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 –OCH3 (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.

Keywords

• Porphyrin
• dipyrromethane