手性樟脑衍生的共价有机骨架材料用作高效液相色谱固定相分离手性化合物  

Covalent Organic Framework Material Derivative of Chiral Camphor Used as High Performance Liquid Chromatography Stationary Phase for Resolution of Racemates

作　　者：付豪 熊婉淇 王祯 段爱红[1] 袁黎明[1] FU Hao;XIONG Wan-Qi;WANG Zhen;DUAN Ai-Hong;YUAN Li-Ming(School of Chemistry and Chemical Engineering,Yunnan Normal University,Kunming 650500,China)

机构地区：[1]云南师范大学化学化工学院,昆明650500

出　　处：《应用化学》2022年第9期1371-1381,共11页Chinese Journal of Applied Chemistry

基　　金：国家自然科学基金(No.91856123)资助。

摘　　要：共价有机骨架材料(COFs)作为一种新型的晶体多孔材料,其手性共价骨架材料在手性分离领域具有良好的应用前景。本文以1,3,5-三醛基间苯三酚(Tp)和3,3′-二硝基联苯胺(BD)反应合成出TpBD(NH_(2))_(2),并以此作为基本共价有机骨架。用(1S)-(+)-10-樟脑磺酰氯对该骨架进行衍生修饰,制备出手性共价有机骨架材料TpBD(NH_(2))_(2)的(1S)-(+)-10-樟脑磺酰氯(Cam)衍生物(TpBD-1S-(+)-Cam)。结果表明,制备的手性共价有机骨架材料TpBD-1S-(+)-Cam能够分离华法林、马来酸氯苯那敏、阿替洛尔、美托洛尔、佐匹克隆、1-(9-蒽基)-2,2,2-三氟乙醇、1,2-二苯乙醇酮、酮洛芬、盐酸美西律和噻吗洛尔共10种外消旋体以及o,m,p-溴苯胺、o,m,p-碘苯胺2种苯系位置异构体,分离效果较好。该材料用作高效液相色谱固定相具有良好的开发潜力和应用价值。Covalent organic framework materials(COFs)are a new type of crystalline porous materials,and their chiral materials have good application prospects in various fields.In this paper,TpBD(NH2)2 synthesized by the reaction of 1,3,5-trialdehyde phloroglucinol(Tp)and 3,3'-dinitrobenzidine(BD)was used as the covalent organic skeleton,and reacts with(1S)-(+)-10-camphorsulfonyl chloride(Cam)to prepare(1S)-(+)-10-camphorsulfonyl chloride derivative TpBD-1S-(+)-Cam.The derivative is a newly synthesized chiral covalent organic framework material.TpBD-1S-(+)-Cam was immobilized on silica gel to prepare a chiral column for high performance liquid chromatography to separate racemates.The experimental results show that the prepared COF,TpBD-1S-(+)-Cam,can separate warfarin,chlorpheniramine maleate,atenolol,metoprolol,zopiclone,10-(9-anthryl)-2,2,2-trifluoroethanol,1,2-benzophenone,ketoprofen,mexiletine hydrochloride,timolol 10 kinds of racemates and o,m,p-bromoaniline,o,m,p-iodoaniline are two kinds of positional isomers of benzene series.This material has potential as the stationary phase of high performance liquid chromatography.

关 键 词：共价有机骨架材料 高效液相色谱 固定相 手性拆分 

分 类 号：O657.7[理学—分析化学]