臺灣博碩士論文加值系統

本論文經由具不同取代的芳香醛製備一系列香豆素醯肼衍生物， 評估其感測陰陽離子之作用。
香豆素醯肼衍生物其芳香環與氮形成不同的空間構型，具有螯合二價銅離子之可能性，結果證明化合物 4d 及 4i 與銅離子作用溶液顏色由無色變為黃色，吸收光譜顯示在 410 nm 處出現新的吸收峰。化合物 4e 與銅離子作用則出現吸收峰在 400 nm。
香豆素結構具親電子性，與氰離子作用可能進行加成反應，本系列香豆素醯肼衍生物與氰離子作用亦進行加成反應，二者作用後，吸收光譜中香豆素環的 300 nm 吸收峰消失，化合物 4a 及 4i 進一步以核磁共振滴定實驗證明與氰離子作用為加成反應。相反地，氟離子與化合物 4a 及 4i 為酸鹼作用，4a 及 4i 中醯基腙結構上 NH 與氟離子產生氫鍵作用，從而導致吸收光譜中 300 nm 處香豆素環的吸收峰藍位移。

In this thesis, a series of coumarin carbohydrazine derivatives were prepared via different substituted aromatic aldehydes to evaluate the effects of sensing anions and cations.
Due to the spatial configuration of the aromatic ring and nitrogen of the coumarin carbohydrazine derivatives, there exist the possibility to chelate the divalent copper ion. The results demonstrated that the treatment of copper ion with compounds 4d and 4i resulted in a color change from colorless to yellow. As can be seen in the absorption spectra, a new absorption peak appears at 410 nm. For compound 4e, the corresponding new absorption peak was at 400 nm.
It is known that coumarin is electrophic and might undergo nucleophic addition reaction with cyanide anion. Our results showed that this series of coumarin carbohydrazine derivative is easily nucleophilically added by cyanide ions. In the absorption spectra, the absorption peak of the coumarin ring at 300 nm was disappeared with adding cyanide anions. This results were futher supported by the NMR titration experiment of cyanide ions with compound 4a and 4i. On the other hand, fluoride ion only acted as a base with coumarin carbohydrazine derivatives 4a and 4i. The fluoride ion formed a hydrogen bond with the NH of the acylhydrazone, and leading to. a blue shift in the absorption of the coumarin ring at 300 nm in the absorption spectra.

摘要 xxvii
Abstract xxviii
第一章
緒論 1
1.1. 前言 1
1.2. 氰離子(Cyanide ion)及氟離子(Fluoride ion) 1
1.3. 銅(Ⅱ)離子(Copper(Ⅱ) ion) 2
1.4. 查耳酮(Chalcone)及其衍生物 3
1.5. 香豆素(Coumarin)及其衍生物 3
1.6. 香豆素查耳酮(Coumarinyl chalcone) 6
1.7. 醯基腙 (Acylhydrazone) 7
1.8. 喹啉(Quinoline )與 8-羥基喹啉(8-hydroxyquinoline) 7
1.9. 化學感測器(Chemosensor) 7
