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a b s t r a c tPorphyrins are key precursors for development of photosensitizers for photodynamic therapy. A new series of ortho-halogenated tetraarylporphyrins with sulfonamide substituents have been synthesized via chlorosulfonation reaction and characterized by MALDI-TOFMS. To predict their partition properties, log K OW of a selected range of the synthesized halogenated amphiphilic porphyrins is described. A significant effect of the number and type of halogen group as well as on the number of sulfonamide side chain was observed. The determined 1-octanol/water partition coefficients showed that it is possible to obtain compounds with a wide range of lipophilicities, from log K OW ¼À2.71 till log K OW >4, which are suitable to optimize the biological efficacy of this class of sensitizers.

This paper describes an environmentally sustainable synthetic method for the preparation of a set of meso-aryl hydroporphyrins, namely chlorins and bacteriochlorins, via reduction of porphyrins with diimide, in the total absence of solvents and bases. Thermomicroscopy studies clearly showed that the process is a typical solvent-free reaction. † Electronic supplementary information (ESI) available: SI_PLTM_por-phyrin_p_toluenesulfonylhydrazide movie file.

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Photodynamic therapy (PDT) is a promising treatment for several types of cancers. It involves the synergetic effect of light, oxygen and an appropriate photosensitizer. Extensive studies on the synthetic modulation of the structure of tetrapyrrolic macrocycles allowed for the optimization of chemical and physical properties of such photosensitizers. The progress from porphyrins to chlorins and more recently to bacteriochlorins clearly shows the improvements achieved in PDT photosensitizers. This paper summarizes our recent contribution to the synthesis of stable amphiphilic halogenated meso-tetraarylbacteriochlorins. Their photophysics, in vitro cytotoxicity and phototoxicity are presented and their potential use as photosensitizer for PDT application is assessed.