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

Abstract

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 ∼730 nm and fluorescence emission at ∼760 nm after excitation with ∼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 Φ△ value of 0.73, which is significantly higher than that of verteporfin. Therefore, Ar4TNPs have great potential as an effective optical material, bio-tracker, and photodynamic drug candidate.