Stereoisomerism in nanohoops with heterogeneous biaryl linkages of E/Z- and R/S-geometries

Parantap Sarkar, Zhe Sun, Toshiki Tokuhira, Motoko Kotani, Sota Sato, Hiroyuki Isobe

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

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/Zand 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.

Original languageEnglish
Pages (from-to)740-747
Number of pages8
JournalACS Central Science
Volume2
Issue number10
DOIs
Publication statusPublished - 2016 Oct 26

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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