Skip to main content
SpringerLink
Log in

Deactivation of the S2 and Two Lowest Triplet States of 4H-1-Benzopyran-4-thione and Its Alkyl Derivatives in Methanol Solution

  • Published:
Journal of Fluorescence Aims and scope Submit manuscript

Abstract

Spectral and photochemical properties of three aromatic thioketones, 4H-1-benzopyran-4-thione and its two alkyl derivatives, in their second excited singlet and two lowest triplet states have been a subject of stationary and time-resolved studies. Quantum yields of emissions from the above-mentioned states as well as lifetimes of these states have been measured. The results indicate an important role of intermolecular solvent-induced processes in deactivation of the excited states of the thioketones studied. The possible mechanism of these processes involves hydrogen atom abstraction and/or formation of exciplex. For relatively high thione concentrations, the contribution of self-quenching in deactivation of the triplet states becomes significant. The effect of the alkyl chain in a thione molecule on deactivation parameters is discussed.

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. A. Maciejewski and R. P. Steer (1993) Chem. Rev. 93, 67-98.

    Google Scholar 

  2. R. P. Steer and V. Ramamurthy (1988) Acc. Chem. Res. 21, 380-386.

    Google Scholar 

  3. J. R. Huber and M. Mahaney (1975) Chem. Phys. Lett. 30, 410-412.

    Google Scholar 

  4. M. Mahaney and J. R. Huber (1975) Chem. Phys. 9, 371-378.

    Google Scholar 

  5. M. H. Hui, P. de Mayo, R. Suau, and W. R. Ware (1975) Chem. Phys. Lett. 31, 257-263.

    Google Scholar 

  6. A. Maciejewski, A. Safarzadeh-Amiri, R. E. Verrall, and R. P. Steer (1984) Chem. Phys. 87, 295-303.

    Google Scholar 

  7. A. Maciejewski, D. R. Demmer, D. R. James, A. Safarzadeh-Amiri, R. E. Verrall, and R. P. Steer (1985) J. Am. Chem. Soc. 107, 2831-2837.

