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Updated: Feb 23, 2026

Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores
Published on: August 19, 2013
Fluorescent chirality recognition by simple boronate ensembles with aggregation-induced emission capability.
Meiko Kawai1, Ayaka Hoshi, Ryuhei Nishiyabu
1Department of Applied Chemistry, Graduate School of Urban Environmental Sciences, Tokyo Metropolitan University, 1-1 Minami-ohsawa, Hachioji, Tokyo 192-0397, Japan. yujik@tmu.ac.jp.
Chiral ensembles spontaneously formed using di(boronic acid)-appended tetraphenylethylene (DB-TPE) and tartaric acid. These ensembles enable enantioselective aggregation and fluorescent recognition of chiral molecules like diamines and cinchona alkaloids.
Area of Science:
- Supramolecular Chemistry
- Organic Chemistry
- Analytical Chemistry
Background:
- Chirality recognition is crucial in pharmaceuticals and chemical synthesis.
- Developing efficient methods for chiral sensing remains a significant challenge.
- Tetraphenylethylene (TPE) derivatives offer unique aggregation-induced emission properties.
Purpose of the Study:
- To develop chiral ensembles for enantioselective molecular recognition.
- To investigate the formation of chiral aggregates via boronate esterification.
- To enable fluorescent detection of chiral analytes.
Main Methods:
- Synthesis of di(boronic acid)-appended tetraphenylethylene (DB-TPE).
- Boronate esterification reaction with chiral tartaric acid (l- or d-).
- Observation of enantioselective aggregation with chiral diamines and cinchona alkaloids.
Main Results:
- Spontaneous formation of chiral ensembles in solution.
- Demonstrated enantioselective aggregation behavior of the chiral ensembles.
- Successful fluorescent recognition of chiral diamines and cinchona alkaloids based on aggregation.
Conclusions:
- DB-TPE and tartaric acid can form effective chiral recognition units.
- The developed system provides a novel fluorescent method for chirality sensing.
- This approach holds potential for analyzing complex chiral mixtures.
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