Issue 20, 2022

CPL on/off control of an assembled system by water soluble macrocyclic chiral sources with planar chirality

Abstract

Herein, we report the synthesis and planar chiral properties of a pair of water-soluble cationic pillar[5]arenes with stereogenic carbons. Interestingly, although units of the molecules were rotatable, only one planar chiral diastereomer existed in water in both cases. As a new type of chiral source, these molecules transmitted chiral information from the planar chiral cavities to the assembly of a water-soluble extended π-conjugated compound, affording circularly polarized luminescence (CPL). The chirality transfer process and resulting CPL were extremely sensitive to the feed ratio of the chiral pillar[5]arenes owing to the combined action of their planar chirality, bulkiness, and strong binding properties. When a limited amount of chiral source was added, further assembly of the extended π-conjugated compound into helical fibers with CPL was triggered. Unexpectedly, larger amounts of chiral source destroyed the helical fiber assemblies, resulting in elimination of the chirality and CPL properties from the assembled structures.

Graphical abstract: CPL on/off control of an assembled system by water soluble macrocyclic chiral sources with planar chirality

Supplementary files

Article information

Article type
Edge Article
Submitted
15 Feb 2022
Accepted
28 Mar 2022
First published
30 Mar 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2022,13, 5846-5853

CPL on/off control of an assembled system by water soluble macrocyclic chiral sources with planar chirality

S. Fa, T. Tomita, K. Wada, K. Yasuhara, S. Ohtani, K. Kato, M. Gon, K. Tanaka, T. Kakuta, T. Yamagishi and T. Ogoshi, Chem. Sci., 2022, 13, 5846 DOI: 10.1039/D2SC00952H

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