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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. |
| Rights: | https://creativecommons.org/licenses/by-nc/3.0/ |
| Type: | article |
| URI: | http://hdl.handle.net/2115/75085 |
| 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)
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Submitter: 上遠野 亮
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