Synthesis and photophysical properties of symmetrical tetraaryltetranaphtho[2,3]porphyrin derivatives

The discovery of new photosensitizers with strong absorption near-infrared region, obvious fluorescence emission, and high reactive oxygen generation ability has attracted great attention as optical agents in life science and material industry. Herein a series of meso-tetraaryltetranaphtho[2,3]porphyrins (Ar 4TNPs) with different substitutions were designed and synthesized. They had strong absorptions at similar to 730 nm and fluorescence emission at 760 nm after excitation with similar to 503 nm light. All compounds possessed excellent reactive oxygen species (ROS) generation ability. The singlet oxygen generation rate of compound 10m (meso-5,10,15,20-tetra[2-(2-hydroxyethoxy)ethylbenzoate]tetrana-phthoporphyrin) is 0.1898 s(-1) with a Phi(Delta) value of 0.73, which is significantly higher than that of verteporfin. Therefore, Ar(4)TNPs have great potential as an effective optical material, biotracker, and photodynamic drug candidate.