Journal of Fluorescence

, Volume 7, Issue 2, pp 113–120 | Cite as

Intramolecular energy transfer in naphthalene-containing polyesters: Experiment and simulation for model compounds derived from five aliphatic dicarboxylic acids and 2-hydroxynaphthalene

  • Ana Sánchez-Camacho
  • Javier Pozuelo
  • Francisco Mendicuti
  • Wayne L. Mattice
Article

Abstract

Steady-state fluorescence depolarization measurements and molecular dynamics simulations have been used to study the efficiency of nonradiative intramolecular singlet energy transfer between 2-naphthoxy groups, denoted N, in model compounds for polyesters derived from 2,6-dihydroxy-naphthalene and aliphatic dicarboxylic acids. The five bichromophoric compounds studied are the diesters abbreviated as N-OOC-(CH2)n-COO-N;n = 2–6, which are condensation products obtained from 2-naphthol and aliphatic dicarboxylic acids. The anisotropy of the fluorescence of these compounds dispersed in a solid matrix of glassy poly(methyl methacrylate) indicates that there is nonradiative singlet energy transfer between naphthoxy groups. The efficiency of this transfer depends onn. A theoretical treatment using molecular dynamics simulations for the conformations of the five model compounds has been performed in order to evaluate the parameters related to the efficiency of the transfer. The experimental and theoretical variation of such parameters withn is consistent with the estimated Förster radius of 9–10 Å for this system.

Key words

Fluorescence anisotropy intramolecular energy transfer methylene spacers naphthalene polyesters 

