Photophysical characterization of hydroxy and ethoxy phenalenone derivatives

C. Sandoval-Altamirano, J. R. De la Fuente, E. Berrios, S. A. Sanchez, N. Pizarro, J. Morales, G. Gunther

Resultado de la investigación: Research - revisión exhaustivaArticle

Resumen

Phenalenone has been extensively studied due to its photophysical behavior. However, fewer are the articles referring to the phenalenone derivatives as singlet oxygen generators. The incorporation of substituents on the phenalenone ring rearranges the molecular electronic states changing its photophysical behavior. In order to rationalize the effect of the presence of electron-donor substituents on the phenalenone ring, we studied two ethoxy derivatives and their corresponding hydroxyl precursors. All derivatives prepared present smaller singlet oxygen quantum yield values than phenalenone. These lower quantum yields can be rationalized by considering non-radiative decay of singlet excited state absent in unsubstituted phenalenone. The hydroxy and alkoxy derivatives substituted in position 6 of phenalenone have larger fluorescence quantum yields than the ones substituted in position 3. Interestingly, 3-hydroxy-phenalenone shows a low emission quantum yield with two emission bands, which can be related with equilibria between diketo and enol tautomers in the first excited singlet state. Flash photolysis spectra for all derivatives were measured and the extinction coefficients of triplet–triplet absorption were evaluated near 500 nm.

IdiomaEnglish
Páginas349-357
Número de páginas9
PublicaciónJournal of Photochemistry and Photobiology A: Chemistry
Volumen353
DOI
EstadoPublished - 15 feb 2018

Huella dactilar

Derivatives
phenalen-1-one
Quantum yield
rings
oxygen
excitation
Excited states
Oxygen
molecular electronics
tautomers
flash
photolysis
extinction
generators
fluorescence
decay
coefficients
electrons
Singlet Oxygen
Molecular electronics

Keywords

    ASJC Scopus subject areas

    • Chemistry(all)
    • Chemical Engineering(all)
    • Physics and Astronomy(all)

    Citar esto

    Sandoval-Altamirano, C., De la Fuente, J. R., Berrios, E., Sanchez, S. A., Pizarro, N., Morales, J., & Gunther, G. (2018). Photophysical characterization of hydroxy and ethoxy phenalenone derivatives. Journal of Photochemistry and Photobiology A: Chemistry, 353, 349-357. DOI: 10.1016/j.jphotochem.2017.11.049
    Sandoval-Altamirano, C. ; De la Fuente, J. R. ; Berrios, E. ; Sanchez, S. A. ; Pizarro, N. ; Morales, J. ; Gunther, G./ Photophysical characterization of hydroxy and ethoxy phenalenone derivatives. En: Journal of Photochemistry and Photobiology A: Chemistry. 2018 ; Vol. 353. pp. 349-357
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    Sandoval-Altamirano, C, De la Fuente, JR, Berrios, E, Sanchez, SA, Pizarro, N, Morales, J & Gunther, G 2018, 'Photophysical characterization of hydroxy and ethoxy phenalenone derivatives' Journal of Photochemistry and Photobiology A: Chemistry, vol. 353, pp. 349-357. DOI: 10.1016/j.jphotochem.2017.11.049

    Photophysical characterization of hydroxy and ethoxy phenalenone derivatives. / Sandoval-Altamirano, C.; De la Fuente, J. R.; Berrios, E.; Sanchez, S. A.; Pizarro, N.; Morales, J.; Gunther, G.

    En: Journal of Photochemistry and Photobiology A: Chemistry, Vol. 353, 15.02.2018, p. 349-357.

    Resultado de la investigación: Research - revisión exhaustivaArticle

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    Sandoval-Altamirano C, De la Fuente JR, Berrios E, Sanchez SA, Pizarro N, Morales J y otros. Photophysical characterization of hydroxy and ethoxy phenalenone derivatives. Journal of Photochemistry and Photobiology A: Chemistry. 2018 feb 15;353:349-357. Disponible desde, DOI: 10.1016/j.jphotochem.2017.11.049