Accurate chiral pattern recognition for amines from just a single chemosensor

• Published in: Chemical science (Cambridge) Vol. 11; no. 15; pp. 379 - 3796
• Main Authors: Sasaki, Yui, Kojima, Soya, Hamedpour, Vahid, Kubota, Riku, Takizawa, Shin-ya, Yoshikawa, Isao, Houjou, Hirohiko, Kubo, Yuji, Minami, Tsuyoshi
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 21.04.2020; Royal Society of Chemistry
• Subjects: Aldehydes; Amines; Artificial neural networks; Chemical sensors; Chemistry; Chemistry, Multidisciplinary; Chemoreceptors; Crystallography; Cyclohexane; Data processing; Diamines; Discriminant analysis; Discrimination; Emission analysis; Emission spectra; Fluorescence; Pattern recognition; Physical Sciences; Science & Technology; Self-assembly; Titration; ENANTIOMERIC EXCESS; FLUORESCENT; DISCRIMINATION; MOLECULAR RECOGNITION; COMPLEXES; SYSTEMS; METAL-IONS; IDENTIFICATION; SENSOR ARRAY; INTRAMOLECULAR CHARGE-TRANSFER
• ISSN: 2041-6520; 2041-6539
• DOI: 10.1039/d0sc00194e

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 (Zn 2+ ). 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. The current work proposes a novel method for accurate pattern recognition of (mono- and di-) amines and determination of enantiomeric excess (ee) using molecular self-assembly.