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Updated: Sep 19, 2025

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Published on: October 10, 2016
Thio-Tetracosulene: A Highly Twisted Molecular Plectoneme
Yiqiang Ou1, Chaoqun Zhao1, Long Jiang2
1School of Chemistry, Sun Yat-Sen University, Guangzhou, 510275, China.
Abstract:
We report the synthesis and characterization of thio-tetracosulene 3, a highly twisted chiral macrocycle constructed via sulfur fluorine annulative substitution from a cyclometaphenylene derivative. It is the first macrocyclic aromatic compound with a plectonemic configuration, and the structure is unambiguously confirmed by single crystal X-ray diffraction study. The two enantiomers of 3 can be resolved to investigate their chiroptical properties. In contrast to the known topological knot-, or Möbius-type macrocycles which induce chirality by specific connection patterns, the asymmetric structure of 3 is formed and maintained by the tendency of a ring in distress to reduce unfavorable strains.
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