1.9.1. Chemodosimeter Approach 8
1.9.2. 金屬離子螯合(Metal chelation) 9
第二章 結果與討論 10
2.1.合成部分 10
2.1.1. 化合物設計 10
2.1.2. 化合物合成步驟設計 11
2.1.3. 3-Acetyl-2H-chromen-2-one 的合成 13
2.1.3.1.3-Acetyl-2H-chromen-2-one 的 1H NMR 討論 15
2.1.3.2.推測的反應機構 15
2.1.4. (E)-3-(3-aryl)-prop-2-enoyl)-2H-chromen-2-one 的合成 16
2.1.4.1.香豆素查耳酮的 1H NMR 討論 17
2.1.4.2.推測的反應機構 17
2.1.5. (E)-3-(3-(4-methoxyphenyl)acryloyl)-2H-chromen-2-one 與硫脲的反應 18
2.1.6. (E)-3-(3-(phenyl)acryloyl)-2H-chromen-2-one 與聯氨的反應 19
2.1.7. Ethoxycarbonylacetohydrazide (2)的製備 20
2.1.7.1.推測的反應機構 23
2.1.8.N'-arylidene-2-oxo-2H-chromene-3-carbohydrazide (4)的製備 23
2.1.8.1.化合物 4a-4c 的製備 24
2.1.8.2. 化合物 4f-4j 的製備 25
2.1.8.3. 化合物 4d 的製備 27
2.1.8.4. 化合物 4e 的製備 27
2.1.8.5. 化合物 3 的鑒定 28
2.1.8.6. 化合物 4 的性質探討 30
2.1.8.7. 化合物 4 的純化 36
2.1.8.8.推測的反應機構 37
2.1.9. Quinoline-2-carbaldehyde 與8-hydroxyquinoline-2-carbaldehyde 的製備 37
2.2.UV-Vis 光譜部分 38
2.2.1. 離子試劑的選擇 38
2.2.1.1.金屬離子試劑選擇 38
2.2.1.2.陰離子試劑選擇 39
2.2.2. 化合物 4 顏色及吸收結果討論 40
2.2.3. 化合物 4a-c 與金屬離子作用 41
2.2.3.1.化合物 4a-4c 與金屬離子作用之吸收光譜 42
2.2.4. 化合物 4d 與金屬離子作用 45
2.2.4.1.化合物 4d 與金屬離子作用之吸收光譜 45
2.2.4.2.化合物 4d 與 Cu2+作用的滴定光譜與 job’s plot 47
2.2.4.3.化合物 4d 與銅的作用形式 49
2.2.5. 化合物 4e 與金屬離子作用 49
2.2.5.1.化合物 4e 與金屬離子作用之吸收光譜 50
2.2.5.2.化合物 4e 與 Cu2+作用的滴定光譜與 job’s plot 51
2.2.5.3.化合物 4e 與銅離子的作用形式 53
2.2.6. 化合物 4i 與金屬離子作用 53
2.2.6.1.化合物 4i 與金屬離子作用之吸收光譜 54
2.2.6.2.化合物 4i 與 Cu2+作用之滴定光譜及 job’s plot 55
2.2.6.3.化合物 4i 與銅離子的作用方式 56
2.2.7. 化合物 4j 與金屬離子作用 57
2.2.7.1.化合物 4j 與金屬離子作用之吸收光譜 58
2.2.7.2.化合物 4j 或 4i 和銅離子的作用不同的原因 59
2.2.8. 化合物 4h 與金屬離子作用 60
2.2.8.1.化合物 4h 與金屬離子作用之吸收光譜 60
2.2.9. 化合物 4f, 4g 與金屬離子作用 62
2.2.9.1.化合物 4f,4g 與金屬離子作用之吸收光譜 62
2.2.9.2.化合物 4f,4g 與 Cu2+作用之滴定光譜 65
2.2.10. 化合物 4 加入 Cu2+離子後吸收光譜討論 66
2.2.11. 化合物 4a-c 和 4g 與陰離子作用 67
2.2.11.1.化合物 4a-c 和 4g 陰離子作用之吸收光譜 67
2.2.12. 化合物 4e 和 4f 與陰離子作用 74
2.2.12.1.化合物 4e 和 4f 陰離子作用之吸收光譜 74
2.2.13. 化合物 4i 和 4j 與陰離子作用之 78
2.2.13.1.化合物 4i 和 4j 與陰離子作用之吸收光譜 78
2.2.14. 化合物 4a-c, 4e-g, 4i-j 對 CN-離子的作用之 job’s plot 82
2.2.15. 化合物 4d 與陰離子作用 87
2.2.15.1.化合物 4d 和陰離子作用之吸收光譜 87
2.2.15.2.化合物 4d 與氰離子作用的滴定光譜與 job’s plot 89
2.2.16. 化合物 4h 與陰離子作用 90
