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.
Highlights
Meso-substituted porphyrins are the great interest for the development of model systems in biomimetic and materials chemistry [1]
This route requires access to meso-substituted dipyrromethane, which can be synthesized from the reaction of aldehyde with excess of pyrrole catalyzed by acid [7,8]
The yields obtained using the dipyrromethane approach are considerably higher for porphyrins substituted by –OCH3 (4) and -F (6) groups than when the binary mixed aldehyde and pyrrole condensation method was used
Summary
Meso-substituted porphyrins are the great interest for the development of model systems in biomimetic and materials chemistry [1]. These porphyrins bearing two different types of meso-substituents can be prepared by a binary mixed aldehyde condensation [4,5]. This route requires access to meso-substituted dipyrromethane, which can be synthesized from the reaction of aldehyde with excess of pyrrole catalyzed by acid [7,8].
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