手性多孔戊基笼用于高效液相色谱拆分手性化合物
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摘要
高效液相色谱法拆分手性化合物是目前较为常用的一种手性分离手段,色谱拆分的关键在于探索新型高效的色谱固定相.手性多孔有机笼是一类新型的纯有机多孔晶体材料.文章合成了一种具有单一手性结构的多孔戊基笼,并将其涂渍在硅胶表面,制备了涂渍型高效液相色谱手性固定相.以正己烷/异丙醇为流动相,研究了该手性固定相对手性化合物的手性识别性能.结果表明,该固定相对手性化合物具有较好的手性识别能力.
High performance liquid chromatography(HPLC) is a commonly used Chiral separation method for the resolution of chiral compounds. The key to chromatographic resolution lies in exploring new and efficient stationary phases. Chiral porous organic cage is a new kind of pure organic porous crystal material. In this study, a chiral porous pentyl cage with homochiral structure was synthesized. The chiral porous pentyl cage was coated on silica gel to prepare a coated HPLC chiral stationary phase. The chiral recognition ability of the chiral stationary phase for chiral compounds was studied using n-hexane/isopropanol as mobile phase. The results show that the chiral column exhibited good recognition ability toward some chiral compounds.
High performance liquid chromatography(HPLC) is a commonly used Chiral separation method for the resolution of chiral compounds. The key to chromatographic resolution lies in exploring new and efficient stationary phases. Chiral porous organic cage is a new kind of pure organic porous crystal material. In this study, a chiral porous pentyl cage with homochiral structure was synthesized. The chiral porous pentyl cage was coated on silica gel to prepare a coated HPLC chiral stationary phase. The chiral recognition ability of the chiral stationary phase for chiral compounds was studied using n-hexane/isopropanol as mobile phase. The results show that the chiral column exhibited good recognition ability toward some chiral compounds.
引文
[1]章俊辉.手性多孔材料用作高分辨率气相色谱和高效液相色谱固定相的研究[D].上海:华东师范大学,2016.Zhang J H.Study on chiral porous materials used as stationary phases in high-resolution gas chromatography and high-performance liquid chromatography[D].Shanghai:East China Normal University,2016.
[2]Zhang G,Mastalerz M.Organic cage compounds-from shape-persistency to function[J].Chemical Society Reviews,2014,43(6):1 934-1 947.DOI:10.1039/C3CS60358J.
[3]Mastalerz M.Shape-persistent organic cage compounds by dynamic covalent bond formation[J].Angewandte Chemie International Edition,2010,49(30):5 042-5 053.DOI:10.1002/anie.v49:30.
[4]Chen L,Chen Q,Wu M,et al.Controllable coordination-driven self-assembly:from discrete metallocages to infinite cage-based frameworks[J].Accounts of Chemical Research,2015,48(2):201-210.DOI:10.1021/ar5003076.
[5]Cook,Timothy R,Stang,Peter J.Recent developments in the preparation and chemistry of metallacycles and metallacages via coordination[J].ChemInform,2015,46(38):7 001-7 045.
[6]Zarra S,Wood D M,Roberts D A,et al.Molecular containers in complex chemical systems[J].Chemical Society Reviews,2014,44(2):419-432.
[7]Jiang S,Bacse J,Wu X,et al.Selective gas sorption in a[2+3]‘propeller’cage crystal[J].Chemical Communications,2011,47(31):8 919-8 921.DOI:10.1039/c1cc12460a.
[8]邢宇博,刘宇奇,王新颖,等.三维配合物{[Mn3(C12H6O4)4]2-(C11H18N4)2+}n的水热合成、晶体结构和磁性研究[J].云南大学学报:自然科学版,2017,39(3):474-480.Xing Y B,Liu Y Q,Wang X Y,et al.Hydrothermal synthesis,crystal structure and magnetic property of a3D coordinated complex{[Mn3(C12H6O4)4]2-(C11H18N4)2+}n[J].Journal of Yunnan University:Natural Sciences Edition,2017,39(3):474-480.
[9]裴翠颖,曲凤玉.羟基官能化共价有机骨架化合物的设计合成及性质[J].高等学校化学学报,2011,32(6):1 234-1 238.Pei C Y,Qu F Y.Preparation and characterization of hydroxyl functional compound with covalent organic framework[J].Chemical Journal of Chinese Universities,2011,32(6):1 234-1 238.
[10]李阳雪,张巍,刘智,等.用环糊精的金属有机框架材料作为模板制备多孔有机笼[J].化学学报,2015(73):641-645.Li Y X,Zhang W,Liu Z,et al.Fabrication of porous covalent organic cages using cyclodextrin metal-organic frameworks as template[J].Acta Chimica Sinica,2015(73):641-645.
[11]Zhang J H,Xie S M,Chen L,et al.Homochiral porous organic cage with high selectivity for the separation of racemates in gas chromatography[J].Analytical Chemistry,2015,87(15):7 817-7 824.DOI:10.1021/acs.analchem.5b01512.
