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Issue 38, 2020
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Guest-induced supramolecular chirality transfer in [2]pseudorotaxanes: experimental and computational study

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Abstract

To reveal the factors governing the chirality transfer from a chiral unimolecule to a supramolecular assembly, we constructed a series of [2]pseudorotaxanes through the intermolecular noncovalent interaction of a pair of chiral binaphthalene crown ethers with achiral secondary ammonium salts with different chromophores, and found that the binaphthalene groups can induce new circular dichroism (CD) signals only in the [2]pseudorotaxane structures between the host crown ethers and the guest molecule with the anthryl group. Density functional theory (DFT) and time-dependent density functional theory (TD-DFT) calculations show that the generation of the new CD signal is mainly due to the intermolecular chiral induction between the anthryl group in the guest and the naphthalene groups in the host.

Graphical abstract: Guest-induced supramolecular chirality transfer in [2]pseudorotaxanes: experimental and computational study

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Article information


Submitted
01 Jul 2020
Accepted
14 Sep 2020
First published
15 Sep 2020

Org. Biomol. Chem., 2020,18, 7649-7655
Article type
Paper

Guest-induced supramolecular chirality transfer in [2]pseudorotaxanes: experimental and computational study

H. Wang, H. Zhang, H. Zhang, G. Liu, X. Dai, H. Wu and Y. Liu, Org. Biomol. Chem., 2020, 18, 7649
DOI: 10.1039/D0OB01347A

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