like Elements, volume 2, Organoiron Polymers, Wiley, New York (2003)

    Google Scholar 

  5. A. S. Abd-El-Aziz, I. Manners, J. Inorg. Organomet. Poly. Mat. 15, 157 (2005)

    Article  CAS  Google Scholar 

  6. A. S. Abd-El-Aziz, E. K. Todd, Coord. Chem. Rev. 246, 3 (2003)

    Article  CAS  Google Scholar 

  7. A. S. Abd-El-Aziz, Macromol. Rapid Commun. 23, 995 (2002)

    Article  CAS  Google Scholar 

  8. P. Nguyen, P. Gomez-Elipe, I. Manners, Chem. Rev. 99, 1515 (1999)

    Article  CAS  Google Scholar 

  9. I. Manners, Can. J. Chem. 76, 371 (1998)

    Article  CAS  Google Scholar 

  10. I. Manners, Chem. Int. Ed. Engl. 35, 1603 (1996)

    Article  CAS  Google Scholar 

  11. I. Manners, J. Polym. Sci. Part A: Polym. Chem. 40, 179 (2002)

    Article  CAS  Google Scholar 

  12. R. D. A. Hudson, J. Organomet. Chem. 47, 637 (2001)

    Google Scholar 

  13. F. S. Arimoto, A. C. Haven Jr., J. Am. Chem. Soc. 77, 6295 (1955)

    Article  CAS  Google Scholar 

  14. A. S. Abd-El-Aziz, E. K. Todd, T. H. Afifi, Macromol. Rapid Commun. 23, 113 (2002)

    Article  CAS  Google Scholar 

  15. A. S. Abd-El-Aziz, S. A. Carruthers, E. K. Todd, T. H. Afifi, J. M. A. Gavina, J. Polym. Sci: Part A: Polym. Chem. 43, 1382 (2005)

    Article  CAS  Google Scholar 

  16. M.-C. Daniel, D. Astruc, Chem. Rev. 104, 293 (2004)

    Article  CAS  Google Scholar 

  17. C. M. Casado, M. Moran, J. Losada, I. Cuadrado, Inorg. Chem. 34, 1668 (1995)

    Article  CAS  Google Scholar 

  18. M. M. Galka, H.-B. Kraatz, Chem. Phys. Chem. 3, 356 (2002)

    CAS  Google Scholar 

  19. Q. Sun, K. Xu, H. Peng, R. Zheng, M. Häussler, B. Z. Tang, Macromolecules 36, 2309 (2003)

    Article  CAS  Google Scholar 

  20. M. Häussler, Q. Sun, K. Xu, J. W. Y. Lam, H. Dong, B. Z. Tang, J. Inorg. Organomet. Polym. Mater. 15, 67 (2005)

    Article  CAS  Google Scholar 

  21. Z. Li, J. W. Y. Lam, Y. Q. Dong, Y. P. Dong, H. H. Y. Sung, I. D. Williams, B. Z. Tang, Macromolecules 38, 6458 (2006)

