Sequential Chiral Induction and Regulator-Assisted Chiral Memory of Pillar[5]arenes

Shixin Fa; Kouichi Egami; Keisuke Adachi; Kenichi Kato; Tomoki Ogoshi

doi:10.1002/anie.202010050

Sequential Chiral Induction and Regulator-Assisted Chiral Memory of Pillar[5]arenes

Angew Chem Int Ed Engl. 2020 Nov 9;59(46):20353-20356. doi: 10.1002/anie.202010050. Epub 2020 Oct 7.

Authors

Shixin Fa¹, Kouichi Egami¹, Keisuke Adachi¹, Kenichi Kato¹, Tomoki Ogoshi^{1

2}

Affiliations

¹ Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto, 615-8510, Japan.
² WPI Nano Life Science Institute (WPI-NanoLSI), Kanazawa University, Kakuma-machi, Kanazawa, Ishikawa, 920-1192, Japan.

PMID: 32845059
DOI: 10.1002/anie.202010050

Abstract

Chirality transfer is widely observed in life processes, and many artificial chiral transfer systems have been developed. In these systems, chiral information is transferred from chiral inducers to chiral acceptors by a direct chiral induction process and a direct chiral memorization process. We have developed ternary nondirect chiral transfer systems based on pillar[5]arenes, in which a third factor was introduced as a regulator. The planar chirality of an acceptor was induced and memorized by a chiral inducer with precise control by a regulator. In the chiral induction period, the feed sequence of the chiral inducer and regulator affected the chiral induction behavior of the chiral acceptor. The chiral memory ability of the acceptor was substantially improved by the combined action of the chiral inducer and regulator.

Keywords: chirality; macrocycles; memory; noncovalent interactions; pillar[n]arenes.

Publication types

Research Support, Non-U.S. Gov't