Synthesis of 5-(4-X-Phenyl)-10,15,20-tris(substituted phenyl) porphyrins using dipyrromethanes

Abstract

5-(4-X-Phenyl)-10,15,20-tris(substituted phenyl) porphyrins (4-6) were synthesized from meso-(substituted phenyl) dipyrromethanes (1-3), which in turn were prepared in yields of 75-92%. This synthetic pathway was compared with the binary mixed aldehyde and pyrrole condensation method. The reported dipyrromethane approach is advantageous for porphyrins substituted by -OCH 3 (4) and -F (6) groups (12-14%), while the yield of porphyrins bearing -N(CH3)2 (5) groups was similar (∼0.3%) by both methods.