期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 24, 期 29, 页码 7489-7497出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201800617
关键词
chiral resolution; circulene; fluorescence; helicene; oxidative fusion reaction
资金
- JSPS KAKENHI [JP25220802, JP16K13952, JP26810021, JP16H00909, JP15H03779, JP15K13642, JP16KK0111, JP17H05261]
- Asahi Glass Foundation
- Cosmetology Research Foundation
- Grants-in-Aid for Scientific Research [16H00909] Funding Source: KAKEN
Polycyclic heteroaromatic compounds including pyrrole units are promising functional scaffolds owing to their electron-rich nature, bright fluorescence, and applicability to anion recognition at the pyrrolic hydrogen atom. We report herein the effective synthesis of pseudo-aza[5]helicene and aza[7]helicene derivatives, and unexpected formation of azahepta[8]circulenes by oxidative fusion reactions. By choosing reaction conditions and peripheral substituents attached at the terminal indole moieties, we obtained aza[7]helicenes 10a-c and azahepta[8]circulenes 11a,c selectively in moderate to good yields. Their solid-state structures have been revealed by X-ray diffraction analysis. UV/Vis absorption, emission, and cyclic voltammetry of these compounds were studied in comparison with those of previously reported tetraaza[8]circulene (TA8C), a symmetric and planar molecule. Furthermore, the enantiomeric separation of dimethyl-substituted aza[7]helicene 10b was achieved, and the racemization kinetics have been elucidated both theoretically and experimentally. This work illustrates a wealth of advantages of pyrrole incorporation into the polycyclic aromatic scaffolds in terms of synthetic aspects, structural variation, and optical tuning.
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