葫芦脲及其衍生物在色谱中的应用研究
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摘要
基于超分子化学作用的大环超分子化合物色谱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。葫芦脲被誉为“第四代超分子化合物”，葫芦脲优良的分子识别能力早已被许多实验证实，研究已表明葫芦脲在色谱领域具有发展潜力，但其应用研究的深度和广度远远不如冠醚、环糊精和杯芳烃。利用葫芦脲的分子识别作用提高色谱分离选择性是色谱学与超分子化学交叉的前沿研究领域，显示出重要的学术价值和应用前景。本学位论文将葫芦脲应用于气相色谱固定相，表征和评价了新固定相的色谱性能，通过各种溶质和实际样品较系统地探讨了色谱保留机理；制备了葫芦[6]脲单轮烷键合硅胶固定相应用于高效液相色谱，对新固定相的制备、表征、色谱性能和保留机理等进行了较为系统的研究。主要内容如下：
1．较全面地综述了大环超分子化合物冠醚、环糊精、杯芳烃在气相色谱和液相色谱固定相方面的研究进展，并侧重概述了第四代超分子化合物葫芦脲在分离科学和超分子自组装领域的研究现状和进展，为本论文选题、研究内容、技术路线设计等提供依据。
2．合成了甘脲、葫芦[6]脲和羟基葫芦[6]脲，并采用红外光谱、质谱、热分析等手段对产物进行了表征，为气相色谱固定相和液相色谱键合相的制备提供原料。
3．设计了一种在酸性条件下均匀涂渍固定液的新方法，首次将羟基葫芦[6]脲(HOCB6)用作气相色谱固定相。将HOCB6填装成气相色谱填充柱后，以烷烃、卤代烃、芳香烃、醇、酮、酯、酸、胺等类物质为探针以及用复杂样品花露水，对它的色谱分离性能进行了研究，探讨了其色谱分离机理。结果表明：HOCB6是一种性能优良的气相色谱分离材料，热稳定性高，柱性能稳定，可用于高温气相色谱。HOCB6柱具有优良的色谱分离性能，对难分离的芳香族位置异构体(如二甲苯)具有良好的分离能力，显示出较好的立体选择性；尤其是对复杂样品的高沸点组分(如花露水中的高沸点组分)有良好的分离效果，可预见其对复杂体系的分离具有广阔的应用前景。
4．制备了葫芦[6]脲和甘脲填充柱，首次将甘脲应用于气相色谱固定相，采用各种溶质探针，评价了甘脲和葫芦[6]脲固定相的色谱性能，探讨了色谱分离机理。结果表明：甘脲固定相热稳定性高、柱性能稳定，是一种良好的气相色谱固定相，该固定相对烷烃、卤代烃、芳香烃、醇、酯、酮、酸、胺等类物质具有良好的分离能力，尤其是对位置异构体(如二取代苯位置异构体)有较好的分离选择性。葫芦[6]脲固定相对气体分子有吸附和捕集作用，在环保领域有应用前景。
5．利用气相色谱法研究了葫芦[6]脲与有机气体分子的相互作用。结果表明：葫芦[6]脲能吸附和捕集气体分子，特别是气体小分子，可用于室内空气污染如甲醛污染的治理。
6．将超分子自组装技术和色谱键合硅胶固定相制备技术相结合，采用γ-[(2，3)-环氧丙氧]丙基三甲氧基硅烷(KH-560)为偶联剂，首次将一种葫芦[6]脲单轮烷(CB6MR)键合到硅胶上，制备了一种新型的高效液相色谱葫芦[6]脲单轮烷键合固定相(CB6MRBS)。通过红外光谱、元素分析、热分析等手段表征了固定相的结构。
7．采用中性、酸性、碱性化合物和二取代苯位置异构体等溶质探针，分别在反相和正相色谱模式下对固定相的色谱性能和保留机理进行了研究。结果表明：CB6MRBS是一种多模式键合固定相，具有良好的正相和反相色谱性能，对位置异构体具有较高的识别能力，特别是可有效地用于碱性化合物的分离分析。其保留机理存在氢键、静电、π-π和疏水作用等多种作用力机制，协同作用提高了CB6MRBS对溶质的分离选择性。由于配体中含有酰胺基和众多羰基，可预见CB6MRBS在络合色谱和生化样品分析方面有应用前景。
8．采用新固定相进行了溶质分离的应用研究，研究了正相和反相色谱模式下嘌呤衍生物在新固定相上的色谱行为并在反相模式下与ODS固定相进行了比较，研究了各种因素对色谱分离的影响，探讨了分离机理，并优化色谱条件，有利于新固定相进一步的推广应用；利用新固定相在正相和反相模式下测定了茶叶中的咖啡因。结果表明：在反相模式下，嘌呤化合物与葫芦[6]脲单轮烷键合相之间存在多种相互作用，除疏水作用外，分离过程中还存在与ODS不同的色谱分离机制，分离效果明显优于ODS。在正相条件下，多作用力的色谱分离机制同样存在。葫芦[6]脲单轮烷键合相与溶质之间存在疏水、氢键、π-π和偶极-偶极等多种作用力，协同作用提高了固定相对它们的分离选择性。CB6MRBS对茶叶中咖啡因的测定在正相和反相模式下均取得了满意的效果。CB6MRBS在嘌呤碱基衍生物的快速分离和测定方面有广阔的应用前景。
9．葫芦脲在毛细管气相色谱等方面的应用以及葫芦[6]脲单轮烷键合硅胶固定相在生化样品分离分析等方面的应用有待于下一步研究。
Macrocycle supramolecular chromatography stationary phases have been gaining great interest for the chromatography due to special molecular recognition based on supramolecular interaction retention mechanism. A great deal of studies have shown that cucurbit[n]urils (CB[n], n=5-10), the macrocyclic host molecules of the fourth generation supramolecular, possess special capacity of the molecular recognition for a wide variety of guest molecules based on supramolecular interactions. Although cucurbit[n]s are potentially as useful as well-known host molecules such as crown ethers, cyclodextrins, and calixarenes, their practical applications are still limited especially in separation science. How to promote separation selectivity via the molecular recognition of CB[n] ligands is an attracting subject in the overlapping area of modern chromatography with supramolecular chemistry, showing great promising prospect for the researches of separation theory and application. In this thesis, CB[n]s was used as stationary phase for gas chromatography for the first time. The preliminary evaluation of the new stationary phases for GC was carried out. Related separation mechanism was systematically studied. Meanwhile, the preparation, characterization, evaluation and retention mechanism of cucurbit[6]uril mono-rotaxane-bonded silica stationary phases for HPLC were studied systematically. The main contents studied are as follows:
