| 研究生: |
張恩銘 Chang, En-Ming |
|---|---|
| 論文名稱: |
吡唑衍生物在藥物合成與有機發光二極體之開發與應用 Development and Application of Pyrazole Derivatives in Medicinal Syntheses and Organic Light-Emiting Diodes |
| 指導教授: |
葉茂榮
Yeh, Mou-Yung |
| 學位類別: |
博士 Doctor |
| 系所名稱: |
理學院 - 化學系 Department of Chemistry |
| 論文出版年: | 2008 |
| 畢業學年度: | 96 |
| 語文別: | 中文 |
| 論文頁數: | 137 |
| 中文關鍵詞: | 有機發光二極體 、光電材料 、幽門桿菌 、吡唑 、酵素抑制劑 、雪梨酮 、雙偶極環化 、電洞層 |
| 外文關鍵詞: | DHODase inhibitors, organic electronic-transporting, OLED, pyrazole, electroluminescent |
| 相關次數: | 點閱:188 下載:14 |
| 分享至: |
| 查詢本校圖書館目錄 查詢臺灣博碩士論文知識加值系統 勘誤回報 |
本論文主要以研究吡唑類之衍生物在藥物與光電材料上之應用。
而吡唑類衍生物之合成係以雪梨酮為起始物進行1,3-雙偶極環化加成反應而得到含吡唑環之化合物,進一步合成各類吡唑類衍生物,再將之分別應用於藥物與發光材料之領域。
論文其中一部分為合成出具有抗幽門桿菌能力之酵素抑制劑,以1,3-雙偶極環化加成反應配合立體效應,得到51-60%之高產率,而另一部分為研究小分子與高分子有機發光二極體之材料,材料之合成以雪梨酮為起始物進行衍生,合成出含有吡唑環與1,3,4-二唑環之化合物,再進一步衍生出含有不同官能基之有機發光二極體材料。利用此類之設計合成出多種光電材料(電子與電洞層),並對其物理性質、化學性質、光電性質做深入之探討。
In this thesis, we developed the new synthesis and application for pyrazole-based derivatives as the DHODase inhibitors, and the organic electronic-transporting and electronic-hole electroluminescent materials derivatives.
In the first part, we developed a new efficient and convenient synthetic method from 3-(p-aryl)-4-cyanosydnone for Pyrazole-based DHODase inhibitors via chemoselective 1,3-diploar cycloaddition, amidation, and Ritter reaction. Overall yields was in 51–60% yield in three steps.
In the second part, 1,3,4-oxadiazole-based pyrazole derivatives have been synthesized and characterized as blue-greenish electroluminescent materials. Those compounds are successfully inducted a pyrazole chromophore and multiple 1,3,4-oxadiazole moieties by 1,3-dipolar-cyclization and dehydration-cyclization to promote the conjugation range and exhibit high thermal stability and good physical properties. Spectroscopic studies, the measurements of cyclic voltammogram, thermal characterization and electroluminescent properties have revealed that 1,3,4-oxadiazole-based pyrazole derivatives are efficient blue-greenish electroluminescent materials
In the third part, we have also prepared the double-layer OLED devices containing new organic electronic-transporting and electronic-hole electroluminescent materials under vacuum onto the ITO-coated glass substrate. The device showed the blue-greenish emission.
1. Stewart F.H.C., Chem. Rev. , 1964, 64, 129.
2. Ohta M. and Kato H., “Non-bezxenoid Aromatics, I”, (Edited by J. P. Suyder), Academic Press, New York, . 1996, 117.
3. Earl, J. C.; Mackney, A. W., J. Chem. Soc., 1935, 899.
4. Simpson, J. C. E., J. Chem. Soc., 1946, 94.
5. Baker, W.; Ollis, W. D.; Poole, V. D., J. Chem. Soc., 1949, 307.
6. Hahn, S. J.; Kim, S. H.; Chane, H. J.; Youn, L. H.; Lyu, H. S., Bull.
Korean Chem. Soc., 1988, 8, 49.
7. Huseya, Y.; Chinone, A.; Ohta, M., Bull. Chem. Soc .Jpn., 1971, 44,
1667.
8. Huseya, Y.; Chinone, A.; Ohta, M., Bull. Chem. Soc. Jpn., 1972, 45,
3202.
