The synthesis of new chromophore architectures based on arrays of phenothiazine and (hetero)aromatic units joint in the meso positions of a porphyrin core (phenothiazinyl A 4 , phenothiazinyl and (hetero)aryl: AB 3 trans-A 2 B 2 and A 3 B), is described. The structures were assigned based on HRMS and NMR spectra. Their optical properties were evaluated according UV–Vis spectroscopic data, which emphasized absorption maxima around 420 nm with molar absorptivities 10 5 M −1 cm −1 and emission characterized in solution by large Stokes shifts (3800–4500 cm −1 ) and fluorescence quantum yields ranging from 0.01 to 0.06. The electron transfer properties of the compounds were estimated using cyclic voltammetry which pointed out three quasi-reversible one-electron oxidations potentials ranging between 800 and 1400 mV (vs. Ag/AgCl). Selected meso-phenothiazinylporphyrins were evaluated as photosensitizers for photodynamic therapy (PDT) by in vitro irradiation of two human skin cell lines (HaCaT and A431) using red and blue light.