1. The progress of the study of crown ethers, cyclodextrins, and calixarenes in HPLC and GC were reviewed in detail. The main subject focused on the preparation, chromatographic property, retention mechanism and application of cucurbituril-bonded stationary phases for HPLC and molecular assembly of cucurbituril. The application prospect of cucurbituril for separation science and related techniques in the future is discussed. Above all provide the basis and start point for further research of the subject.
2. Glycoluril, cucurbit[6]uril and perhydroxycucurbit[6]uril were synthesized. Their structures were characterized by infared fourier transform spectroscopy, elemental analysis, thermal analysis and mass spectrometry. This provided material for the preparation of GC stationary phases and bonded silica stationary for HPLC.
3. A novel method of well-proportionally coating perhydroxycucurbit[6]uril stationary phase (PSP) on a packed column under acidic condition was developed, perhydroxycucurbit[6]uril has been used successfully as stationary phase for packed column gas chromatography for the first time. Perhydroxycucurbit[6]uril stationary phase exhibited wide operational temperature, outstanding thermostability and good selectivities for various organic compounds, such as alkanes, aromatic hydrocarbons, alcohols, esters, ketones and amines, etc. It was also found that some positional isomers, such as disubstituted benzenes could be well separated on this column. PSP has excellent separation abilities to some complicate samples, for example commercial toilet waters. PSP exhibits the promising application in the separation of complicate samples. Separation mechanism of the new packing for GC-separation was preliminary discussed.
4. Cucurbit[6]uril and glycoluril packed column was prepared and glycoluril was used as stationary phase in packed column gas chromatography for the first time. Their chromatographic properties were studied by using different probes. The results showed that the glycoluril stationary phase (GSP) was a good GC stationary phase with wide operational temperature, outstanding thermostability and good separation ability for alkanes, halohydrocarbons, aromatic hydrocarbons, alcohols, esters, ketones, carboxylic acids and amines, etc. It was also found that some positional isomers such as disubstituted benzene can be well separated on GSP. The GC-separation mechanism of GSP was preliminary discussed. The results also showed that cucurbit[6]uril can absorbed and capture gas molecules. Cucurbituril will be well application prospect in environmental protection.
5. The interactions between cucurbit[6]uril and organic volatile molecules were studied by using gas chromatography method. The results show that cucurbit[6]uril can absorb and capture gas molecules especially for small molecules, cucurbit[6]uril can be used in control indoor air pollution such as the treatment of indoor formaldehyde pollution.
