Comparison of the photocatalytic activity of novel hybrid photocatalysts based on phthalocyanines, subphthalocyanines and porphyrins immobilized onto nanoporous gold

A series of different singlet oxygen photosensitizers was immobilized onto nanoporous gold powder with a mean pore size of 40 nm via copper catalyzed azide–alkyne cycloaddition. The attachment of phthalocyanine and porphyrin derivatives was performed on the peripheral substituent of the macrocycle, whereas the subphthalocyanine derivatives were attached via the axial substituent with respect to the macrocyclic ring system. All obtained hybrid systems were studied in the photooxidation of 2,5-diphenylfuran as a chemical singlet oxygen quencher and showed increased photocatalytic activity compared to the same amount of the corresponding photosensitizer in solution due to photoinduced interactions of the plasmon resonance of the nanostructured gold support and the attached photosensitizer. The understanding of the different photophysical interactions depending on the coordination mode of the macrocycle as well as the position of the absorbance in the electromagnetic spectrum is an important point in the development towards highly active hybrid photocatalysts covering a broad absorption range within the spectrum of visible light.