臺灣博碩士論文加值系統

本論文以開發新型態整體成形管柱，應用於毛細管電層析(capillary electrochromatography, CEC)與奈升級液相層析(nano liquid chromatography, nano-LC)之靜相及固相微萃取(solid phase microextraction, SPME)技術之吸附劑，將分為三部分探討。
在本研究的第一部分，以單體三烯丙基異三聚氰酸酯(triallyl isocyanurate, TAIC)、二甲基丙烯酸乙酯(ethylene dimethacrylate, EDMA)、十八烷基甲基丙烯酸酯(stearyl methacrylate, SMA)及2-丙烯醯胺基-2-甲基丙烷磺酸(2-acrylamido-2-methylpropanesulfonic acid, AMPS)聚合形成整體成形管柱，應用在奈升級液相層析進行酚酸之分離。藉由動相梯度沖提可在90分鐘內使分析物分離，並以van Deemter曲線探討管柱之效能，在0.1 - 1.0 μL/min的線性流速下其理論板高仍小於20 μm，顯示其良好的管柱效能。實驗最後與常見親水性整體成形管柱相比較，顯示poly(TAIC-EDMA-AMPS)管柱對酚酸分離有顯著的效果。
第二部分為金屬有機骨架(metal-organic framework, MOF)在層析靜相之研究，研究首先以MIL-101(Cr)材料填充至毛細管柱中，並應用在毛細管電層析系統上，由於填充式管柱產生較高的背壓使得無法應用在奈升級液相層析中，因此，本研究首次開發金屬有機骨架高分子整體成形管柱，以解決填充式管柱背壓高的缺點。實驗中將MIL-101(Cr)與單體丁基甲基丙烯酸酯(butyl methacrylate, BMA)及二甲基丙烯酸乙酯，以離子液體1-hexyl-3-methylimidazolium tetrafluoroborate ([C6mim][BF4])為溶劑混合均勻，並結合微波輔助加熱法可成功快速製備MIL-101(Cr)高分子整體成形管柱，與填充式管柱相比較其管柱通透率大幅提升約20倍。此外，藉由掃描式電子顯微鏡、X光繞射儀、表面積測定儀及紅外線光譜儀完成靜相相關性質的鑑定。
此新型態MIL-101(Cr)高分子整體成形管柱成功應用於毛細管電層析、奈升級液相層析系統中，針對多種芳香環化合物進行分離，顯示其良好的分離效果及管柱再現性。此外，MIL-101(Cr)高分子整體成形管柱也應用在蛋白質水解胜肽的分析，在牛血清蛋白水解胜肽成功鑑定出46個胜肽片段及其胜肽覆蓋率(sequence coverage)為64 %。
實驗最後一部分，以第二部分開發之MOF高分子整體成形管柱應用在固相微萃取技術中，針對盤尼西林分析物進行萃取，並以毛細管電層析方法檢測其萃取效果。實驗中首先在25 wt% (0.04 mg/μL)的MOF含量下，以MIL-101(Cr)高分子為吸附劑，探討脫附溶劑種類及體積、平衡溶液體積、清洗溶液種類、樣品進樣流速、樣品pH值等條件對盤尼西林萃取效果之影響，並由貫穿曲線(breakthrough curve)得知，MIL-101(Cr)對盤尼西林的最大吸附量為9.1 - 11.1 μg/mg。
比較不同系列MOF材料對盤尼西林萃取之差異，結果顯示在25 wt% (0.04 mg/μL)的MOF含量下，MIL-101(Cr)顯示其有最好的回收率範圍在63.0 % - 96.2 %；而同為籠狀型的MIL-100(M)回收率範圍分別是MIL-100(Cr)：23.9 % - 78.4 %、MIL-100(Fe)：7.0 % - 22.5 %、MIL-100(Al)：15.6 % - 81.5 %。通道型結構的MIL-53(Al)回收率範圍是54.7 % - 67.7 %，而將MIL-53(Al)含量提高至37.5 wt% (0.06 mg/μL)後，回收率範圍可提升至76.4 % - 94.0 %，與MIL-101(Cr)的效果相當。在分析物濃度0.01 - 1.0 μg/mL範圍內，MIL-101(Cr)高分子萃取所得檢量線之R2值範圍在0.9982 - 0.9993，及其LOD與LOQ範圍分別在1.2 - 4.5 ng/mL與4.0 - 14.8 ng/mL。將此方法應用至河水樣品中，添加0.05 μg/mL及0.10 μg/mL濃度至河水中，所得到的回收率範圍分別是67.9 % - 91.2 %與62.5 % - 90.8 %，最後在重複使用之探討，結果顯示MIL-101(Cr)高分子可重複使用至少45次，顯示其耐用性佳。本實驗證明MOF-polymer在SPME技術之可行性。

In this dissertation, novel monolithic columns were developed and were applied as stationary phases for capillary electrochromatography (CEC), nano liquid chromatography (nano-LC) and sorbents for solid phase microextraction (SPME).
