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

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 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 m² g^-1 after desolvation.

SUBMITTER: Wagner P

PROVIDER: S-EPMC8048989 | biostudies-literature | 2021 Apr

REPOSITORIES: biostudies-literature

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

Wagner Philippe P Rominger Frank F Zhang Wen-Shan WS Gross Jürgen H JH Elbert Sven M SM Schröder Rasmus R RR Mastalerz Michael M

Angewandte Chemie (International ed. in English) 20210308 16

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 ...[more]

PMID: 33476442

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