Synthesis and electrochemical properties of a novel mono-meso-ferrocenyl porphyrin

FERNANDO NIEMEVZ; JUAN MANUEL LÁZARO MARTÍNEZ; ROMINA CARBALLO; IRENE REZZANO; GRACIELA YOLANDA BULDAIN

SYNTHESIS-STUTTGART

Georg Thieme Verlag Stuttgart

Lugar: New York; Año: 2006 vol. 2006 p. 870 - 874

0039-7881

A synthetic route to mono meso-ferrocenyl porphyrins using a MacDonald type 2+2 condensation is described. In this method, the substituted diformyldipyrrylmethane is treated with the dicarboxydipyrrylmethane. The 5-ferrocenyldipyrrylmethane was obtained by condensation of the benzyl 3-methyl-4-ethylpyrrol-2-carboxylate with ferrocenecarboxaldehyde in presence of p-toluenesulfonic acid. The unequivocal assignment of all proton resonances in the new porphyrin was achieved by means of a detailed analysis of its H-H NOESY correlations. Interestingly, we noticed that the ferrocenyl group introduces an element of asymmetry in the molecule. The corresponding Co(II) and Ni(II) complexes were also prepared. Cyclic voltammograms of the free base and the Co or Ni complexes show that all voltammetric peaks disappear after four consecutive scans. This result suggest no film formation in any of them.