The Fold-In Approach to Bowl-Shaped Aromatic Compounds: Synthesis of Chrysaoroles


  • Financial support from the National Science Center (grant N N204 199340) is gratefully acknowledged. Quantum-chemical calculations were performed in the Wrocław Center for Networking and Supercomputing. We thank Prof. Tadeusz Lis for solving the X-ray crystal structure of 4 and for helpful discussions. We thank Dr. Piotr Stefanowicz and Dr. Piotr Jakimowicz for their assistance with mass spectrometry.


original image

Molecular jellyfish: A new family of bowl-shaped aromatic compounds swims into view (see picture). Quite unlike true jellyfish, chrysaoroles possess a rigid skeleton, which is assembled from fused carbazole units. Their synthesis involves a fold-in step to convert a macrocyclic precursor into the bowl-shaped target molecule.