9. Bhat, V,; Dixit, V. M.; Ugarker, B. G.; Trozzolo, A. M.; George,
M. V., J.Org. Chem., 1979, 44, 2957.
10. Gotthardt, H.; Reiter, F., Chem. Ber., 1979, 112, 1193.
11. Tien, J. M. ; Hunsberger, I. M., J. Am. Chem. Soc., 1955, 77, 1843.
12. Shetty, B. V., J. Org. Chem., 1961, 26, 3002.
13. Baker, W.; Ollis, W. D.; Poole, V. D., J. Chem. Soc. ,1949, 307.
14. Earl, J. C., Tetrahedron., 1957, 1, 338.
15. Huisgen, R.; Gotthardt, H.; Grashey, R., Angew. Chem., 1962, 74, 30.
16. Gotthardt, H.; Huisgen, R., Chem. Ber., 1968, 101, 552.
17. Stille, J. K.; Harris, F. W.; Bedford, M. A., J. Heterocyclic Chem., 1966, 3, 55.
18. Gotthardt, H.; Teiter, F., Chem. Ber., 1979, 112, 1193.
19. Gotthardt, H.; Teiter, F., Chem. Ber., 1979, 112, 1635.
20. Kato, H.; Sato, S.; Ohta, M., Tetrahedron Lett., 1967, 4261.
21. Thoman, C. J.; Voaden, D. J.; Hunsberger, I. M., J. Org. Chem., 1964, 29, 2044.
22. Dallacker, F.; Kern, J., Chem. Ber., 1966, 99, 3830.
23. Masuda, K.; Kikuchi, K.; Imajo, Y., Japan Patent., 1972, 29, 511.
24. Yeh, M.Y. ; Tien, H. J. ; Huang, L. Y. ; Chen, M. H. , J. Chin. Chem. Soc., 1983, 30, 29.
25. Yeh, M.Y. ; Tien, H. J., J. Chin. Chem. Soc., 1986, 33, 83.
26. Jugie, G.; Smith, J. A. S.; Martin, G. J., J. Chem. Soc., Perkin Trans.1, 1975, 2, 925.
27. Tien, H.J. ; Yeh, M. Y. ; Wu, C. H.; Chen, H. T., J. Chin. Chem. Soc., 1984, 31, 191.
28. Yeh, M. Y. ; Tien, H. J., J. Chin. Chem. Soc., 1986, 33, 83.
29. Destriau G., J. Chem. Phys., 1936, 33, 587.
30. Ohnishi, H., Ann. Rev. Mater. Res., 1989, 19, 83.
31. Matsumoto, S., Electronic display devices, New York, Wiley, 1990, Chapt 5, 180.
32. Pope, M. ; Kallmann, H.P. ; Magnante, P., J. ;Chem. Phys., 1963, 38(8), 2042.
33. Helfrich, W., Schneider, W.G., Phys. Rev. Lett., 1965, 14(7), 229.
34. Helfrich, W.; Schneider, W.G.; J. Chem. Phys., 1966, 44(8), 2902.
35. Vincett, P.S.; Barlow, W.A.; Hann, R.A.; Roberts, G.G.; Thin Solid Films, 1982, 94, 476.
36. Partridge, R.H.; Polymer, 1983, 24(6), 733.
37. Tang, C.W.; Van Slyke, S.A., Appl. Phys. Lett., 1987, 51(12), 913.
38. Adachi, C.; Tokito, S.; Tsutsui; Saito,T. S., Jpn. J. Appl. Phys., 1988, 27(2), 219.
39. Adachi, C.; Tsutsui,T.; Saito, S., Appl. Phys. Lett., 1989, 1489.
40. Kido, J.; Khodo, M.; Okuyana, K.; Nagai, K., Appl. Phys. Lett., 1992, 61(7), 761.
41. Kido, J.; Hongavwa, K.; Khoda, M.; Nagai, K.; Okuyama,K., Jpn, J. Appl. Phys., 1992, 31(7B), 960.
42. Cleary,D.; Polymer technology-after years in the dark, electric plastic
finally shines, 1994, 263(5139), 1700.
43. Burroughes, J. H.; Bradley, D.D.C.; Brown, A.R.; Marks, R.N.; Mackay, K.; Friend, R.H.; burn, P.L.; Holmes, A.B.; Nature, 1990, 347, 539.
44.徐玉娟;科學月刊,374期,P.126,2001年2月號.
45. Shirota, Y.; Kuwabara, Y.; Inada, H.; Appl. Phys., 1994, 65(7), 807.
46. Friend,R.H.; Gymer, R.W.; Holmes, A.B.; Byrroughes, J.H.; Marks, R.N. C.; Talianii, D.D.C.; Bradley, DosSantos, D.A.; Bredas, J.L.; Loglund, M.; salaneck, W.R.; Nature, 1999, 397, 121.
47. Cao, Y.; Treacy, G.M.; Smith, P.; Heeger, A.T. Appl. Phys. Lett., 1992,
60(22), 2711.
48. Kido, J.; Nagai, K.; Okamoto, Y.; Skotheim, T. Appl. Phys. Lett., 1991, 59, 2760.
49. Zhang, A.; Von Seggen, H.; Pakbag, K.; Kraable, B.; Schmidt, K.H.V.; Heeger, A.T. Synth. Met. 1994, 62, 35.
50. Broun, A.R.; Bradley, D.D.C.; Burroughs, J.H.; Friend, R.H.;
Greenham, N.C.; Burn, P.L.; Kraft, A. Appl. Phys. Lett., 1992, 61(23), 2793.
