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| 研究生： |
許瑋倫 Hsu, Wei-Lun |
|---|---|
| 論文名稱： |
合成二苯并[a,j]蒽為主體之大環分子及以核磁共振光譜研究其對銀離子之感測 Dibenzo[a,j]anthracene-Based Macrocycle as A Receptor of Silver Cation: A NMR Study |
| 指導教授： |
吳耀庭
Wu, Yao-Ting |
| 學位類別： |
碩士 Master |
| 系所名稱： |
理學院 - 化學系 Department of Chemistry |
| 論文出版年： | 2020 |
| 畢業學年度： | 108 |
| 語文別： | 中文 |
| 論文頁數： | 56 |
| 中文關鍵詞： | 大環分子 、二苯并[a,j]蒽 、銀離子感測 、麥克默里反應 |
| 外文關鍵詞： | macrocycle, dibenzo[a,j]anthracene, sensor of silver cation, McMurry reaction |
| 相關次數： | 點閱：59 下載：0 |
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大環化合物因其結構的特殊性，可以使分子或離子進入大環分子的內部，在主客化學、奈米材料、生醫材料及記憶材料等都有發展的潛力。本篇論文利用適宜的麥克默里反應條件及簡易的操作方法合成出二苯并[a,j]蒽為主體之大環分子14，並透過化合物14的核磁共振光譜的訊號位移及變寬成功證明了與銀離子的結合。
此外，原期望透過增加鍵長，來擴大大環分子內部的空間，進而增加與銀離子結合的能力。透過將化合物14進行氫化反應，以增加空間，但因化合物14的立體障礙，無法得到預期產物，化合物15。另外也嘗試合成另一大環分子，將原先麥克默里反應產生的雙鍵設計為苯環共振之碳-碳鍵，以增加鍵長，在最後氧化環化去氫反應中沒有產生預期的產物，化合物16。改變合成條件、提升產率及克服溶解度的問題是未來合成大環分子的方向。
Macrocycles which have association capability with molecules and ions are often utilized in host-guest chemistry, nano materials, bio materials, information storage, etc. Dibenzo[a,j]anthracene-based macrocycle 14 was successfully synthesized; besides, the preferred condition of McMurry reaction and well-operated approach were proposed. Additionally, the association between compound 14 and silver cation is proved by the shift of 1H NMR spectrum. In order to improve the association capability between macrocycle and silver cation, compound 15 is designed to increase the bond length and expand the cavity via hydrogenation of compound 14; however, compound 15 was synthesized unsuccessfully. In another way, compound 16 is designed to have the bond length of benzene instead of double bond, but it is failed to synthesize compound 16 because of the final oxidative cyclodehydrogenation. Based on the synthesis of compound 14, the further research is changing the synthetic approach, raising up the yield and solving the solubility.
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校內：2025-08-31公開校外：不公開