Quaterrylenebis(dicarboximide)s: near infrared absorbing and emitting dyes

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

Yves Geerts, Heribert Quante, Harald Platz, Rainer Mahrt, M. Hopmeier, Arno Böhm and Klaus Müllen


New ladder-type chromophores, the quaterrylenebis(dicarboxdiimide)s 2, 18 and 23, have been synthesised which, despite their extended π-system, exhibit good solubility in organic solvents and film forming properties when adequately substituted. These unprecedented dyes, which absorb and even emit light in the NIR window, are also characterized by oustanding chemical, thermal and photochemical stability with regard to their absorption range. The potential formation of J-aggregates in strongly acidic media has been investigated and has been ruled out by combined 1H NMR and UV-VIS-NIR spectroscopy experiments. In addition, their photophysical and electrochemical characteristics have been explored and are discussed.

References

  1. J. Fabian and R. Zahradnik, Angew. Chem., 1989, 101, 693 CAS; Angew. Chem., Int. Ed. Engl., 1989, 28, 677 Search PubMed; J. Fabian, M. Nakazumi and T. J. Matsuoka, Chem. Rev., 1992, 92, 1197 Search PubMed.
  2. Y. Suzuki, in Infrared Absorbing DyesPlenum Press, New York, 1990 Search PubMed.
  3. Y. Nagao and T. Misono, Dyes Pigm., 1984, 5, 171 CrossRef CAS.
  4. A. Rademacher, S. Märkle and H. Langhals, Chem. Ber., 1982, 115, 2927 CrossRef CAS.
  5. H. Langhals, Heterocycles, 1995, 40, 477 CrossRef CAS.
  6. M. Burghard, C. Fischer, M. Schmelzer, S. Roth, M. Hanack and W. Göpel, Chem. Mater., 1995, 7, 2104 CrossRef CAS.
  7. D. Schlettwein, D. Wöhrle, E. Karmann and U. Melville, Chem. Mater., 1994, 6, 3 CrossRef CAS.
  8. H. O. Loutfy, A. M. Hor, P. Kazmaier and M. Tam, J. Imaging Sci., 1989, 33, 151 Search PubMed.
  9. M. P. O'Neil, M. P. Niemczyk, W. A. Svec, D. Gosztola, G. L. Gaines III and M. R. Wasielewski, Science, 1992, 257, 63 CrossRef CAS.
  10. R. Gvishi, R. Reisfeld and Z. Bursheim, Chem. Phys. Lett., 1993, 213, 338 CrossRef CAS.
  11. G. Seybold and G. Wagenblast, Dyes Pigm., 1989, 11, 303 CrossRef.
  12. E. Clar, W. Kelly and R. M. Laird, Monatsh. Chem., 1956, 87, 391 CAS.
  13. E. Clar and J. C. Speakman, J. Chem. Soc., 1958, 2492 RSC.
  14. (a) K.-H. Koch and K. Müllen, Chem. Ber., 1991, 124, 2091 CrossRef CAS; A. Bonhen, K.-H. Koch, W. Lüttke and K. Müllen, Angew. Chem., Int. Ed. Engl., 1990, 29, 525 CrossRef; (b) S. De Backer, M. R. Negri, S. De Feyter, G. B. Dutt, M. Ameloot, F. C. De Schryver, K. Müllen and F. Holtrup, Chem. Phys. Lett., 1995, 233, 538 CrossRef CAS; A. Schmidt, N. R. Armstrong, C. Goeltner and K. Müllen, J. Phys. Chem., 1994, 98, 11780 CrossRef CAS; S. De Backer, G. B. Dutt, M. Ameloot, F. C. De Schryver, K. Müllen and F. Holtrup, J. Phys. Chem., 1996, 100, 512 CrossRef; Y. H. Meyer, P. Plaza and K. Müllen, Chem. Phys. Lett., 1997, 264, 643 CrossRef CAS.
