Skip to main content
SpringerLink
Log in

Photophysical study of bay substituted perylenediimides

  • Paper
  • Published:
Photochemical & Photobiological Sciences Aims and scope Submit manuscript

Abstract

A detailed investigation of the photophysical properties of a series of perylenediimide systems bearing three different types of bay substituents is presented. Single photon timing and femtosecond transient absorption experiments reveal that the dynamics of interconversion between two conformational arrangements of these substituents occurs with a time constant of 550 ps. In addition, charge transfer from the electron-rich units attached to the bay area of the electron-poor perylenediimide core is observed. This process leads to a fast non-radiative deactivation of the locally excited state of the perylenediimide in polar solvents. When the experimental results of the investigated systems are compared we observe a shift from a conformational dynamics towards competitive excited state processes involving charge transfer in the -meta and -para substituted perylenediimidechromophore.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. P. F. Barbara, A. J. Gesquiere, S. J. Park and Y. J. Lee, Acc. Chem. Res., 2005, 38, 602–610.

    Article  CAS  PubMed  Google Scholar 

  2. F. Schindler, J. M. Lupton, J. Müller, J. Feldmann and U. Scherf, Nat. Mater., 2006, 5, 141–146.

    Article  CAS  PubMed  Google Scholar 

  3. M. Van Der Auweraer and I. Scheblykin, Chem. Phys., 2002, 275, 285–306.

    Article  Google Scholar 

  4. H. Uji-i, S. M. Melnikov, A. Deres, G. Bergamini, F. De Schryver, A. Herrmann, K. Müllen, J. Enderlein and J. Hofkens, Polymer, 2006, 47, 2511–2518.

    Article  CAS  Google Scholar 

  5. F. C. De Schryver, T. Vosch, M. Cotlet, M. Van der Auweraer, K. Müllen and J. Hofkens, Acc. Chem. Res., 2005, 39, 514–522.

    Article  CAS  Google Scholar 

  6. L. Schmidt-Mende, A. Fechtenkötter, K. Müllen, E. Moons, R. H. Friend and J. D. MacKenzie, Science, 2001, 293, 1119–1122.

    Article  CAS  PubMed  Google Scholar 

  7. L. Y. Park, D. G. Hamilton, E. A. McGehee and K. A. McMenimen, J. Am. Chem. Soc., 2003, 12, 10586–10590.

    Article  CAS  Google Scholar 

  8. F. Würthner, Z. Chen, F. J. M. Hoeben, P. Osswald, C.-C. You, P. Jonkheijm, J. v. Herrikhuyzen, A. P., H. J. Schenning, P. P. A. M. van der Schoot, E. W. Meijer, E. H. A. Beckers, S. C. J. Meskers, R. A. J. Janssen, J. Am. Chem. Soc., 2004, 126, 10611–10618.

    Article  PubMed  CAS  Google Scholar 

  9. A. Prodi, C. Chiorboli, F. Scandola, E. Iengo, E. Alessio, R. Dobrawa, F. Würthner, J. Am. Chem. Soc., 2005, 127, 1454–1462.

    Article  CAS  PubMed  Google Scholar 

  10. A. Sautter, B. K. Kaletaş, D. G. Schmid, R. Dobrawa, M. Zimine, G. Jung, I. H. M. van Stokkum, L. De Cola, R. M. Williams, F. Würthner, J. Am. Chem. Soc., 2005, 127, 6719–6729.

