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

submitted on 29.03.2020, 17:26 and posted on 30.03.2020, 13:29 by Marc Kielmann, Keith Flanagan, Mathias O.. Senge
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.


Science Foundation Ireland (SFI IvP 13/IA/1894)

Horizon 2020 FET Open grant agreement no. 828779


Email Address of Submitting Author


Trinity College Dublin, The University of Dublin



ORCID For Submitting Author


Declaration of Conflict of Interest

The authors declare no conflict of interest.

Version Notes

Version 1.0