Wagner Philippe, Rominger Frank, Zhang Wen-Shan, Gross Jürgen H, Elbert Sven M, Schröder Rasmus R, Mastalerz Michael
Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Centre for Advanced Materials, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 225, 69120, Heidelberg, Germany.
Angew Chem Int Ed Engl. 2021 Apr 12;60(16):8896-8904. doi: 10.1002/anie.202016592. Epub 2021 Mar 8.
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 d =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 m g after desolvation.
手性自分类与自然界中观察到的复杂手性过程有着错综复杂的联系，化学家尚未构建出具有同等复杂性的人工体系。然而，迄今为止仅报道了少数几例能够控制自分类过程的纯有机分子。在此，我们描述了基于手性TBTQ前体的大立方[8 + 12]水杨基亚胺笼状化合物的手性自分类。在23种可能的笼状异构体中，仅观察到对映体纯的笼状化合物和一种内消旋笼状化合物形成，通过单晶X射线衍射对其进行了明确表征。此外，通过仔细选择溶剂，可以控制内消旋笼状化合物的形成。这些笼状化合物的内径d = 3.3 - 3.5 nm，是已表征的最大有机笼状化合物之一，脱溶剂后比表面积高达约1500 m² g。
