Narcissistic chiral self-sorting of molecular face-rotating polyhedra

Narcissistic chiral self-sorting prevailed in the assembly of molecular face-rotating polyhedra from a C 3h 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...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2018-01, Vol.16 (1), p.34-37
Main Authors: Wang, Xinchang, Peng, Pixian, Xuan, Wei, Wang, Yu, Zhuang, Yongbin, Tian, Zhongqun, Cao, Xiaoyu
Format: Article
Language:English
Subjects:
Assembly
Diamines
Narcissism
Polyhedra
Stereoisomers
Triazine
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Summary:Narcissistic chiral self-sorting prevailed in the assembly of molecular face-rotating polyhedra from a C 3h 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 (1 R ,2 R )-diamines were segregated in AAAA polyhedra and (1 S ,2 S )-diamines in CCCC polyhedra. This chiral self-sorting process is regulated by facial non-covalent interactions in the polyhedra. In contrast, D 3h 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. Narcissistic chiral self-sorting prevailed in the assembly of molecular face-rotating polyhedra from a C 3h building block 5,5,10,10,15,15-hexabutyl-truxene-2,7,12-tricarbaldehyde and racemic mixtures of 1,2-diamines.
ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob02727c