Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 28, Issue 3, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202104024
Keywords
chirality transfer; helic[6]arene; macrocyclic arenes; pseudo[1]rotaxane; [1]rotaxane
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Funding
- National Natural Science Foundation of China [22031010, 21772205, 21521002]
- Youth Innovation Promotion Association CAS [2021035]
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The study presented the discovery of chiral pseudo[1]rotaxanes formed by self-inclusion of helic[6]arene, and demonstrated the convenient synthesis of chiral [1]rotaxanes through a specific blocking strategy with successful chirality transfer. This finding provides a new avenue for the synthesis of chiral [1]rotaxanes.
Chiral pseudo[1]rotaxanes and [1]rotaxanes constructed from macrocyclic arenes still remain a big challenge mainly owing to the lack of such chiral macrocycles. In this work, a new system of chiral pseudo[1]rotaxanes formed by self-inclusion of helic[6]arene containing amide linked with the terminal tertiary amines was first discovered. Based on an atom-economic stopping strategy, a pair of chiral [1]rotaxanes were conveniently obtained in almost quantitative yields by blocking the pseudo[1]rotaxanes with monobenzyl bromide of tetraphenylethene. The structures of pseudo[1]rotaxanes and [1]rotaxanes were characterized by 2D NMR spectra in solution, combined with DFT calculations. The photophysical properties further revealed the efficient chirality transfer of helic[6]arene to the tetraphenylethene moiety, compared to their unthreaded chiral isomers. The discovery of the chiral pseudo[1]rotaxanes allows for a wide and available synthesis of chiral [1]rotaxanes, and also opening a new avenue to the design of chiral supramolecular materials.
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