Synthesis of alanine-based colorimetric sensors and enantioselective recognition of aspartate and malate anions

Abstract

Two chiral colorimetric sensors (1,2) were synthesized and characterized by spectroscopic techniques and their enantioselective recognition of chiral dicarboxylic anions (D/L-aspartate and D/L-malate) was examined by UV-vis and (1)H NMR spectroscopy. Interaction of the receptors 1 and 2 with the enantiomers of aspartate or malate caused different color changes, and they act as optical chemosensors for the recognition of D-aspartate vs. L-aspartate and d-malate vs.l-malate. Receptor 1 exhibits high enantioselective binding for aspartate anions [K(A(D))/K(A(L)) = 12.15].