大环超分子高效液相色谱键合固定相制备和性能研究
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摘要
基于超分子化学作用的大环化合物键合硅胶固定相由于具有特殊的分离选择性、稳定性一直受到广大色谱工作者的极大关注。制备稳定的键合硅胶固定相是新型硅胶固定相发展的必要条件，而环糊精和杯芳烃作为第二和第三代超分子化学主体分子，由于具有特殊的分子识别能力，已经成为分离科学与生物医药、材料科学等基础和应用学科交叉的前沿领域研究课题，因此，探讨新型、稳定的环糊精和杯芳烃键合硅胶固定相的新制备方法具有重要的学术和应用价值。本学位论文对高效液相色谱环糊精和杯芳烃键合硅胶固定相的固相缩合反应制备、表征、色谱性能和保留机理进行较为系统的研究。主要内容如下：
1．比较系统地综述了目前环糊精和杯芳烃高效液相色谱应用及键合固定相制备和保留机理等方面研究进展，这是本学位论文选题、研究内容、技术路线设计的依据。
2．首次利用氯丙基三乙氧基硅烷与硅胶反应制各氯丙基硅胶中间体(CPS)，再在催化剂的作用下通过固相表面缩合反应制备新型的对—叔丁基杯[8]芳烃键合硅胶固定相(CBS)。采用元素分析、红外光谱及热分析等手段对固定相进行表征。以苯的同系物、PAHs和二取代苯位置异构体为溶质考察固定相的色谱性能，与间隔基氯丙基柱及ODS进行对比研究，探讨固定相的保留机理，并考察其柱效与色谱峰对称性。结果表明该固定相具有反相色谱性能，并具有特殊的分离选择性。对二取代苯位置异构体尤其是碱性胺类溶质有良好的分离选择性，峰形对称，柱效高；可以极大地弥补ODS柱的不足。其保留机理包括疏水作用及电荷转移、偶极—偶极、π—π、静电、氢键以及包结等超分子作用。
3．研究对—叔丁基杯[8]芳烃键合硅胶固定相分离激素类药物的应用。考察流动相有机改性剂含量、pH值、离子强度等因素对溶质保留及分离选择性的影响；并与CPS和ODS进行对比。结果表明溶质在CBS、CPS和ODS上分别获得有效分离并且出峰顺序与分离选择性存在明显差异，可见，三种固定相的保留和分离机理不—致。CBS对溶质由于超分子保留机理(如：疏水作用、π—π作用、氢键作用、偶极—偶极作用等)的存在，提高了对溶质的分离选择性尤其是疏水差异较小，而能与CBS形成其它作用力(如π—π作用、氢键作用)的溶质。另外，由于CBS的疏水性较ODS弱，因而对溶质间疏水差异太大的溶质可实现快速分离并避免梯度洗脱；提高分离效率并
且节约有机溶剂的用量。
4.首次利用氯丙基三乙氧基硅烷与硅胶反应制备氯丙基硅胶中间体，再通过固相表面
缩合反应制备新型的p一环糊精键合硅胶固定相(盯仆Bs)。采用元素分析和红外光
谱等手段对固定相进行表征。以苯的同系物、PAHs、ODS难分离物质对、二取代苯位
置异构体、苯的单取代物、酚类、胺类及丹磺酞化氨基酸为溶质考察固定相的色谱性
能与CPS和ODS进行对比研究，探讨固定相的保留机理。结果表明采用此法布咯
的p一环糊精键合硅胶固定相虽然键合量宁剐氏，但具有较好的分离选择性。采用三个
亚甲基短链间隔基有效避免了含氮间隔基对固定相色谱性能的不利影响并且很好地保
持了环糊精的天然构型，突出了环糊精的包结等超分子作用，增强了固定相的分离选
择性。
5.考察筋沛组备的p一环糊精键合硅胶固定相又创敏素和磺胺类药物的色谱保留行为。通
过优化流动相条件使溶质达选择性分离，并与CPS及ODS进行对比，探讨其保留机
理。结果发现，卜CD一s对激素类药物具有较好的分离选择性，较ODs有一定的优势。
而对磺胺类药物的分离，卜CD-Bs显示出良好的分离选择性，溶质达快速分离，色谱
峰对称、柱效高，明显改善硅胶对胺类化合物拖尾现象，这进一步证明采用此法制备
的环糊精柱，通过短链连接到硅胶表面，有效屏蔽硅轻基，改进硅胶柱的色谱性能。
Macrocycle supramolecular bonded silica stationary phases have been gaining great interest for the chromatography due to especial molecular recognition based on supramolecular interaction retention mechanism. It is necessary to explore new preparation process of the stable bonded silica stationary phases with macrocycle molecules. In addition, cyclodextrin and calixarene as host molecules of the second and third generation supramolecular to possess molecular recognition ability is an attractive research object in overlapping area of modern separation science with biomedical and material sciences, showing great promising prospect to develop the supramolecular theory and application in chromatography. In the dissertation, the preparation method and characterization of novel p-cyclodextrin andp0terf-calix[8]arene bonded silica stationary phases for high performance liquid chromatography were studied, their chromatographic performance were evaluated systematically and retention mechanisms were researched. The ma
jor contents are as follows:
l.The preparation, evaluation, application and retention mechanism of p-cyclodextrin and calixarene bonded silica stationary phases for high performance liquid chromatography were reviewed in detail, which provides the basis for further research of other new bonded stationary phases and which is the foundation for new ideas, object and design of technical scheme of the dissertation.
