共价有机框架材料TpBD-(NH_(2))_(2)-D-(-)-α-苯甘氨酸用作高效液相色谱手性固定相的研究

Preparation of a Covalent Organic Framework TpBD-(NH_(2))_(2)-D-(-)-α-phenylglycine and Its Application Used as Chiral Stationary Phase for High Performance Liquid Chromatography

该文采用溶剂热法合成了一种共价有机框架材料(COFs)TpBD-(NO_(2))_(2),将TpBD-(NO_(2))_(2)还原为TpBD-(NH_(2))_(2)后用D-(-)-α-苯甘氨酸对其进行手性修饰得到手性COFs材料TpBD-(NH_(2))_(2)-D-(-)-α-苯甘氨酸。对TpBD-(NO_(2))_(2)、TpBD-(NH_(2))_(2)及TpBD-(NH_(2))_(2)-D-(-)-α-苯甘氨酸3种COFs材料进行表征,并采用“网包法”制备了TpBD-(NH_(2))_(2)-D-(-)-α-苯甘氨酸手性固定相。为考察该固定相的分离性能,将其用于制备高效液相色谱(HPLC)手性柱,并使用正己烷-异丙醇(体积比9∶1)和甲醇-水(体积比9∶1)为流动相,实现了13种手性化合物和5种苯系位置异构体的分离。且该色谱柱具有较好的重现性。实验表明TpBD-(NH_(2))_(2)-D-(-)-α-苯甘氨酸用作HPLC固定相用于手性物质和苯系位置异构体分离具有良好的研究意义。

In this work,a covalent organic framework(COF)material TpBD-(NO_(2))_(2) was firstly syn⁃thesized by solvothermal method,which was then reduced to TpBD-(NH_(2))_(2),and finally,a chiral COF material TpBD-(NH_(2))_(2)-D-(-)-α-phenylglycine was obtained by chirally modifying the TpBD-(NH_(2))_(2) with D-(-)-α-phenylglycine.Three COF materials,i.e.TpBD-(NO_(2))_(2),TpBD-(NH_(2))_(2) and TpBD-(NH_(2))_(2)-D-(-)-α-phenylglycine were characterized,and a chiral stationary phase of TpBD-(NH_(2))_(2)-D-(-)-α-phenylglycine was prepared by“net-wrap method”.In order to investigate the sepa⁃ration performance of the stationary phase,it was used to prepare a chiral column for high performance liquid chromatography(HPLC),n-hexane-isopropanol(9∶1,by volume)and methanol-water(9∶1,by volume)were used as mobile phases.13 chiral compounds and 5 benzene positional isomers were sep⁃arated on this column with good reproducibility.The experiment showed that the separation effect of TpBD-(NH_(2))_(2)-D-(-)-α-phenylglycine chromatographic column was excellent.It was of a certain re⁃search significance to use the chiral COF material TpBD-(NH_(2))_(2)-D-(-)-α-phenylglycine as HPLC sta⁃tionary phase for the separation of chiral substances and benzene isomers.