設計以鄰苯二胺為核心架構的化學感測分子，外層接上咔唑來修
飾核心架構上的共軛系統和推拉電子性，另外在二胺官能基的地方做
乙二胺的延伸，使整體具有一個離子結合位置。先藉由UV-Vis測量
其最大吸收波長 ，接著再用不同金屬離子的無機鹽纇來滴定此化合
物透過UV-Vis來觀察吸收波長變化 。

Synthesis of heavy metal cation sensing molecules based on 0-Phenylenediamine. It possesses conjugate property, and push-pull system. It can be a good Organic Light Emitting Diode. We employ 0-Phenylenediamine’s amino group to synthetize a good binding site. Finally, we titrate with solution which include heavy metal cation following measure the maximum UV- Vis wavelength. We observe color change

目錄
中文摘要................................................................................................i
英文摘要..............................................................................................ii
第一章 緒論…………………………………………………………..1
1-1 重金屬污染………………………………………………..2
1-2 偵測重金屬陽離子的方法………………………………..8
1-3 化學感測器………………………………………………10
第二章 結果與討論…………………………………………………20
2-1 兩端為推電子官能基的鄰苯二胺分子合成……………20
2-2 發光性質討論……………………………………………44
2-3 金屬離子的滴定…………………………………………46
第三章 實驗與儀器…………………………………………………51
3-1 實驗儀器與測試方法……………………………………51
3-2 溶劑的乾燥………………………………………………54
3-3 反應條件及實驗步驟……………………………………56
第四章 結論…………………………………………………………68
第五章 光譜…………………………………………………………70
第六章 參考資料……………………………………………………82

Scheme目錄
Scheme 1-1………………………………………...…………………10
Scheme 1-2…………………………………………………………...12
Scheme 1-3…………………………………………………………...13
Scheme 1-4…………………………………………………………...14
Scheme 1-5………………………………………………………...…15
Scheme 1-6…………………………………………………………...16
Scheme 1-7…………………………………………………………...16
Scheme 1-8…………………………………………………………...17
Scheme 1-9…………………………………………………………...18
Scheme 1-10………………………………………………………….18
Scheme 1-11……………………………………………………….....19
Scheme 2-1…………………………………………………………...21
Scheme 2-2…………………………………………………………...22
Scheme 2-3…………………………………………………………...22
Scheme 2-4…………………………………………………………...23
Scheme 2-5…………………………………………………………...23
Scheme 2-6…………………………………………………………...24
Scheme 2-7…………………………………………………………...24
Scheme 2-8…………………………………………………………...24
Scheme 2-9…………………………………………………………...25
Scheme 2-10………………………………………………………….26
Scheme 2-11………………………………………………………….27
Scheme 2-12………………………………………………………….27
Scheme 2-13………………………………………………………….28
Scheme 2-14………………………………………………………….29
Scheme 2-15………………………………………………………….30
Scheme 2-16………………………………………………………….31
Scheme 2-17………………………………………………………….32
Scheme 2-18………………………………………………………….33
Scheme 2-19………………………………………………………….33
Scheme 2-20………………………………………………………….34
Scheme 2-21………………………………………………………35-36
Scheme 2-22………………………………………………………….37
Scheme 2-23………………………………………………………….39
Scheme 2-24………………………………………………………….40
Scheme 2-25………………………………………………………….41
Scheme 2-26………………………………………………………….41
Scheme 2-27………………………………………………………….41
Scheme 2-28………………………………………………………….42
Scheme 2-29………………………………………………………….42
Scheme 2-30………………………………………………………….43
Scheme 2-31………………………………………………………….44
Scheme 2-32………………………………………………………….47
Scheme 2-33………………………………………………………….47
Scheme 2-34………………………………………………………….48
Scheme 2-35………………………………………………………….49
Scheme 2-36………………………………………………………….49
Scheme 2-37………………………………………………………….50
Scheme 4-1…………………………………………..……………….68
Scheme 4-2…………………………………………………..……….69
Scheme 4-3…………………………………………………..……….69


光譜目錄

2,1,3-Benzothiadiazole………………………………………………………………70
4,7-Dibromo-2,1,3-benzothiadiazole…………………..…………………………… 71
Tributyl(thiophen-2-yl)stannane……………………………………………………..72
4,7-Dibromo-2,1,3-benzothiadiazole…………………………..…………………….73
4,4,5,5-tetramethyl-2-(thiophen-2-yl)-1,3,2-dioxaborolane………………………….74
5-(4-(thiophen-2-yl)benzo[c][1,2,5]thiadiazol-7-yl)thiophene-2-carbaldehyde...……75


3-((5-(4-(thiophen-2-yl)
benzo[c][1,2,5]thiadiazol-7-yl)thiophen-2-yl)mehyleneamino)propan-1-ol……….…76


3-methyl-1-phenyl-4-((5-(4-(thiophen-2-yl)
benzo[c][1,2,5]thiadiazol-7-yl)thiophen-2-yl)methylene)-1H-pyrazol-5-one…….. …77


Diethyl -2-((5-(4-(thiophen-2-yl)
benzo[c][1,2,5]thiadiazol-7-yl)thiophen-2-yl)methylene)malonate…………………..78


2-((5-(4-(thiophen-2-yl)
benzo[c][1,2,5]thiadiazol-7-yl)thiophen-2-yl)methylene)malonic acid………………79


9-(4-(9H-carbazol-9-yl)benzo[c][1,2,5]thiadiazol-7-yl)-9H-carbazole …. ………….80


N,N'-
(3,6-di(9H-carbazol-9-yl)-1,2-phenylene)bis(2-acetamidoacetamide)……………….81

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