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研究生:邱德倫
研究生(外文):De-Lun Chiu
論文名稱:離子液體塗覆毛細管電泳分離類黃酮素鏡像異構物與喹諾酮類抗生素
論文名稱(外文):Ionic liquids for separation enantiomeric flavanones and quinolones by capillary electrophoresis
指導教授:王書蘋
指導教授(外文):Shu-Ping Wang
學位類別:碩士
校院名稱:靜宜大學
系所名稱:應用化學研究所
學門:自然科學學門
學類:化學學類
論文種類:學術論文
論文出版年:2009
畢業學年度:97
語文別:中文
論文頁數:96
中文關鍵詞:離子液體鏡像分離類黃酮素喹諾酮動力塗覆毛細管電泳
外文關鍵詞:chiral ionic liquidenantioseparation of flavanonequinolonedynamic coating capillary electrophoresis
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離子液體有綠色溶劑之稱,具有獨特的物理及化學性質,廣泛應用在各化學領域中,例如電化學、觸媒化學、有機化學及分析化學。近年來在毛細管電泳中,離子液體可應用在藥物、除草劑、殺蟲劑及食品添加物等分離中,證實離子液體在分離上的潛力。
本研究首次以 imidazolium 為主體的離子液體作為鏡像選擇劑,合成單一鏡像離子液體 ((R)-3-(3-hydroxy-2-methylpropyl
-1-methylimidazolium bromide, IL*-OH ),分離類黃酮素之鏡像異構物,並對其分離機制做探討。分離條件為 60 mM 四硼酸鈉溶液 (pH 9.0),30 mM IL*-OH,電壓 12 kV,Hesperetin (I) 及 Naringenin (II) 鏡像異構物分別在 15 及 16 分鐘分離,解析度達 2.5。此外並藉由 1H NMR 滴定結果推測離子液體與類黃酮素 C(5) 上氧負電荷有氫鍵作用力,此點亦利用理論計算得到證實。離子液體具有分離鏡像物的潛力,並可嘗試應用在藥物分析上。本研究同時亦使用不同碳鏈之離子液體分離四種喹諾酮類抗生素,條件為 15 mM 磷酸鹽溶液 (pH 6.0),30 mM 1-butyl-3-methylimizolium bromide (1B-3MI-Br),電壓 25 kV,5 分鐘完成分離且解析度達 1.2,回收率介於 95-116 %。其分離機制可能為庫倫靜電力、偶極-偶極力及氫鍵作用力。
There has been growing interest in ionic liquids (ILs) for their potential in various field such as electrochemistry, catalysis, organic chemistry, and analytical chemistry. With the last one, it has proven especially useful in separating determination. Generally, ILs has versatile physico-chemical properties and really attractive as so called green solvents. In recent years, application of ILs for pharmaceutical, agricultural industry and the food additive in capillary electrophoresis has been reported. It also indicated ILs has powerful potential for separation.
It is the first time in this study for using ionic liquid based on imidazolium as a chiral selector for separating enantimeric flavanones as well as studing on separation mechanism.(R)-3-(3-hydroxy-
2-methylpropyl)-1-methylimidazolium bromide (IL*-OH) was synthesized and applied to separate enantiomeric flavanones in this work. The optimal separation was 60 mM of borate at pH 9.0, 30 mM of IL*-OH and applied voltage of 12 kV. Under the optimum conditions, enantiomers of Naringenin and Hesperetin has successfully separation within 16 min and resolution of 2.5. The presence of hydrogen-bonding interaction between IL*-OH and oxygen at C(5) of flavanones was confirmed by 1H NMR titration and computational chemistry. It is important to prove that the ionic liquid has potential for separation enantiomer and may be applied to pharmaceutical industry. In addition, we discussed on various alkyl group of ILs for separating to four quinolones and studying separation mechanism. The optimal separation was 15 mM phosphate at pH 6.0, 30 1-butyl-3-methylimizolium bromide and applied voltage of 25 kV which has successfully separation within 5 min and resolution of 1.2. The recovery between 95-116 %.The separation mechanism seems to be the hydrogen-bonding, coulomb and dipole-dipole interaction.
目錄 I
謝誌 IV
中文摘要 VI
英文摘要 VII
表目錄 VIII
圖目錄 IX
第一章 緒論 1
第一節 前言 1
一、離子液體的簡介 1
二、離子液體的特性 2
三、離子液體的應用 3
第二節 離子液體結構及性質 5
第三節 分析物結構及性質 7
一、類黃酮素 (flavanone) 7
二、喹諾酮 (quinolone) 類抗生素 9
第四節 相關文獻 11
一、CZE 11 I
二、IL-Cyclodextrins (IL-CDs) 13
三、NACE 14
四、鏡像 IL 14
第五節 研究動機 16
第二章 毛細管電泳法 17
第一節 原理 17
ㄧ、發展簡介 17
二、儀器裝置 18
三、分離原理 18
四、操作模式 23
第二節 實驗部分 26
一、儀器設備 26
二、藥品 28
三、藥品配置 29
四、毛細管的清理方式 37
第三節 結果與討論. 38
一、分離類黃酮素鏡像異構物 38
二、分離喹諾酮類之抗生素 70
第三章 真實樣品之檢測 81 II
第一節 實驗部份 81
第二節 結果與討論 90
第四章 結論 92
第五章 參考文獻 93
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