2.2.16.1.化合物 4h 和陰離子作用之吸收光譜 90
2.2.16.2.化合物 4h 與氰離子作用之滴定光譜與 job’s plot 92
2.2.17.化合物 4d, 4e, 4g, 4h, 4j 與氟離子作用的滴定光譜 94
2.2.17.1.化合物 4d, 4e, 4g, 4h, 4j 與氟離子作用的滴定光譜 95
2.2.18. 化合物 4d 和 4i 使用 job’s plot 方法測定與氟離子作用比例 98
2.2.19. 水存在下化合物氟離子或氰離子作用 100
2.2.19.1.水存在下化合物與氟離子或氰離子作用之吸收光譜 100
2.2.20. 化合物 4 加入氰離子以及氟離子後的光譜討論 106
2.3.NMR titration 107
2.3.1.溶劑及化合物選擇 107
2.3.2.化合物 4a、4i 與氰離子之 NMR 滴定 107
2.3.3.化合物 4a、4i 與氟離子之 NMR 滴定 110
2.4.螢光光譜部分 112
2.4.1.化合物 4d 的螢光光譜 113
2.4.2.化合物 4d 出現螢光的推測 114
第三章 結論 116
第四章 實驗部分 118
4.1.實驗儀器、藥品及試藥 118
4.2.實驗步驟 119
4.2.1.合成方法 119
4.2.1.1. 3-Acetyl-2H-chromen-2-one 的合成 119
4.2.1.2. (E)-3-(3-phenyl)-prop-2-enoyl)-2H-chromen-2-one 119
4.2.1.3.(E)-3-(3-(4-methoxyphenyl)acryloyl)-2H-chromen-2-one 的合成 120
4.2.1.4. (E)-3-(3-(4-chlorophenyl)acryloyl)-2H-chromen-2-one 的合成 121
4.2.1.5. (E)-3-(3-(p-tolyl)acryloyl)-2H-chromen-2-one 的合成 121
4.2.1.6. 8-Hydroxyquinoline-2-carbaldehyde 的合成 122
4.2.1.7. Quinoline-2-carbaldehyde 的合成 122
4.2.1.8. Ethoxycarbonylacetohydrazide（2）的合成 123
4.2.1.9. (E)-N'-benzylidene-2-oxo-2H-chromene-3-carbohydrazide (4a)的合成 124
4.2.1.10.(E)-N'-(4-methoxybenzylidene)-2-oxo-2H-chromene-3-carbohydrazide (4b)的合成125
4.2.1.11.(E)-N'-(4-chlorobenzylidene)-2-oxo-2H-chromene-3-carbohydrazide (4c)的合成 127
4.2.1.12.(E)-N'-(2-hydroxybenzylidene)-2-oxo-2H-chromene-3-carbohydrazide (4d)的合成 128
4.2.1.13.(E)-2-oxo-N'-(pyridin-2-ylmethylene)-2H-chromene-3-carbohydrazide (4e)的合成 129
4.2.1.14.(E)-2-oxo-N'-(thiophen-2-ylmethylene)-2H-chromene-3-carbohydrazide (4f)的合成 130
4.2.1.15.(E)-N'-(furan-2-ylmethylene)-2-oxo-2H-chromene-3-carbohydrazide (4g)的合成 131
4.2.1.16.(E)-N'-((1H-pyrrol-2-yl)methylene)-2-oxo-2H-chromene-3-carbohydrazide (4h）的合成 132
4.2.1.17.(E)-2-oxo-N'-(quinolin-2-ylmethylene)-2H-chromene-3-carbohydrazide (4i)的合成 133
4.2.1.18.(E)-N'-((8-hydroxyquinolin-2-yl)methylene)-2-oxo-2H-chromene-3-carbohydrazide (4j)的合成 135
4.2.2.測量方法 136
4.2.2.1. 金屬離子測定 136
4.2.2.2. 陰離子測定 136
4.2.2.3. UV 滴定實驗 137
4.2.2.4. Job’s plot 實驗 137
4.2.2.5. 螢光實驗 138
4.2.2.6. NMR 滴定實驗 138
第五章 參考資料 140
附錄 154

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