1. Accurate chiral pattern recognition for amines from just a single chemosensor
- Author
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Vahid Hamedpour, Hirohiko Houjou, Soya Kojima, Yuji Kubo, Yui Sasaki, Shin-ya Takizawa, Riku Kubota, Tsuyoshi Minami, and Isao Yoshikawa
- Subjects
chemistry.chemical_classification ,Cyclohexane ,010405 organic chemistry ,business.industry ,Imine ,Pattern recognition ,General Chemistry ,010402 general chemistry ,01 natural sciences ,Aldehyde ,Fluorescence ,0104 chemical sciences ,chemistry.chemical_compound ,chemistry ,Diamine ,Artificial intelligence ,Enantiomer ,business ,Enantiomeric excess ,Derivative (chemistry) - 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.
- Published
- 2020