| 研究生: |
吳建聖 Wu, Chien-Sheng |
|---|---|
| 論文名稱: |
苝-3,4,9,10-四羧酸酐衍生物的合成、鑑定與應用 Synthesis, Characterization and Application of Perylene-3,4,9,10-tetracarboxylic Dianhydride's Derivatives |
| 指導教授: |
葉茂榮
Yeh, Mou-Yung |
| 學位類別: |
碩士 Master |
| 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: | 83 |
| 中文關鍵詞: | 苝-3 4 9 10-四羧酸酐 、Suzuki-Coupling 、酯化 、太陽能電池 |
| 外文關鍵詞: | Perylene-3 4 9 10-tetracarboxylic dianhydride, esterification, Suzuki-Coupling, Solar Cell |
| 相關次數: | 點閱:79 下載:1 |
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太陽能電池發電是現今非常熱門的研究課題,其中又以有機薄膜太陽能電池最具有發展潛力。苝是具有良好電子遷移率的化合物,已經有許多將其應用在有機薄膜太陽能電池的研究。
本論文討論從苝-3,4,9,10-四羧酸酐出發,將之溴化,再進行酯化反應,製備三種不同碳數的1,7-二溴苝-3,4,9,10-四羧酸酯。再經由Suzuki-Coupling合成一系列帶有多共軛系統的衍生物;所合成之產物的光學能階差在2.32~2.49電子伏特之間。最後透過UV-Vis、PL和CV來探討其結構與光電性質之關係。
The development of solar cell has been a popular topic, recently the researches focus on the organic-thin-film-type . Various perylene derivatives with good electron mobility are promising materials for organic solar cells .
New compounds with aromatic group were synthesized via esterification with simple phase transfer catalysis (PTC) method and Suzuki-coupling.
Several perylene-3,4,9,10-tetracarboxylic dianhydride’s have been synthesized. The optical energy gap (Eg) of these new compounds are between 2.32eV to 2.49eV. The relationship between the structure and photoelectric property of these new compounds were studied .
1. 楊素華 蔡泰成 科學發展2005年6月,390期51
2. G. P. Smestad, Solar Energy Mater. Solar Cells, 82, 227 (2004).
3. a. M. A. Green, Prog. Photovolt: Res. Appl., 8, 127 (2000).
b. M. A. Green, Prog. Photovolt: Res. Appl., 8, 443 (2000).
c. M. A. Green, Prog. Photovolt: Res. Appl., 9, 123 (2001).
d. M. A. Green, Prog. Photovolt: Res. Appl., 13, 447 (2005).
4. T. Surek, J. Cryst. Growth, 275, 292 (2005).
5. H. Spanggaard, and F. C. Krebs, Solar Energy Mater. Solar Cells, 83, 125 (2004).
6. W. E. Spear and P. G. LeComber, Solid State Commun., Vol. 17, p.1193, 1975.
7. D. E. Carlson and C. R. Wronski, Appl. Phys. Lett., Vol. 28, 671-673, 1975.
8. E.Ruud ,I.Schropp and Miro Zeman, IEEE Trans. on Electron Devices, Vol. 46, 2086-2092, 1999.
9. A. Shah, P. Torres, R. Tscharner, N. Wyrsch, H. Keppner
Science 30 July 1999: Vol. 285. no. 5428, 692–698
10. E. B. Yousfi, B. Weinberger, F. Donsanti, P. Cowache and D. Lincot Thin Solid Films Volume 387, Issues 1-2, 29 May 2001, 29-32
11. T.L. Chu, S.S. Chu, J. Britt, C. Ferekides, C. Wang,
C. Q. Wu, H. S. Ullal, Electron Device Letters, IEEE Volume 13, Issue 5, May 1992 303–304
12. Y. Endo, T. Fujiwara, S. Nishizaki, K. Nishioka, and H. Matsumura 22nd European Photovoltaic Solar Energy Conference (PVSEC) and Exhibition Milan, Italy September 3–7, 2007
13. K. Fujimoto, F. Nakabeppu, Y. Sogawa, Y. Okayasu, K. Kumagai, Photovoltaic Specialists Conference, 1993., Conference Record of the Twenty Third IEEE Volume , Issue , 10-14 May 1993 83–87
14 .J. Kuendig, M. Goetz, X. Niquille, A. Shah, S. Vaccaro,
J. Mosig, L. Gerlach, P. de Maagt, E. Fernandez,
Photovoltaic Specialists Conference, 2000. Conference Record of the Twenty-Eighth IEEE Volume , Issue , 2000 1079 – 1082
15. M. A. Green, K. Emery, D. L. King, Y. Hishikawa, and W. Warta, Prog. Photovoltaics Res. Appl. 14, 455-461 (2006).
16. Brian O'Regan and Michael Grätzel
Nature 353, 737 - 740 (1991).
