Synthesis and reactions of meso-(p-nitrophenyl)porphyrins

Synthesis of Highly Substituted Nitro/Ha­lo-meso-tetraaryl­porphyrins by Tandem Cyclocondensation/Aromatic Electrophilic Nitration Reactions

“…Preparation of porphyrins, [12] substituted with electrophilic highly functionalized aryl rings in mesopositions , by the Rothemund synthesis [14] (and its crosscondensation modifications [15] ), from the corresponding aldehydes and pyrrole, is an extremely difficult task (yields below 3 %), [16] or even impossible.…”

Phenyl Substituted Porphyrins. Part 5. Acylation of Aminophenylporphyrins

“…5-(4-Nitrophenyl)-10,15,20-triphenylporphyrin (1, 4-NO 2 ) was also obtained by nitration of meso-tetraphenylporphyrin 2 (side product of the "mixed aldehyde" condensation) with sodium nitrite in trifluoroacetic acid, similarly to [29,30] (Scheme 2), with subsequent reduction, which afforded significantly increased total yield of aminophenylporphyrin 5 (4-NH 2 ).…”

Model Systems for Fluorescence and Singlet Oxygen Quenching by Metalloporphyrins

“…nophenyl)-10,15,20-triphenylporphyrin 3 was chosen as our starting material, as it is easily synthesized from the corresponding 5,10,15,20-tetraphenylporphyrin (TPP, 1) by nitration with NaNO 2 followed by reduction with SnCl 2 ·2 H 2 O, as reported previously (Scheme 1). [22] Aminophenylporphyrin 3 can be further functionalized with a five-carbon linker terminating in an acid moiety by reaction with glutaric anhydride to give compound 4.…”