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Title Page

Abstract

Contents

CHAPTER 1. Introduction 16

1.1. Deep eutectic solvents 17

1.2. Preparation of deep eutectic solvents 18

1.3. Properties of deep eutectic solvents 22

1.4. Deep Eutectic Solvent based Mesoporous Siliceous Materials 26

1.5. Deep Eutectic Solvent based Molecularly Imprinted Polymers 28

1.6. Deep Eutectic Solvent based hexagonal Boron Nitride Molecularly Imprinted Polymers 31

CHAPTER 2. Experimental 34

2.1. Deep Eutectic Solvent based Mesoporous Siliceous Materials 35

2.1.1. Chemicals 35

2.1.2. Instruments 35

2.1.3. Preparation of deep eutectic solvent based mesoporous siliceous materials 36

2.1.4. Size exclusion chromatography for separation of polysaccharides 38

2.2. Deep Eutectic Solvent based Molecularly Imprinted Polymers 40

2.2.1. Chemicals 40

2.2.2. Instruments 40

2.2.3. Preparation of deep eutectic solvent based molecularly imprinted polymers 41

2.2.4. Evaluation of the selective adsorption capacity of materials 45

2.2.5. Extraction of antibiotics from millet extract 45

2.3. Deep Eutectic Solvent based hexagonal Boron Nitride-Molecularly Imprinted Polymers 47

2.3.1. Chemicals 47

2.3.2. Instruments 47

2.3.3. Preparation of deep eutectic solvent based hexagonal boron nitride molecularly imprinted polymers 48

2.3.4. Theoretical methodology 51

2.3.5. Extraction of flavonoids 51

CHAPTER 3. Results and Discussions 54

3.1. Deep eutectic solvent based mesoporous siliceous materials 55

3.1.1. Preparation of deep eutectic solvent based mesoporous siliceous materials 55

3.1.2. Characterization of materials 55

3.1.3. Size exclusion chromatography for separation of polysaccharides 63

3.2. Deep eutectic solvent based molecularly imprinted polymers 69

3.2.1. Preparation of deep eutectic solvent based molecularly imprinted polymers 69

3.2.2. Characteristics of the materials 71

3.2.3. Evaluation of the selective adsorption capacity of materials 73

3.2.4. Validation of the SPE-HPLC method 76

3.2.5. Extraction of antibiotics from the millet extract 78

3.3. Deep eutectic solvent based hexagonal Boron Nitride-molecularly imprinted polymers 80

3.3.1. Preparation of deep eutectic solvent based hexagonal boron nitride molecularly imprinted polymers 80

3.3.2. Theoretical studies 81

3.3.3. Characteristics of the materials 85

3.3.4. Extraction of flavonoids 90

Conclusions 95

References 96

Appendix 109

1. Exploration of Mesoporous Stationary Phases Prepared Using Deep Eutectic Solvents Combining Choline Chloride with 1,2-Butanediol or Glycerol for Use in Size-Exclusion Chromatography 109

2. Synthesis of Mesoporous Siliceous Materials in Choline Chloride Deep Eutectic Solvents and the Application of These Materials to High-Performance Size Exclusion Chromatography 110

3. Development of deep eutectic solvents applied in extraction and separation 111

4. Application of Deep Eutectic Solvents in Hybrid Molecularly Imprinted Polymers and Mesoporous Siliceous Material for Solid-Phase Extraction of Levofloxacin from Green Bean Extract 112

5. Separation of Polysaccharides by a SEC based on Deep Eutectic Solvents Modified Mesoporous Siliceous Materials 113

6. Application of novel ternary deep eutectic solvents as a functional monomer in molecularly imprinted polymers for purification of levofloxacin 114

7. Purification of Antibiotics from the Millet Extract Using Hybrid Molecularly Imprinted Polymers Based on Deep Eutectic Solvents 115

8. Preparation and Application of Porous Materials based on Deep Eutectic Solvents 116

9. Preparation of two-dimensional magnetic molecularly imprinted polymers based on boron nitride and a deep eutectic solvent for the selective recognition of flavonoids 117

11. Preparation of Deep Eutectic Solvent-based Hexagonal Boron Nitride-Molecularly Imprinted Polymer Nanoparticles for Solid Phase Extraction of Flavonoids 118