    Article  CAS  PubMed  Google Scholar 

  11. W. Herbst, and K. Hunger, Industrial Organic Pigments: Production, Properties, Applications, Wiley-VCH, 1997.

    Google Scholar 

  12. M. P. O’Neil, M. P. Niemczyk, W. A. Svec, D. Gosztola, G. L. Gaines and M. R. Wasielewski, Science, 1992, 257, 63.

    Article  PubMed  Google Scholar 

  13. F. Würthner, Chem. Commun., 2004, 1564–1579.

    Google Scholar 

  14. V. Balzani, F. Scandola, Supramolecular Photochemistry, Ellis Horwood, Chichester, 1991.

    Google Scholar 

  15. P. Osswald, F. Würthner, Chem. Eur. J., 2007, 13, 7395–7409.

    Article  CAS  PubMed  Google Scholar 

  16. P. Osswald, D. Leusser, D. Stalke, F. Würthner, Angew. Chem., Int. Ed., 2005, 44, 250.

    Article  CAS  Google Scholar 

  17. F. Würthner, Pure Appl. Chem., 2006, 78, 2341–2349.

    Article  CAS  Google Scholar 

  18. J. Hofkens, T. Vosch, M. Maus, F. Kohn, M. Cotlet, T. Weil, A. Herrmann, K. Müllen, F. C. De Schryver, Chem. Phys. Lett., 2001, 333, 255–263.

    Article  CAS  Google Scholar 

  19. E. Fron, R. Pilot, G. Schweitzer, J. Qu, A. Herrmann, K. Müllen, J. Hofkens, M. Van der Auweraer, F. C. De Schryver, Photochem. Photobiol. Sci., 2008, 7, 597–604.

    Article  CAS  PubMed  Google Scholar 

  20. M. Cotlet, S. Masuo, E. Fron, M. Van der Auweraer, K. Müllen, J. Hofkens, F. C. De Schryver, Angew. Chem., Int. Ed., 2004, 43, 6116.

    Article  CAS  Google Scholar 

  21. M. Cotlet, S. Masuo, G. Luo, J. Hofkens, M. Van der Auweraer, J. Verhoeven, K. Müllen, X. S. Xie, F. C. De Schryver, Proc. Natl. Acad. Sci. USA, 2004, 101, 14343.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  22. J. Hofkens, T. D. M. Bell, A. Stefan, E. Fron, K. Müllen, F. C. De Schryver, Pure Appl. Chem., 2006, 78, 2261–2266.

    Article  CAS  Google Scholar 

  23. R. Gvishi, R. Reisfeld and Z. Burshstein, Chem. Phys. Lett., 1993, 213, 338–344.

    Article  CAS  Google Scholar 

  24. C. Hippius, F. Schlosser, M. O. Vysotsky, V. r. Böhmer, F. Würthner, J. Am. Chem. Soc., 2006, 128, 3870–3871.

    Article  CAS  PubMed  Google Scholar 

  25. E. Lang, R. Hildner, H. Engelke, P. Osswald, F. Würthner, J. Köhler, ChemPhysChem, 2007, 8, 1487–1496.

    Article  CAS  PubMed  Google Scholar 

  26. G. D. Scholes, D. S. Larsen and G. R. Fleming, Phys. Rev. B, 2000, 61, 13670–13678.

    Article  CAS  Google Scholar 

  27. C. Hippius, I. H. M. van Stokkum, E. Zangrando, R. M. Williams, F. Würthner, J. Phys. Chem. C, 2007, 111, 13988–13996.

    Article  CAS  Google Scholar 

  28. R. A. L. Vallée, M. Van Der Auweraer, F. C. De Schryver, D. Beljonne and M. Orrit, ChemPhysChem, 2005, 6, 81–91.

    Article  PubMed  CAS  Google Scholar 

  29. D. V. O’ Connor and W. R. Ware, J. Am. Chem. Soc., 1976, 98, 4706.

    Article  Google Scholar 

  30. T. Higuchi, C. Satake and M. Hirobe, J. Am. Chem. Soc., 1995, 117, 8879–8880.

    Article  CAS  Google Scholar 

  31. T. Higuchi, C. Satake and M. Hirobe, J. Am. Chem. Soc., 1995, 117, 8879–8880.

    Article  CAS  Google Scholar 

  32. A. Zweig, W. G. Hodgson and W. H. Jura, J. Am. Chem. Soc., 1964, 86, 4124–4129.

    Article  CAS  Google Scholar 

  33. D. Gosztola, M. P. Niemczyk, W. A. Svec, A. S. Lukas and M. R. Wasielewski, J. Phys. Chem. A, 2000, 104, 6545–6551.

    Article  CAS  Google Scholar 

  34. T. Kircher, H.-G. Löhmannsröben, Phys. Chem. Chem. Phys., 1999, 1, 3987–3992.

    Article  CAS  Google Scholar 

  35. R. A. Marcus, and P. Siddarth, Theory of electron transfer reactions and comparison with experiments, Photoprocesses in transition metal complexes, biosystems and other molecules. Experiment and theory, Natoasi series, ed. E. Kochanski, Kluwer Academic Publishers, Netherlands, 1991, 49.

