Journal
ACS CENTRAL SCIENCE
Volume 2, Issue 10, Pages 740-747Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscentsci.6b00240
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Funding
- KAKENHI [24241036, 25102007, 16K04864]
- Grants-in-Aid for Scientific Research [15K13432, 25102001, 16K04864, 25102007] Funding Source: KAKEN
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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.
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