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

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Title: Chiral diversification through the assembly of achiral phenylacetylene macrocycles with a two-fold bridge
Authors: Katoono, Ryo Browse this author →KAKEN DB
Kusaka, Keiichi Browse this author
Saito, Yuki Browse this author
Sakamoto, Kazuki Browse this author
Suzuki, Takanori Browse this author →KAKEN DB
Issue Date: 14-May-2019
Journal Title: Chemical Science
Volume: 10
Issue: 18
Start Page: 4782
End Page: 4791
Publisher DOI: 10.1039/C9SC00972H
PMID: 31160955
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.
Type: article
Appears in Collections:理学院・理学研究院 (Graduate School of Science / Faculty of Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 上遠野 亮

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