The synthesis of ideal photosensitizers (PSs) is considered to be the most significant bottleneck in photodynamic therapy (PDT). To discover novel PSs with excellent photodynamic anti-tumor activities, a series of novel photosensitizers 5,15-diaryl-10,20-dibromoporphyrins (I_1–6) were synthesized by a facile method. Compared with hematoporphyrin monomethyl ether (HMME) as the representative porphyrin-based photosensitizers, it is found that not only the longest absorption wavelength of all compounds was red-shifted to therapeutic window (660 nm) of photodynamic therapy, but also the singlet oxygen quantum yields were significantly increased. Furthermore, all compounds exhibited lower dark toxicity (except I₂) and stronger phototoxicity (except I₄) against Eca-109 tumor cells than HMME. Among them, I₃ possessed the highest singlet oxygen quantum yield (Φ_Δ = 0.205), the lower dark toxicity and the strongest phototoxicity (IC₅₀ = 3.5 μM) in vitro. The findings indicated the compounds I₃ had the potential to become anti-tumor agents for PDT.

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