Journal
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
Volume 91, Issue 4, Pages 531-537Publisher
CHEMICAL SOC JAPAN
DOI: 10.1246/bcsj.20170384
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Funding
- MEXT [JP26102002]
- JSPS KAKENHI [JP26288020]
- JST (ACT-C) [JPMJCR12YZ]
- Japan Society for the Promotion of Science (JSPS)
- WCU (World Class University) program, Korea [R31-10059]
- Ogasawara Foundation for the Promotion of Science Engineering
- Iketani Science and Technology Foundation
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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.
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