2024-03-29T06:06:40Zhttps://eprints.lib.hokudai.ac.jp/dspace-oai/requestoai:eprints.lib.hokudai.ac.jp:2115/750852022-11-17T02:08:08Zhdl_2115_20039hdl_2115_116Chiral diversification through the assembly of achiral phenylacetylene macrocycles with a two-fold bridge1000060432142Katoono, RyoKusaka, KeiichiSaito, YukiSakamoto, Kazuki1000070202132Suzuki, Takanoriopen accessCreative Commons Attribution-NonCommercial 3.0 Unported430We 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.2019-05-14engjournal articleVoRhttp://hdl.handle.net/2115/75085https://doi.org/10.1039/C9SC00972H311609552041-65202041-6539Chemical Science101847824791https://eprints.lib.hokudai.ac.jp/dspace/bitstream/2115/75085/1/Chem%20sci10-18_4782-4791.pdfapplication/pdf2.36 MB2019-05-14https://eprints.lib.hokudai.ac.jp/dspace/bitstream/2115/75085/3/Supplementary%20Information.pdfapplication/pdf3.86 MB2019-05-14