How does chiral self-sorting take place in the formation of homochiral Pd6 L8 capsules consisting of cyclotriveratrylene-based chiral tritopic ligands?

Chemical Science
Shumpei KaiShuichi Hiraoka

Abstract

The chiral self-sorting process during the self-assembly of homochiral Pd6L8 capsules from cyclotriveratrylene (CTV)-based chiral tritopic ligands (L) and (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 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.

References

Dec 10, 2002·Inorganic Chemistry·Jason Cooper, Tom Ziegler
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Oct 19, 2017·Chemistry : a European Journal·Shumpei KaiShuichi Hiraoka

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Citations

Aug 12, 2021·Chemical Communications : Chem Comm·Masaki YamamuraTatsuya Nabeshima
Feb 2, 2019·Journal of the American Chemical Society·Jean-François AymeDavid A Leigh
Dec 15, 2018·Organic Letters·Augustin LongAlexandre Martinez
Mar 12, 2019·Organic Letters·Estelle GodartAlexandre Martinez
Nov 26, 2019·Journal of the American Chemical Society·Tomoki TateishiShuichi Hiraoka
Aug 14, 2020·Journal of the American Chemical Society·Shuta IsekiJunpei Yuasa
Oct 2, 2021·The Journal of Organic Chemistry·Chunyang LiAlexandre Martinez

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Software Mentioned

QASAP

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