Skip to main content
Log in

Influence of local excitation of octupolar Oligophenylenevinylenes on their dipole moments

  • Published:
Journal of Applied Spectroscopy Aims and scope

Absorption and fluorescence spectra of octupolar centrosymmetric oligophenylenevinylene dyes (E,E)-bis[2-(4-hexyloxyphenyl)ethenyl]-(E,E)-3,6-bis-[2-(4-N,N-dipropylaminophenyl)ethenyl]pyrazine and (E,E,E,E)-2,3,5,6- tetra-[2-(4-hexyloxyphenyl)ethenyl]pyrazine were measured in various solvents. An electro-optical absorption method was used to determine their dipole moments as μ g  = 6.1∙10–30 and 3.4∙10–30 C∙m in the equilibrium ground state and the increased values a μ = 11.9∙10–30 and 8.2∙10–30 C∙m upon excitation into a Franck–Condon state. Quantum-chemical calculations showed that the molecules had non-planar configurations. The π,π-conjugated system was localized on the most planar part of the molecule that was responsible for light absorption in the range 300–450 nm due to a change in the geometry of the molecules in the ground state. Localized excitation of the molecules caused their dipole moments a μ to change significantly.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. J. H. Burroughes, D. D. C. Bradley, A. R. Brown, R. N. Marks, K. Mackay, R. H. Friend, P. L. Burn, and A. B. Holmes, Nature, 347, 539–541 (1990).

    Article  ADS  Google Scholar 

  2. T. Goodson III, W. Li, A. Gharavi, and L. Yu, Adv. Mater., 9, 639–643 (1997).

    Article  Google Scholar 

  3. K. Mullen and G. Wegner, Electronic Materials: The Oligomer Approach, Wiley-VCH, Weinheim, New York (1998).

    Book  Google Scholar 

  4. J. Gierschner, M. Ehni, H.-J. Egelhaaf, B. Millian, D. Beljonne, H. Benmansour, and G. C. Bazan, J. Chem. Phys., 123, 144914-1–144914-9 (2005).

    Article  ADS  Google Scholar 

  5. A. Mathy, K. Ueberhofen, R. Schenk, H. Gregorius, R. Garay, K. Mullen, and C. Bubeck, Phys. Rev. B: Condens. Matter Mater. Phys., 53, 4367–4376 (1996).

    Article  ADS  Google Scholar 

  6. R. M. Gurge, M. Hickl, G. Krause, P. M. Lahti, B. Hu, Z. Yang, and F. E. Karasz, Polym. Adv. Technol., 9, 504–510 (1998).

    Article  Google Scholar 

  7. B. Strehmel, A. M. Sarker, and H. Detert, Chem. Phys. Chem., 4, 249–259 (2003).

    Article  Google Scholar 

  8. T. A. Skotheim and J. R. Reynolds, Handbook of Conducting Polymers, Part III: Properties and Characterization of Conducting Polymers, CRC Press, Boca Raton (2007).

    Google Scholar 

  9. A. E. Stiegman, E. Graham, K. J. Perry, L. R. Khundkar, L.-T. Cheng, and J. W. Perry, J. Am. Chem. Soc., 113, 7658–7666 (1991).

    Article  Google Scholar 

  10. J. O. Morley, Int. J. Quantum Chem., 46, 19–26 (1993).

    Article  Google Scholar 

  11. M. Tomonari, N. Ookubo, and T. Takada, Chem. Phys. Lett., 215, 45–52 (1993).

    Article  ADS  Google Scholar 

  12. D. Jacquemin, B. Champagne, and J.-M. Andre, Int. J. Quantum Chem., 65, 679–688 (1997).

    Article  Google Scholar 

  13. B. Champagne and B. Kirtman, Chem. Phys., 245, 213–226 (1999).

    Article  Google Scholar 

  14. J. Y. Lee, S. B. Suh, and K. S. Kim, J. Chem. Phys., 112, 344–348 (2000).

    Google Scholar 

  15. H. Detert and V. Schmitt, J. Phys. Org. Chem., 17, 1051–1056 (2004).

    Article  Google Scholar 

  16. R. Stahl, C. Lambert, C. Kaiser, R. Wortman, and R. Jakober, Chem. Eur. J., 12, 2358–2370 (2006).

    Article  Google Scholar 

  17. N. G. Bakhshiev (ed.), Solvatochromism: Problems and Methods [in Russian], Izd. Leningr. Gos. Univ., Leningrad (1989).