    Google Scholar 

  8. D. S. Blackwell, C. C. Liao, R. O. Loufty, P. de Mayo, and S. Paszyc (1972) Mol. Photochem. 4, 171-188.

    Google Scholar 

  9. D. A. Capitanio, H. J. Pownall, and J. R. Huber (1974) J. Photochem. 3, 225-236.

    Google Scholar 

  10. A. Safarzadeh-Amiri, R. E. Verrall, and R. P. Steer (1983) Can. J. Chem. 61, 894-900.

    Google Scholar 

  11. M. Szymański, R. P. Steer, and A. Maciejewski (1987) Chem. Phys. Lett. 135, 243-248.

    Google Scholar 

  12. A. Maciejewski, M. Szymański, and R. P. Steer (1988) J. Phys. Chem. 92, 6939-6944.

    Google Scholar 

  13. P. de Mayo (1976) Acc. Chem. Res. 9, 52-59.

    Google Scholar 

  14. N. J. Turro, V. Ramamurthy, W. Cherry, and W. Farneth (1978) Chem. Rev. 78, 125-145.

    Google Scholar 

  15. V. Ramamurthy (1986) Org. Photochem. 7, 231-338.

    Google Scholar 

  16. J. D. Coyle (1985) Tetrahedron 41, 5393-5425.

    Google Scholar 

  17. A. Cox, D. R. Kemp, R. Lapouyade, P. de Mayo, J. Joussot-Dubien, and R. Bonneau, Can. J. Chem. 53, 2386-2393.

  18. A. Maciejewski and R. P. Steer (1983) Chem. Phys. Lett. 100, 540-545.

    Google Scholar 

  19. A. Maciejewski and R. P. Steer (1983) J. Am. Chem. Soc. 105, 6738-6740.

    Google Scholar 

  20. M. Mahaney and J. R. Huber (1984) Chem. Phys. Lett. 105, 395-399.

    Google Scholar 

  21. C.-J. Ho, A. L. Motyka, and M. R. Topp (1989) Chem. Phys. Lett. 158, 51-59.

    Google Scholar 

  22. M. Milewski, A. Maciejewski, and W. Augustyniak (1997) Chem. Phys. Lett. 272, 225-231.

    Google Scholar 

  23. M. Szymański, A. Maciejewski, and R. P. Steer (1988) Chem. Phys. 124, 143-154.

    Google Scholar 

  24. J. Kozlowski, A. Maciejewski, M. Milewski, and W. Urjasz (1999) J. Phys. Org. Chem. 12, 47-58.

    Google Scholar 

  25. A. Maciejewski (1990) J. Photochem. Photobiol. A 51, 87-131.

    Google Scholar 

  26. S. J. Formosinho (1976) J. Chem. Soc. Faraday Trans. 2 72, 1332-1338.

    Google Scholar 

  27. A. Maciejewski (1988) J. Photochem. Photobiol. A 43, 303-312.

    Google Scholar 

  28. A. H. Lawrence, P. de Mayo, R. Bonneau, and J. Joussot-Dubien (1973) Mol. Photochem. 5, 361-365.

    Google Scholar 

  29. U. Brühlaman and J. R. Huber (1978) Chem. Phys. Lett. 54, 606-610.

    Google Scholar 

  30. V. Ramesh, N. Ramnath, and V. Ramamurthy (1983) J. Photochem. Photobiol. A 23, 141.

    Google Scholar 

  31. M. Sikorski, W. Augustyniak, I. V. Khmielinski, V. V. Korolev, and N. M. Bazhin (1993) Chem. Phys. Lett. 209, 403-407.

    Google Scholar 

  32. A. H. Lawrence, C. C. Liao, P. de Mayo, and V. Ramamurthy (1976) J. Am. Chem. Soc. 98, 2219-2226.

    Google Scholar 

  33. N. J. Turro and V. Ramamurthy (1977) Mol. Photochem. 8, 239-253.

    Google Scholar 

  34. U. Brühlaman and J. R. Huber (1979) J. Photochem. 10, 205-213.

    Google Scholar 

  35. L. W. Molenkamp, D. P. Weitekamp, and D. A. Wiersma (1983) Chem. Phys. Lett. 99, 382-387.

    Google Scholar 

  36. D. Tittelbach-Helmrich and R. P. Steer (1996) Chem. Phys. Lett. 262, 369-373.

    Google Scholar 

  37. A. Maciejewski, M. Szymański, and R.P. Steer (1986) J. Phys. Chem. 90, 6314-6318.

    Google Scholar 

  38. M. Szymański, A. Maciejewski, and R. P. Steer (1991) J. Photochem. Photobiol. A 57, 405-418.

    Google Scholar 

  39. M. Sikorski, I. V. Khmelinskii, W. Augustyniak, and F. Wilkonson (1996) J. Chem. Soc. Faraday Trans. 92, 3487-3490.

    Google Scholar 

  40. V. Ramesh and V. Ramamurthy (1982). J. Photochem. 20, 47-52.

    Google Scholar 

  41. A. Maciejewski, A. Jakubowska, E. Dutkiewicz, and W. Augustyniak (1996) J. Colloid Interface Sci. 177, 528-541.

    Google Scholar 

  42. M. Milewski, M. Sikorski, A. Maciejewski, M. Mir, and F. Wilkinson (1997) J. Chem. Soc. Faraday Trans. 93, 3029-3034.

    Google Scholar 

  43. M. Milewski, W. Augustyniak, and A. Maciejewski (1998) J. Phys. Chem. A 102, 7427-7434.

    Google Scholar 

  44. M. A. Winnik (1977) Acc. Chem. Res. 10, 173-179.

    Google Scholar 

  45. M. Milewski, W. Urjasz, A. Maciejewski, and W. Augustyniak (1998) Polish J. Chem. 72, 2405-2417.

    Google Scholar 

  46. S. Meech and D. Phillips (1983) J. Photochem. 23, 193-217.

    Google Scholar 

  47. J. B. Birks (1976) J. Res. Natl. Bur. Stand. 80A, 389.

    Google Scholar 

  48. J. Karolczak, D. Komar, J. Kubicki, M. Szymański, T. Wrózÿowa, and A. Maciejewski (1999) Bull. Pol. Acad. Sci. 47, 361-380.

