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Updated: Apr 14, 2026

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Benzene-Fused Azacorannulene Bearing an Internal Nitrogen Atom
Shingo Ito1, Yuki Tokimaru2, Kyoko Nozaki3
1Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656 (Japan). ito_shingo@chembio.t.u-tokyo.ac.jp.
Abstract:
A novel nitrogen-doped corannulene derivative, 8-tert-butyl-6b(2) -azapentabenzo[bc,ef,hi,kl,no]corannulene, was synthesized by 1,3-dipolar cycloaddition of a polycyclic aromatic azomethine ylide with a diarylethyne and subsequent palladium-catalyzed intramolecular cyclization. This molecule represents the first example of a corannulene derivative bearing an internal heteroatom, and exhibits unique structural and physical properties caused by the introduction of the nitrogen atom and extended π-conjugation, as compared to the parent corannulene.
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