  18. W. Rettig and W. Baumann, in: Progress in Photochemistry and Photophysics, J. F. Ralek (ed.), VI, CRC Press, Boca Raton (1992).

  19. N. A. Nemkovich and W. Baumann, J. Photochem. Photobiol. A: Chem., 185, 26–31 (2007).

    Article  Google Scholar 

  20. S. Wachsmann-Hogiu, L. A. Peteanu, L. A. Liu, D. J. Yaron, and J. Wildeman, J. Phys. Chem., 107, 5133–5143 (2003).

    Article  Google Scholar 

  21. N. A. Nemkovich, Yu. V. Kruchenok, A. N. Sobchuk, H. Detert, N. Vrobel’, and E. A. Chernyavskii, Opt. Skektrosk., 107, 288–295 (2009).

    Article  Google Scholar 

  22. N. A. Nemkovich, H. Detert, and V. Schmitt, Chem. Phys., 378, 37–41 (2010).

    Article  ADS  Google Scholar 

  23. P. R. Bangal, D. M. K. Lam, L. A. Peteanu, and M. V. Auweraer, J. Phys. Chem. B, 108, 16834–16840 (2004).

    Article  Google Scholar 

  24. V. Schmitt, "Syntheses und Charakterisierung Aza-Analoger Oligo(phenylenvinylen)e mit Umgebungsabhagiger UV-Vis-Absorption und Fluoreszenz," Diss. Doctor der Naturwissenschaften am Fachbereich Chemie, Pharmazie und Geowissenschaften, Johannes Gutenberg Universitat, Mainz (2009).

  25. W. Liptay, in: Excited States, E. C. Lim (ed.), 1, Academic Press, New York (1974).

  26. W. Baumann, Z. Nagy, H. Reis, and N. Detzer, Chem. Phys. Lett., 224, 517–524 (1994).

    Article  ADS  Google Scholar 

  27. N. A. Nemkovich, W. Baumann, H. Reis, and N. Detzer, J. Photochem. Photobiol. A: Chem., 89, 127–133 (1995).

    Article  Google Scholar 

  28. N. A. Nemkovich, A. N. Rubinov, and V. I. Tomin, in: Topics Fluorescence Spectroscopy, 2 : Principles, J. R. Lakowicz (ed.), Kluver Academic/Plenum Publ., New York (1991), pp. 367–428.

  29. W. Liptay, R. Wortman, H. Schaffrin, O. Burkhard, W. Reitinger, and N. Detzer, J. Chem. Phys., 120, 429–438 (1998).

    Google Scholar 

  30. F. Terenziani, A. Painelli, C. Katan, M. Charlot, and M. Blanchard-Desce, J. Am. Chem. Soc., 128, 15742–15755 (2006).

    Article  Google Scholar 

  31. R. A. Friesner and R. Silbey, J. Chem. Phys., 75, 3925–3936 (1981).

    Article  ADS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to N. A. Nemkovich.

Additional information

Translated from Zhurnal Prikladnoi Spektroskopii, Vol. 79, No. 3, pp. 375–381, May–June, 2012.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Nemkovich, N.A., Detert, H., Schmitt, V. et al. Influence of local excitation of octupolar Oligophenylenevinylenes on their dipole moments. J Appl Spectrosc 79, 353–359 (2012). https://doi.org/10.1007/s10812-012-9608-0

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10812-012-9608-0

Keywords

Navigation