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Issue 17, 2018
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How does chiral self-sorting take place in the formation of homochiral Pd6L8 capsules consisting of cyclotriveratrylene-based chiral tritopic ligands?

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Abstract

The chiral self-sorting process during the self-assembly of homochiral Pd6L8 capsules from cyclotriveratrylene (CTV)-based chiral tritopic ligands (L) and Image ID:c8sc01062e-t1.gif (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 Image ID:c8sc01062e-t2.gif 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.

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

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Publication details

The article was received on 06 Mar 2018, accepted on 26 Mar 2018 and first published on 26 Mar 2018


Article type: Edge Article
DOI: 10.1039/C8SC01062E
Citation: Chem. Sci., 2018,9, 4104-4108
  • Open access: Creative Commons BY-NC license
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    How does chiral self-sorting take place in the formation of homochiral Pd6L8 capsules consisting of cyclotriveratrylene-based chiral tritopic ligands?

    S. Kai, T. Kojima, Flora L. Thorp-Greenwood, M. J. Hardie and S. Hiraoka, Chem. Sci., 2018, 9, 4104
    DOI: 10.1039/C8SC01062E

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