Abstract: The enantiomers show similar physical and chemical properties, while optical, biochemical, and pharmacological activities are often different. Therefore, it is important to selective recognition of one enantiomer from the other. In this contribution, a pair of chiral cyclic compounds based on triphenylamine, 1,2-dicyanoethylene, and optically pure 1,2-cyclohexanediamine were synthesized. These probes were verified by the nuclear magnetic resonance, high resolution mass spectroscopies, and single crystal X-ray diffraction. Then, the photophysical properties of the probes were investigated. The results indicated that the probes show red emission (622 nm) with high quantum yield (QY up to 35.2%) in the crystal states. The photophysical properties exhibited that the probes are typically aggregation-induced emission compounds. Further, the probes show satisfactory enantiorecognition property, the fluorescence intensity ratio of the complexes were 14.2 to R/S-1,2-diaminocyclohexane and 4.28 to R/S-1,2,3,4-tetrahydronaphthalen-2-amine. This work not only enriches the variety of AIE-type cyclic compounds but also extends the emission wavelength of chiral probes. The obtained compound can serve as a simple and convenient measurement tool for enantioselectively recognizing racemic compounds.

Key words: Aggregation-induced emission, Triphenylamine, Cyclohexylenediamine, Chiral recognition, Fluorescent probe