期刊
CHEMISTRY-AN ASIAN JOURNAL
卷 13, 期 5, 页码 510-514出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201701805
关键词
donor-acceptor systems; isomerization; overcrowded ethylene; solvatochromism; twisted system
资金
- JSPS KAKENHI Grant from the Ministry of Education, Culture, Sports, Science and Technology, Japan [JP15K05475, 2408, JP15H00942]
The twisted form of bianthrone is known as a metastable state provided by a photo-induced or thermal-induced isomerization of the folded form, and thus prevents the isolation and the detailed analysis of its electronic structure. In this study, an unsymmetrical bianthrone (2), consisting of the electron-withdrawing anthrone and electron-donating acridane, have been synthesized and shown to exhibit a solvent-polarity-dependent isomerization reaction between the folded and twisted isomers. With increasing the polarity of the solvent, 2 showed an isomerization reaction from the folded form to the twisted form. The stabilization of the twisted isomer in polar solvents can be interpreted as proof of its relatively large zwitterionic character. The DMF solution of 2 displayed paramagnetically-broadened NMR signals from the thermally populated triplet state resulting from rotation of the weakened ethylenic double bond of the twisted isomer.
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