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.

中文翻译：

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硫代-四硫磺烯：一种高度扭曲的分子 Plectoneme

我们报道了硫代-四硫烯 3 的合成和表征，硫代四硫烯 3 是一种高度扭曲的手性大环，通过硫氟环环缩取代从环偏苯衍生物构建。它是第一个具有 plectonemic 构型的大环芳香族化合物，其结构通过单晶 X 射线衍射研究得到明确证实。可以解析 3 的两个对映异构体以研究它们的手性特性。与已知的拓扑结或莫比乌斯型大环相比，它们通过特定的连接模式诱导手性，3 的不对称结构是通过处于困境中的环的趋势形成和维持的，以减少不利的应变。