Photophysical properties of 2,3,6,7,10,11-hexakis(n-hexylsulfanyl)triphenylene and 2,3,6,7,10,11-hexakis(n-hexylsulfonyl)triphenylene in solution

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Dorrit Baunsgaard, Mogens Larsen, Niels Harrit, John Frederiksen, Robert Wilbrandt and Henrik Stapelfeldt


Abstract

The photophysical properties of 2,3,6,7,10,11-hexakis(n-hexylsulfanyl)triphenylene and 2,3,6,7,10,11-hexakis(n-hexylsulfonyl)triphenylene have been investigated by absorption, fluorescence and phosphorescence spectroscopy and compared with parent triphenylene and 2,3,6,7,10,11-hexakis(n-hexyloxy)triphenylene. It is concluded that alkylsulfanyl substituents interact more strongly with the triphenylene core than alkylsulfonyl and alkyloxy substituents, as revealed by the absorption and emission spectra as well as by the rate constants for the radiative and non-radiative processes. In terms of photophysical properties, 2,3,6,7,10,11-hexakis(n-hexylsulfonyl)triphenylene and 2,3,6,7,10,11-hexakis(n-hexyloxy)triphenylene are very much alike. 2,3,6,7,10,11-Hexakis(n-hexylsulfanyl)triphenylene aggregates in cyclohexane at concentrations above ca. 10-3M.


References

  1. C. Destrade, Nguyen Huu Tinh, H. Gasparoux, J. Malthête and A. M. Levelut, Mol. Cryst. Liq. Cryst., 1981, 71, 111 CAS.
  2. C. Destrade, P. Foucher, H. Gasparoux, Nguyen Huu Tinh, A. M. Levelut and J. Malthête, Mol. Cryst. Liq. Cryst., 1984, 106, 121 CrossRef CAS.
  3. J. Billard, J. C. Dubois, Nguyen Huu Tinh and A. Zahn, Nouv. J. Chim., 1978, 2, 535 Search PubMed.
  4. C. Destrade, M. C. Mondon and J. Malthête, J. Phys. (Paris), 1979, 40, 17 Search PubMed.
  5. D. Markovitsi, I. Lécuyer, P. Lianos and J. Malthête, J. Chem. Soc., Faraday Trans., 1991, 87, 1785 RSC.
  6. D. Markovitsi, F. Rigaut and M. Mouallem, Chem. Phys. Lett., 1987, 135, 236 CrossRef CAS.
  7. O. Braitbart, R. Sasson and A. Weinreb, Mol. Cryst. Liq. Cryst., 1988, 159, 233 CAS.
  8. D. Markovitsi, A. Germain, P. Millié, P. Lécuyer, L. K. Gallos, P. Argyrakis, H. Bengs and H. Ringsdorf, J. Phys. Chem., 1995, 99, 1005 CrossRef CAS.
  9. D. Adam, F. Closs, T. Frey, D. Funhoff, D. Haarer, H. Ringsdorf, P. Schuhmacher and K. Siemensmeyer, Phys. Rev. Lett., 1993, 70, 457 CrossRef CAS.
  10. F. Closs, K. Siemensmeyer, T. Frey and D. Funhoff, Liq. Cryst., 1993, 14, 629 CrossRef CAS.
  11. B. Kohne, W. Poules and K. Praefcke, Chem. Z., 1984, 108, 113 Search PubMed.
  12. K. Praefcke, B. Kohne, W. Poules and E. Poetsch, Ger. Pat. DE 3346980A1, 1983 Search PubMed.
  13. D. Adam, P. Schuhmacher, J. Simmerer, L. Häussling, K. Siemensmeyer, K. H. Etzbach, H. Ringsdorf and D. Haarer, Nature (London), 1994, 371, 141 CrossRef CAS.
  14. A. van der Craats, J. M. Warman, M. P. de Haas, D. Adam, J. Simmerer, D. Haarer and P. Schuhmacher, Adv. Mater., 1996, 8, 823 CrossRef CAS.
  15. F. D. Saeva and G. A. Reynolds, Mol. Cryst. Liq. Cryst., 1986, 132, 29 CAS.
  16. E. Y. Sheu, K. S. Liang and L. Y. Chiang, J. Phys. (Paris), 1989, 50, 1279 Search PubMed.
  17. D. Markovitsi, H. Bengs and H. Ringsdorf, J. Chem. Soc., Faraday Trans., 1992, 88, 1275 RSC.
  18. T. Sato, Y. Goto and K. Hata, Bull. Chem. Soc. Jpn., 1967, 40, 1994 CAS.
  19. T. Sato, S. Shimada and K. Hata, Bull. Chem. Soc. Jpn., 1969, 42, 766 CAS.
  20. T. Sato, S. Shimada and K. Hata, Bull. Chem. Soc. Jpn., 1971, 44, 2484 CAS.
  21. J. R. Lakowicz, Principles of Fluorescence Spectroscopy, Plenum Press, New York, 1983, p. 53 Search PubMed.
  22. J. R. Lakowicz, H. Cherek and A. Balter, J. Biochem. Biophys. Methods, 1981, 5, 131 CrossRef CAS.
  23. J. B. Birks, Photophysics of Aromatic Molecules, Wiley-Interscience, London, 1970, pp. 103, 104 Search PubMed.
  24. M. Zander, Angew. Chem., Int. Ed. Engl., 1965, 4, 930 CrossRef.
  25. R. S. Becker, Theory and Interpretation of Fluorescence and Phosphorescence, Wiley Interscience, New York, 1969, p. 54 Search PubMed.
  26. C. Hansch, A. Leo and R. W. Taft, Chem. Rev., 1991, 91, 165 CrossRef CAS.
  27. H. H. Jaffé and M. Orchin, Theory and Applications of Ultraviolet Spectroscopy, Wiley, New York, 1962 Search PubMed.
  28. R. S. Becker, A. D. Jordan and J. Kolc, J. Chem. Phys., 1972, 59, 4024 CrossRef.
  29. R. S. Becker, I. S. Singh and E. A. Jackson, J. Chem. Phys., 1963, 38, 2144 CrossRef CAS.
  30. M. Nakayama, H. Shimizu, S. Akiyama, Y. Komura, K. Suzuki and Y. J. Ihaya, Nippon Kag. Kai., 1996, 3, 231 Search PubMed.
  31. G. W. King, Spectroscopy and Molecular Structure, Holt, Rinehart and Winston, New York, 1965, pp. 404–411 Search PubMed.
  32. N. J. Turro, Modern Molecular Photochemistry, Benjamin/Cummings, Menlo Park, 1978, p. 183 Search PubMed.
  33. N. Nishi, K. Matsui, M. Kinoshita and J. Higuchi, Mol. Phys., 1979, 38, 1 CAS.
  34. G. G. Giachino and D. R. Kearns, J. Chem. Phys., 1970, 53, 3886 CrossRef CAS.
  35. M. Zander, Z. Naturforsch., A, 1984, 39, 1145.
  36. D. Markovitsi, C. Jallabert, H. Strzelecka and M. Veber, J. Chem. Soc., Faraday Trans., 1990, 86, 2819 RSC.
  37. S. L. Murov, I. Carmichael and G. L. Hug, Handbook of photochemistry, Marcel Dekker, New York, 1993, p. 51 Search PubMed.
  38. H. W. Offen and D. E. Hein, J. Chem. Phys., 1969, 50, 5274 CrossRef CAS.
  39. C. Ecoffet, D. Markovitsi, C. Jallabert, H. Strzelecka and M. Veber, J. Chem. Soc., Faraday Trans., 1992, 88, 3007 RSC.