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Updated: Sep 12, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Synthesis of a Highly Luminescent Pyrrole-Fused Dicorannulene as a Corrugated π-Extended Carbazole
Koki Kise1, Aoi Nakagawa2, Shu Seki2
1Department of Chemistry, Graduate School of Science, Kyoto University, Kitashirakawa Oiwake-cho, Sakyo-ku, Kyoto 606-8502, Japan.
Abstract:
A pyrrole-fused dicorannulene was designed and synthesized via Pd-catalyzed reactions. This molecule can be regarded as a corrugated π-extended carbazole, which exhibited efficient blue fluorescence (ΦF = 0.56) in contrast to fairly nonemissive pristine corannulene. In addition, deprotonation of the pyrrolic NH by tetrabutylammonium hydroxide gave stable anionic species with a perturbed optical response. Its tetrabutylammonium salt was isolable under ambient conditions, owing to the extensive charge delocalization onto the π-extended chromophore.
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