Benzene-Fused Azacorannulene Bearing an Internal Nitrogen Atom.
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.
Department 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.
Shingo
S
Ito
Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656 (Japan).
Yuki
Y
Tokimaru
Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656 (Japan). nozaki@chembio.t.u-tokyo.ac.jp.
Kyoko
K
Nozaki
azomethine ylide; corannulenes; polycycles; supramolecular chemistry; synthetic methods