    Article  CAS  Google Scholar 

  22. D. A. Foucher, B. Z. Tang, I. Manners, J. Am. Chem. Soc. 114, 6246 (1992)

    Article  CAS  Google Scholar 

  23. R. Rulkens, A. J. Lough, I. Manners, J. Am. Chem. Soc. 116, 797 (1994)

    Article  CAS  Google Scholar 

  24. Y. Ni, R. Rulkens, J. K. Pudelski, I. Manners, Makromol. Chem. Rapid Commun. 16, 637 (1995)

    Article  CAS  Google Scholar 

  25. X.-H. Liu, D. W. Bruce, and I. Manners, Chem. Commun. 289 (1997)

  26. K. T. Kim, J. Han, C. Y. Ryu, F. C. Sun, S. S. Sheiko, M. A. Winnik, I. Manners, Macromolecules 39, 7922 (2006)

    Article  CAS  Google Scholar 

  27. A. Bartole-Scott, A. J. Lough, I. Manners, Polyhedron 25, 429 (2006)

    Article  CAS  Google Scholar 

  28. S. Nlate, J. Ruiz, J.-C. Blais, and D. Astruc, Chem. Commun. 417 (2000)

  29. C. Valerio, J.-L. Fillaut, J. Ruiz, J. Guittard, J.-C. Blais, D. Astruc, J. Am. Chem. Soc. 119, 2588 (1997)

    Article  CAS  Google Scholar 

  30. E. Alonso, C. Valerio, J. Ruiz, D. Astruc, New J. Chem. 21, 1139 (1997)

    CAS  Google Scholar 

  31. S. Nlate, J. Ruiz, V. Sartor, R. Navarro, J.-C. Blais, D. Astruc, Chem. Eur. J. 6, 2544 (2000)

    Article  CAS  Google Scholar 

  32. M.-C. Daniel, J. R. Aranzaes, S. Nlate, D. Astruc, J. Inorg. Organomet. Polym. Mat. 15, 107 (2005)

    Article  CAS  Google Scholar 

  33. H. Nishihara, M. Murata, J. Inorg. Organomet. Polym. Mat. 15, 147 (2005)

    Article  CAS  Google Scholar 

  34. M. Yamada, H. Nishihara, Eur. Phys. J. 24, 257 (2003)

    CAS  Google Scholar 

  35. H. Nishihara, Cood. Chem. Rev. 249, 1468 (2005)

    Article  CAS  Google Scholar 

  36. T. Yutaka, I. Mori, M. Kurihara, J. Mizutani, N. Tamai, T. Kawai, M. Irie, H. Nishihara, Inorg. Chem. 41, 7143 (2002)

    Article  CAS  Google Scholar 

  37. S. Itsuno, Y. Sakurai, K. Ito, T. Maruyama, S. Nakahama, J. M . J. Fréchet, J. Org. Chem. 55, 304 (1990)

    Article  CAS  Google Scholar 

  38. G. C. S. Riera, H. F. Azurmendi, M. E. Ramia, H. E. Bertorello, C. A. Martin, Polymer, 39 3515 (1998)

    Article  CAS  Google Scholar 

  39. C. D. Wood, K. Senoo, C. Martin, J. Cuellar, A. I. Cooper, Macromolecules 35, 6743 (2002)

    Article  CAS  Google Scholar 

  40. Y. Li, B. S. Lokitz, S. P. Armes, C. L. McCormick, Macromolecules 39, 2726 (2006)

    Article  CAS  Google Scholar 

  41. W. Zhang, V. Gogel, K. A. Friedrich, J. Kerres, J. Power Sources 155, 3 (2006)

    Article  CAS  Google Scholar 

  42. C. Tarducci, W. C. E. Schofield, J. P. S. Badyal, Macromolecules. 35, 8724 (2002)

    Article  CAS  Google Scholar 

  43. Z. Zhang, D. Sherlock, R. West, R. West, Macromolecules. 36, 9176 (2003)

    Article  CAS  Google Scholar 

  44. T. Liu, J. M. DeSimone, G. W. Roberts, Polymer, 47. 4276 (2006)

    Article  CAS  Google Scholar 

  45. J. M. Pollino, K. P. Nair, L. P. Stubbs, J. Adams, M. Weck, Tetrahedron, 60. 7205 (2004)

    Article  CAS  Google Scholar 

  46. A. S. Abd-El-Aziz, R. M. Okasha, P. O. Shipman, T. H. Afifi, Macromol. Rapid Commun. 25, 1497 (2004)

    Article  CAS  Google Scholar 

  47. A. S. Abd-El-Aziz, R. M. Okasha, T. H. Afifi, J. Inorg. Organomet. Polym. Mat. 14, 269 (2004)

    Article  CAS  Google Scholar 

  48. A. S. Abd-El-Aziz, T. H. Afifi, W. R. Budakowski, K. J. Friesen, E. K. Todd, Macromolecules 35, 8929 (2002)

    Article  CAS  Google Scholar 

  49. A. S. Abd-El-Aziz, R. M. Okasha, T. H. Afifi, E. K. Todd, Macromol. Chem. Phys. 204, 555 (2003)

    Article  CAS  Google Scholar 

  50. A. S. Abd-El-Aziz, N. M. Pereira, W. Boraie, E. K. Todd, T. H. Afifi, W. R. Budakowski, K. J. Friesen, J. Inorg. Organomet. Polym. Mat. 15, 497 (2006)

    Article  CAS  Google Scholar 

  51. A. S. Abd-El-Aziz, S. A. Carruthers, P. M. Aguiar, S. Kroeker, J. Inorg. Organomet. Polym. Mat. 15, 349 (2005)

    Article  CAS  Google Scholar 

  52. S. Aitipamula, A. Nangia, Supramol. Chem. 17, 17 (2005)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

Financial support provided by the Natural Sciences Engineering and Research Council of Canada (NSERC) and the Canada Foundation for Innovation is gratefully acknowledged.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Alaa S. Abd-El-Aziz.

Additional information

This article is dedicated to Professor Ian Manners for his outstanding contribution to the field of metal-containing polymers.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Abd-El-Aziz, A.S., Pereira, N.M., Winram, D.J. et al. Synthesis and Polymerization of a Four-Arm Star with Pendent Cyclopentadienyliron Moieties. J Inorg Organomet Polym 17, 275–282 (2007). https://doi.org/10.1007/s10904-007-9097-4

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10904-007-9097-4

Keywords

Navigation