含吡啶-2,6-二羧酸衍生物的合成與離子辨識 行為探討

本篇論文研究的目標為合成一系列含吡啶-2,6-二羧酸衍生物之化學感測器，並藉由核磁共振光譜儀(1H NMR)、紅外線光譜儀(IR)等儀器鑑定其結構及特性。含酯基官能基的化合物11、12在甲醇溶液中測定吸收光譜實驗，含羧酸根的化合物13、14則在THF溶液中測定。在UV-vis吸收光譜圖中，化合物11~14的吸收峰主要都出現在270-280 nm，是來自芳香環中π-π*的躍遷。離子辨識實驗中，發現化合物11可以透過顏色變化有效地檢測汞(II)離子。在UV-vis光譜圖中，汞離子加入後，在330 nm會產生新的吸收帶，推測是化合物11與汞離子配位造成的結果。在Job’s plot實驗中，化合物11與汞離子是以1:1的方式鍵結。在滴定實驗觀察出逐漸加入汞離子時，化合物11的UV-vis光譜中280 nm的吸收峰隨著汞離子當量增加而下降且產生些微的紅位移；而330 nm產生的新吸收帶隨著汞離子當量增強而上升，結合常數Ka為8.05×103 M-1。由可逆實驗證實化合物11對汞離子的辨識行為是具有可逆性的，可以重複測驗。

關鍵字

化學感測器；吡啶二羧酸；分子辨識

並列摘要

In this research, we have synthesized a series of chemosensor containing pyridine-2,6-dicarboxylic acid and its derivative. Its characters were identified by nuclear magnetic resonance spectroscopy and infrared spectroscopy. Compound 11, 12 which bearing ester functional group were proceed its absorption spectra with methanol, while compound 13, 14 which bearing acetic acid group were taken with tetrahydrofuran. All the compounds showed an absorption peaks around 270~280 nm in the UV-vis absorption spectra, which is attributed to the π-π* transition from aromatic ring. In the recognition behavior, it was found that compound 11 can detected of Mercury (II) effectively. When Mercury ion was added in compound 11, a new absorption band was appears in 330 nm, which could be the result of the coordination between compound 11 and Mercury (II). In Job’s plot experiments, the bonding mode of compound 11 with Mercury (II) is 1 : 1. In titration experiment, it was observed that the absorption intensity of 280 nm was decreases upon the addition of Mercury (II), along with a small redshift. However, the absorption intensity of 330 nm was increase gradually. We found the binding constant was 8.05×103 M-1. In the reversible experiment, we confirmed that compound 11 has reversibility to sensing of Mercury (II).