Thiophenotribenzoporphyrazines: novel near-IR absorbing dyes

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Michael J. Cook and Ali Jafari-Fini


Abstract

The first examples of thiophenotribenzoporphyrazines have been synthesised. The compounds obtained bear either six or eight alkyl chains and show Q-band absorptions which are red shifted relative to analogous phthalocyanine derivatives. Their formulations as spin coated films show broad band absorption extending into the near IR. The compounds exhibit discotic mesophase behaviour.


References

  1. (a) Phthalocyanines—Properties and Applications, ed. C. C. Leznoff and A. B. P. Lever, VCH, New York, 1989 Search PubMed; (b) M. J. Cook, in Spectroscopy of New Materials, eds. R. J. H. Clark and R. E. Hester, Wiley, Chichester, 1993, p. 87 Search PubMed.
  2. (a) N. Kobayashi, in Phthalocyanines—Properties and Applications, eds. C. C. Leznoff and A. B. P. Lever, VCH, New York, 1993, vol. 2, p. 101 Search PubMed; (b) M. J. Cook, A. J. Dunn, S. D. Howe, A. J. Thomson and K. J. Harrison, J. Chem. Soc., Perkin Trans. 1, 1988, 2453 RSC.
  3. (a) R. Bonnett, Chem. Soc. Rev., 1995, 19 RSC; (b) P. Margaron, R. Langlois, J. E. van Lier and S. Gaspard, J. Photochem. Photobiol. B: Biol., 1992, 14, 187 CrossRef CAS.
  4. (a) P. A. Hunt, in Chemistry and Technology of Printing and Imaging Systems, ed. P. Gregory, Blackie Academic & Professional, Glasgow, 1996, p. 168 Search PubMed; (b) R. Ao, L. Kummerl and D. Haarer, Adv. Mater., 1995, 7, 495 CrossRef CAS.
  5. P. Gregory, High-Technology Applications of Organic Colorants, Plenum Press, New York, 1991, p. 45 Search PubMed.
  6. R. P. Linstead, E. G. Noble and J. M. Wright, J. Chem. Soc., 1937, 911 RSC.
  7. J. Morel, C. Paulmier and P. Pastour, C. R. Acad. Sci. Paris, Ser. C, 1968, 266, 1300 Search PubMed.
  8. I. Chambrier, M. J. Cook, S. J. Cracknell and J. McMurdo, J. Mater. Chem., 1993, 3, 841 RSC.
  9. (a) A. S. Cherodian, A. N. Davies, R. M. Richardson, M. J. Cook, N. B. McKeown, A. J. Thomson, J. Feijoo, G. Ungar and K. J. Harrison, Mol. Cryst. Liq. Cryst., 1991, 196, 103 CrossRef CAS; (b) J. Simon and P. Bassoul, in ref. 2(a), p. 223; (c) D. W. Bruce, J. Chem. Soc., Dalton Trans., 1993, 2983 RSC.
  10. (a) J. A. Elvidge, J. H. Golden and R. P. Linstead, J. Chem. Soc., 1957, 2466 RSC; (b) N. Kobayashi, R. Kondo, S. Nakajima and T. Osa, J. Am. Chem. Soc., 1990, 112, 9640 CrossRef CAS; (c) T. F. Baumann, J. W. Sibert, M. M. Olmstead, A. G. M. Barrett and B. M. Hoffman, J. Am. Chem. Soc., 1994, 116, 2639 CrossRef CAS; (d) N. Kobayashi, M. Togashi, T. Osa, K. Ishii, S. Yamauchi and H. Hino, J. Am. Chem. Soc., 1996, 118, 1073 CrossRef CAS.
  11. S. M. Critchley, M. R. Willis, M. J. Cook, J. McMurdo and Y. Maruyama, J. Mater. Chem., 1992, 2, 157 RSC.
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