Synthesis, Characterization, Singlet-Oxygen Photogeneration, DNA Photocleavage and Two-Photon-Absorption Properties of Some (4-Cyanophenyl)porphyrins

A series of (4-cyanophenyl)porphyrins have been prepared and structurally characterized by H-1 NMR, IR and UV/Vis spectroscopy, mass spectrometry, and elemental analysis. The relative singlet-oxygen quantum yields, two-photon absorption cross-sections and DNA photocleavage activities of these porphyrins were measured. The results show that (4-cyanophenyl)porphyrins with a properly designed hydrophobic/hydrophilic balance for better cellular uptake have potential application in two-photon-absorption photodynamic therapy. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)