In the first part, triallyl isocyanurate (TAIC), ethylene dimethacrylate (EDMA), stearyl methacrylate (SMA) and 2-acrylamido-2-methylpropanesulfonic acid (AMPS) were polymerized to produce poly(TAIC-EDMA-AMPS) monolithic column and applied in nano-LC for the separation of phenolic acids. The phenolic acids were successfully separated using gradient elution for 90 min. The column efficiency was determined by using the van Deemter curve and results indicated that the plate heights was lower than 20 μm at linear flow rate of 0.1-1.0 μL/min. In comparison with the common hydrophilic monolithic column, the poly(TAIC-EDMA-AMPS) revealed more efficient in separating the phenolic acids.
In the second part, metal-organic framework (MOF) (MIL-101(Cr)) was studied as chromatographic stationary phases. At first, the MIL-101(Cr) was packed into capillary and applied in CEC system. However, due to high back pressure of MIL-101(Cr) column, attempts in applying for nano-LC system was deemed impossible. Thus, in this case, novel MOF-polymer monolith was successfully developed with improved effectiveness against high back pressure problems caused by packing. For the preparation of MOF-polymer, MIL-101(Cr), butyl methacrylate (BMA) and EDMA were homogeneously mixed in [C6mim][BF4] ionic liquid solvent via microwave assisted heating. In comparison with MOF packed column, the permeability of MOF-polymer was increased approximately to 20-fold. The MOF-polymer monoliths were characterized by scanning electron microscope (SEM), powder x-ray diffraction (PXRD), surface area analyzer and fourier transform infrared spectroscopy (FTIR).
The novel MOF-polymer monolithic columns were successfully applied for CEC, and nano-LC for several aromatic compounds, and revealed a good column efficiency and column reproducibility, respectively. Moreover, MIL-101(Cr)-polymer monolithic column was also applied in peptides analyses, the result showed that 46 peptides were identified with sequence coverage of 64 % from tryptic digest of Bovine Serum Albumin (BSA).
For the last part, MOF-polymer monoliths were applied to SPME technique for penicillins extraction, and quantitatively analyzed by CEC method to determine extraction efficiency. Using 25 wt% MOF, the desorption solvent and volume, condition solution volume, washing solution type, sample flow rate, and sample pH were optimized in the extraction of penicillin using MIL-101(Cr)-polymer as sorbent. The maximun penicillins adsorption for MIL-101(Cr) were 9.1 - 11.1 μg/mg obtained from breathrough curve.
At 25 wt%, different MOFs (cage and tunnel type) were also used to expore their extraction efficiencies. The result revealed that the recovery for cage type MIL-101(Cr) was 63.0 % - 96.2 %, while with the same cage structure MIL-100(M), the recoveries for MIL-100(Cr), MIL-100(Fe) and MIL-100(Al) were 23.9 % - 78.4 %, 7.0 % - 22.5 % and 15.6 % - 81.5 %, respectively. Meanwhile, for the tunnel type MOF, the recovery for MIL-53(Al) was 54.7 % - 67.7 %. With the results, it suggests that MIL-101(Cr) and MIL-53(Al) have greater adsorption capacities in extracting the penicillin. Further studies have conducted on MIL-101(Cr) and MIL-53(Al) by increasing the MOF wt% to 37.5. Based on the results, the recovery for MIL-53(Al) further increased to 76.4 % - 94.0 % and was comparable to MIL-101(Cr).
