Chiroptical features and luminescence behaviour of macrocyclic tetra(4-quinolyl)-complexes: surprising absence of exciton coupling

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Linda J. Govenlock, Judith A. K. Howard, Janet M. Moloney, David Parker, Robert D. Peacock and Giuliano Siligardi


Abstract

The C4-symmetric (S[hair space])-tetra(4-quinolyl) tetraamide derivative of dota has been prepared. The sodium complex has been characterised by X-ray crystallography and although the quinolyl groups are appropriately oriented for exciton coupling in the solid-state, in solution no evidence for coupling was found for the free ligand nor its protonated, Na, Ca or Eu complexes. Instead, excimer formation was observed in emission consistent with a coplanar arrangement of the quinolyl groups.


References

  1. J. H. Perlstein, in Electrical Properties of Polymers, ed. D. Seaner, Academic Press, New York, 1982, pp. 59–91 Search PubMed.
  2. T. Nishimi, M. Tachikawa, T. Meada, Y. Ishikawa and T. Kunitake, Chem. Lett., 1994, 331 CAS; D. G. Whitten, Acc. Chem. Res., 1993, 26, 502 CrossRef CAS.
  3. N. Harada and K. Nakanishi, Circular Dichroic Spectroscopy—Exciton Coupling in Organic Stereochemistry, University Science Books, Mill Valley, CA, 1983 Search PubMed; G. E. Ficken, J. Photogr. Sci., 1973, 21, 11 Search PubMed.
  4. K. Liang, M. S. Farahat, J. Perlstein, K.-Y. Law and D. G. Whitten, J. Am. Chem. Soc., 1997, 119, 830 CrossRef CAS.
  5. S. F. Mason, Molecular Optical Activity and the Chiral Discriminations, Cambridge University Press, Cambridge, 1982 Search PubMed.
  6. J. Canceill, A. Collet, G. Gotarelli and P. Palmieri, J. Am. Chem. Soc., 1987, 109, 6454 CrossRef CAS.
  7. S. Matile, N. Berova, K. Nakanishi, J. Fleischhauer and R. W. Woody, J. Am. Chem. Soc., 1996, 118, 5798 CrossRef CAS.
  8. A. Harriman, V. Heitz and J.-P. Sauvage, J. Phys. Chem., 1993, 97, 5940 CrossRef CAS.
  9. S. F. Mason and B. J. Heart, J. Chem. Soc., Dalton Trans., 1973, 949 RSC.
  10. R. S. Dickins, J. A. K. Howard, J. M. Moloney, D. Parker, R. D. Peacock and G. Siligardi, Chem. Commun., 1997, 1747 RSC.
  11. R. S. Dickins, J. A. K. Howard, C. L. Maupin, J. M. Moloney, D. Parker, R. D. Peacock, J. P. Riehl and G. Siligardi, New J. Chem., 1998, 891 RSC.
  12. D. Parker and R. J. Taylor, Tetrahedron, 1987, 46, 5451 CrossRef CAS; D. Parker, Chem. Rev., 1991, 91, 1441 CrossRef CAS.
  13. J. R. Platt, J. Chem. Phys., 1949, 17, 484 CrossRef CAS.
  14. R. Kataky, K. E. Matthes, P. E. Nicholson, D. Parker and H.-J. Buschmann, J. Chem. Soc., Perkin Trans. 2, 1990, 1425 RSC.
  15. G. A. Epling and K.-Y. Lin, J. Heterocycl. Chem., 1984, 21, 1205 CAS.
  16. R. P. Blaunstein and R. S. Gant, Photochem. Photobiol., 1973, 18, 347 CAS.
  17. G. M. Sheldrick( 1996), SADABS, Program for the correction of area detector data, University of Göttingen, Germany.
  18. Bruker Analytical X-ray Instruments ( 1998) SHELX96. Suite of programs for the data reduction, solution and refinement of crystal structures.
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