Synthesis of a phthalocyanine derivative containing easily oxidised sterically-hindered phenolic substituents

Abstract

A novel phthalocyanine containing four redox-active 3,5-di-tert-butyl-4-hydroxyphenyl substituents is readily oxidised in aerated, basified solution to give a complex product mixture; the oxidation is apparently localised on the phenolic moieties without disturbing the structure of the phthalocyanine core.

References

1. N. B. McKeown, Phthalocyanine Materials: Synthesis, Structure and Function, Cambridge University Press, Cambridge, in the press.
2. Z. Jin, K. Nolan, C. R. McArthur, A. B. P. Lever and C. C. Leznoff, J. Organomet. Chem., 1994, 468, 205.
3. T. G. Linβen, K. Durr, M. Hanack and A. Hirsch, J. Chem. Soc., Chem. Commun., 1995, 103.
4. M. J. Cook, G. Cooke and A. Jafarifini, Chem. Commun., 1996, 1925.
5. T. G. Traylor, K. B. Kolan, R. Hildreth and T. A. Evans, J. Am. Chem. Soc., 1983, 105, 6149; L. R. Milgrom, Tetrahedron, 1983, 39, 3895.
6. A. J. Golder, L. R. Milgrom, K. B. Nolan and D. C. Povey, J. Chem. Soc., Chem. Commun., 1989, 1751.
7. W. O. Siegl, J. Heterocycl. Chem., 1981, 18, 1613; S. A. Mikhalenko, V. M. Derkacheva and E. A. Luk'yanets, Zh. Obshch. Khim., 1981, 51, 1650; I. Guerol, V. Ahsen and O. Bekaroghi, J. Chem. Soc., Dalton Trans., 1994, 497.
8. I. N. Chechulina, E. R. Milaeva, A. I. Prokofev and Y. G. Bundel, Zh. Obshch. Khim., 1988, 58, 1075; J. Wright and E. C. Jorgensen, J. Org. Chem., 1968, 33, 1245; G. P. Stahly, J. Org. Chem., 1985, 50, 3091.
9. C. C. Leznoff, S. Greenburg, S. M. Marcuccio, P. C. Minor, P. Seymour and A. B. P. Lever, Inorg. Chim. Acta, 1984, 89, L35.
10. A. Nishinaga, T. Itahara and T. Matsuura, J. Am. Chem. Soc., 1978, 100, 1826; A. Nishinaga, T. Shimizu and T. Matsuura, J. Org. Chem., 1979, 44, 2983.
11. P. Humberstone, G. J. Clarkson, N. B. McKeown and K. E. Treacher, J. Mater. Chem., 1996, 6, 315.