For MIL-101(Cr)-polymer SPME, the fabricated method exhibited a good linearity (with R2 between 0.9982 and 0.9993) from 0.01 - 1.0 μg/mL, low limits of detection (1.2 - 4.5 ng/mL), and limit of quantification (4.0 - 14.8 ng/mL). The MOF-polymer SPME was applied in river sample and the recovery ranges from 67.9 % - 91.2 % and 62.5 % - 90.8 % at spiked 0.05 μg/mL and 0.10 μg/mL concentration, respectively. Finally, the MIL-101(Cr)-polymer can be re-used at least 45 times which shows high column life-time. With these results, it showed the potential application of MOF-polymer SPME.

目錄
摘要 I
Abstract III
謝誌 VI
目錄 VIII
圖目錄 XIII
表目錄 XVII
英文縮寫對照表 XX
1. 緒論 1
1-1. 有機整體成形管柱簡介 1
1-1-1. 聚丙烯醯胺類整體成形管柱(polyacrylamide-based monolithic column) 1
1-1-2. 聚甲基丙烯酸酯類整體成形管柱(polymethacrylate-based monolithic column) 2
1-1-3. 聚苯乙烯類整體成形管柱(polystyrene-based monolithic column) 3
1-1-4. 聚三烯丙基異三聚氰酸酯類整體成形管柱(polytriallyl isocyanurate-based monolithic column) 4
1-2. 微波輔助加熱法製備有機整體成形管柱 5
1-3. 填充式管柱製備方法 7
1-4. 毛細管電層析簡介 8
1-5. 奈升級液相層析法簡介 9
1-5-1. van Deemter方程式 9
1-6. 固相微萃取技術簡介 11
1-6-1. Fiber SPME簡介 12
1-6-2. SBSE簡介 13
1-6-3. In-tube SPME簡介 13
1-6-4. Syringe SPME簡介 14
1-6-5. In-tip SPME簡介 14
1-7. PMME萃取管柱發展現況 15
1-8. 金屬有機骨架簡介 26
1-8-1. mesoMOF之有機配位基 28
1-8-2. mesoMOF孔洞形態 30
1-9. 金屬有機骨架於層析靜相的應用 34
1-10. 金屬有機骨架在萃取技術的應用 40
1-11. 盤尼西林 48
2. 奈升級液相層析在親水性物質分離之應用 53
2-1. 研究動機 53
2-2. 實驗簡介 54
2-2-1. 儀器設備及裝置 54
2-2-2. 實驗藥品 54
2-2-3. 毛細管壁改質前處理 57
2-2-4. 高分子整體成形管柱製備 59
2-2-4-1. 高分子共聚物聚合溶液製備 59
2-2-4-2. 整體成形管柱製備方法 59
2-3. 結果與討論 62
2-3-1. Poly(TAIC-EDMA-SMA-AMPS)管柱於逆相層析機制之探討 62
2-3-2. Poly(TAIC-EDMA-SMA-AMPS)與poly(TAIC-EDMA-AMPS)管柱在奈升級液相層析對酚酸化合物之分離 63
2-3-3. TAIC管柱在奈升級液相層析效能之探討 70
2-3.4. 不同靜相種類於奈升級液相層析中對酚酸分離之比較 71
2-4. 結論 72
3. 金屬有機骨架整體成形管柱之開發 73
3-1. 研究動機 73
3-2. 實驗簡介 74
3-2-1. 儀器設備及裝置 74
3-2-2. 實驗藥品 75
3-2-3. 金屬有機骨架之製備 80
