Effective enantioselective recognition by steady-state fluorescence spectroscopy: Towards a paradigm shift to optical sensors with unusual chemical architecture

• Published in: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy Molecular and biomolecular spectroscopy, 2023-06, Vol.294, p.122526, Article 122526
• Main Authors: Debia, Natalí P., Muller, Jenifer M., Gonçalves, Paulo F.B., Rodembusch, Fabiano S., Lüdtke, Diogo S.
• Format: Article
• Language: English
• Subjects: Amino acid-derived 1,2,3-triazole; Benzazole; Carbohydrate; Enantioselective sensing
• ISSN: 1386-1425
• DOI: 10.1016/j.saa.2023.122526

[Display omitted] •Amino acid-derived triazoles with a fluorescent benzazole fluorophore were prepared.•Sensing interaction investigated only by fluorescence emission spectroscopy.•Different interaction between fluorophores with two pairs of enantiomers.•Full photophysical and theoretical calculations have been performed. A series of amino acid-derived 1,2,3-triazoles presenting the amino acid residue and the benzazole fluorophore connected by a triazole-4-carboxylate spacer was studied for enantioselective recognition using only steady-state fluorescence spectroscopy in solution. In this investigation, the optical sensing was performed with D-(−) and L-(+)-Arabinose and (R)-(−) and (S)-(+)-Mandelic acid as chiral analytes. The optical sensors showed specific interactions with each pair of enantiomers, allowing photophysical responses, which were used for their enantioselective recognition. DFT calculations confirm the specific interaction between the fluorophores and the analytes corroborating the observed high enantioselectivity of these compounds with the studied enantiomers. Finally, this study investigated nontrivial sensors for chiral molecules by a mechanism different than turn-on fluorescence and has the potential to broad chiral compounds with fluorophoric units as optical sensors for enantioselective sensing.