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Benzene‐Fused Azacorannulene Bearing an Internal Nitrogen Atom
Author(s) -
Ito Shingo,
Tokimaru Yuki,
Nozaki Kyoko
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201502599
Subject(s) - corannulene , chemistry , heteroatom , nitrogen atom , cycloaddition , intramolecular force , molecule , nitrogen , derivative (finance) , benzene , photochemistry , catalysis , stereochemistry , ring (chemistry) , organic chemistry , financial economics , economics
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.