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Comparison of the photophysical properties of three phenothiazine derivatives: transient detection and singlet oxygen production

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Abstract

New methylene blue (NMB+) and methylene violet (MV) are known for their photosensitizing properties for singlet oxygen (1O2) generation upon visible-light irradiation, and various examples of their use in the photodynamic inactivation of microorganisms and for photomedicinal purposes have been reported. However, their photophysical properties have never been extensively and systematically analyzed and compared. In the current work, we studied their absorption and fluorescence behavior relative to their parent compound, methylene blue (MB+), detected the transient species generated upon excitation of the photosensitizers and determined their quantum yields of singlet oxygen production. We could measure very high quantum yields of singlet oxygen production for all the studied compounds. NMB+ appeared similar to MB+, even though it produces 1O2 much more efficiently, and was slightly influenced by the solvent. MV, in contrast, was much more sensitive to the chemical environment, and the transient species formed upon irradiation were different in methanol and acetonitrile. It appeared to be a very good singlet oxygen sensitizer, but the influence of the chemical environment should be carefully considered for any application. The comparative characterization of these sensitizers will represent a support for the determination and the understanding of the photochemical mechanisms occurring by using these phenothiazine dyes for various photobiological applications.

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Authors and Affiliations

  1. IPREM, UMR CNRS 5254, Université de Pau et des Pays de l’Adour, Hélioparc, 2 rue du Président Angot, F-64053, Pau Cedex 9, France

    Filippo Ronzani, Sylvie Blanc & Sylvie Lacombe

  2. ICCF, UMR CNRS 6296, Université Blaise Pascal, Campus des Cézeaux, 24 avenue des Landais, BP 80026, F-63171, Aubière Cedex, France

    Aurélien Trivella, Mohamed Sarakha & Claire Richard

  3. Laboratoire des IMRCP, UMR CNRS 5623, Université Toulouse III (Paul Sabatier, UPS), 118 route de Narbonne, F-31062, Toulouse Cedex 9, France

    Emmanuel Arzoumanian & Esther Oliveros

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  1. Filippo Ronzani
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  2. Aurélien Trivella
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  3. Emmanuel Arzoumanian
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  4. Sylvie Blanc
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  7. Esther Oliveros
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Correspondence to Sylvie Lacombe.

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Electronic supplementary information (ESI) available. See DOI: 10.1039/c3pp50246e

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Ronzani, F., Trivella, A., Arzoumanian, E. et al. Comparison of the photophysical properties of three phenothiazine derivatives: transient detection and singlet oxygen production. Photochem Photobiol Sci 12, 2160–2169 (2013). https://doi.org/10.1039/c3pp50246e

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