2 A newp-tert-calix[8]arene bonded silica stationary phase (CBS) for high performance liquid chromatography was prepared firstly by condensation reaction on solid surface of silica between the sodium of p-terr-calix[8]arene and bonded chloropropyl groups which were obtained by reaction of chloropropyltriethoxysilane with silica. The stationary phase was characterized by elemental analysis, FTIR and thermoanalysis. The chromatographic performance of CBS was studied by using PAHs, allkylbenzene and disubstituted benzenes as solutes and compared with mat of CPS and ODS; and the retention mechanism, column efficiency and peak symmetry were also studied. The result shows that the stationary phase has reversed-phase chromatographic performance and especial separation selectivity. Good selectivity, symmetry peak and high column efficiency were obtained for disubstituted benzenes particularly aniline compounds, which make up the disadvantage of ODS. Chromatographic process exist various retention mechanism based on
the supramolecular interaction, such as hydrogen-bonding, p-p charge-transfer, dipole-dipole interaction and
inclusion complexation and hydrophobic interaction.
3.The high performance liquid chrornatographic behavior of some steroid hormone medicines was studied on CBS. The effect of mobile phase variable such as methanol content, pH values, ionic strength and cation type of buffer was investigated. It is found that the solutes were separated respectively on CBS, CPS and ODS, but the elution order and separation selectivity were difference among three stationary phases, which means the different retention mechanism exist among three stationary phases. For multi-retention mechanisms exhibit on CBS, the separation selectivity was improved for solutes with the similar hydrophobicity whennd hydrogen-bonding interaction exist between solutes and stationary phase. In addition, the separation speed was increased due to weaker hydrophobicity of CBS compared with ODS, gradient elution was avoided and consumption of organic solvent was decreased for me separation of the solutes with very different hydrophobicity.
4. A novel P -cyclodextrin bonded silica stationary phase ( 3 CD-BS) for high performance liquid chromatography was prepared firstly by condensation reaction on solid surface of the bonded silica between the sodium of cyclodextrin and bonded chloropropyl groups. The stationary phase was characterized by elemental analysis and FTIR. The chromatographic performance and retention mechanism of 3 -CD-BS were studied by using PAHs, allcylbenzene, disubstituted benzenes, substituted benzene, phenol c
1．比较系统地综述了目前环糊精和杯芳烃高效液相色谱应用及键合固定相制备和保留机理等方面研究进展，这是本学位论文选题、研究内容、技术路线设计的依据。
2．首次利用氯丙基三乙氧基硅烷与硅胶反应制各氯丙基硅胶中间体(CPS)，再在催化剂的作用下通过固相表面缩合反应制备新型的对—叔丁基杯[8]芳烃键合硅胶固定相(CBS)。采用元素分析、红外光谱及热分析等手段对固定相进行表征。以苯的同系物、PAHs和二取代苯位置异构体为溶质考察固定相的色谱性能，与间隔基氯丙基柱及ODS进行对比研究，探讨固定相的保留机理，并考察其柱效与色谱峰对称性。结果表明该固定相具有反相色谱性能，并具有特殊的分离选择性。对二取代苯位置异构体尤其是碱性胺类溶质有良好的分离选择性，峰形对称，柱效高；可以极大地弥补ODS柱的不足。其保留机理包括疏水作用及电荷转移、偶极—偶极、π—π、静电、氢键以及包结等超分子作用。
3．研究对—叔丁基杯[8]芳烃键合硅胶固定相分离激素类药物的应用。考察流动相有机改性剂含量、pH值、离子强度等因素对溶质保留及分离选择性的影响；并与CPS和ODS进行对比。结果表明溶质在CBS、CPS和ODS上分别获得有效分离并且出峰顺序与分离选择性存在明显差异，可见，三种固定相的保留和分离机理不—致。CBS对溶质由于超分子保留机理(如：疏水作用、π—π作用、氢键作用、偶极—偶极作用等)的存在，提高了对溶质的分离选择性尤其是疏水差异较小，而能与CBS形成其它作用力(如π—π作用、氢键作用)的溶质。另外，由于CBS的疏水性较ODS弱，因而对溶质间疏水差异太大的溶质可实现快速分离并避免梯度洗脱；提高分离效率并
且节约有机溶剂的用量。
4.首次利用氯丙基三乙氧基硅烷与硅胶反应制备氯丙基硅胶中间体，再通过固相表面
缩合反应制备新型的p一环糊精键合硅胶固定相(盯仆Bs)。采用元素分析和红外光
谱等手段对固定相进行表征。以苯的同系物、PAHs、ODS难分离物质对、二取代苯位
置异构体、苯的单取代物、酚类、胺类及丹磺酞化氨基酸为溶质考察固定相的色谱性
能与CPS和ODS进行对比研究，探讨固定相的保留机理。结果表明采用此法布咯
的p一环糊精键合硅胶固定相虽然键合量宁剐氏，但具有较好的分离选择性。采用三个
亚甲基短链间隔基有效避免了含氮间隔基对固定相色谱性能的不利影响并且很好地保
持了环糊精的天然构型，突出了环糊精的包结等超分子作用，增强了固定相的分离选
择性。
5.考察筋沛组备的p一环糊精键合硅胶固定相又创敏素和磺胺类药物的色谱保留行为。通
过优化流动相条件使溶质达选择性分离，并与CPS及ODS进行对比，探讨其保留机
理。结果发现，卜CD一s对激素类药物具有较好的分离选择性，较ODs有一定的优势。
而对磺胺类药物的分离，卜CD-Bs显示出良好的分离选择性，溶质达快速分离，色谱
峰对称、柱效高，明显改善硅胶对胺类化合物拖尾现象，这进一步证明采用此法制备
的环糊精柱，通过短链连接到硅胶表面，有效屏蔽硅轻基，改进硅胶柱的色谱性能。