6. A novel cucurbit[6]uril monorotaxane bonded silica stationary phase (CB6MRBS) for high performance liquid chromatography has been prepared successfully by combining supramolecular self-assembly technology with the immobilization technique of chromatographic stationary phase. A cucurbit[6]uril monorotaxane (CB6MR) was, for the first time, grafted to silica gel by usingγ-glycidoxypropyl-trimethoxysilane (KH-560) as a coupling reagent. CB6MRBS was characterized by FTIR, elemental analysis and thermal analysis.
7. The chromatographic performance and retention mechanism of CB6MRBS were evaluated by using organic components including acidic, basic, neutral analytes and positional isomers of disubstituted benzene as probe molecules under both reversed-phase and normal-phase modes. The results show that CB6MRBS is a kind of multimode bonded stationary phase with excellent reversed-phase and normal-phase chromatographic properties. CB6MRBS shows obvious priority for separation of positional isomers, especially for the better separation of basic compounds. The new packing material can provide various action sites for different analytes, such as those of hydrogen-bonding,π-π, electrostatic and hydrophobic interactions. It may have good prospect for complexation chromatography, which is required to further stduy.
8. The new cucurbit[6]uril monorotaxane-bonded stationary phases were used for the separation of solute series. The chromatographic behavior of purine derivatives on CB6MRBS were studied by high performance liquid chromatography under normal and reversed phase modes. A comparative study with ODS was carried out as well. The various influence factors on the chromatographic behavior of the solutes on CB6MRBS were investigated. The chromatographic conditions were optimized partially, which paid the way for further applications. Coffeine has been determined by using CB6MRBS under both reversed-phase and normal-phase modes. The results show that various interactions occurred between the analytes and CB6MRBS besides hydrophobic interaction under reversed-phase mode, which was different from that on ODS. CB6MRBS were superior to ODS in the above separations. According to the chromatographic analysis, the separation mechanism of multiple interactions also existed under normal-phase chromatography. CB6MRBS can provide various sites for analytes, such as the hydrophobic, hydrogen-bonding,π-πand dipole-dipole interactions. Separations of purine derivatives on CB6MRBS were achieved with satisfaction due to the various retention mechanisms both under reversed and normal phase modes. CB6MRBS exhibits the promising application in the rapid separation and determination of purine derivatives.
9. Applying of cucurbituril in capillary column gas chromatography and the chromatographic application of CB6MRBS such as for biochemical samples will still be requiring to be developed in the next step.
1．较全面地综述了大环超分子化合物冠醚、环糊精、杯芳烃在气相色谱和液相色谱固定相方面的研究进展，并侧重概述了第四代超分子化合物葫芦脲在分离科学和超分子自组装领域的研究现状和进展，为本论文选题、研究内容、技术路线设计等提供依据。
2．合成了甘脲、葫芦[6]脲和羟基葫芦[6]脲，并采用红外光谱、质谱、热分析等手段对产物进行了表征，为气相色谱固定相和液相色谱键合相的制备提供原料。
3．设计了一种在酸性条件下均匀涂渍固定液的新方法，首次将羟基葫芦[6]脲(HOCB6)用作气相色谱固定相。将HOCB6填装成气相色谱填充柱后，以烷烃、卤代烃、芳香烃、醇、酮、酯、酸、胺等类物质为探针以及用复杂样品花露水，对它的色谱分离性能进行了研究，探讨了其色谱分离机理。结果表明：HOCB6是一种性能优良的气相色谱分离材料，热稳定性高，柱性能稳定，可用于高温气相色谱。HOCB6柱具有优良的色谱分离性能，对难分离的芳香族位置异构体(如二甲苯)具有良好的分离能力，显示出较好的立体选择性；尤其是对复杂样品的高沸点组分(如花露水中的高沸点组分)有良好的分离效果，可预见其对复杂体系的分离具有广阔的应用前景。
