Journal
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES
Volume 13, Issue 3, Pages 376-381Publisher
WORLD SCIENTIFIC PUBL CO PTE LTD
DOI: 10.1142/S1088424609000462
Keywords
photodynamic therapy; photosensitizers; porphycenes; porphyrinoids; singlet oxygen
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Funding
- Spanish Ministerio de Ciencia e Innovacion [CTQ2007-67763C03-01/BQU]
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The effects of 9-substitution on the photophysical properties of tetraphenylporphycenes (TPPo) have been examined using an electron acceptor, an electron donor, and an electroneutral substituent as model compounds. Introduction of the acetoxy group enhances the fluorescence ability of the compound, with only a small reduction in the singlet oxygen quantum yield. The optical and photophysical properties of a nitro-porphycene are reported for the first time. The compound is emerald green, contrasting with the typical blue color of porphycenes. While this compound is much less fluorescent than unsubstituted TPPo, its singlet oxygen quantum yield is only slightly lower, almost identical to that of the 9-acetoxy compound (9-AcOTPPo). Finally, the electron-donor amino group is found to induce the greatest changes in the porphycene photophysics, decreasing strongly its fluorescence and singlet oxygen quantum yields. With the exception of such electron donors, introduction of substituents at the 9 (meso) position of tetraphenylporphycenes is not detrimental to their photophysics
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