Synthesis of Octafluoroporphyrin.

ABSTRACT

Despite the long list of known fluoroporphyrinoids, the most fundamental 2,3,7,8,12,13,17,18-octafluoroporphyrin (OFP) has not been synthesized until now. It is achieved by condensation of two molecules of tetrafluoro-dipyrrylmethane-2-carboxaldehyde in the presence of magnesium(II) salts. The fluorinated dipyrrylmethane also gives 5,15-bis(pentafluorophenyl)-OFP (F18P) with a reasonable yield. Both Mg/OFP and Zn/F18P in the solid-state reveal an essentially flat structure. The fluoro groups impart as much as a 0.5 V anodic shift for porphyrin ring oxidation/reduction, as well as hypsochromic shifts in the Uv-vis spectra.