Preparation and characterisation of electrodes modified with iron porphyrins immobilised in a poly(amino acid) matrix

(Note: The full text of this document is currently only available in the PDF Version )

Martin Devenney, James Grimshaw and Jadwiga Trocha-Grimshaw


Abstract

Controlled reaction of 1-(3-aminopropyl)imidazole with poly(γ-ethyl L-glutamate) leads to conversion of some side-chain ester groups to amides. The functionalised polymer is characterised by 1H NMR spectroscopy. Imidazole complexes have been formed between this functionalised polymer and 5,10,15,20-tetraphenylporphyrin iron(III) chloride and also deuteroporphyrin-IX dimethyl ester iron(III) chloride. Films of the polymer-porphyrin complexes formed on platinum and on tin oxide coated glass show reversible redox activity in acetonitrile and in aqueous electrolytes. Both redox states of iron are characterised as bis-imidazole ligated by their UV–VIS spectra. The influence of the degree of polymerisation of the starting poly(γ-ethyl L-glutamate), the composition of the aqueous electrolyte and the oxidation state of the iron centre on the stability of the hydrogel films towards redox cycling is examined.


References

  1. Molecular Design at Electrode Surfaces (Techniques of Chemistry vol. 22), ed. R. W. Murray, Wiley, New York, 1992 Search PubMed.
  2. F. Bedioui, J. Devynck and C. Bied-Charrenton, Acc. Chem. Res., 1995, 28, 30 CrossRef CAS; A. Deronzier, J. Chim. Phys. Phys.-Chim. Biol., 1996, 93, 611 CAS.
  3. A. M. Abeysekera, J. Grimshaw, S. D. Perera and S. D. Vipond, J. Chem. Soc., Perkin Trans. 2, 1989, 43 RSC; J. Grimshaw and S. D. Perera, J. Chem. Soc., Perkin Trans. 2, 1989, 1711 RSC.
  4. A. M. Abeysekera, J. Grimshaw and J. Trocha-Grimshaw, J. Chem. Soc., Perkin Trans. 2, 1992, 43 RSC.
  5. J. Grimshaw and J. Trocha-Grimshaw, J. Chem. Soc., Perkin Trans. 2, 1991, 751 RSC.
  6. For a comprehensive review on porphyrins and metalloporhyrins see: The Porphyrins, ed. D. Dolfin, Academic Press, New York, 1978 Search PubMed.
  7. R. D. Jones, D. A. Somerville and F. Basolo, Chem. Rev., 1979, 79, 139 CrossRef CAS; E. Tsuchide and H. Nishide, Top. Curr. Chem., 1986, 132, 63 CAS; B. Meunier, Chem. Rev., 1992, 92, 1411 CrossRef CAS.
  8. A. P. Brown, C. Koval and F. C. Anson, J. Electroanal. Chem., 1976, 72, 379 CrossRef CAS; A. Bettelheim, R. J. H. Chan and T. Kuwana, J. Electroanal. Chem., 1979, 99, 391 CrossRef CAS.
  9. R. L. McCarley, D. J. Dunaway and R. J. Willicut, Langmuir, 1993, 9, 2775 CrossRef CAS.
  10. J. E. Hutchinson, T. A. Postlethwaite, C. H. Chen, C. W. Heathcock, R. S. Ingram, W. Qu, R. W. Linton, R. W. Murray, D. A. Tyvoll, L. L. Chng and J. P. Collman, Langmuir, 1997, 13, 2143 CrossRef CAS.
  11. C. Shi and F. C. Anson, Inorg. Chem., 1992, 31, 5078 CrossRef CAS.
  12. R. D. Locklin and R. W. Murray, J. Electroanal. Chem., 1979, 100, 271 CrossRef; N. Kobayashi, T. Mabue, M. Fujihara and T. Osa, J. Electroanal. Chem., 1979, 103, 427 CrossRef CAS; F. Arifuku, K. Mori, T. Muratuni and H. Kurihara, Bull. Chem. Soc. Jpn., 1992, 65, 1491 CAS.
  13. K. W. Willman, R. D. Rocklin, R. Nowak, K.-N. Kuo, F. A. Shultz and R. W. Murray, J. Am. Chem. Soc., 1980, 102, 7629 CrossRef CAS.
  14. F. Bedioui, S. Trevin, M. G. G. Villegas and J. Devynck, Anal. Chim. Acta, 1997, 341, 177 CrossRef CAS.
  15. F. Bedioui, A. Merino, J. Devynck, C.-E. Mestres and C. Bied-Charreton, J. Electroanal. Chem., 1988, 239, 433 CrossRef CAS.
