关键词: cage compounds chiral imine self-sorting tribenzotriquinacene

来  源:   DOI:10.1002/anie.202016592   PDF(Sci-hub)   PDF(Pubmed)

Abstract:
Chiral self-sorting is intricately connected to the complicated chiral processes observed in nature and no artificial systems of comparably complexity have been generated by chemists. However, only a few examples of purely organic molecules have been reported so far, where the self-sorting process could be controlled. Herein, we describe the chiral self-sorting of large cubic [8+12] salicylimine cage compounds based on a chiral TBTQ precursor. Out of 23 possible cage isomers only the enantiopure and a meso cage were observed to be formed, which have been unambiguously characterized by single crystal X-ray diffraction. Furthermore, by careful choice of solvent the formation of meso cage could be controlled. With internal diameters of din =3.3-3.5 nm these cages are among the largest organic cage compounds characterized and show very high specific surface areas up to approx. 1500 m2  g-1 after desolvation.
摘要:
手性自分选与自然界中观察到的复杂手性过程密切相关,化学家没有产生具有相当复杂性的人工系统。然而,到目前为止,仅报道了一些纯有机分子的例子,可以控制自分类过程。在这里,我们描述了基于手性TBTQ前体的大立方[8+12]水杨亚胺笼化合物的手性自分选。在23种可能的笼型异构体中,仅观察到形成了对映纯和内消旋笼。已通过单晶X射线衍射明确表征。此外,通过仔细选择溶剂,可以控制内消旋笼的形成。内径为din=3.3-3.5nm,这些笼子是表征最大的有机笼子化合物之一,并显示出非常高的比表面积,最高约为。去溶剂化后1500m2g-1。
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