Boosting the singlet oxygen photosensitization abilities of Zn(ii) phthalocyanines through functionalization with bulky fluorinated substituents

Miguel A. Revuelta-Maza, Santi Nonell, Gema De La Torre, Tomás Torres

Research output: Indexed journal article Articlepeer-review

23 Citations (Scopus)

Abstract

In-depth, systematic photophysical studies have been performed on a series of ABAB, A3B and A4 ZnPcs functionalized with a varying number of bis(trifluoromethyl)phenyl units (i.e. at the B isoindoles) and other electron-withdrawing/electron-donating moieties (i.e. at the A isoindoles), to determine the influence of the susbtitution pattern on the aggregation features, fluorescence quantum yields and singlet oxygen (1O2) generation abilities of these molecules. As a general trend, the larger the number of bis(trifluoromethyl)phenyl units (i.e.ABAB crosswise functionalized ZnPcs), the lower the fluorescence quantum yield and the higher the 1O2 photosensitization. On the other hand, the electronic character of the substituents at the A isoindoles do not seem to have a clear effect on the photophysical properties of these ABAB ZnPcs. Overall, 1O2 quantum yields determined by the direct observation of the 1O2 phosphorescence are very high, with values ranging from 1 to 0.74 in THF solutions.

Original languageEnglish
Pages (from-to)7448-7454
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume17
Issue number32
DOIs
Publication statusPublished - 2019

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