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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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Publication details

The article was received on 26 Feb 2019, accepted on 30 Mar 2019 and first published on 02 Apr 2019


Article type: Edge Article
DOI: 10.1039/C9SC00972H
Chem. Sci., 2019,10, 4782-4791
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    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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