Dynamic cis/trans isomerisation in a porphyrin–fullerene conjugate

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

Jean-François Nierengarten and Jean-François Nicoud


Abstract

A porphyrin with two fullerene substituents is prepared by condensation of a C60 aldehyde derivative and dipyrrol-2-yl methane and by reaction of a preconstructed porphyrin with C60 itself; it is obtained as a mixture of two conformers in slow equilibrium, as shown by a variable temperature NMR study.


References

  1. P. A. Liddell, J. P. Sumida, A. N. Macpherson, L. Noss, G. R. Seely, K. N. Clark, A. L. Moore, T. A. Moore and D. Gust, Photochem. Photobiol., 1994, 60, 537 Search PubMed.
  2. H. Imahori, K. Hagiwara, T. Akiyama, S. Taniguchi, T. Okada and Y. Sakata, Chem. Lett., 1995, 265 CAS; T. Drovetskaya, C. A. Reed and P. Boyd, Tetrahedron Lett., 1995, 36, 7971 CrossRef CAS; H. Imahori and Y. Sakata, Chem. Lett., 1996, 199 CAS; H. Imahori, K. Hagiwara, M. Aoki, T. Akiyama, S. Taniguchi, T. Okada, M. Shirakawa and Y. Sakata, J. Am. Chem. Soc., 1996, 118, 11 771 CrossRef CAS; M. G. Ranasinghe, A. M. Olivier, D. F. Rothenfluh, A. Salek and M. N. Paddon-Row, Tetrahedron Lett., 1996, 37, 4797 CrossRef CAS; H. Imahori, K. Yamada, M. Hasegawa, S. Taniguchi, T. Okada and Y. Sakata, Angew. Chem., Int. Ed. Engl., 1997, 36, 2626 CrossRef CAS; I. G. Safanov, P. S. Baran and D. I. Schuster, Tetrahedron Lett., 1997, 38, 8133 CrossRef.
  3. H. Imahori and Y. Sakata, Adv. Mater., 1997, 9, 537 CAS.
  4. J.-F. Nierengarten, C. Schall and J.-F. Nicoud, Angew. Chem., in the press Search PubMed.
  5. R. Young and C. K. Chang, J. Am. Chem. Soc., 1985, 107, 898 CrossRef CAS.
  6. J.-F. Nierengarten, V. Gramlich, F. Cardullo and F. Diederich, Angew. Chem., Int. Ed. Engl., 1996, 35, 2101 CrossRef CAS; J.-F. Nierengarten, A. Herrmann, R. R. Tykwinski, M. Rüttimann, F. Diederich, C. Boudon, J.-P. Gisselbrecht and M. Gross, Helv. Chim. Acta, 1997, 80, 293 CrossRef CAS; J.-F. Nierengarten, T. Habicher, R. Kessinger, F. Cardullo, F. Diederich, V. Gramlich, J.-P. Gisselbrecht, C. Boudon and M. Gross, Helv. Chim. Acta, 1997, 80, 2238 CrossRef CAS.
  7. H. Günther, NMR-Spektroskopie, 2nd edn., Thieme, Stuttgart, 1983 Search PubMed.
  8. E. L. Eliel, S. H. Wilen and L. N. Mander, Stereochemistry of Organic Compounds, Wiley, New York, 1994 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.