Macrocycle supramolecular bonded silica stationary phases have been gaining great interest for the chromatography due to especial molecular recognition based on supramolecular interaction retention mechanism. It is necessary to explore new preparation process of the stable bonded silica stationary phases with macrocycle molecules. In addition, cyclodextrin and calixarene as host molecules of the second and third generation supramolecular to possess molecular recognition ability is an attractive research object in overlapping area of modern separation science with biomedical and material sciences, showing great promising prospect to develop the supramolecular theory and application in chromatography. In the dissertation, the preparation method and characterization of novel p-cyclodextrin andp0terf-calix[8]arene bonded silica stationary phases for high performance liquid chromatography were studied, their chromatographic performance were evaluated systematically and retention mechanisms were researched. The ma
jor contents are as follows:
l.The preparation, evaluation, application and retention mechanism of p-cyclodextrin and calixarene bonded silica stationary phases for high performance liquid chromatography were reviewed in detail, which provides the basis for further research of other new bonded stationary phases and which is the foundation for new ideas, object and design of technical scheme of the dissertation.
2 A newp-tert-calix[8]arene bonded silica stationary phase (CBS) for high performance liquid chromatography was prepared firstly by condensation reaction on solid surface of silica between the sodium of p-terr-calix[8]arene and bonded chloropropyl groups which were obtained by reaction of chloropropyltriethoxysilane with silica. The stationary phase was characterized by elemental analysis, FTIR and thermoanalysis. The chromatographic performance of CBS was studied by using PAHs, allkylbenzene and disubstituted benzenes as solutes and compared with mat of CPS and ODS; and the retention mechanism, column efficiency and peak symmetry were also studied. The result shows that the stationary phase has reversed-phase chromatographic performance and especial separation selectivity. Good selectivity, symmetry peak and high column efficiency were obtained for disubstituted benzenes particularly aniline compounds, which make up the disadvantage of ODS. Chromatographic process exist various retention mechanism based on
the supramolecular interaction, such as hydrogen-bonding, p-p charge-transfer, dipole-dipole interaction and
inclusion complexation and hydrophobic interaction.
3.The high performance liquid chrornatographic behavior of some steroid hormone medicines was studied on CBS. The effect of mobile phase variable such as methanol content, pH values, ionic strength and cation type of buffer was investigated. It is found that the solutes were separated respectively on CBS, CPS and ODS, but the elution order and separation selectivity were difference among three stationary phases, which means the different retention mechanism exist among three stationary phases. For multi-retention mechanisms exhibit on CBS, the separation selectivity was improved for solutes with the similar hydrophobicity whennd hydrogen-bonding interaction exist between solutes and stationary phase. In addition, the separation speed was increased due to weaker hydrophobicity of CBS compared with ODS, gradient elution was avoided and consumption of organic solvent was decreased for me separation of the solutes with very different hydrophobicity.
4. A novel P -cyclodextrin bonded silica stationary phase ( 3 CD-BS) for high performance liquid chromatography was prepared firstly by condensation reaction on solid surface of the bonded silica between the sodium of cyclodextrin and bonded chloropropyl groups. The stationary phase was characterized by elemental analysis and FTIR. The chromatographic performance and retention mechanism of 3 -CD-BS were studied by using PAHs, allcylbenzene, disubstituted benzenes, substituted benzene, phenol c
引文
1．肖湘竹，高效液相色谱杯芳烃键合硅胶固定相制备、表征与性能研究 博士论文 2000，1
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