期刊
CHEMISTRY-AN ASIAN JOURNAL
卷 17, 期 12, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.202200244
关键词
amidine; circulene; pyridine; antiaromaticity; protonation
资金
- MEXT, Japan [2903, JP20H04668]
- JSPS Research Fellowship for Young Scientists [JP18J22906]
- National Research Foundation of Korea (NRF) - Korean government (MSIT) [2021R1A2C300630811]
In this study, C-4h-symmetric octaaza[8]circulenes were synthesized and exhibited enhanced antiaromaticity upon protonation. The protonation of the pyridine rings enhanced the contribution of the octaaza[8]circulenes' antiaromatic character.
The switching of cyclic pi-conjugation pathways using external stimuli is an attractive research topic in the field of organic chemistry. Here, we synthesized C-4h-symmetric octaaza[8]circulenes with four peripherally arranged amidine moieties that exhibit enhanced antiaromaticity upon protonation. Titration experiments with methanesulfonic acid revealed the formation of the tetraprotonated forms of the octaaza[8]circulenes in solution. Single-crystal X-ray diffraction analyses and theoretical calculations indicated that the contribution of the 8 pi antiaromatic character of the octaaza[8]circulenes is enhanced by the delocalization of charge through the protonation of the pyridine rings.
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