  36. J. Qu, N. G. Pschirer, D. Liu, A. Stefan, F. C. De Schryver, K. Müllen, Chem.-Eur. J., 2004, 10, 528.

    Article  CAS  PubMed  Google Scholar 

  37. G. Seybold and G. Wagenblast, Dyes Pigm., 1987, 11, 303–317.

    Article  Google Scholar 

  38. G. Seybold, and A. Stange, BASF AG, Ger. Pat., DE 3545004, 1987, Chem. Abstr. 1988, 108, 77 134c.

    Google Scholar 

  39. CRC Handbook of Physics and Chemistry, ed. D. R. Lide, CRC Press, Boca Raton, FL, 73rd edn, 1992.

    Google Scholar 

  40. J. Olmsted, J. Phys. Chem., 1979, 83, 2581.

    Article  CAS  Google Scholar 

  41. M. Maus, E. Rousseau, M. Cotlet, G. Schweitzer, J. Hofkens, M. Van der Auweraer, F. C. De Schryver, Rev. Sci. Instrum., 2001, 72, 36–40.

    Article  CAS  Google Scholar 

  42. Program developed in a cooperation between the Management of Technology Institute (Belarusian State University) and The Division of Photochemistry and Spectroscopy (University of Leuven).

  43. D. V. O’Connor, and D. Philips, Time-Correlated Single Photon Counting, Academic Press, London, 1984.

    Google Scholar 

  44. G. Schweitzer, L. Xu, B. Craig, F. C. De Schryver, Opt. Commun., 1997, 142, 283–288.

    Article  CAS  Google Scholar 

  45. A. K. Rappé, C. J. Casewit, K. S. Colwell, W. A. Goddard III and W. M. Skiff, J. Am. Chem. Soc., 1992, 114, 10024.

    Article  Google Scholar 

  46. J. A. Pople, D. Beveridge and P. Dobosh, J. Chem. Phys., 1967, 47, 2026.

    Article  CAS  Google Scholar 

  47. R. A. L. Vallée, P. Marsal, E. Braeken, S. Habuchi, F. C. De Schryver, J. Hofkens, D. Beljonne, M. Van Der Auweraer, J. Am. Chem. Soc., 2005, 127, 12011.

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry and Institute for Nanoscale Physics and Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200F, 3001, Heverlee, Belgium

    Eduard Fron, Gerd Schweitzer, Frans C. De Schryver & Mark Van der Auweraer

  2. Institut für Organische Chemie, Am Hubland, Universität Würzburg, D-97074, Würzburg, Germany

    Peter Osswald & Frank Würthner

  3. Laboratory for Chemistry ofNovel Materials, University of Mons-Hainaut, Place du Parc 20, B-7000, Mons, Belgium

    Philippe Marsal & David Beljonne

  4. Max-Planck-Institut für Polymerforschung, Ackermannweg 10, 55128, Mainz, Germany

    Klaus Müllen

Authors
  1. Eduard Fron
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Gerd Schweitzer
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Peter Osswald
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Frank Würthner
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Philippe Marsal
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. David Beljonne
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Klaus Müllen
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Frans C. De Schryver
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Mark Van der Auweraer
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Frank Würthner or Mark Van der Auweraer.

Additional information

This paper was published as part of the themed issue in honour of Nicholas Turro.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Fron, E., Schweitzer, G., Osswald, P. et al. Photophysical study of bay substituted perylenediimides. Photochem Photobiol Sci 7, 1509–1521 (2008). https://doi.org/10.1039/b813737d

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1039/b813737d

Search

Navigation