List of publication 119

List of Tables

Table 1-1. Physical property measurements. 25

Table 2-1. Compositions of the DESs in the synthesis of DES-based mesoporous siliceous materials. 37

Table 2-2. Specific information of the preparation of the proposed materials. 43

Table 3-1. Characteristics of the DES-based mesoporous siliceous materials. 62

Table 3-2. Separation of dextran compounds by B-EG and B-U based HP-SEC columns. 68

Table 3-3. Calibration curves for levofloxacin and tetracycline. 76

Table 3-4. SPE-HPLC method recoveries (n＝3) and RSD values of levofloxacin and tetracycline standard solution. 77

Table 3-5. Thermodynamic properties △H, △G, △E and T△S for complexes. Values are given in kcal mol-1.(이미지참조) 83

Table 3-6. Analysis of BET. 88

Table 3-7. Validation of re-usability recoveries (n＝3) and RSD values of quercetin standard solution. 92

Table 3-8. Comparison with other reported methods for recognition of quercetin. 94

List of Figures

Figure 1-1. Interaction of a HBD with the quaternary ammonium salt choline chloride. 19

Figure 1-2. Some HBD and HBA counterparts that can be combined to form a DES. 21

Figure 2-1. Synthesis of the ChCl DES-based mesoporous siliceous spheres. 38

Figure 2-2. Same Structure of the different dextrans. 39

Figure 2-3. Preparation of based-betaine DES. 41

Figure 2-4. Schematic illustration of the proposed materials formation. 44

Figure 2-5. Schematic diagram of the mechanism for the formation of the h-BN-... 50

Figure 3-1. TGA results for DES-based mesoporous siliceous materials. 57

Figure 3-2. SEM images of the No-DES-based (a), B-G-based (b), B-DG-based (c),... 58

Figure 3-3. FT-IR spectra of DES-based mesoporous siliceous materials. 60

Figure 3-4. Size exclusion chromatogram of the dextran mixture (5K, 25K, 50K,... 65

Figure 3-5. Size exclusion chromatogram of a single dextran (5K, 25K, 50K, 270K,... 66

Figure 3-6. Retention factor for 2 ㎎ mL-1 dextran in the difference column. The...(이미지참조) 67

Figure 3-7. The loss rates of materials for levofloxacin and tetracycline. Column 70

Figure 3-8. Scanning electron micrograph of NIP (a) and (b), LMIP (c), DES-LMIP... 71

Figure 3-9. FT-IR spectrum of materials. 73

Figure 3-10. The static adsorption capacity of the proposed materials for antibiotics. 75

Figure 3-11. The recoveries of levofloxacin and tetracycline. 78

Figure 3-12. The chromatograms of levofloxacin (ng mL-1) and tetracycline (ng...(이미지참조) 79

Figure 3-13. Electrostatic potential map highlighting the three most susceptible... 82

Figure 3-14. B3LYP/6-311G+(d,p)-optimized structures for the CA/target... 84

Figure 3-15. Image of DES monomer (a) and proposed materials (b) before washing. Scanning electron micrograph of h-... 89

Figure 3-16. Static adsorption capacity (a) and dynamic adsorption capacity (b) of... 91

초록보기

 With the development of sustainable chemistry, eco-friendly solvents have drawn an increasing attention. Over the past 30 years, room-temperature ionic liquids have attracted considerable interest, particularly in relation to separation and chemical reactions. Deep eutectic solvents (DESs) are a common successor to ionic liquids (ILs) with similar physicochemical properties. Based on the specific properties of DESs, it has the superiority in preparation of porous materials than conventional method. DESs based porous materials have attracted increasing attention for the extraction and separation of bioactive compounds from natural products. DESs was applied to preparation of mesoporous silica. The DES based silica was packed into a size exclusion chromatography (SEC) column for separation of polysaccharose. On the other hand, DES had been introduced in preparation of molecularly imprinted polymers (MIPs). The synthetic environment ofMIPs was improved by the introduction of DESs. DES-based MIPs are also used widely in the solid phase extraction of antibiotics and flavonoids. The affinity and selectivity of MIPs was improved significantly. MIPs based on DESs have better molecular recognition efficiency than conventional MIPs. Based on the development of DESs, the exploitation of new DES-based materials is expected to diversify into chemical research.

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