Crosswise Phthalocyanines with Collinear Functionalization: New Paradigmatic Derivatives for Efficient Singlet Oxygen Photosensitization

摘要： We describe here the preparation of a number of trans-ABAB Zn(II) phthalocyanines (ZnPcs) 1a-g, which combine several interesting features. First, these compounds present high solubility and hindered aggregation, due to the functionalization of two facing isoindole constituents (B) of the ZnPc with bis(trifluoromethylphenyl) units. Second, the other two isoindoles (A) hold extra-annulated phthalimide units containing different substituents in the nitrogen positions, this feature resulting in a collinear arrangement of a variety of functional groups. Some of these collinearly functionalized ZnPcs are interesting building blocks for constructing either homo- or heteroarrays containing ZnPc units. On the other hand, the amphiphilic nature of some members of the series renders them interesting candidates for photosensitization of singlet oxygen. Photophysical studies on ZnPc 1c, selected as model compound of the series, have proven these molecules efficient singlet oxygen photosensitizers in both polar and apolar media, with 1O2 quantum yields (ΦΔ) as high as 0.74.