4．制备了葫芦[6]脲和甘脲填充柱，首次将甘脲应用于气相色谱固定相，采用各种溶质探针，评价了甘脲和葫芦[6]脲固定相的色谱性能，探讨了色谱分离机理。结果表明：甘脲固定相热稳定性高、柱性能稳定，是一种良好的气相色谱固定相，该固定相对烷烃、卤代烃、芳香烃、醇、酯、酮、酸、胺等类物质具有良好的分离能力，尤其是对位置异构体(如二取代苯位置异构体)有较好的分离选择性。葫芦[6]脲固定相对气体分子有吸附和捕集作用，在环保领域有应用前景。
5．利用气相色谱法研究了葫芦[6]脲与有机气体分子的相互作用。结果表明：葫芦[6]脲能吸附和捕集气体分子，特别是气体小分子，可用于室内空气污染如甲醛污染的治理。
6．将超分子自组装技术和色谱键合硅胶固定相制备技术相结合，采用γ-[(2，3)-环氧丙氧]丙基三甲氧基硅烷(KH-560)为偶联剂，首次将一种葫芦[6]脲单轮烷(CB6MR)键合到硅胶上，制备了一种新型的高效液相色谱葫芦[6]脲单轮烷键合固定相(CB6MRBS)。通过红外光谱、元素分析、热分析等手段表征了固定相的结构。
7．采用中性、酸性、碱性化合物和二取代苯位置异构体等溶质探针，分别在反相和正相色谱模式下对固定相的色谱性能和保留机理进行了研究。结果表明：CB6MRBS是一种多模式键合固定相，具有良好的正相和反相色谱性能，对位置异构体具有较高的识别能力，特别是可有效地用于碱性化合物的分离分析。其保留机理存在氢键、静电、π-π和疏水作用等多种作用力机制，协同作用提高了CB6MRBS对溶质的分离选择性。由于配体中含有酰胺基和众多羰基，可预见CB6MRBS在络合色谱和生化样品分析方面有应用前景。
8．采用新固定相进行了溶质分离的应用研究，研究了正相和反相色谱模式下嘌呤衍生物在新固定相上的色谱行为并在反相模式下与ODS固定相进行了比较，研究了各种因素对色谱分离的影响，探讨了分离机理，并优化色谱条件，有利于新固定相进一步的推广应用；利用新固定相在正相和反相模式下测定了茶叶中的咖啡因。结果表明：在反相模式下，嘌呤化合物与葫芦[6]脲单轮烷键合相之间存在多种相互作用，除疏水作用外，分离过程中还存在与ODS不同的色谱分离机制，分离效果明显优于ODS。在正相条件下，多作用力的色谱分离机制同样存在。葫芦[6]脲单轮烷键合相与溶质之间存在疏水、氢键、π-π和偶极-偶极等多种作用力，协同作用提高了固定相对它们的分离选择性。CB6MRBS对茶叶中咖啡因的测定在正相和反相模式下均取得了满意的效果。CB6MRBS在嘌呤碱基衍生物的快速分离和测定方面有广阔的应用前景。
9．葫芦脲在毛细管气相色谱等方面的应用以及葫芦[6]脲单轮烷键合硅胶固定相在生化样品分离分析等方面的应用有待于下一步研究。
Macrocycle supramolecular chromatography stationary phases have been gaining great interest for the chromatography due to special molecular recognition based on supramolecular interaction retention mechanism. A great deal of studies have shown that cucurbit[n]urils (CB[n], n=5-10), the macrocyclic host molecules of the fourth generation supramolecular, possess special capacity of the molecular recognition for a wide variety of guest molecules based on supramolecular interactions. Although cucurbit[n]s are potentially as useful as well-known host molecules such as crown ethers, cyclodextrins, and calixarenes, their practical applications are still limited especially in separation science. How to promote separation selectivity via the molecular recognition of CB[n] ligands is an attracting subject in the overlapping area of modern chromatography with supramolecular chemistry, showing great promising prospect for the researches of separation theory and application. In this thesis, CB[n]s was used as stationary phase for gas chromatography for the first time. The preliminary evaluation of the new stationary phases for GC was carried out. Related separation mechanism was systematically studied. Meanwhile, the preparation, characterization, evaluation and retention mechanism of cucurbit[6]uril mono-rotaxane-bonded silica stationary phases for HPLC were studied systematically. The main contents studied are as follows:
1. The progress of the study of crown ethers, cyclodextrins, and calixarenes in HPLC and GC were reviewed in detail. The main subject focused on the preparation, chromatographic property, retention mechanism and application of cucurbituril-bonded stationary phases for HPLC and molecular assembly of cucurbituril. The application prospect of cucurbituril for separation science and related techniques in the future is discussed. Above all provide the basis and start point for further research of the subject.
2. Glycoluril, cucurbit[6]uril and perhydroxycucurbit[6]uril were synthesized. Their structures were characterized by infared fourier transform spectroscopy, elemental analysis, thermal analysis and mass spectrometry. This provided material for the preparation of GC stationary phases and bonded silica stationary for HPLC.
