A macrocyclic [60]fullerene–porphyrin dyad involving π–π stacking interactions

Abstract

The very regioselective twofold cyclopropanation of C₆₀ with a porphyrin bismalonate leads to a C₂ symmetrical [60]fullerene–porphyrin dyad with pronounced electronic interactions between the two π–π stacked chromophores.

References

1. E. Dietel, A. Hirsch, J. Zhou and A. Rieker, J. Chem. Soc., Perkin Trans. 2, 1998, 1357.
2. J.-F. Nierengarten, V. Gramlich, F. Cardullo and F. Diederich, Angew. Chem., 1996, 108, 2242.
3. F. Li, K. Yang, J. S. Tyhonas, K. A. MacCrum and J. S. Lindsey, Tetrahedron, 1997, 53, 12339.
4. (a) C. Bingel, Chem. Ber., 1993, 126, 1957; (b) C. Bingel, presentation at the meeting ‘New Perspectives in Fullerene Chemistry and Physics’, October 10–12, 1994, Rome.
5. F. Djojo, A. Herzog, I. Lamparth, F. Hampel and A. Hirsch, Chem. Eur. J., 1996, 2, 1537.
6. (a) B. Röder, Biophys. Chem., 1990, 35, 303; (b) S. Oelkers, SPIE Proc., 1994, 2325, 116; (c) B. Röder, C. Zimmermann and R. Herter, SPIE Proc., 1994, 2325, 80; (d) W. Spiller and S. Hackbarth, J. Porphyrins Phthalocyanines, 1998, 2, 145.
7. J. W. Arbogast, A. P. Darmanyan, C. S. Foote, Y. Rubin, F. Diederich, M. M. Alvarez, S. J. Anz and R. L. Whetten, J. Phys. Chem., 1991, 95, 11.