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

preprint
submitted on 29.03.2020 and posted on 30.03.2020 by Marc Kielmann, Keith Flanagan, Mathias 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.

Funding

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

Horizon 2020 FET Open grant agreement no. 828779

History

Email Address of Submitting Author

sengem@tcd.ie

Institution

Trinity College Dublin, The University of Dublin

Country

Ireland

ORCID For Submitting Author

0000-0002-7467-1654

Declaration of Conflict of Interest

The authors declare no conflict of interest.

Version Notes

Version 1.0

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