  16. A. Deronzier, R. Devaux, D. Limosin and J.-M. Latour, J. Electroanal. Chem., 1992, 324, 325 CrossRef CAS; F. Bedioui, M. Voisin, J. Devynck and C. Bied-Charreton, J. Electroanal. Chem., 1991, 297, 257 CrossRef CAS; F. Bedioui, A. Merino, J. Devynck, C.-E. Mestres and C. Bied-Charreton, J. Electroanal. Chem., 1990, 277, 197 CrossRef CAS.
  17. S. Gutierrez-Grandadors, F. Bedioui and J. Devynck, Electrochim. Acta, 1993, 38, 1747 CrossRef CAS; F. Bedioui, J. Devynck and C. Bied-Charreton, J. Mol. Catal., 1996, 113, 3 Search PubMed.
  18. C. Couiquis, S. Cosnier, A. Deronzier, B. Galland, D. Limosin, J.-C. Moutet, J. Bizot, D. Deprez and J.-P. Pulicani, J. Electroanal. Chem., 1993, 352, 181 CrossRef CAS.
  19. A. Bettelheim, R. J. H. Chan and T. Kuwana, J. Electroanal. Chem., 1980, 110, 93 CrossRef CAS.
  20. G.-X. Wan, K. Shigehara, E. Tsuchida and F. C. Anson, J. Electroanal. Chem., 1984, 179, 239 CrossRef CAS.
  21. S. E. J. Bell, M. Devenney, J. Grimshaw, J. Trocha-Grimshaw and J. J. McGarvey, J. Chem. Soc., Chem. Commun., 1992, 221 RSC.
  22. W. E. Hanby, S. G. Waley and J. Watson, J. Chem. Soc., 1950, 3239 RSC.
  23. E. R. Blout and R. H. Karlson, J. Am. Chem. Soc., 1956, 78, 941 CrossRef CAS.
  24. M. Goodman, E. Pelggion, M. Szwarc and C. H. Bamford, Macromolecules, 1977, 10, 1299 CrossRef CAS.
  25. A. Costani, G. d'Este, E. Pelggion and E. Scoffone, Biopolymers, 1966, 4, 595 CrossRef.
  26. H. Fujita, A. Teramoto, T. Yamashita, K. Okita and S. Ikeda, Biopolymers, 1966, 4, 781 CAS; P. Doty, J. H. Bradbury and A. H. Holtzer, J. Am. Chem. Soc., 1956, 78, 947 CrossRef CAS Their combined results yield the equation: log([η]/dm3 g–1)=–5.09 ± 0.21 +(0.77 ± 0.04)log M.
  27. H. Tanaka, T. Endo and M. Okawara, Nippon Kagaku Kaishi, 1973, 1770 CAS.
  28. A. Kotai, Acta. Chim. Acad. Sci. Hung., 1967, 54, 65 CAS.
  29. A. Kotai, Gy. Szokan, I. Ferencz and M. Almas, Acta. Chim. Acad. Sci. Hung., 1969, 62, 293 CAS.
  30. M. Momenteau, Biochim. Biophys. Acta, 1973, 304, 814 CrossRef CAS.
  31. F. A. Walker, M.-L. Lo and M. T. Ree, J. Am. Chem. Soc., 1976, 98, 5552 CrossRef CAS.
  32. R. Quinn, M. Nappa and J. S. Valentine, J. Am. Chem. Soc., 1982, 104, 2588 CrossRef CAS.
  33. E. B. Fleisher and T. S. Srivastava, J. Am. Chem. Soc., 1969, 91, 2403 CrossRef CAS.
  34. D. K. Geiger, Y. J. Lee and W. R. Scheidt, J. Am. Chem. Soc., 1984, 106, 6339 CrossRef CAS.
  35. W. J. Albery, M. G. Boutelle, P. J. Colby and A. R. Hillman, J. Electroanal. Chem., 1982, 133, 135 CrossRef CAS; M. F. Dautaras, E. F. Bowden and J. P. Evans, J. Electroanal. Chem., 1987, 219, 71 CrossRef CAS.
  36. J. Grimshaw and J. Trocha-Grimshaw, J. Chem. Soc., Chem. Commun., 1990, 157 RSC.
  37. S.-M. Oh and L. R. Faulkner, J. Am. Chem. Soc., 1989, 111, 5613 CrossRef CAS.
  38. A. J. Kelly, T. Ohsaka, N. Oyama, R. J. Forster and J. G. Vos, J. Electroanal. Chem., 1990, 287, 185 CrossRef CAS.
  39. A. R. Hillman and S. Brukenstein, J. Chem. Soc., Faraday Trans., 1993, 89, 339 RSC.
  40. S.-M. Oh and L. R. Faulkner, J. Electroanal. Chem., 1989, 269, 77 CrossRef CAS.
  41. A. Bettelheim, D. Ozer, R. Harth and R. W. Murray, J. Electroanal. Chem., 1989, 266, 93 CrossRef CAS.
  42. A. Bettelheim, B. A. White, B. A. Raybuck and R. W. Murray, Inorg. Chem, 1987, 26, 1009 CrossRef; A. Bettelheim, B. A. White and R. W. Murray, J. Electroanal. Chem., 1987, 217, 271 CrossRef CAS.
  43. J. Geibel, J. Cannon, D. Campbell and T. G. Traylor, J. Am. Chem. Soc., 1978, 100, 3575 CrossRef CAS.
  44. J. E. Falk, Porphyrins and Metalloporphyrins, Elsevier, Amsterdam, 1964, p. 179 Search PubMed.
  45. A. D. Adler, F. R. Longo, F. Kampas and J. J. Kim, J. Inorg. Nucl. Chem., 1970, 32, 2443 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.