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Issue 18, 2019
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Chiral diversification through the assembly of achiral phenylacetylene macrocycles with a two-fold bridge

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Abstract

We demonstrate so-called “chiral diversification”, which is a design strategy to create multiple chiral molecules through the assembly and double-bridging of achiral components. We used phenylacetylene macrocycles (PAMs) as an achiral element. In a molecule, two achiral rings of [6]PAM are stacked one above the other, or bound to each other mechanically. As an alternative, a single enlarged ring of [12]PAM was also assumed to be a doubled form of [6]PAM. In any case, one or two ring(s) are doubly-bridged by covalent bonds to exert chirality. Through intramolecular two-bond formation, these multiple chiral molecules were obtained as a set of products in one reaction. The dynamic chirality generated in molecules with either two helically-stacked rings of [6]PAM or a single helically-folded ring of [12]PAM was characterized by induced Cotton effects with the aid of an external chiral source. Thus, a chiral structure based on [12]PAM could be demonstrated as the first success. Alternatively, enantiomeric separation was achieved for molecules with two interlocked rings of [6]PAM to show remarkable chiroptical properties.

Graphical abstract: Chiral diversification through the assembly of achiral phenylacetylene macrocycles with a two-fold bridge

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Supplementary files

Article information


Submitted
26 Feb 2019
Accepted
30 Mar 2019
First published
02 Apr 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 4782-4791
Article type
Edge Article

Chiral diversification through the assembly of achiral phenylacetylene macrocycles with a two-fold bridge

R. Katoono, K. Kusaka, Y. Saito, K. Sakamoto and T. Suzuki, Chem. Sci., 2019, 10, 4782
DOI: 10.1039/C9SC00972H

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