Mechanistic Study on a BINOL–Coumarin-Based Probe for Enantioselective Fluorescent Recognition of Amino Acids
Xuedan Wu, Qin Wang, Diane A. Dickie, Lin Pu
Abstract
A detailed investigation was conducted on the reaction of a 1,1′-bi-2-naphthol–coumarin-based fluorescent probe with amino acids. On the basis of the studies, including fluorescence spectroscopy, 1H NMR, UV–vis, mass spectroscopy, single-crystal X-ray analysis, and molecular modeling, it was found that the distinctively different fluorescent responses of the probe toward the amino acid at the two excitation wavelengths are due to two different reaction pathways that generate different intermediates and products.
Topics & Concepts
CoumarinFluorescenceChemistryFluorescence spectroscopyAmino acidEnantioselective synthesisExcitation wavelengthMass spectrometrySpectroscopyMolecular modelPhotochemistryAromatic amino acidsOrganic chemistryStereochemistryCombinatorial chemistryChromatographyCatalysisBiochemistryQuantum mechanicsPhysicsMolecular Sensors and Ion DetectionSulfur Compounds in BiologyAnalytical Chemistry and Chromatography