（1）雙環型三唑離子液體[R-4C-tr][NTf2]之合成與量化製備（2）冠醚型離子液體及其在親和性萃取胜肽/蛋白質之應用（3）親和性離子液體應用於銅離子之萃取

（1）Improved and Scalable Synthesis of Bicyclic 1,2,3-Triazolium Ionic Liquids [R-4C-tr][NTf2] （2）Crowned Ionic Liquids and Their Applications to Affinity Extraction of Peptides/Proteins （3）Affinity Ionic Liquids Tailored for Chemoselective Extraction of Copper (II) Ions

袁子鈞(Tsu-Chun Yuan)

指導教授 ： 朱延和

國立中正大學/理學院/化學暨生物化學系/碩士(2016年)

摘要

第一章，我們開發全新的合成路徑，使得雙環型三唑離子液體的製備與量化更為容易。此合成策略所建構出的雙環骨架，是以氧化劑碘苯二乙酸做為環化試劑，再由鈀碳催化劑 鈀碳催化劑 將吡啶結構還原，即可得 吡啶結構還原，即可得 吡啶結構還原，即可得 吡啶結構還原，即可得 吡啶結構還原，即可得 吡啶結構還原，即可得 到目標分子 到目標分子 ，此 反應 溫和且快速 溫和且快速 ，更適合量化生產 更適合量化生產 更適合量化生產 。 第二章，我們以冠醚的分子辨識為基礎，設計一系列具有冠醚結構的離子液體。透過離子液體上的冠醚結構與銨根離子之親和性，辨識側鏈含有銨根離子的胜肽。我們預期此性質可將水層含有lysine或arginine的胜肽萃入離子液體層，並進一步討論與研究將此冠醚型離子液體應用於純化及分離含有Lysine的蛋白質。 第三章，我們開發了對銅離子具有親合性之離子液體，並將其應用於萃取水中的銅離子。透過改變親合性離子液體之陽離子及側鏈結構，推測其與銅離子配位形式。並加入其他金屬離子，探討此離子液體的選擇性。

關鍵字

離子液體 ； 雙環形三唑 ； 冠醚

並列摘要

The first research project—” Improved and Scalable Synthesis of Bicyclic
1,2,3-Triazolium Ionic Liquids [R-4C-tr][NTf2]”—developed novel synthetic routes to bicyclic triazolium ionic liquids. These synthetic routes successfully constructed bicyclic triazoles by taking advantage of an iodosobenzene diacetate-mediated oxidative cyclization as well as the Pd/C catalytic hydrogenation. Our preparation of bicyclic triazoles can be conveniently scalable and proceeds under mild experimental conditions.

The second research project—”Crowned Ionic Liquids and Their Applications to Affinity Extraction of Peptides/Proteins”—designed and synthesized a series of crowned ionic liquids containing different sizes of crown ethers. Based on specific recognition of crown ethers to organoammonium ions, these crowned ionic liquids chemoselectively extract lysine or arginine containing peptides and lysine-rich proteins.

The third research project—”Affinity Ionic Liquids Tailored for Chemoselective Extraction of Copper(II) Ions”—designed and synthesized affinity ionic liquids and used for chemoselective extraction of copper(II) ions from aqueous solution. The mode of binding interaction of affinity ionic liquid with the copper(II) ion was proposed by comparing with interactions with analogous ionic liquids. Chemoselectivity of copper(II) extraction by affinity ionic liquid was achieved relative to that of other divalent transition-metal cations such as cobalt(II) and nickel(II).

參考文獻

4. Wilkes, J. S. Green Chem., 2002, 4, 73.

7. Hurley, F. H.; Wier, T. P. J. Electrochem. Soc., 1951, 98, 230.

9. Wilkes, J. S.; Zaworotko, M. J. J. Chem. Soc. Chem. Commun., 1992, 13, 965.

10. Davis, J. H.; Fox, P. A. Chem. Commun., 2003, 1209.

12. Yoshizawa, M.; Narita, A.; Ohno, H. Aust. J. Chem., 2004, 57, 139.