Interaction of 3,4-diiodopyrrole with 4-trifluoromethylbenzaldeyde under carefully optimized, Lindsey-type conditions at -10 degrees C has led to the synthesis of the first beta-octaiodoporphyrin, H-2[I(8)TpCF(3)PP]. The free ligand readily yielded Ni, Cu, and Zn complexes, which all proved amenable to single-crystal X-ray structure analyses. The zinc complex Zn[I8TpCF3PP] exhibits the most saddled porphyrin core for any simple porphyrin known to date and a dramatically red-shifted optical spectrum with a Soret maximum at 495 nm.