Related Experiment Video
Updated: Jun 2, 2025

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Fluoride binding-modulated supramolecular chirality of urea-containing triarylamine and its photo-manifestation
Sijia Ma1,2,3, Xin Wen1,2, Yuqian Jiang3
1Beijing National Laboratory for Molecular Science, CAS Key Laboratory of Colloid, Interface and Chemical Thermodynamics, Institute of Chemistry, Chinese Academy of Sciences, No. 2 ZhongGuanCun BeiYiJie, 100190, Beijing, P. R. China. zhangli@iccas.ac.cn.
Abstract:
In recent years, the regulation of anion-mediated chiral assemblies has gained significant interest. This study investigated the modulation of supramolecular chiroptical signals and chiral assembled structures in a triarylamine system containing a urea moiety through fluoride ion-urea bond interactions, aiming to understand the chiral sense amplification in supramolecular assemblies. Chiral triarylamine derivatives containing urea or amide units were synthesized and the self-assemblies were examined in the absence and presence of fluoride ions. The results revealed that the addition of F- led to an increase in the circular dichroism (CD) intensity for the triarylamine compounds containing urea, accompanied by a transformation of the nanofiber structure into chiral twists. Comparative studies with other anions confirmed the selective specificity for F-. Additionally, the combination of photo-induced triarylamine anion radicals allowed the F- in the system to be visualized through photoirradiation, resulting in distinct colour changes that were detectable by the naked eye. The research demonstrates that F- can selectively amplify supramolecular chirality through urea-F- interactions, which may have promising applications in the fields of sensing and chiroptical devices.
Related Concept Videos
Structure of Amines
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
Diazonium Group Substitution: –OH and –H
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
Chirality at Nitrogen, Phosphorus, and Sulfur
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...

