Development of Low-Molecular-Weight Organogelators from Cyclic β-Amino Acid: Effect of Stereochemistry and their Application on Visual Chiral Recognition of Amines.
chirality
molecular recognition
noncovalent interaction
organogelator
β-amino acid
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
21 Feb 2023
21 Feb 2023
Historique:
received:
29
08
2022
pubmed:
4
12
2022
medline:
4
12
2022
entrez:
3
12
2022
Statut:
ppublish
Résumé
This study reports the formation of low-molecular-weight gelators based on carboxylic acids derived from chiral cyclicβ-amino acids. The effect of their stereochemistry on the gelation of organic solvents was investigated, and their assemblies with the intermolecular interactions in the xerogels were proposed via infrared spectroscopy, X-ray diffraction, scanning electron microscopy, and crystallographic details of the related model compounds. The effect of the alkyl chain length on the gelators was studied, and they were applied to the chiral recognition of amines. Only one diastereomeric salt with amines afforded gels, whereas the others resulted in precipitates. Chiral recognition was also achieved in the gel state, and the appearance of the as-prepared gel changed upon the addition of each amine enantiomer, thus enabling the visual detection of their chirality.
Identifiants
pubmed: 36461621
doi: 10.1002/chem.202202692
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202202692Informations de copyright
© 2022 Wiley-VCH GmbH.
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