Synthesis, Absorption and Fluorescence Spectral Investigation of Phorphyrazines with Eight 2-Naphthalenecarboxy Esters

New magnesium porphyrazines substituted with eight naphthalenecarboxy groups on the peripheral positions were synthesized through a stepped reaction; first, cyclo tetramerization of 1,2-dicyano-1,2-bis(2-hydroxyethylthio)ethylene led to a porphyrazine formation which was subsequently esterified with 2-naphthoic acid. A metal-free derivative was prepared by treatment with trifluoroacetic acid. Metalloporphyrazines were prepared by insertion of Zn(II), Co(II) and Ni(II) ions. These porphyrazines were characterized by elemental analysis, 1H NMR, 13C NMR, LC-MS, FT-IR, and UV-Vis spectral data. In addition, fluorescence emissions of the compounds with naphthalene were obtained and the emissions due to the naphthalene moieties covalently-bonded to the porphyrazine were partially quenched.