Organic Chemistry

Targeted Synthesis of Regioisomerically Pure Dodecasubstituted Type I Porphyrins Through the Exploitation of Peri-Interactions



A targeted synthesis of dodecasubstituted type I porphyrins that utilizes the reaction of unsymmetrical 3,4-difunctionalized pyrroles and sterically demanding aldehydes was developed. This way, type I porphyrins could be obtained as the only type isomers, likely due to a minimization of the steric strain arising from peri-interactions. Uniquely, this method does not depend on lengthy precursor syntheses, the separation of isomers, or impractical limitations of the reaction scale. In addition, single crystal X-ray analysis elucidated the structural features of the macrocycles.

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Type I Porphyrin Isomers - SI - ChemRxiv