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References

  1. 1.
    J. R. Lakowicz (1983)Principles of Fluorescence Spectroscopy, Plenum Press, New York.Google Scholar
  2. 2.
    J. Guillet (1985)Polymer Photochemistry and Photophysics: An Introduction to the Study of Photoprocesses in Macromolecules, Cambridge University Press, Cambridge.Google Scholar
  3. 3.
    D. Phillips (Ed.) (1985)Polymer Photophysics: Luminescence, Energy Migration and Molecular Motion in Synthetic Polymer, Chapman and Hall, London.Google Scholar
  4. 4.
    J. F. Rabeck (1987)Mechanisms of Photophysical Processes and Photochemical Reactions in Polymers: Theory and Applications, John Wiley and Sons, Chichester.Google Scholar
  5. 5.
    Th. Förster (1948)Ann. Phys. 2, 55.CrossRefGoogle Scholar
  6. 6.
    I. B. Berlman (1973)Energy Transfer Parameters of Organic Compounds, Academic Press, New York.Google Scholar
  7. 7.
    A. S. Jones, T. J. Dickson, B. E. Wilson, J. Duhamel, and M. A. Winnik (1996)Polym. Prepr. (Am. Chem. Soc. Div. Polym. Chem.) 37(1), 229.Google Scholar
  8. 8.
    J. R. Lakowicz, I. Gryczynski, H. C. Cheung, C.-K. Wang, and M. L. Jhonson (1988)Biopolymers 27, 821.PubMedCrossRefGoogle Scholar
  9. 9.
    I. Gryczynski, W. Wiczk, M. L. Jhonson, H. C. Cheung, C.-K. Wang, and J. R. Lakowicz (1988)Biophys. J. 54, 577.PubMedCrossRefGoogle Scholar
  10. 10.
    I. Gryczynski, W. Wiczk, M. L. Jhonson, and J. R. Lakowicz (1988)Chem. Phys. Lett. 145, 439.CrossRefGoogle Scholar
  11. 11.
    J. R. Lakowicz, J. Kusba, H. Szmacinski, I. Gryczynski, P. S. Eis, W. Wiczk, and M. L. Jhonson (1991)Biopolymers 31, 1363.PubMedCrossRefGoogle Scholar
  12. 12.
    J. R. Lakowicz, W. Wizck, I. Gryczynski, M. Fishman, and M. L. Jhonson (1993)Macromolecules 26, 349.CrossRefGoogle Scholar
  13. 13.
    G. Liu and J. E. Guillet (1990)Macromolecules 23, 1388.CrossRefGoogle Scholar
  14. 14.
    G. Liu, J. E. Guillet, E. T. B. Al-Takrity, A. D. Jenkins, and D. R. M. Walton (1990)Macromolecules 23, 1393.CrossRefGoogle Scholar
  15. 15.
    G. Liu and J. E. Guillet (1990)Macromolecules 23, 2969.CrossRefGoogle Scholar
  16. 16.
    G. Liu, J. E. Guillet, E. T. B. Al-Takrity, A. D. Jenkins, and D. R. M. Walton (1990)Macromolecules 23, 4165.Google Scholar
  17. 17.
    G. Liu, J. E. Guillet, E. T. B. Al-Takrity, A. D. Jenkins, and D. R. M. Walton (1991)Macromolecules 24, 68.CrossRefGoogle Scholar
  18. 18.
    G. Liu, J. E. Guillet, M. Vlegels, and E. J. Goethals (1991)Macromolecules 24, 4094.CrossRefGoogle Scholar
  19. 19.
    M. Guo (1996)Polym. Prepr. (Am. Chem. Soc. Div. Polym. Chem.) 37(1), 227, 827.Google Scholar
  20. 20.
    M. Guo and H. G. Zachmann (1996)Polym. Prepr. (Am. Chem. Soc. Div. Polym. Chem.) 37(1), 825, 829, 831.Google Scholar
  21. 21.
    F. Mendicuti, B. Patel, and W. L. Mattice (1990)Polymer 31, 453.CrossRefGoogle Scholar
  22. 22.
    F. Mendicuti, E. Saiz, I. Zúniga, B. Patel, and W. L. Mattice (1992)Polymer 33, 2031.CrossRefGoogle Scholar
  23. 23.
    O. Martin, F. Mendicuti, E. Saiz, and W. L. Mattice (1996)J. Polym. Sci. Part B Polym. Phys. 34, 2623.CrossRefGoogle Scholar
  24. 24.
    O. Martin, A. Sanchez-Camacho, F. Mendicuti, and W. L. Mattice (1997)J. Polym. Sci. Part B Polym. Phys. 35, 1127.CrossRefGoogle Scholar
  25. 25.
    P. G. de Gennes (1982) in A. Ciferri, W. R. Krigbaum, and R. B. Meyer (Eds.)Polymer Liquid Crystals; Academic Press, New York, Chap. 8.Google Scholar
  26. 26.
    F. Mendicuti, E. Saiz, and W. L. Mattice (1992)Polymer 33, 4908.CrossRefGoogle Scholar
  27. 27.
    J. Gallego, F. Mendicuti, E. Saiz, and W. L. Mattice (1993)Polymer 34, 2475.CrossRefGoogle Scholar
  28. 28.
    F. Mendicuti, E. Saiz, J. Bravo, and W. L. Mattice (1995)Polym. Int. 36, 137.CrossRefGoogle Scholar
  29. 29.
    J. Bravo, F. Mendicuti, E. Saiz, and W. L. Mattice (1994)Makromol. Chem. 195, 3411.CrossRefGoogle Scholar
  30. 30.
    J. Bravo, F. Mendicuti, E. Saiz, and W. L. Mattice (1996)Macromol. Chem. Phys. 197, 1349.CrossRefGoogle Scholar
  31. 31.
    J. Bravo, F. Mendicuti, E. Saiz, and W. L. Mattice (1996)J. Fluoresc. 6, 41.CrossRefGoogle Scholar
  32. 32.
    P. J. Flory (1974)Macromolecules 7, 381.CrossRefGoogle Scholar
  33. 33.
    W. L. Mattice and U. W. Suter (1994)Conformational Theory of Large Molecules. The Rotational Isomeric State Model in Macromolecular Systems, Wiley, New York.Google Scholar
  34. 34.
    F. Mendicuti and W. L. Mattice (1989)Polym. Bull. 22, 557.CrossRefGoogle Scholar
  35. 35.
    J. R. Lakowicz (1983)Principles of Fluorescence Spectroscopy, Plenum Press, New York, p 134.Google Scholar
  36. 36.
    I. B. Berlman (1973)Energy Transfer Parameters of Organic Compounds, Academic Press, New York, p 308.Google Scholar
  37. 37.
    I. B. Berlman (1973)Handbook of Fluorescence Spectra of Aromatic Molecules, Academic Press, New York, p. 421.Google Scholar
  38. 38.
    Sybyl 6.0, Tripos Associates, Inc., St. Louis, MO.Google Scholar
  39. 39.
    M. Clark, R. D. Cramer, III, and N. Van Opdenbosch (1989)Cornput. Chem. 10, 982.CrossRefGoogle Scholar

Copyright information

© Plenum Publishing Corporation 1997

Authors and Affiliations

  • Ana Sánchez-Camacho
    • 1
  • Javier Pozuelo
    • 1
  • Francisco Mendicuti
    • 1
  • Wayne L. Mattice
    • 2
  1. 1.Departamento de Quimica FisicaUniversidad de AlcaláMadridSpain
  2. 2.Institute of Polymer ScienceUniversity of AkronAkron

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