Pyridino[3,4]tribenzoporphyrazines: edge-to-faceversus face-to-face assemblies among phthalocyanine analogues

Abstract

The metal-free and nickel derivatives of hexaoctylpyridino[3,4]tribenzoporphyrazine generate conventional face-to-face aggregates in solution, exhibit columnar mesophases and form columnar assemblies upon evaporation of solutions. By contrast, the zinc derivative forms alternative edge-to-face complexes through axial ligation of one molecule to the zinc atom of another, a process which inhibits mesophase behaviour and leads to new types of visible region absorption signatures.

References

1. Phthalocyanines—Properties and Applications, ed. C. C. Leznoff and A. B. P. Lever, VCH, New York, 1989.
2. M. J. Cook, in Spectroscopy of New Materials, ed. R. J. H. Clark and R. E. Hester, Wiley, Chichester, 1993, p 87.
3. J. Simon and P. Bassoul, in Phthalocyanines—Properties and Applications, ed. C. C. Leznoff and A. B. P. Lever, VCH, New York, 1993, vol. 2, p 223.
4. See, for example, R. Mason, G. A. Williams and P. E. Fielding, J. Chem. Soc., Dalton Trans., 1979, 676.
5. A. D. Pomogailo and D. Wöhrle, in Macromolecule-Metal Complexes, ed. F. Ciardelli, E. Tsuchida and D. Wöhrle, Springer, Berlin-Heidleberg, 1996, p 11; M. Hanack and M. Lang, Adv. Mater., 1994, 6, 819.
6. E.g. A. M. Shachter, E. B. Fleischer and R. C. Haltiwanger, J. Chem. Soc., Chem. Commun., 1988, 960; E. B. Fleischer and A. M. Shachter, Inorg. Chem., 1991, 30, 3763; C. A. Hunter and L. D. Sarson, J. Chem. Soc., Chem. Commun., 1994, 33, 2313; K. Funatsu, A. Kimura, T. Immanura and Y. Sasaki, Chem. Lett., 1995, 765; S. Anderson, H. L. Anderson, A. Bashall, M. McPartlin and J. K. M. Sanders, Angew. Chem., Int. Ed. Engl., 1995, 34, 1096; E. Alessio, M. Macchi, S. Heath and L. G. Marzilli, Chem. Commun., 1996, 1411.
7. R. P. Linstead, E. G. Noble and J. M. Wright, J. Chem. Soc., 1937, 911.
8. M. Yokote and F. Shibamiya, Kogyo Kagaku Zasshi, 1959, 62, 224 (Chem. Abstr., 1961, 55, 24 019); M. Yokote, F. Shibamiya and H. Hayakawa, Yuki Gosei Kagaka Kyokai-Shi, 1965, 23, 151 (Chem. Abstr., 1965, 62, 14 859); K. Sakamoto, M. Yoshioka and F. Shibamiya, J. Jpn. Soc. Colour Mater., 1985, 58, 121 (Chem. Abstr., 1985, 103, 38 688); K. Sakamoto and F. Shibamiya, J. Jpn. Soc. Colour Mater., 1986, 59, 517 (Chem. Abstr., 1987, 106, 103 797).
9. I. Chambrier, M. J. Cook, S. J. Cracknell and J. McMurdo, J. Mater. Chem., 1993, 3, 841.
10. Cf. N. Kobayashi, M. Togashi, T. Osa, K. Ishii, S. Yamauchi and H. Hino, J. Am. Chem. Soc., 1996, 118, 1073; M. J. Cook and A. Jafari-Fini, J. Mater. Chem., 1997, 7, 5.
11. C. F. van Nostrum, S. J. Picken and R. J. M. Nolte, Angew. Chem., Int. Ed. Engl., 1994, 33, 2173; C. F. van Nostrum, S. J. Picken, A.-J. Schouten and R. J. M. Nolte, J. Am. Chem. Soc., 1995, 117, 9957.
12. 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.