We created chiral assemblies of planar and achiral macrocycles by saccharide recognition. To achieve this, we synthesized stackable meta-arylene ethynylene macrocycles consisting of pyridine–acetylene–phenol and pyridine–acetylene–aniline units. ¹H NMR, absorption, and fluorescence emission spectroscopy indicated that these macrocycles formed 1:1 and 2:1 complexes with lipophilic alkyl glycosides. The 2:1 complex of the pyridine–acetylene–phenol macrocycle showed induced circular dichroism (ICD) bands, meaning that two achiral macrocycles are arranged in an asymmetrically twisted manner. CD spectroscopy revealed that the helical sense was affected by the chirality of guest saccharides. On the other hand, strong CD bands were observed after solid–liquid extraction of native saccharides into lipophilic solvents using the pyridine–acetylene–aniline macrocycle.

中文翻译：

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糖类识别诱导的平面和非手性间亚芳基乙炔基大环的手性组装

我们通过糖识别创建了平面和非手性大环的手性组装体。为此，我们合成了由吡啶-乙炔-苯酚和吡啶-乙炔-苯胺单元组成的可堆叠间亚芳基乙炔基大环化合物。¹H NMR、吸收和荧光发射光谱表明这些大环化合物与亲脂性烷基糖苷形成 1:1 和 2:1 复合物。吡啶-乙炔-苯酚大环的 2:1 配合物显示出诱导圆二色性 (ICD) 带，这意味着两个非手性大环以不对称扭曲的方式排列。CD光谱显示螺旋意义受客体糖的手性影响。另一方面，在使用吡啶-乙炔-苯胺大环化合物将天然糖类固液萃取到亲脂性溶剂中后，观察到强 CD 条带。