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Narcissistic chiral self-sorting of molecular face-rotating polyhedra

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Abstract

Narcissistic chiral self-sorting prevailed in the assembly of molecular face-rotating polyhedra from a C3h building block 5,5,10,10,15,15-hexabutyl-truxene-2,7,12-tricarbaldehyde and racemic mixtures of 1,2-diamines. Out of 124 possible stereoisomers, a pair of racemic polyhedra dominated, wherein (1R,2R)-diamines were segregated in AAAA polyhedra and (1S,2S)-diamines in CCCC polyhedra. This chiral self-sorting process is regulated by facial non-covalent interactions in the polyhedra. In contrast, D3h facial building blocks 1,3,5-tris-(4-formyl-phenyl)triazine and racemic mixtures of 1,2-diamines assembled into polyhedra without facial interactions, and their assembly process did not undergo apparent chiral self-sorting.

Graphical abstract: Narcissistic chiral self-sorting of molecular face-rotating polyhedra

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Publication details

The article was received on 07 Nov 2017, accepted on 20 Nov 2017 and first published on 27 Nov 2017


Article type: Communication
DOI: 10.1039/C7OB02727C
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Narcissistic chiral self-sorting of molecular face-rotating polyhedra

    X. Wang, P. Peng, W. Xuan, Y. Wang, Y. Zhuang, Z. Tian and X. Cao, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C7OB02727C

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