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系統識別號 U0002-1308200908290500
中文論文名稱 感測重金屬離子的有機分子合成研究
英文論文名稱 Synthesis of Heavy Metal Cation Sensing Molecules
校院名稱 淡江大學
系所名稱(中) 化學學系碩士班
系所名稱(英) Department of Chemistry
學年度 97
學期 2
出版年 98
研究生中文姓名 林振弘
研究生英文姓名 Jen- Hung Lin
學號 696160208
學位類別 碩士
語文別 中文
口試日期 2009-06-16
論文頁數 85頁
口試委員 指導教授-李世元
委員-林俊成
委員-蔡厚仁
委員-王伯昌
中文關鍵字 鉗合  重金屬  化學感測器 
英文關鍵字 Chelating  Heavy metal  Chemosensor 
學科別分類 學科別自然科學化學
中文摘要 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 。


英文摘要 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
論文目次 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
參考文獻 1. Cheng-Ju Yu, and Wei-Lung Tseng, Langmuir, 2008, 24 (21),
12717-12722.
2. Younghun Kim, and Jongheop Yi, Langmuir, 2006, 22 (24),
9805-9808.
3. Philippe Bu¨hlmann,*,† Erno¨ Pretsch,‡ and Eric Bakker, Chem. Rev.,
1998, 98, 1593-1687.
4. C. J. Pedersen, J. Am. Chem. Soc., 1967, 89(26), 7017–7036.
5. A. Prasanna de Silva, H. Q. Nimal Gunaratne, Thorfinnur
Gunnlaugsson, Allen J. M. Huxley, Colin P. McCoy, Jude T.
Rademacher, and Terence E. Rice, Chem. Rev., 1997, 97 (5),
1515-1566.
6. Dmitry Aldakov, Manuel A. Palacios, and Pavel Anzenbacher,
Chem. Mater., 2005, 17 (21), 5238-5241.
7. M. JAYAKANNAN, PAUL A. VAN HAL, RENE´ A. J. JANSSEN
Journal of Polymer Science: Part A: Polymer Chemistry, 2002, 40,
251–261.
8. Roncali, J, Chem Rev, 1997, 97, 173.
9. Brabec, C. J.; Shaheen, S. E.; Fromherz, T.; Padinger, F.; Hummelen, J.
C.; Dhanabalan, A.;Janssen, R. A. J.; Sariciftci, N. S., Synth Met., 2001,
121, 1517.
10. J. F. Lame`re, P. G. Lacroix, N. F. J. M. Rivera, R. Santillan and K.
Nakatani, J. Mater. Chem., 2006, 16, 2913–2920.
11. J. Casado, M. C. R. Delgado, M. C. R. Mercha´n, V. Herna´ndez, J. T.
L. Navarrete, T. M. Pappenfus, N. Williams, W. J. Stegner, J. C.
Johnson, B. A. Edlund, D. E. Janzen, K. R. Mann, J. Orduna and B.
Villacampa, Chem.–Eur. J., 2006, 12, 5485–5470.
83
12. M. M. C. Oliva, J. M. M. M. Raposo, A. M. C. Fonseca, H. Hartmann,
V. Hernandez and J. T. Lopez Navarrete, J. Org. Chem., 2006, 71,
7509–7520.
13. Ste´phane Dufresne, Marie Bourgeaux and W. G. Skene* J. Mater.
Chem., 2007, 17, 1166–1177.
14. Yu Liu, Zhong-Yu Duan, Heng-Yi Zhang, Xiao-Lu Jiang, and
Jian-Rong Han, J. Org. Chem., 2005, 70 (4), 1450-1455.
15. Prodi, L.; Bolletta, F.; Montalti, M.; Zaccheroni, N., Tetrahedron
Lett., 1998, 39, 5451.
16. Arunkumar, E.; Chithra, P.; Ajayaghosh, A., J. Am. Chem. Soc., 2004,
126, 6590.
17. Chao-Tsen Chen, and Wan-Pei Huang, J. Am. Chem. Soc., 2002, 124
(22), 6246-6247.
