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新型香豆素螢光探針的合成與應用 = Synthesis and Application of Novel Coumarin-Based Fluorescence Probe / 黃婷苡.

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本研究以7-羥基- 4-甲基香豆素(7-Hydroxy-4-methylcoumarin)為起始物，利用Duff反應，與環六亞甲基四胺(Hexamine)反應，合成出8-甲醯基-7-羥基-4-甲基香豆素(8-Formyl-7-hydroxy-4-methylcoumarin；FHM)，再以異菸酸醯肼(Isonicotinic acid hydrazide)與香豆素8號位置上的醛基進行縮合反應，合成出探針FHM-INH，以FTIR光譜、1H NMR核磁共振光譜及MS質譜來鑑定其結構，並嘗試應用於螢光感測。 研究結果顯示，以乙醇作為溶劑，將FHM-INH探針應用在金屬離子的螢光感測時，與FHM-INH原始的螢光相比，當鋁離子加入時，會使螢光大幅增強，而其他離子則無明顯變化。在選擇性實驗上也可看出FHM-INH對鋁離子的感測不受到其他離子干擾，說明FHM-INH探針對鋁離子具有高選擇性及高靈敏度，並且透過Job’s plot圖說明FHM-INH與鋁離子是以1：1的配位形式結合。 FHM-INH-Al3+錯合物亦能應用於氟離子的螢光感測，當加入氟離子後螢光明顯淬熄，並且確認FHM-INH-Al3+中的鋁離子可與氟離子的反應是以1：6的方式配位，因此FHM-INH可以成為二元順序識別的螢光探針，用來順序檢測鋁離子與氟離子。FHM-INH可先對鋁離子做偵測形成錯合物後，使螢光開啟，再與氟離子反應，使螢光淬熄。. In this study, a novel coumarin-based fluorescent probe (FHM-INH) has been designed and synthesized by the condensation of 8-formyl-7-hydroxy-4-methylcoumarin with isonicotinic acid hydrazide. The 8-formyl-7-hydroxy-4-methylcoumarin (FHM) was prepared via the Duff reaction of 7-hydroxy-4-methylcoumarin with hexamine. The structure of FHM-INH was characterized by FTIR, 1H NMR and MS. The absorption and fluorescence spectra of FHM-INH in ethanol were investigated after adding different metal ions (Al3+, K+ , Mg2+, Sn2+, Na+, Hg2+ , Ca2+, Zn2+, Cu2+ and Li+). Compared with other metal ions, the fluorescence of FHM-INH exhibited remarkable enhancements in the presence of Al3+. In the selective experiment, it was also seen that FHM-INH fluorescence sensing of Al3+ is not interfered by other ions. These results clearly showed that FHM-INH probe exhibited excellent selectivity and sensitivity for Al3+. The Job’s plot indicated a 1:1 stoichiometry between FHM-INH and Al3+. Furthermore, the FHM-INH-Al3+ complex was also used for fluorescence sensing of F-. When F- was added, the fluorescence of FHM-INH-Al3+ was obviously quenched. The 1:6 stoichiometry of complex FHM-INH-Al3+ and F- was confirmed by fluorescence titration. Therefore FHM-INH could be a fluorescent probe for binary sequential detection of Al3+ and F-. FHM-INH coordinated with Al3+ to form complex [FHM-INH-Al3+], leading fluorescence turn-on, then released Al3+ from complex with addition of F-, making fluorescence turn-off..

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