Synthesis And Properties Of Naphthylporphyrin Compounds And Their Anthraquinone Derivatives

Porphyrin derivatives, due to their exclusive biological and optical properties, have been wildly used as photosensitizer for photodynamic therapy of cancer and cardiovascular diseases. Nowadays, the investigation on porphyrin mainly focused on phenylporphyrin-anthraquinone and its derivatives. Nevertheless, porphyrins containing high-conjugated groups, such as naphyl, substituted in the meso positions of the tetrapyrrole ring exhibit increased tumor localization properties compared with the corresponding phenyl substituted compounds.In the present paper, several novel porphyrins bearing naphthyl group and their metal complexes were synthesized by Adler and Guo method and characterized by IR, 1H NMR and FAB-MS. Naphthylporphyrin-anthraquinone compounds were also synthesized and characterized by IR, 1H NMR, FAB-MS and Element Analysis. The crystal structure of one of these compounds was investigated by single crystal X-ray diffraction.The absorption properties, fluorescence spectra and oxidation-reduction potential were studied. The result exhibit that the introduction of naphthyl group can enhance the conjugate degree of the porphyrin and make them more difficult to be oxidated. In the naphthylporphyrin-anthraquinone molecule, the fluorescence quenching was observed due to the photoinduced intramolecular electron transfer from the excited porphyrin singlet state to the appended anthraquinone.