51. Antomiadis, H.; Hsieh, Br.; Abkowitz, Ma.; Jenekhe, Sa.; Stolka, M.; Synth.Met., 1994, 62(3), 265.
52. Kido, J.; Hongawa, K.; Okuyama, K.; Naga, K. Appl. Phys. Lett.,
1994,64(7), 815.
53. Strukelj, M.; Papadimitrakopoulos, F.; Miller, T.M.; Rothberg, L.J.;
Science, 1995, 267(5206), 1969.
54. Kido, J.; Ohtali, C.; Hongawa, K.; Okuyama, K.; Nagai, K. Jpn. J.
Appl.Phys., 1993, 32(7A), 917.
55. 劉佳明、翁文國、陳良吉;科學月刊,374期,P.115,2001年2月號.
56. Chen, S.A.; Chao, C.I. Synth. Met. 1996, 79, 93.
57. Ranger, M. D.; Rondeau, M. Leclerc, Macromolecules, 1999, 30, 7686.
58. Yu, W.L.; Pei, J.; Cao, Y.; Huang, W.; Heeger, A.T. Chem. Comnun., 1999, 1837.
59. 周宣良、林金福、韓于凱、王鼎章;台大工程學刊,2003年10月,P.111.
60. Bouche,C.M.; Berdague, P.; Facoetti, H.; Robin, P.; Lebarny,P.;
M.Schott, Synth. Met., 1996, 81, 191.
61. Tomopkins;falkow S., Scince, 1995, 267,1621.
62. Leunk, R. D.;Johnson, P. T.;David, B. C., J. Med. Microbiol., 1991, 26, 93.
63. Marshall, B. J.;Royce, H.;Warren, J. R., Microbio. Lett., 1984, 25, 83.
64. Robert, A. C.;Jovita, M.;Tasir, S. H., J. Biol. Chem., 2002, 275,
33373.
65. Marcinkeviciene, J.; Rogers, M. J.; Kopcho, L., Biochem. Pharmacol., 2000, 60, 339.
66. Muri, E. M. F.;Williamson, J. S., Mini-Reviews in Med. Chem., 2004, 4, 201.
67. Tasir, S. H.;Seifu, T.;Jovita, M., J. Med. Chem., 2002, 45, 4669.
68. Tasir, S. H.;Seifu, T.;Jovita, M., J. Med. Chem., 2002, 45, 4669.
69. John, R.;Steffen, B.;Pier, C., J. Med. Chem., 2002, 45, 2994.
70. Chiara, B. V.;Donatella, M.;Alfredo, T., J. Agric. Food. Chem., 2004, 52, 1898.
71. En-Ming Chang ; Fung-Fuh Wong ; Tse-Hsin Cheng ; Kuo-Chen Chiang ; Mou-yung Yeh Heterocycles , 2006, 68, 1007.
72. Adachi, C.; Tsutsui T. and Saito, S. Appl. Phys. Lett. 1989, 55, 1489.
73. Hamada, Y.; Adachi, C.; Tsusui T.; and Saito, S. Jpn. J. Appl.Phys. 1991, 1540.
74. Hamada, Y.; Adachi, C.; Tsusui T.; and Saito, S. Jpn. J.Appl. Phys.
1992, 31, 1812.
75. Bradley D. O'and Tsutsui, T. J. Appl. Phys. 1997, 82, 2662.
76. Kawate, K.; Ohkura, K. –I.; Yamazaki, M.; Kuroda M.; and Nabeta,O. Proc.SPIE Int. Soc. Opt. Eng. 1994, 2174, 200.
77. Reddy, P.S.N.; Reddy, P.P.; Indian J.Chem.Sect B ,1987,26B ,890
78. Ueda, H.; Kitahora, T.; Furukawa K.; and Terasaka, Y. Synth. Met. 1997, 91,257.
79. Bettenhausen, J. P.; Strohriegl, W.; Brutting, H.; Tokuhisa and T. Tsutsui, J. Appl. Phys. 1997, 82, 4957.
80. Shirota, Y.; Kuwabara,Y.; Okuda,D.; Okuda, R.; Ogawa,H.; Inada, H.; Wakimoto,T.; Nakada, H ; Yonemoto, Y.; Kawami, S., Luminesc. 1997, 72, 985.
81. Tokito, S.; Tanaka, H.; Noda, K.; Okada, A.; Taga, Y., Macromol. Symp. 1997,125, 181.
82. Haque, T. S.; Tadesse, S. J.; Marcinkeviciene, J. Med. Chem. 2002, 45, 4669
83. Klupfel, K. W.; Sus, O.; Behmenburg, H.; and Neugebauer, W.; Us 3, 1965, 180, 730.
84. Brantly, T. B.; Contois, L. E.; and Fox, C. J., Us 3, 1971, 567, 450.
85. Brantly, T. B.; Contois, L. E.; and Fox, C. J., Us 3, 1972, 658, 520.