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Issue 15, 2020
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Accurate chiral pattern recognition for amines from just a single chemosensor

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Abstract

The current work proposes a novel determination method for enantiomeric excess (ee) in (mono- and di-) amines using molecular self-assembly. A pyridine-attached binaphthyl derivative ((R)-1) exhibits fluorescence responses based on imine formation between the aldehyde group of (R)-1 and target chiral amines (i.e. cyclohexane diamine (CHDA), 2-amino-1,2-diphenylethanol (ADPE), 1,2-diphenylethylenediamine (DPDA), 1-amino-2-indanol (AID), and leucinol) in the presence of zinc(II) ions (Zn2+). Because of the multi-optical responses which are derived from the variation of chiral complexes, pattern recognition-based discrimination (i.e. linear discriminant analysis (LDA)) has been achieved for five types of enantiomeric pairs of amines. Possessing such a discrimination capability in combination with data processing (LDA and an artificial neural network) allows accurate determination (prediction error < 1.8%) of the % ee of individual targets such as CHDA which is one of the main components of pharmaceutical drugs. The simple molecular self-assembled system enabled simultaneous multi-chiral discrimination and % ee determination of unknown samples.

Graphical abstract: Accurate chiral pattern recognition for amines from just a single chemosensor

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Supplementary files

Article information


Submitted
12 Jan 2020
Accepted
24 Feb 2020
First published
24 Feb 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 3790-3796
Article type
Edge Article

Accurate chiral pattern recognition for amines from just a single chemosensor

Y. Sasaki, S. Kojima, V. Hamedpour, R. Kubota, S. Takizawa, I. Yoshikawa, H. Houjou, Y. Kubo and T. Minami, Chem. Sci., 2020, 11, 3790
DOI: 10.1039/D0SC00194E

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