Issue 47, 2018

Chiral molecular face-rotating sandwich structures constructed through restricting the phenyl flipping of tetraphenylethylene

Abstract

Chiral tetraphenylethylene (TPE) derivatives have great potential in chiral recognition and circularly polarized luminescence. However, they were mainly constructed through introducing chiral substituents at the periphery of the TPE moiety, which required additional chemical modifications and limited the variety of chiralities of products. Herein, we constructed a series of chiral face-rotating sandwich structures (FRSs) through restricting the phenyl flipping of TPE without introducing any chiral substituents. In FRSs, the complex arrangements of TPE motifs resulted in a variety of chiralities. We also found that non-covalent repulsive interactions in vertices caused the facial hetero-directionality of FRSs, and the hydrogen bonds between imine bonds and hydroxy groups induced excited-state intramolecular proton transfer (ESIPT) emission of FRSs. In addition, the fluorescence intensity of FRSs decreases with the addition of trifluoroacetic acid. This study provides new insights into the rational design of chiral assemblies from aggregation-induced emission (AIE) active building blocks through restriction of intramolecular rotation (RIR).

Graphical abstract: Chiral molecular face-rotating sandwich structures constructed through restricting the phenyl flipping of tetraphenylethylene

Supplementary files

Article information

Article type
Edge Article
Submitted
31 Jul 2018
Accepted
13 Sep 2018
First published
14 Sep 2018
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., 2018,9, 8814-8818

Chiral molecular face-rotating sandwich structures constructed through restricting the phenyl flipping of tetraphenylethylene

H. Qu, X. Tang, X. Wang, Z. Li, Z. Huang, H. Zhang, Z. Tian and X. Cao, Chem. Sci., 2018, 9, 8814 DOI: 10.1039/C8SC03404D

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