Triazasumanene: An isoelectronic heteroanalogue of sumanene

Qitao Tan, Patcharin Kaewmati, Shuhei Higashibayashi, Masaki Kawano, Yumi Yakiyama, Hidehiro Sakurai

Research output: Contribution to journalArticlepeer-review

33 Citations (Scopus)


Buckybowls, which are represented by sumanene and corannulene, have attracted considerable attention for their unique bowl structures and interesting physicochemical properties. However, still few heteroatom-doped buckybowls have been reported to date. Here we show the successful synthesis of triazasumanene, an isoelectronic heteroanalogue of sumanene, which possesses a deeper bowl with stable bowl chirality and unique helical columnar packing in the crystal as an enantiopure form. In contrast, the crystal packing of the racemate shows a unidirectional columnar structure, which resembles that of the pristine sumanene. Doping of nitrogen atoms into the periphery of the sumanene framework also leads to perturbations of the electronic structure as shown by a significant decrease of the lowest unoccupied molecular orbital (LUMO) level and the optical band gap in comparison to all-carbon sumanene. The pyridine ring of triazasumanene shows unusual susceptibility towards acidic hydrolysis due to the highly strained curved structure.

Original languageEnglish
Pages (from-to)531-537
Number of pages7
JournalBulletin of the Chemical Society of Japan
Issue number4
Publication statusPublished - 2018

ASJC Scopus subject areas

  • General Chemistry


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