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

• Katoono, Ryo

• Kusaka, Keiichi

• Saito, Yuki

• Sakamoto, Kazuki

• Suzuki, Takanori

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 doublybridged 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.

Journal

• Chemical Science

  Chemical Science 10 (18), 4782-4791, 2019-05-14

  Royal Society of Chemistry (RSC)

Keywords

• General Chemistry

Details

• CRID: 1050282814039060992
• NII Article ID: 120006709315
• DOI: 10.1039/c9sc00972h
• ISSN: 20416539
• ISSN: 20416520
• HANDLE: 2115/75085
• Web Site: http://pubs.rsc.org/en/content/articlepdf/2019/SC/C9SC00972H
• Text Lang: en
• Article Type: journal article
• Data Source:
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