    Google Scholar 

  49. J. Karolczak, J. Kubicki, D. Komar, T. Wrózÿowa, M. Szymański, B. Ciesielska, A. Cencek, and A. Maciejewski (in press).

  50. M. Binkowski, M. Szymański, J. Baksalary, and A. Maciejewski (1996) Opt. Appl. 26, 159-169.

    Google Scholar 

  51. K. J. Rosenberg (1962) Acta Chem. Scand. 16, 2284-2292.

    Google Scholar 

  52. H. Eisenberger and B. Nickel (1996) J. Chem. Soc. Faraday Trans. 92, 733-740.

    Google Scholar 

  53. M. Milewski, J. Kubicki, T. Wrózÿowa, A. Maciejewski, and W. Augustyniak (in press).

  54. M. Szymański, A. Maciejewski, and R. P. Steer (1988) J. Phys. Chem. 92, 2485-2489.

    Google Scholar 

  55. M. Milewski (1998) Ph.D. thesis (Faculty of Chemistry, A. Mickiewicz University, Poznań, Poland).

  56. A. Maciejewski and R. P. Steer (1984) J. Photochem. 24, 303-307.

    Google Scholar 

  57. A. Maciejewski (1989) Chem. Phys. Lett. 164, 166-172; W. Augustyniak, J. Koput, A. Maciejewski, M. Sikorski, R. P. Steer, and M. Szymański (1993) Polish J. Chem. 67, 1409-1423; A. Maciejewski. M. Sikorski,W. Augustyniak, and M. Fidecka (1996) J. Photochem. Photobiol. A 94, 119-127.

    Google Scholar 

  58. M. Szymański, M. Balicki, M. Binkowski, J. Kubicki, A. Maciejewski, E. Pawlowska, and T. Wrózÿowa (1996) A. Phys. Pol. A 89, 527-546.

    Google Scholar 

  59. A. Maciejewski, M. Szymański, and R. P. Steer (1988) Chem. Phys. Lett. 143, 559-564.

    Google Scholar 

  60. R. Rajee and V. Ramamurthy (1979) J. Photochem. 11, 135-138.

    Google Scholar 

  61. J. Saltiel, G. R. Marchand, W. K. Smothers, S. A. Stout, and J. L. Charlton (1981) J. Am. Chem. Soc. 103, 7159-7164.

    Google Scholar 

  62. H. Eisenberger, B. Nickel, A. A. Ruth, and R. P. Steer (1996) J. Chem. Soc. Faraday Trans. 92, 741-746.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Faculty of Chemistry, Adam Mickiewicz University, 60–780, Poznań, Poland

    Marek Milewski

  2. Institute of Physics, Adam Mickiewicz University, 61–614, Poznań, Poland

    Justyna Baksalary, Paweł Antkowiak, Michał Binkowski, Jerzy Karolczak, Dariusz Komar & Marian Szymański

  3. Faculty of Chemistry, Adam Mickiewicz University, 60–780, Poznań, Poland

    Włodzimierz Augustyniak, Andrzej Maciejewski & Wojciech Urjasz

Authors
  1. Marek Milewski
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Justyna Baksalary
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Paweł Antkowiak
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Włodzimierz Augustyniak
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Michał Binkowski
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Jerzy Karolczak
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Dariusz Komar
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Andrzej Maciejewski
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Marian Szymański
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Wojciech Urjasz
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Milewski, M., Baksalary, J., Antkowiak, P. et al. Deactivation of the S2 and Two Lowest Triplet States of 4H-1-Benzopyran-4-thione and Its Alkyl Derivatives in Methanol Solution. Journal of Fluorescence 10, 89 (2000). https://doi.org/10.1023/A:1009478606314

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1009478606314

Search

Navigation