3-2-4. 毛細管壁改質前處理 80
3-2-5. 填充式管柱製備 80
3-2-6. MOF整體成形管柱之製備 82
3-3. 結果與討論 83
3-3-1. MIL-101(Cr)-polymer與MIL-101(Cr)填充式管柱之鑑定 83
3-3-2. MOF填充式管柱在毛細管電層析的應用 90
3-3-3. MOF整體成形管柱在毛細管電層析的應用 92
3-3-4. MOF整體成形管柱應用於奈升級液相層析 101
3-3-5. MOF整體成形管柱再現性及效能 105
3-3-6. MOF整體成形管柱於蛋白質水解胜肽之分離應用 106
3-4. 結論 108
4. 金屬有機骨架高分子整體成形管柱於微萃取技術之開發 109
4-1. 研究動機 109
4-2. 實驗簡介 111
4-2-1. 儀器設備及裝置 111
4-2-2. 實驗藥品 112
4-2-3. 毛細管壁改質前處理 113
4-2-4. MOF-polymer SPME整體成形管柱製備 113
4-2-5.實驗裝置介紹 114
4-2-6. MOF-polymer SPME實驗操作流程 114
4-2-7. 盤尼西林檢測方法 115
4-2-7-1. Poly(SMA-DVB-VBTA)管柱製備 115
4-2-7-2. 儀器操作參數 116
4-2-7-3. 回收率計算 116
4-3. 結果與討論 117
4-3-1. 萃取管柱內徑影響 117
4-3-2. 萃取管中MOF對盤林西林吸附之差異性 117
4-3-3. 脫附溶劑之影響 119
4-3-4. 清洗溶液種類的影響 120
4-3-5. 平衡溶液體積之影響 123
4-3-6. 樣品溶液在不同流速下之影響 125
4-3-7. 脫附溶劑體積之探討 127
4-3-8. 樣品pH值不同對萃取效果之影響 130
4-3-9. 樣品體積及不同樣品濃度之吸附效果 133
4-3-10. 不同MOF材料對盤尼西林萃取之影響 139
4-3-11. 不同MOF含量對盤尼西林吸附之影響 143
4-3-12. MOF-polymer SPME萃取效能評估 145
4-3-13. 檢量曲線及偵測極限 146
4-3-14. 實際樣品之應用 146
4-3-15. MOF-polymer SPME重複萃取次數之探討 149
4-4. 結論 151
5. 參考文獻 152
作者簡歷 164
附錄I. 166
附錄II. 168
附錄III. 169

圖目錄
圖1-1 不同種類離子液體對整體成形高分子聚合之變化 6
圖1-2 毛細管填充式管柱製備示意圖 7
圖1-3 (a)壓力驅動與(b)電動驅動效應示意圖 8
圖1-4 SPME方法之分類及其裝置示意圖 12
圖1-5 PMME使用裝置示意圖 15
圖1-6 石墨烯與石墨烯氧化物鍵結在poly(GMA-EDMA)機制示意圖 17
圖1-7 近年來MOF及coordination polymer文獻發表數 26
圖1-8 MOF材料構建示意圖 27
圖1-9 MOF應用於藥物分子示意圖 28
圖1-10 合成mesoMOF之常見有機配位基結構 29
圖1-11 MIL-100(Cr)與MIL-101(Cr)結構示意圖 31
圖1-12 IRMOF-n結構示意圖 32
圖1-13 不同比例BDC/BTB合成之MOF 33
圖1-14 UMCM-1結構示意圖 33
圖1-15 MIL-101(Cr) coated管柱之SEM圖 35
圖1-16 Silica-MOF之SEM圖 36
圖1-17 MOF-199 SPME fiber之SEM圖 40
圖1-18 ZIF-90共價鍵結在探針之示意圖 41
圖1-19 MALDI-MS分析不同MOF對胜肽分子濃縮之結果 42
圖1-20 MIL-101(Cr) on-line SPE HPLC裝置圖 44
圖2-1 毛細管內壁改質示意圖 57
圖2-2 自由基反應聚合示意圖 59
圖2-3 防腐劑分析物在不同ACN比例對log k 62
圖2-4 Poly(TAIC-EDMA-SMA-AMPS)分離酚酸之層析圖 65
圖2-5 Poly(TAIC-EDMA-SMA-AMPS)管柱在不同ACN動相條件下分離酚酸之電層析圖 66
圖2-6 不同流速下之管柱背壓 67
