Skip to main content
Log in

Design of Star-Shaped Organoiron Oligomers with Azo Dye Bridges

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

Abstract

A series of star-shaped macromolecules bearing distinct symmetrical branches with alternating organoiron complexes and azobenzene moieties were synthesized using both convergent and divergent approaches. The various azo dye and organoiron-containing branches were reacted with multifunctional cores via metal-mediated nucleophilic aromatic substitution and ester condensation reactions to afford multi-substituted three- and four-arm star-shaped oligomers. UV–vis spectral studies of complexes 15 and 22 (λ max = 435 and 427 nm, respectively) show bathochromic shifts (λ max = 576 and 558, respectively) at various HCl concentrations indicating their use as potential acid sensors. Cyclic voltammetric studies of the octa-iron oligomer 22 were reversibly reduced at E 1/2 = −1.53 V.

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
Fig. 1
Scheme 3
Scheme 4
Scheme 5
Scheme 6
Scheme 7
Fig. 2
Scheme 8
Scheme 9
Scheme 10
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. J.M.J. Fréchet, Science 263, 1710 (1994)

    Article  Google Scholar 

  2. 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 

  3. X. Shen, H. Liu, Y. Li, S. Liu, Macromolecules 41, 2421 (2008)

    Article  CAS  Google Scholar 

  4. T. Tuuttila, J. Lipsonen, M. Lahtinen, J. Huuskonen, K. Rissanen, Tetrahedron 64, 10590 (2008)

    Article  CAS  Google Scholar 

  5. A.O. Moughton, R.K. O’Reilly, Macromol. Rapid Commun. 31, 37 (2010)

    Article  CAS  Google Scholar 

  6. P. Rempp, J.E. Herz, Encyclopedia of Polymer Science and Engineering, 2nd edn. (Wiley, New York, 1989), p. 793

    Google Scholar 

  7. T.H. Higashihara, K. Sugiyama, H.S. Yoo, M. Hayashi, A. Hirao, Macromol. Rapid Commun. 31, 1031 (2010)

    Article  CAS  Google Scholar 

  8. A.S. Abd-El-Aziz, P.O. Shipman, B.N. Boden, W.S. McNeil, Prog. Polym. Sci. 35, 714 (2010)

    Article  CAS  Google Scholar 

  9. S. Wang, X. Wang, L. Li, R.C. Advincula, J. Org. Chem. 69, 9073 (2004)

    Article  CAS  Google Scholar 

  10. R.L.M. Allen, In Colour Chemistry (Appleton-Century-Crofts, New York, 1971)

    Google Scholar 

  11. H. Zollinger, In Azo and Diazo Chemistry (Interscience Publishers, New York, 1961)

    Google Scholar 

  12. 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 

  13. A.S. Abd-El-Aziz, I. Manners, J. Inorg. Organomet. Polym. Mater. 15, 157 (2005)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  16. A.S. Abd-El-Aziz, P.O. Shipman, P.R. Shipley, Macromol. Rapid Commun. 31, 459 (2010)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  18. A.S. Abd-El-Aziz, E.K. Todd, R.M. Okasha, P.O. Shipman, T.E. Wood, Macromolecules 38, 9411 (2005)

    Article  CAS  Google Scholar 

  19. A.K. Prajapati, N.L. Bonde, J. Chem. Sci. 118, 203 (2006)

    Article  CAS  Google Scholar 

  20. Z. Seferoğlu, N. Ertan, Heteroa. Chem. 18, 622 (2007)

    Article  Google Scholar 

  21. K. Tawa, K. Kamada, K. Kiyohara, K. Ohta, D. Yasumatsu, Z. Sekkat, S. Kawata, Macromolecules 34, 8232 (2001)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

Download references

Acknowledgements

Financial support was provided by the Natural Sciences and Engineering Research Council of Canada (NSERC) and the University of British Columbia, Okanagan and is gratefully acknowledged. We would also like to thank Professor Edward G. Neeland for his invaluable contribution to this article.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Alaa S. Abd-El-Aziz.

Additional information

This paper is dedicated to Professor Charles U. Pittman, Jr. in recognition of his outstanding contribution to the field of inorganic and organometallic polymers.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Abd-El-Aziz, A.S., Strohm, E.A., Ding, M. et al. Design of Star-Shaped Organoiron Oligomers with Azo Dye Bridges. J Inorg Organomet Polym 20, 592–603 (2010). https://doi.org/10.1007/s10904-010-9393-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10904-010-9393-2

Keywords

Navigation