3. A novel method of well-proportionally coating perhydroxycucurbit[6]uril stationary phase (PSP) on a packed column under acidic condition was developed, perhydroxycucurbit[6]uril has been used successfully as stationary phase for packed column gas chromatography for the first time. Perhydroxycucurbit[6]uril stationary phase exhibited wide operational temperature, outstanding thermostability and good selectivities for various organic compounds, such as alkanes, aromatic hydrocarbons, alcohols, esters, ketones and amines, etc. It was also found that some positional isomers, such as disubstituted benzenes could be well separated on this column. PSP has excellent separation abilities to some complicate samples, for example commercial toilet waters. PSP exhibits the promising application in the separation of complicate samples. Separation mechanism of the new packing for GC-separation was preliminary discussed.
4. Cucurbit[6]uril and glycoluril packed column was prepared and glycoluril was used as stationary phase in packed column gas chromatography for the first time. Their chromatographic properties were studied by using different probes. The results showed that the glycoluril stationary phase (GSP) was a good GC stationary phase with wide operational temperature, outstanding thermostability and good separation ability for alkanes, halohydrocarbons, aromatic hydrocarbons, alcohols, esters, ketones, carboxylic acids and amines, etc. It was also found that some positional isomers such as disubstituted benzene can be well separated on GSP. The GC-separation mechanism of GSP was preliminary discussed. The results also showed that cucurbit[6]uril can absorbed and capture gas molecules. Cucurbituril will be well application prospect in environmental protection.
5. The interactions between cucurbit[6]uril and organic volatile molecules were studied by using gas chromatography method. The results show that cucurbit[6]uril can absorb and capture gas molecules especially for small molecules, cucurbit[6]uril can be used in control indoor air pollution such as the treatment of indoor formaldehyde pollution.
6. A novel cucurbit[6]uril monorotaxane bonded silica stationary phase (CB6MRBS) for high performance liquid chromatography has been prepared successfully by combining supramolecular self-assembly technology with the immobilization technique of chromatographic stationary phase. A cucurbit[6]uril monorotaxane (CB6MR) was, for the first time, grafted to silica gel by usingγ-glycidoxypropyl-trimethoxysilane (KH-560) as a coupling reagent. CB6MRBS was characterized by FTIR, elemental analysis and thermal analysis.
7. The chromatographic performance and retention mechanism of CB6MRBS were evaluated by using organic components including acidic, basic, neutral analytes and positional isomers of disubstituted benzene as probe molecules under both reversed-phase and normal-phase modes. The results show that CB6MRBS is a kind of multimode bonded stationary phase with excellent reversed-phase and normal-phase chromatographic properties. CB6MRBS shows obvious priority for separation of positional isomers, especially for the better separation of basic compounds. The new packing material can provide various action sites for different analytes, such as those of hydrogen-bonding,π-π, electrostatic and hydrophobic interactions. It may have good prospect for complexation chromatography, which is required to further stduy.
8. The new cucurbit[6]uril monorotaxane-bonded stationary phases were used for the separation of solute series. The chromatographic behavior of purine derivatives on CB6MRBS were studied by high performance liquid chromatography under normal and reversed phase modes. A comparative study with ODS was carried out as well. The various influence factors on the chromatographic behavior of the solutes on CB6MRBS were investigated. The chromatographic conditions were optimized partially, which paid the way for further applications. Coffeine has been determined by using CB6MRBS under both reversed-phase and normal-phase modes. The results show that various interactions occurred between the analytes and CB6MRBS besides hydrophobic interaction under reversed-phase mode, which was different from that on ODS. CB6MRBS were superior to ODS in the above separations. According to the chromatographic analysis, the separation mechanism of multiple interactions also existed under normal-phase chromatography. CB6MRBS can provide various sites for analytes, such as the hydrophobic, hydrogen-bonding,π-πand dipole-dipole interactions. Separations of purine derivatives on CB6MRBS were achieved with satisfaction due to the various retention mechanisms both under reversed and normal phase modes. CB6MRBS exhibits the promising application in the rapid separation and determination of purine derivatives.
9. Applying of cucurbituril in capillary column gas chromatography and the chromatographic application of CB6MRBS such as for biochemical samples will still be requiring to be developed in the next step.
引文
[1] Fishbein L, Chromatography of environmental hazards, Amsterdam, Elsevier, Pub. Co., 1982
[2] 师治贤，王俊德．生物大分子的液相色谱分离和制备[M]．北京，科学出版社，1992
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