He Lisi, Ng Chun-Fai, Li Yuke, Liu Zhifeng, Kuck Dietmar, Chow Hak-Fun
Department of Chemistry, The Chinese University of Hong Kong, Shatin, Hong Kong, Hong Kong.
Department of Chemistry and Center for Molecular Materials (CM2), Bielefeld University, Universitätsstraße 25, 33615, Bielefeld, Germany.
Angew Chem Int Ed Engl. 2018 Oct 8;57(41):13635-13639. doi: 10.1002/anie.201808461. Epub 2018 Sep 17.
Porous curved polycyclic aromatic compounds 6 and 14 bearing a tribenzotriquinacene (TBTQ) core encircled by an m,p,p,m,m,p,p,m,m,p,p,m-cyclododecaphenylene belt were synthesized and characterized by NMR spectroscopy and mass spectrometry. These trefoil hydrocarbon macrocycles were constructed in high yield using an intramolecular three-fold Scholl macrocyclization. X-ray crystal analysis of 14 demonstrated a large wizard-hat-shaped structure with three pores (radii 2.9-3.0 Å). The π-stacking aggregation of the hexa-n-dodecyloxy derivative 6 a and the chloride anion binding properties of 14 were studied by NMR spectroscopy. Such stacking and anion binding properties were much weaker in the singly 11 and doubly macrocyclized products 12.
合成了带有由间、对、对、间、间、对、对、间、间、对、对-环十二苯带环绕的三苯并三喹吖啶（TBTQ）核心的多孔弯曲多环芳烃6和14，并通过核磁共振光谱和质谱对其进行了表征。这些三叶烃大环化合物通过分子内三重重排肖尔大环化反应以高产率构建而成。14的X射线晶体分析表明其具有一个带有三个孔（半径为2.9 - 3.0 Å）的大巫师帽形状的结构。通过核磁共振光谱研究了六正十二烷氧基衍生物6 a的π-堆积聚集以及14的氯离子结合特性。在单重11和双重大环化产物12中，这种堆积和阴离子结合特性要弱得多。