18. Deo, S.; Godwin, H. A., J. Am. Chem. Soc., 2000, 122, 174-175.
19. Fabiana S. Mancilha,[a] Brenno A. DaSilveira Neto,[a] Aline S.
Lopes,[a]Paulo F. Moreira Jr.,[b] Frank H. Quina,[b] Reinaldo S.
Gonçalves,[a] and Jaïrton Dupont*[a], Eur. J. Org. Chem., 2006,
4924–4933.
20. Mohand Melaimi, François Mathey and Pascal Le Floch, JOC, 2001,
197-199
21. Norio Miyaura, Kinji Yamada and Akira Suzuki, Tetrahedron Lett.,
1979, 20, 3437-3440.
22.Petent No. U.S. 7,217,824
23.Lee,A. S.-Y.; Dai, W.-C. Tetrahedron. Lett. 1996, 37, 495.
24. Lee,A. S.-Y.; Dai, W.-C. Tetrahedron. 1997, 53, 859.
25. D. Milstein, J. K. Stille, J. Am. Chem. Soc., 1978, 100 (11),
3636–3638.
26. W. G. Jackson et al., J. Am. Chem. Soc., 1981, 103, 533.
27. Joseph A. Sclafani, Maria T. Maranto, Thomas M. Sisk, and Scott A.
Van Arman, J. Org. Chem.,1996, 61, 3221-3222.
28. Wanlapa Aeungmaitrepirom, Zouhair Asfari, and Jacques Vicens,
Tetrahedron Lett., 1997, 38, 1907-1910.
29. W CUN-DE, LU JUN, S XIN-ZHONG, F YUN-HUA, Synth.
Commun., 1999, 29(17), 3057-3061.
30. Rajender S. Varma,*l, 2 Rajender Dahiya I and Sudhir Kumar 2
Tetrahedron Lett., 1997, 38(12), 2039-2042.
31. H. K. Jr. Hall, Anne Buyle Padias, Paul A. Williams,
Jan-Michael Gosau, Harold W. Boone, Dong-Kyu Park
Macromolecules, 1995, 28(1), 1–8.
32. Carlson, R.; Larsson, U.; Hansson, L., Acta Chem. Scand., 1992,
28, 517.
33. Carlson, R.; Nordahl, A.; Kraus, W., Acta Chem. Scand., 1991, 45,
46.
34. Oldrich Kocian, Kwok W. Chiu, Roger Demeure, Bernard Gallez,
Christopher J. Jones and John R. Thornback, J. Chem. Soc., Perkin
Trans. 1, 1994, 527.
35. Constantinos G. Screttas* and Barry R. Steele, J. Org. Chem., 1989,
54, 1013-1017.
36. Man-kit Leung, Chin-Chuan Chang, Meng-Hsiu Wu, Kai-Hsiang
Chuang, Jiun-Haw Lee, Shwu-Ju Shieh, Shien-Chang Lin, and
85
Chi-Feng Chiu, Org. Lett., 2006, 8(12), 2623-2626.
37. Kwon, P-S.; Kim, Y-M.; Kang, C-J.; Kwon, T-W., Synth. Commun.,
1997, 27, 4091-4100.
38. Vassiliki Theodorou, Konstantinos Skobridis, Andreas G. Tzakos and
Valentine Ragoussis, Tetrahedron Lett., 2007, 48, 8230–8233.
39. P.E. Fanta, Chem. Rev., 1964, 64, 613.
40. Yoshiaki Tsubata, Takanori Suzuki, Tsutomu Miyashi, and Yoshiro
Yamashita, J. Org. Chem., 1992, 57(25), 6749-6755.
41. Asuman Durmus, Gorkem E. Gunbas, and Levent Toppare,
Chem. Mater., 2007, 19(25), 6247-6251.
42. Olga L. Hoyos, Manuel R. Bermejo, Matilde Fondo, Ana
García-Deibe, Ana M. González, Marcelino Maneiro and Rosa
Pedrido, J. Chem. Soc., Dalton Trans., 2000, 3122–3127.
43. Sebastien G. Gouin, Jean-Francois Gestin, Laurence Monrandeau,
Fabienne Segat-Dioury, Jean Claude Meslin and David Deniaud, Org.
Biomol. Chem., 2005, 3, 454–461.
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