Journal
CHEMISTRY LETTERS
Volume 46, Issue 9, Pages 1368-1371Publisher
CHEMICAL SOC JAPAN
DOI: 10.1246/cl.170566
Keywords
Sumanene; Buckybowl; Cross-coupling
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Funding
- Japan Society for the Promotion of Science (JSPS) [JP26102002, JP26102008]
- Dynamic Alliance for Open Innovation Bridging Human, Environment and Materials from MEXT
- Grants-in-Aid for Scientific Research [26102008, 26102002] Funding Source: KAKEN
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2,3,5,6,8,9-hexabromosumanene (2) with Br groups at all the peripheral aromatic carbons was successfully synthesized. Single-crystal X-ray structural analysis of 2 revealed the formation of a one-dimensional columnar structure in the solid state, where the molecules overlapped in an eclipsed manner. The Suzuki-Miyaura cross-coupling of 2 and various aryl-boronic acids gave hexaarylsumanene derivatives (3a-3h) in good-to-moderate yields. The NMR spectroscopic analysis and theoretical calculations of 2 and hexaphenylsumanene (3a) revealed that the six peripheral functional groups do not significantly affect the original bowl structure or bowl-to-bowl inversion behavior of sumanene.
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