[12]Zhang J H,Xie S M,Wang B J,et al.Highly selective separation of enantiomers using a chiral porous organic cage[J].Journal of Chromatography A,2015,1426:174-183.DOI:10.1016/j.chroma.2015.11.038.
[13]Xie S M,Zhang J H,Fu N,et al.A chiral porous organic cage for molecular recognition using gas chromatography[J].Analytica Chimica Acta,2016,903:156-163.DOI:10.1016/j.aca.2015.11.030.
[14]Xie S M,Zhang J H,Fu N,et al.Application of homochiral alkylated organic cages as chiral stationary phases for molecular separations by capillary gas chromatography[J].Molecules,2016,21(11):1 466.DOI:10.3390/molecules21111466.
[15]Xie S M,Fu N,Li L,et al.Homochiral metal-organic cage for gas chromatographic separations[J].Analytical Chemistry,2018,90(15):9 182-9 188.DOI:10.1021/acs.analchem.8b01670.
[16]Giri N,Davidson C,Melaugh G,et al.Alkylated organic cages:from porous crystals to neat liquids[J].Chemical Science,2012,3(6):2 153-2 157.DOI:10.1039/c2sc01007k.
[2]Zhang G,Mastalerz M.Organic cage compounds-from shape-persistency to function[J].Chemical Society Reviews,2014,43(6):1 934-1 947.DOI:10.1039/C3CS60358J.
[3]Mastalerz M.Shape-persistent organic cage compounds by dynamic covalent bond formation[J].Angewandte Chemie International Edition,2010,49(30):5 042-5 053.DOI:10.1002/anie.v49:30.
[4]Chen L,Chen Q,Wu M,et al.Controllable coordination-driven self-assembly:from discrete metallocages to infinite cage-based frameworks[J].Accounts of Chemical Research,2015,48(2):201-210.DOI:10.1021/ar5003076.
[5]Cook,Timothy R,Stang,Peter J.Recent developments in the preparation and chemistry of metallacycles and metallacages via coordination[J].ChemInform,2015,46(38):7 001-7 045.
[6]Zarra S,Wood D M,Roberts D A,et al.Molecular containers in complex chemical systems[J].Chemical Society Reviews,2014,44(2):419-432.
[7]Jiang S,Bacse J,Wu X,et al.Selective gas sorption in a[2+3]‘propeller’cage crystal[J].Chemical Communications,2011,47(31):8 919-8 921.DOI:10.1039/c1cc12460a.
[8]邢宇博,刘宇奇,王新颖,等.三维配合物{[Mn3(C12H6O4)4]2-(C11H18N4)2+}n的水热合成、晶体结构和磁性研究[J].云南大学学报:自然科学版,2017,39(3):474-480.Xing Y B,Liu Y Q,Wang X Y,et al.Hydrothermal synthesis,crystal structure and magnetic property of a3D coordinated complex{[Mn3(C12H6O4)4]2-(C11H18N4)2+}n[J].Journal of Yunnan University:Natural Sciences Edition,2017,39(3):474-480.
[9]裴翠颖,曲凤玉.羟基官能化共价有机骨架化合物的设计合成及性质[J].高等学校化学学报,2011,32(6):1 234-1 238.Pei C Y,Qu F Y.Preparation and characterization of hydroxyl functional compound with covalent organic framework[J].Chemical Journal of Chinese Universities,2011,32(6):1 234-1 238.
[10]李阳雪,张巍,刘智,等.用环糊精的金属有机框架材料作为模板制备多孔有机笼[J].化学学报,2015(73):641-645.Li Y X,Zhang W,Liu Z,et al.Fabrication of porous covalent organic cages using cyclodextrin metal-organic frameworks as template[J].Acta Chimica Sinica,2015(73):641-645.
[11]Zhang J H,Xie S M,Chen L,et al.Homochiral porous organic cage with high selectivity for the separation of racemates in gas chromatography[J].Analytical Chemistry,2015,87(15):7 817-7 824.DOI:10.1021/acs.analchem.5b01512.
[12]Zhang J H,Xie S M,Wang B J,et al.Highly selective separation of enantiomers using a chiral porous organic cage[J].Journal of Chromatography A,2015,1426:174-183.DOI:10.1016/j.chroma.2015.11.038.
[13]Xie S M,Zhang J H,Fu N,et al.A chiral porous organic cage for molecular recognition using gas chromatography[J].Analytica Chimica Acta,2016,903:156-163.DOI:10.1016/j.aca.2015.11.030.
[14]Xie S M,Zhang J H,Fu N,et al.Application of homochiral alkylated organic cages as chiral stationary phases for molecular separations by capillary gas chromatography[J].Molecules,2016,21(11):1 466.DOI:10.3390/molecules21111466.
[15]Xie S M,Fu N,Li L,et al.Homochiral metal-organic cage for gas chromatographic separations[J].Analytical Chemistry,2018,90(15):9 182-9 188.DOI:10.1021/acs.analchem.8b01670.
[16]Giri N,Davidson C,Melaugh G,et al.Alkylated organic cages:from porous crystals to neat liquids[J].Chemical Science,2012,3(6):2 153-2 157.DOI:10.1039/c2sc01007k.