| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1334856 | Polyhedron | 2011 | 9 Pages |
Two novel zinc(II) phthalocyanines bearing non-peripheral ester-alkyloxy substituents (Pc-4 and Pc-5) were synthesized, by a two-step procedure starting from 2,3-dicyanohydroquinone. Both sensitizers show promising photophysical properties, including solvatochromic study, qualitative evaluation of emission, aggregation behavior and singlet oxygen generation. It was proven that the photodynamic activity of the compounds studied depends on the molecular oxygen level. Comparison of the quantum yields of singlet oxygen generation as well as the oxidation rate constants using 1,3-diphenylisobenzofurane before and after deaeration proved the photodynamic effect of Pc-4 and Pc-5 to be governed by the photosensitization mechanism II. Changes in the quantities of the compounds exposed to irradiation were also estimated. Upon their exposure to light the changes in intensity of the Q band were monitored. The photodecomposition of Pc-4 and Pc-5 in DMSO or DMF solutions was found to proceed according to the first order kinetic reaction in two stages.The photosensitizing effect of Pc-4 in HSC-3 cells was significantly lower than that of ZnPc. Pc-4 was ineffective at 0.1 μM, while a low, approx. 15% photocytotoxicity was observed at 5 μM, at a distance of 5 and 10 cm. The efficacy of Pc-4 in photokilling of cultured cells is affected by hydrophobicity and the aggregation status of the photosensitizer.
Graphical abstractTwo novel zinc(II) phthalocyanines bearing non-peripheral ester-alkyloxy substituents (Pc-4 and Pc-5) were synthesized. Both sensitizers present promising photophysical properties, including singlet oxygen generation. The photosensitizing effect of Pc-4 was significantly lower than that of ZnPc.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Novel phthalocyanines bearing non-peripheral ester-alkyloxy substituents were synthesized. ► Sensitizers showed promising photophysical properties, including singlet oxygen generation. ► The photodecomposition of phthalocyanines was examined. ► The photosensitizing effect of novel phthalocyanine in HSC-3 cells was tested.
