How does chiral self-sorting take place in the formation of homochiral Pd6L8 capsules consisting of cyclotriveratrylene-based chiral tritopic ligands?

The chiral self-sorting process during the self-assembly of homochiral Pd6L8 capsules from cyclotriveratrylene (CTV)-based chiral tritopic ligands (L) and [Formula Omitted] (Py*: 3-chloropyridine) was investigated by an NMR-based approach (QASAP: quantitative analysis of the self-assembly process)....

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Bibliographic Details
Published in:Chemical science (Cambridge) 2018, Vol.9 (17), p.4104-4108
Main Authors: Shumpei Kai, Kojima, Tatsuo, Thorp-Greenwood, Flora L, Hardie, Michaele J, Hiraoka, Shuichi
Format: Article
Language:English
Subjects:
Chemistry
Chirality
Isomers
Ligands
NMR
Nuclear magnetic resonance
Quantitative analysis
Self-assembly
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Summary:The chiral self-sorting process during the self-assembly of homochiral Pd6L8 capsules from cyclotriveratrylene (CTV)-based chiral tritopic ligands (L) and [Formula Omitted] (Py*: 3-chloropyridine) was investigated by an NMR-based approach (QASAP: quantitative analysis of the self-assembly process). From the beginning to the formation of the [Formula Omitted] immature capsules (ICs), enantiomeric ligands are distributed in the intermediates in a non-self-sorting manner, which leads to the isomers of heterochiral ICs over 99% yield. The mismatch of the chirality in the heterochiral ICs prevents intramolecular ligand exchanges in ICs to form the heterochiral capsules. The correction of the chirality in the heterochiral ICs (chiral self-sorting) takes place very slowly to finally lead to the homochiral capsules. The reason why the chiral self-sorting took place in the late stage of the self-assembly (after the formation of the heterochiral ICs) would be due to the relatively high flexibility of the CTV-based ligand.
ISSN:2041-6520
2041-6539
DOI:10.1039/c8sc01062e