圖2-7 Poly(TAIC-EDMA-AMPS)分離酚酸之層析圖 68
圖2-8 Poly(TAIC-EDMA-AMPS)在不同流速下對酚酸分離之層析圖 69
圖2-9 Poly(TAIC-EDMA-AMPS)與poly(TAIC-EDMA-SMA-AMPS)管柱之van Deemter曲線比較 70
圖2-10 常見親水性靜相對酚酸化合物分離之層析圖 71
圖3-1 [C6mim][BF4]之1H NMR圖譜 77
圖3-2 填充式管柱製備流程 81
圖3-3 MOF整體成形管柱合成示意圖 82
圖3-4 (a) MIL-101(Cr) packed column、(b)MIL-101(Cr)-polymer與(c) neat poly(BMA-EDMA)管柱之SEM圖 84
圖3-5 (a) MIL-101(Cr)-polymer與(b) neat poly(BMA-EDMA)之光學顯微鏡照片 85
圖3-6 MIL-101(Cr)、MIL-101(Cr)-polymer及neat polymer之PXRD圖 85
圖3-7 MIL-101(Cr)、MIL-101(Cr)-polymer及neat polymer之氮氣等溫吸附圖 86
圖3-8 MIL-101(Cr)、MIL-101(Cr)-polymer及neat polymer之孔洞分佈 87
圖3-9 MIL-101(Cr)、MIL-101(Cr)-polymer及neat polymer之FTIR光譜圖 88
圖3-10 SEM-EDS mapping (a) MIL-101(Cr)-polymer、(b) neat polymer 89
圖3-11 MOF填充管柱分離位置異構物之電層析圖 91
圖3-12 文獻中以MIL-101(Cr)在GC(左圖)與HPLC(右圖)分離xylene之層析圖 91
圖3-13 MOF整體成形管柱分離位置異構物之電層析圖 93
圖3-14 Neat polymer管柱分離位置異構物之電層析圖 94
圖3-15 文獻中以MIL-53分離cymene之層析圖 95
圖3-16 MOF整體成形管柱分離cymene異構物之電層析圖 96
圖3-17 MOF整體成形管柱在不同pH值動相之影響 97
圖3-18 不同ACN比例動相對xylene分離之影響 98
圖3-19 不同ACN比例動相對chlorotoluene分離之影響 99
圖3-20 不同ACN比例動相對cymene分離之影響 100
圖3-21 有無MOF之整體成形管柱對PAHs分離之影響 102
圖3-22 有無MOF之整體成形管柱對aromatic acids分離之影響 103
圖3-23 MOF整體成形管柱之van Deemter曲線比較 (a) aromatic acids (b) ethylbenzene 104
圖4-1 以SBSE方法吸附及脫附盤尼西林之效果 110
圖4-2 各種MOF-polymer管柱 113
圖4-3 SPME裝置示意圖 114
圖4-4 MOF-polymer SPME實驗流程示意圖 114
圖4-5 MOF-polymer SPME對盤尼西林吸附之效果 118
圖4-6 脫附溶劑之影響 119
圖4-7 清洗溶液之影響 120
圖4-8 不同清洗溶液影響之電層析圖 121
圖4-9 不同清洗溶液下所得之回收率 122
圖4-10 平衡溶液體積之影響 123
圖4-11 以不同體積pH2 PBS緩衝液作平衡溶液之電層析圖 124
圖4-12 樣品流速變化對萃取效果之影響 125
圖4-13 不同樣品流速之電層析圖 126
圖4-14 脫附溶劑體積之影響 127
圖4-15 脫附溶劑體積之電層析圖 128
圖4-16 不同脫附溶劑體積之樣品回收率 129
圖4-17 樣品pH值不同對萃取效果之影響 130
圖4-18 樣品pH值不同之電層析圖 131
圖4-19 不同樣品pH值之回收率 132
圖4-20 樣品體積之影響 134
圖4-21 樣品體積變化之電層析圖 135
圖4-22 不同樣品體積之回收率 136
圖4-23 MOF-polymer SPME對盤尼西林吸附之貫穿曲線 137
圖4-24 不同MOF-polymer SPME對盤尼西林萃取效果之影響 140