17. U. Bach , D. Lupo , P. Comte , J. E. Moser , F. Weissortel , J. Salbeck , H. Spreitzer , M. Gratzel Nature 1998, vol. 395,number 6702, 583-585
18. G.P. Smestad, M. Grätzel, J. Chem. Educ. 75, 752 (1998).
19. A. Kay, M. Grätzel, J. Phys. Chem. 97, 6272 (1993).
20. F. O. Lenzmann and J. M. Kroon Advances in OptoElectronics
Volume 2007 (2007), Article ID 65073, 10 pages
21. C.W. Tang, APPl. Phys. Lett. 1985, 48, 183
22. 莊嘉琛, "太陽能工程-太陽電池篇," 全華科技圖書股份有限公司,中華民國九十年十月初版三刷。
23. M. M. Shi, H.Z. Chen, J.Z. Sun, J. Ye, M. Wang, Chem. Commun. 14 (2003) 1710.
24. M. M. Shi, H.Z. Chen, J.Z. Sun, J. Ye, M. Wang, Chem. Phys.
Lett. 381 (2003) 666.
25. L. Schmidt-Mende, A. Fechtenkötter, K. Müllen, E. Moons, R. H. Friend, J. D. MacKenzie Science 10 August 2001:
Vol. 293. no. 5532, 1119 - 1122
26. B. A. Gregg, Chem. Phys. Lett. 258 (1996) 376.
27. H. Langhals , R. Ismael , O. Yuruk Tetrahedron 56 (2000) 5435-5441
28. Shengxiong Xiao, Matthew Myers, Qian Miao, Sebastien Sanaur,Keliang Pang , Michael L. Steigerwald,and Colin Nuckolls Angew. Chem. Int. Ed. 1998, 37,1434
29. Jwanro Hassan, Marc Sevignon, Christel Gozzi Emmanuelle Schulz, and MarcLemaire , Chem. Rev. 2002, 102, 1359-1469
30. Chun-Chieh Chao, Man-kit Leung, Yuhlong Oliver Su, Kuo-Yuan Chiu, Tsung-Hsien Lin, Shwu-Ju Shieh, and Shien-Chang Lin J. Org. Chem. 2005, 70, 4323-4331
31. Y. Liu, Ms. Nishiura , Y. Wang ,Z. M. Hou J.AM.CHEM. SOC. 2003, 125, 437-443
32. Hualei Qian, Zhaohui Wang, Wan Yue, and Daoben Zhu J. Am. Chem. Soc.; (Communication); 2007; 129(35);
10664-10665
33. Timothy E. Barder, Shawn D. Walker, Joseph R. Martinelli, and Stephen L. Buchwald J. AM. CHEM. SOC. 2005, 127, 4685-4696
34. Steven V. Ley, Prof. Dr., Andrew W. Thomas, Dr.
Angew. Chem. Int. Ed. 2003, 42, 5400–5449
35. Michael J. Ahrens, Louise E. Sinks, Boris Rybtchinski, Wenhao Liu, Brooks A. Jones, Jovan M. Giaimo, Alexy V. Gusev, Andrew J. Goshe, David M. Tiede, and Michael R. Wasielewski J. AM. CHEM. SOC. 2004, 126, 8284-8294
36. Tamar van der Boom, Ryan T. Hayes, Yongyu Zhao, Patrick J. Bushard, Emily A. Weiss, and Michael R. Wasielewski
J. AM. CHEM. SOC. 2002, 124, 9582-9590
37. Alix Arnaud, Jol Belleney, Francois Boue, Laurent Bouteiller,* Geraldine Carrot, and Veronique Wintgens Angew. Chem. Int. Ed. 2004, 43, 1718–1721
38. J. H. Kirchhoff, M. R. Netherton, I. D. Hill, G. C. Fu,
J. Am. Chem. Soc., 2002, 124, 13662-13663.
39. X. Cui, T. Qin, J.-R. Wang, L. Liu, Q.-X. Guo, Synthesis,
2007, 393-399.
40. S. Li, Y. Lin, J. Cao, S. Zhang, J. Org. Chem., 2007, 72,
4067-4072.
41. G. Altenhoff, R. Goddard, C. W. Lehmann, F. Glorius, Angew.
Chem. Int. Ed., 2003, 42, 3690-3693.
42. W.-J. Liu, Y.-X. Xie, Y. Liang, J.-H. Li, Synthesis, 2006,
860-864.
43. J. V. Kingston, J. G. Verkade, J. Org. Chem., 2007, 72,
2816-2822.
44. Marion, O. Navarro, J. Mei, E. D. Stevens, N. M. Scott,
S. P. Nolan, J. Am. Chem. Soc., 2006, 128, 4101-4111.
45. Billingsley, K. W. Anderson, S. L. Buchwald, Angew. Chem.
Int. Ed., 2006, 45, 3484-3488.
46. C. Song, Y. Ma, Q. Chai, C. Ma, W. Jiang, M. B. Andrus,
Tetrahedron, 2005, 61, 7438-7446.
47. A. S. Guram, X. Wang, E. E. Bunel, M. M. Faul, R. D. Larsen,
M. J. Martinelli, J. Org. Chem., 2007, 72, 5104-5112.
48. J. Baxter, D. Steinhuebel, M. Palucki, I. W. Davies,
Org. Lett., 2005, 7, 215-218.
49. K. R. Buszek, N. Brown, Org. Lett., 2007, 9, 707-710.
50. J. K. Stille, K. S. Y. Lau, Acc. Chem. Res. 1977, 10,
434–442.
51. A. L. Casado, P. Espinet, Organometallics 1998, 17,
954–959.
52. B. H. Ridgway, K. A. Woerpel, J. Org. Chem. 1998, 63,
458–460.
53. 史銘翔;”含1,3,4-二唑吡啶衍生物之合成及發光性質研究”
國立成功大學化學研究所碩士論文,民國93年.