Clamp-shaped chiral organic small molecules (COSM) are designed through the linkage between one (1R,2R)-(+)-1,2-diphenyl-1,2-ethylenediamine molecule and two 5-methylsalicylic acid molecules by amidation reaction. Aldehyde groups are introduced to the ortho position of the hydroxyl groups of the two 5-methylsalicylic acid units of the COSM via Duff reaction. The COSM is then coordinated with Zn(II) to enhance its rigidity and strengthen its chirality. Imine bonds can be formed between the amino groups of tyrosine (Tyr) and the aldehyde groups of the COSM via Schiff base reaction, which play an important role in the enhanced intramolecular charge transfer (ICT). Therefore, the Zn(II) coordinated COSM can be used as the chiral fluorescent probe for discrimination and detection of Tyr enantiomers, and the limit of detection is 2.77 and 3.35 μM for D-Tyr and L-Tyr, respectively.

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