Chiral Self-sorting of Giant Cubic [8+12] Salicylimine Cage Compounds.

Chiral Self-sorting of Giant Cubic [8+12] Salicylimine Cage Compounds.
Angew Chem Int Ed Engl. 2021 Jan 21;:
Authors: Mastalerz M, Wagner P, Rominger F, Zhang WS, Gross JH, Elbert SM, Schröder RR
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. Among those systems a handful of shape-persistent organic cages were studied and rarely narcisstic or social self-sorting 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 in = 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 2 /g after desolvation.
PMID: 33476442 [PubMed - as supplied by publisher]

Source: Angewandte Chemie - January 21, 2021 Category: Chemistry Authors: Mastalerz M, Wagner P, Rominger F, Zhang WS, Gross JH, Elbert SM, Schröder RR Tags: Angew Chem Int Ed Engl Source Type: research