期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 56, 期 12, 页码 3374-3378出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201610434
关键词
carbohelicenes; cyclodehydrogenation; double helicenes; isomerization barrier; optical resolution
资金
- Alexander von Humboldt Foundation
- European Commission through the FET-Proactive Project MoQuaS [610449]
- Graphene Flagship [CNECT-ICT-604391]
A benzo-fused double [7]carbohelicene (D7H) was synthesized through a regioselective cyclodehydrogenation of a tetranaphthyl-p-terphenyl-based precursor. The twisted (D7H-1) and anti-folded (D7H-2) conformers of D7H were separated by recrystallization, and their double helicene structures with overlapping terminal benzene rings were unambiguously elucidated by X-ray crystallography. A record-high isomerization barrier (46.0 kcal mol(-1)) in double helicenes was estimated based on density functional theory (DFT) calculation, which resulted in the excellent conformational stability of D7H. The physicochemical properties of D7H-1 and D7H-2 were investigated by UV/Vis absorption spectroscopy and cyclic voltammetry, displaying the variation of electronic structure upon conformational changes. The optical resolution of the racemic D7H-1 was carried out by chiral HPLC, offering enantiopure D7H-1-(P,P) and D7H-1(M,M), which were further characterized by circular dichroism spectroscopy.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据