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: Contribución a la publicaciónArticle

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

Quantum yield
Derivatives
Excited states
molecular electronics
rings
tautomers
oxygen
Singlet Oxygen
excitation
flash
photolysis
extinction
generators
Molecular electronics
Oxygen
Photolysis
Electronic states
fluorescence
decay
coefficients

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
    @article{50f2f3ac36b4464cb3db42773a85e387,
    title = "Photophysical characterization of hydroxy and ethoxy phenalenone derivatives",
    abstract = "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.",
    keywords = "Phenalenone derivatives, Phenlenone, Singlet Oxygen",
    author = "C. Sandoval-Altamirano and {De la Fuente}, {J. R.} and E. Berrios and Sanchez, {S. A.} and N. Pizarro and J. Morales and G. Gunther",
    note = "Enviada a pago 02-02-2018",
    year = "2018",
    month = "2",
    day = "15",
    doi = "10.1016/j.jphotochem.2017.11.049",
    language = "English",
    volume = "353",
    pages = "349--357",
    journal = "Journal of Photochemistry and Photobiology A: Chemistry",
    issn = "1010-6030",
    publisher = "Elsevier",

    }

    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: Contribución a la publicaciónArticle

    TY - JOUR

    T1 - Photophysical characterization of hydroxy and ethoxy phenalenone derivatives

    AU - Sandoval-Altamirano,C.

    AU - De la Fuente,J. R.

    AU - Berrios,E.

    AU - Sanchez,S. A.

    AU - Pizarro,N.

    AU - Morales,J.

    AU - Gunther,G.

    N1 - Enviada a pago 02-02-2018

    PY - 2018/2/15

    Y1 - 2018/2/15

    N2 - 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.

    AB - 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.

    KW - Phenalenone derivatives

    KW - Phenlenone

    KW - Singlet Oxygen

    UR - http://www.scopus.com/inward/record.url?scp=85036521605&partnerID=8YFLogxK

    U2 - 10.1016/j.jphotochem.2017.11.049

    DO - 10.1016/j.jphotochem.2017.11.049

    M3 - Article

    VL - 353

    SP - 349

    EP - 357

    JO - Journal of Photochemistry and Photobiology A: Chemistry

    T2 - Journal of Photochemistry and Photobiology A: Chemistry

    JF - Journal of Photochemistry and Photobiology A: Chemistry

    SN - 1010-6030

    ER -

    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