圖4-25 提高MOF含量對盤尼西林吸附之回收率 142
圖4-26 不同含量MIL-101(Cr)對盤尼西林回收率之影響 143
圖4-27不同含量MIL-53(Al)對盤尼西林回收率之影響 144
圖4-28不同含量DUT-5(Al)對盤尼西林回收率之影響 144
圖4-29 MOF-polymer SPME對實際樣品之處理 147
圖4-30 MIL-101(Cr)-polymer SPME重複萃取之結果 149
圖4-31 MOF-polymer萃取前後之SEM圖 150

表目錄
表1-1 液相層析系統於不同流速等級之主要應用 9
表1-2 Poly(MAA-EGDMA)於PMME技術之應用 18
表1-2續 Poly(MAA-EGDMA)於PMME技術之應用 19
表1-2續 Poly(MAA-EGDMA)於PMME技術之應用 20
表1-2續 Poly(MAA-EGDMA)於PMME技術之應用 21
表1-3 Poly(GMA-EDMA)於PMME技術之應用 22
表1-4 其他高分子於PMME技術之應用 23
表1-4續 其他高分子於PMME技術之應用 24
表1-5 高分子結合奈米粒子於PMME技術之應用 25
表1-6 MOF應用在GC靜相中文獻整理 37
表1-7 MOF應用在HPLC靜相中文獻整理 38
表1-7續 MOF應用在HPLC靜相中文獻整理 39
表1-8 MOF於SPME方法中之文獻整理 45
表1-9 MOF應用於吸附劑之文獻整理 46
表1-10 MOF於SPE方法中之文獻整理 47
表1-11 歐盟對盤尼西林藥物之法規 48
表1-12 以SPE方法對盤尼西林檢測之文獻 (2005 - 2013年) 50
表1-12續 以SPE方法對盤尼西林檢測之文獻 (2005 - 2013年) 51
表1-12續 以SPE方法對盤尼西林檢測之文獻 (2005 - 2013年) 52
表2-1 儀器設備名稱及廠牌規格 54
表2-2 常用試藥之名稱 54
表2-3 製備高分子靜相所需試藥 55
表2-4 酚酸標準品 56
表2-5 Poly(TAIC-EDMA-AMPS)及poly(TAIC-EDMA-SMA-AMPS)聚合溶液比例 61
表2-6 Poly(EDMA-BMA)及poly(EDMA-SMA)聚合溶液比例 61
表3-1 儀器設備名稱及廠牌規格 74
表3-1續 儀器設備名稱及廠牌規格 75
表3-2 常用試藥之名稱 75
表3-3製備高分子靜相所需試藥 76
表3-4 標準品介紹 78
表3-4 續 標準品介紹 79
表3-5 Poly(S-DVB)檔板之聚合溶液比例 80
表3-6 MOF整體成形管柱聚合溶液配製 82
表3-7 不同管柱之表面積、孔洞尺寸及通透率 86
表3-8 MOF整體成形管柱在CEC遷移時間、面積再現性及管柱效能 105
表3-9 MOF整體成形管柱在nano-UHPLC遷移時間、面積再現性及管柱效能 106
表3-10 不同管柱對牛血清蛋白水解胜肽分離之效果 107
表4-1儀器設備名稱及廠牌規格 111
表4-2 盤尼西林標準品介紹 112
表4-3 MOF-polymer聚合溶液比例 113
表4-4 MOF-polymer SPME實驗最佳化條件 115
表4-5 Poly(SMA-DVB-VBTA)聚合溶液配製 115
表4-6 不同脫附溶劑體積之回收率 129
表4-7 MOF對盤尼西林之吸附量(μg/mg MOF) 138
表4-8 不同MOF對盤尼西林吸附之回收率 141
表4-9 各種MOF-polymer表面積 141
表4-10提高MOF含量對盤尼西林吸附之回收率值 142
表4-11 MIL-101(Cr)-polymer SPME對盤尼西林萃取再現性 145
表4-12 MIL-53(Al)-polymer SPME對盤尼西林萃取再現性 145
表4-13 MIL-101(Cr)-polymer SPME方法之檢量曲線及偵測極限 146
表4-14 河水樣品之回收率 148

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吳靜宜，中原大學化學研究所碩士論文，中華民國一○○年七月。