Synthesis of 3,5-dichlorobenzene isocyanate-derived β-cyclodextrin and 3,5-dimethyl phenyl isocyanate-derived β-cyclodextrin chiral stationary phases and their applications in the separation of chiral compounds

•A new stationary phase (β-CD-DCIPI@SiO2) with chiral separation properties was constructed.•Chlorine substituents in β-CD-DCIPI@SiO2 provided the possibility for separation of chiral enantiomers.•Separation performance of β-CD-DCIPI@SiO2 in chiral compounds was explored by reversed-phase HPLC. β-Cyclodextrin (β-CD) has a unique three-dimensional structure and chemical properties, and has a strong chiral separation ability. In this study, we linked 3,5-dichlorobenzene isocyanate to β-cyclodextrin and named this newly synthesized molecule β-CD-DCIPI. 3,5-Dimethylbenzene isocyanate was attached to β-cyclodextrin and named β-CD-DPIC. A modified polymerization-induced colloidal aggregation (PICA) method and self-made silica sol were used to synthesize mesoporous silica microspheres with a particle size of 2.38 μm-5.51 μm. A green non-toxic diazoresin (DR) is used as a coupling agent, which is connected to the surface of silica microspheres through electrostatic interaction. After ultraviolet light irradiation, ionic bonds are transformed into covalent bonds, and a new chiral stationary phase with chiral separation properties (β-CD-DCIPI@SiO2 and β-CD-DPIC@SiO2) is constructed. This article first characterizes the properties of mesoporous silica microspheres and β-CD-DCIPI@SiO2 and β-CD-DPIC@SiO2. Through reversed-phase high-performance liquid chromatography (RP-HPLC), the separation performance of two new chiral stationary phases in chiral compounds was explored and compared, and five chiral enantiomers were effectively separated.