  15. F. Holtrup, G. R. Müller, H. Quante, S. De Feyter, F. C. De Schryver and K. Müllen, Chem. Eur. J., 1997, 3, 219 CrossRef CAS.
  16. H. Quante, Y. Geerts and K. Müllen, Chem. Mater., 1997, 9, 495 CrossRef CAS.
  17. H. Quante and K. Müllen, Angew. Chem., Int. Ed. Engl., 1995, 34, 1323 CrossRef CAS; H. Quante, Ph.D. Dissertation, Mainz, 1995.
  18. Y. Nagao and T. Misono, Bull. Chem. Soc. Jpn., 1981, 54, 1191 CAS.
  19. Y. Nagao, Y. Abe and T. Misono, Dyes Pigm., 1991, 16, 19 CrossRef CAS.
  20. T. Yamamoto, A. Morita, Y. Miyazaki, Y. Maruyama, H. Wakayama, Z. Zhou, Y. Nakamura and T. Kanbara, Macromolecules, 1992, 25, 1214 CrossRef CAS.
  21. H. Azizian, C. Eaborn and A. Pidcock, J. Organomet. Chem., 1981, 215, 49 CrossRef CAS.
  22. (a) J. K. Stille, Angew. Chem., 1986, 98, 504 CAS; Angew. Chem., Int. Ed. Engl., 1986, 25, 508 Search PubMed; (b) I. P. Beletskaya, J. Organomet. Chem., 1983, 250, 551 CrossRef CAS.
  23. Ullmanns Enzyclopädie der technischen Chemie, 4th edn., Verlag Chemie, Weinheim, 1974, vol. 18, p. 686 Search PubMed.
  24. W. Bradly and F. W. Pexton, J. Chem. Soc., 1954, 4432 RSC.
  25. D. Dotcheva, M. Klapper and K. Müllen, Macromol. Chem. Phys., 1994, 195, 1905 CrossRef CAS; H. Quante, P. Schlichting, U. Rohr, Y. Geerts and K. Müllen, Macromol. Chem. Phys., 1996, 197, 4029 CrossRef CAS.
  26. R. H. Mitchell, Y.-H. Lai and R. V. Williams, J. Org. Chem., 1979, 44, 4733 CrossRef CAS.
  27. I. T. Storie and F. Sontheimer, Tetrahedron Lett., 1978, 19, 4567 CrossRef.
  28. (a) M. Iyoda, M. Sakaitami, H. Otsuka and M. Oda, Chem. Lett., 1985, 127 CAS; (b) M. Iyoda, M. Sakaitami, A. Kojima and M. Oda, Tetrahedron Lett., 1985, 26, 3719 CrossRef CAS.
  29. A. S. Kende, L. S. Liebeskind and D. Braitsch, Tetrahedron Lett., 1975, 16, 3375 CrossRef.
  30. S. Prathapan, T. E. Johnson and J. Lindsey, J. Am. Chem. Soc., 1993, 115, 7519 CrossRef CAS.
  31. M. Emmelius, G. Pawlowski and H. W. Vollmann, Angew. Chem., 1989, 101, 1475.
  32. (a) G. Scheibe, Angew. Chem., 1937, 50, 51; (b) G. Scheibe, Kolloid Zeitsch., 1938, 82, 1 Search PubMed; (c) E. E. Jelley, Nature, 1936, 138, 1009 CrossRef CAS; (d) E. Jelley, Nature, 1937, 139, 631 CrossRef CAS; (e) S. F. Mason, Proc. Chem. Soc., 1964, 119 RSC; (f) D. Möbius, Adv. Mater., 1995, 7, 437 CrossRef.
  33. K. A. Connors, Binding Constants, Wiley, New York, 1987 Search PubMed.
  34. Y. Geerts and K. Müllen, Novel Light Emitting Dyes, Oligomers, Polymers, and Organic-Inorganic Hybrid Materials, in Applied Fluorescence in Chemistry, Biology, and Medicine, ed. W. Rettig, B. Strehmel and S. Schrader, Springer Verlag, in the press Search PubMed.
  35. S. J. Strickler and R. A. Berg, J. Chem. Phys., 1962, 37, 814 CrossRef CAS.
  36. Electronic processes in organic crystals, ed. M. Pope and C. E. Swenberg, Clarendon Press, Oxford, New York, 1982 Search PubMed.
  37. A. J. Bard, personnal communication.