Abstract
Synthesis of highly functionalized nitro/halo-5,10,15,20-tetraaryl porphyrins is described. meso-Tetraphenylporphyrin derivatives (halo-substituted in meso-phenyl rings; with F, Cl, Br, and I), in the reaction with fuming yellow nitric acid (d = 1.52), result in the formation of mono-, di-, tri-, and even tetranitro-substituted porphyrins (with summary yields of 28–81%), depending on the reaction temperature (0 °C to 5 °C or at r. t.), amounts of the acid used, and reaction time. In some cases moderate selectivity was observed. The starting halo-substituted meso-tetraarylporphyrins were prepared in the cyclocondensation reaction of pyrrole with the respective aromatic aldehydes (usually carried out according to known procedures). By this route, the preparation of the synthetic porphyrins (bearing up to ten halo-/ nitro-substituents) was demonstrated.
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