The synthesis and structural analysis of a quintuple [6]helicene with a corannulene core is reported. The compound was synthesized from corannulene in three steps including a five‐fold intramolecular direct arylation. X‐ray crystallographic analysis revealed a C₅‐symmetric propeller‐shaped structure and one‐dimensional alignment in the solid state. The enantiomers of the quintuple [6]helicene were successfully separated by HPLC, and the chirality of the two fractions was identified by CD spectroscopy. A kinetic study yielded a racemization barrier of 34.2 kcal mol⁻¹, which is slightly lower than that of pristine [6]helicene. DFT calculations indicate a rapid bowl‐to‐bowl inversion of the corannulene moiety and a step‐by‐step chiral inversion pathway for the five [6]helicene moieties.

中文翻译：

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具有Corannulene核心的五元组[6]螺旋形螺帽，作为C5对称螺旋桨形π系统

报道了具有氢化萘芯的五元[6]螺旋烯的合成和结构分析。该化合物是通过三步合成的，由Corannulene合成，包括五倍的分子内直接芳基化。X射线晶体学分析表明，C ₅对称的螺旋桨状结构和固态一维排列。通过HPLC成功分离了五元组[6]螺旋烯的对映异构体，并通过CD光谱法鉴定了这两个馏分的手性。动力学研究得出消旋化势垒为34.2 kcal mol ^-1，比原始的[6]螺旋烯稍低。DFT计算表明，对五个[6]螺旋烯部分，Corannulene部分具有快速的碗对碗倒置和逐步的手性倒置路径。