Modifying carbon dots with l-phenylalanine for rapid discrimination of tryptophan enantiomers

Abstract

New chiral carbon dots (CDs), L-PCDs, for discriminating tryptophan (Trp) enantiomers were prepared in this work. Firstly, original CDs were synthesized through a hydrothermal method using pyridine-2,6-dicarboxylic acid and o-phenylenediamine as raw materials. Then, the surface of original CDs was modified with L-phenylalanine to create chiral fluorescent carbon L-PCDs. In the presence of D-Trp, the fluorescence intensity of L-PCDs decreased significantly while it remained unchanged in the presence of L-Trp. The chiral sensing system used in this study has a rapid response time of 3 minutes and can identify enantiomers with an enantioselectivity (I_D/I_L) of up to 3.3. For D-Trp, a good linear relationship can be obtained in the range of 0.3–4.2 mM with a limit of detection of 0.06 mM. This sensor allows for both quantitative detection of D-Trp and determination of enantiomeric percentage in the racemate. The chiral recognition mechanism is attributed to the different interaction between D-/L-Trp and L-PCDs.