Stereoisomerism in Nanohoops with Heterogeneous Biaryl Linkages of E/Z- and R/S-Geometries.
Stereoisomerism in Nanohoops with Heterogeneous Biaryl Linkages of E/Z- and R/S-Geometries.
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DOI：
10.1021/acscentsci.6b00240
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发表时间：
2016-10-26
影响因子：
18.2
通讯作者：
Isobe, Hiroyuki
中科院分区：
文献类型：
--
作者：
Sarkar, Parantap;Sun, Zhe;Tokuhira, Toshiki;Kotani, Motoko;Sato, Sota;Isobe, Hiroyuki
The stereochemistry of cycloarylene nanohoops gives rise to unique cyclostereoisomerism originating from hoop-shaped molecular shapes. However, cyclostereoisomerism has not been well understood despite the ever-increasing number of structural variants. The present work clarifies the cyclostereoisomerism of a cyclophenanthrenylene nanohoop possessing both E/Z- and R/S-geometries at the biaryl linkages. Involvement of the R/S axial chirality in the nanohoop leads to the deviation of the structure from a coplanar belt shape and allows for structural variations with 51 stereoisomers with E/Z- and R/S-geometries. Experimental investigations of the dynamic behaviors of the cyclophenanthrenylene nanohoop revealed the presence of two-stage isomerization processes taking place separately at the E/Z- and R/S-linkages. Consequently, despite the presence of E/Z-fluctuations, the R/S axial chirality resulted in a separable pair of enantiomers. The structural information reported here, such as geometric descriptors and anomalous dynamics, may shed light on the common structures of various nanohoops. Anomalous cyclostereoisomerism comprising E/Z and R/S biaryl linkages has been disclosed by a cyclophenanthrenylene nanohoop.
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影响因子：
2.8
作者：
Bauernschmitt, R;Ahlrichs, R
通讯作者：
Ahlrichs, R
DOI：
10.1039/jr9630002365
发表时间：
1963-01-01
期刊：
JOURNAL OF THE CHEMICAL SOCIETY
影响因子：
--
作者：
COOKE, AS;HARRIS, MM
通讯作者：
HARRIS, MM
影响因子：
0.8
作者：
Leroux, Fredric R.;Simon, Roger;Nicod, Nathalie
通讯作者：
Nicod, Nathalie
DOI：
10.1139/v78-451
发表时间：
1978-01-01
期刊：
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE
影响因子：
--
作者：
OKAZAWA, N;SORENSEN, TS
通讯作者：
SORENSEN, TS
影响因子：
64.8
作者：
IIJIMA, S
通讯作者：
IIJIMA, S