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 7 2018
Accepted
13 9 2018
First published
14 9 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

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements