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Solvent-dependent radiationless transitions in fluorenone: A probe for hydrogen bonding interactions in the cyclodextrin cavity

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Abstract

Fluorescence lifetimes fluorescence quantum yields and triplet yields were measured for fluorenone in various hydroxylic and non-hydroxylic solvents, and inβ-cyclodextrin complexes. The rate of singlet-triplet intersystem crossing, which decreases with increasing polarity, was found to be a good indicator of nonspecific solvent-solute interactions, while the rate of direct internal conversion from the singlet excited state was correlated with hydrogen bonding. The fast internal conversion of singlet excited fluorenone/β-cyclodextrin complexes shows that the probe molecule, while embedded within the cyclodextrin cavity, still remains hydrogen bonded.

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References

  1. J. Szejtli:Cyclodextrins and Their Inclusion Complexes, Akademiai Kiado, Budapest (1982).

    Google Scholar 

  2. J. Szejtli:Cyclodextrin Technology, Kluwer Academic Publishers, Dordrecht (1988).

    Google Scholar 

  3. A. Nag and K. Bhattacharyya:Chem. Phys. Lett. 151, 474 (1988) A. Nag, R. Dutta, N. Chattopadhyay, and K. Bhattacharyya:Chem. Phys. Lett. 157, 83 (1989). A. Nag and K. Bhattacharyya:J. Chem. Soc. Faraday Trans. 86, 534 (1990).

    Google Scholar 

  4. A. Nag, T. Chakrabarty, and K. Bhattacharyya:J. Phys. Chem. 94, 4203 (1990).

    Google Scholar 

  5. G. S. Cox, P. J. Hauptman, N. J. Turro:Photochem. Photobiol. 39 597 (1984).

    Google Scholar 

  6. F. V. Bright, G. C. Catena, and J. Huang:J. Am. Chem. Soc. 112, 1343 (1990).

    Google Scholar 

  7. D. F. Eaton:Tetrahedron 43, 1551 (1987).

    Google Scholar 

  8. A. Heredia, G. Requena, and F. G. Sanchez:J. Chem. Soc. Chem. Commun. 1814 (1985).

  9. G. S. Cox, N. J. Turro, N. C. Yang, and M.-J. Chen:J. Am. Chem. Soc. 106, 422 (1984).

    Google Scholar 

  10. L. Biczok and T. Berces:J. Phys. Chem. 92, 3842 (1988).

    Google Scholar 

  11. L. Biczok, T. Berces, and F. Marta:J. Phys. Chem. 97, 8895 (1993).

    Google Scholar 

  12. L. J. Andrews, A. Deroulede, and H. Linschitz,J. Phys. Chem. 82, 2304 (1978).

    Google Scholar 

  13. T. Kobayashi and S. Nagakura:Chem. Phys. Lett. 43, 429 (1976).

    Google Scholar 

  14. B. Laszlo, S. Forgeteg, T. Berces, and F. Marta:J. Photochem. 27, 49 (1984).

    Google Scholar 

  15. C. A. Parker:Photoluminescence of Solutions Elsevier Publ. Co. Amsterdam (1968).

    Google Scholar 

  16. J. K. Hurley, N. Sinai, and H. Linschitz:Photochem. Photobiol. 38, 9 (1983).

    Google Scholar 

  17. C. Reichardt:Solvents and Solvent Effects in Organic Chemistry, VCH: Weinheim (1988).

    Google Scholar 

  18. S. Li and W. C. Purdy:Chem. Rev. 92, 1457 (1992).

    Google Scholar 

  19. H. Yamaguchi, K. Ninomiya, and M. Ogata:Chem. Phys. Lett. 75, 593 (1980).

    Google Scholar 

  20. S. Hamai:J. Phys. Chem. 92, 6140 (1988).

    Google Scholar 

  21. S. Hamai:Bull. Chem. Soc. Jpn. 55, 2721 (1982).

    Google Scholar 

  22. R. L. Van Etten, J. F. Sebastian, G. A. Clowes, and M. L. Bender:J. Am. Chem. Soc. 89, 3242 (1967).

    Google Scholar 

  23. K. W. Street Jr. and W. E. Acree:Appl. Spectrosc. 42, 1315 (1988).

    Google Scholar 

  24. T. Soujanya, T. S. R. Krishna, and A. Samanta:J. Phys. Chem. 96, 8544 (1992).

    Google Scholar 

  25. S. Hamai:J. Phys. Chem. 94, 2595 (1990).

    Google Scholar 

  26. S. Hamai:Bull. Chem. Soc. Jpn. 64, 431 (1991).

    Google Scholar 

  27. K. W. Street Jr.:J. Liq. Chromatogr. 10, 655 (1987).

    Google Scholar 

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Dedicated to Professor Szejtli.

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Biczók, L., Jicsinszky, L. & Linschitz, H. Solvent-dependent radiationless transitions in fluorenone: A probe for hydrogen bonding interactions in the cyclodextrin cavity. J Incl Phenom Macrocycl Chem 18, 237–245 (1994). https://doi.org/10.1007/BF00708730

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  • DOI: https://doi.org/10.1007/BF00708730

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