Enantioselective synthesis of a chiral nitrogen-doped buckybowl

Qitao Tan, Shuhei Higashibayashi, Sangita Karanjit, Hidehiro Sakurai

Research output: Contribution to journalArticle

91 Citations (Scopus)

Abstract

Bowl-shaped aromatic compounds, namely buckybowls constitute a family of curved polycyclic aromatic carbons along with fullerenes and carbon nanotubes. Doping of heteroatoms to the carbon frameworks of such aromatic compounds drastically modulates their physical and chemical properties. In contrast to nitrogen-doped azafullerenes or carbon nanotubes, synthesis of azabuckybowls, nitrogen-doped buckybowls, remains an unsolved challenging task. Here we report the first enantioselective synthesis of a chiral azabuckybowl, triazasumanene. X-ray crystallographic analysis confirmed that the doping of nitrogen induces a more curved and deeper bowl structure than in all-carbon buckybowls. As a result of the deeper bowl structure, the activation energy for the bowl inversion (thermal flipping of the bowl structure) reaches an extraordinarily high value (42.2 kcal per mol). As the bowl inversion corresponds to the racemization process for chiral buckybowls, this high bowl inversion energy leads to very stable chirality of triazasumanene.

Original languageEnglish
Article number891
JournalNature Communications
Volume3
DOIs
Publication statusPublished - 2012
Externally publishedYes

Fingerprint

Carbon Nanotubes
Nitrogen
Carbon
aromatic compounds
Aromatic compounds
inversions
nitrogen
carbon
nanotubes
synthesis
carbon nanotubes
Doping (additives)
Fullerenes
Chirality
chirality
chemical properties
Chemical properties
fullerenes
Activation energy
Physical properties

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Chemistry(all)
  • Physics and Astronomy(all)

Cite this

Enantioselective synthesis of a chiral nitrogen-doped buckybowl. / Tan, Qitao; Higashibayashi, Shuhei; Karanjit, Sangita; Sakurai, Hidehiro.

In: Nature Communications, Vol. 3, 891, 2012.

Research output: Contribution to journalArticle

Tan, Qitao ; Higashibayashi, Shuhei ; Karanjit, Sangita ; Sakurai, Hidehiro. / Enantioselective synthesis of a chiral nitrogen-doped buckybowl. In: Nature Communications. 2012 ; Vol. 3.
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