Synthesis and characterization of biocompatible bimodal meso-sulfonamide-perfluorophenylporphyrins

Efficient and selective synthetic method for preparing a set of meso-aryl sulfonamide-perfluorinated aryl porphyrins is reported. The new compounds showed a broad range of 1-octanol/water partition coefficients and singlet oxygen quantum yield from 0.59 to 0.74. •Development of a selective synthetic method for preparing a set of meso-aryl sulfonamide-perfluorinated porphyrins.•The meso-aryl sulfonamide-perfluorinated porphyrins presented a broad range of 1-octanol/water partition coefficients.•Singlet oxygen quantum yields for the perfluorinated porphyrins was in the range of 0.59–0.74. Herein we describe a synthetic strategy for preparing a set of meso-aryl sulfonamide-perfluorinated porphyrins by covalent binding in order to obtain new chemical entities that can potentially target bacteria and act both as bacteriostatic and photosensitizing agents. The conditions optimized allow to selectively obtain porphyrins containing the desired number of sulfonamide substituents. The new compounds showed a broad range of 1-octanol/water partition coefficients and singlet oxygen quantum yields from 0.59 to 0.74. Our results demonstrate that sulfonamide-perfluorinated porphyrins are a promising platform for biomedical applications, particularly in aPDT and medical imaging.