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標題: 具推拉電子基的紫質合成
The synthesis of porphyrins with electron-withdrawing and -donating groups
作者: 陳鴻儀
Cheng, Hong-Yi
關鍵字: porphyrins;紫質;electron-withdrawing;-donating groups;推拉電子基
出版社: 化學系所
引用: 參考資料 1. Omura, T.; Sato, R. J. Biol. Chem. 1994, 239, 2370. 2. Dophin, D. Ed. The porphyrins, New York, 1978. 3. Anderson, H. L. Chem. Commun. 1999, 2323-2330. 4. Kadish, K. M.; Smith , K. M.; Gruilard, R. Eds. The porphyrin handbook 2000, Vol. 1. 5. Vollmer, M. S.; Würthner, F.; Effenberger, F. ; Emele, P.; Meyer, D. U.; Stümpfig, T.; Port, H.; Wolf, H. C. Chem. Eur. J. 1998, 4, 260 -269 6. Kawao, M.; Ozawa, H.; Tanaka, H.; Ogawa, T. Thin Solid Films. 2006, 499, 23 – 28 7.Imahori, D.; Tamaki, K.; Araki, Y.; Sekiguchi, Y.; Ito, O.; Sakata, Y.; Fukuzumi, S. J. Am. Chem. Soc. 2002, 124, 5165-5174 8.Zhang, T. G.; Zhao, Y.; Asselberghs, I.; Persoons, A.; Clays, K ; Therien, M. J. J. Am. Chem .Soc. 2005, 127, 9710-9720 9. Kadish, K. M.; Smith, K. M.; Gruilard,R. Eds. The porphyrin handbook 2000, 8, 156 10. Robertson, N; McGowan, C. A. Chem. Soc. Rev. 2003, 32, 96–103 11. Launay, J. P. Chem. Soc. Rev., 2001, 30, 386-397 12. Reimers, J. R.; Hall, L. E ; Crossley, M. J ; Hush , N. S. J. Phys. Chem. A 1999, 103, 4385-4397 13. Aratani, N.; Cho, H. S.; Ahn, T. K.; Cho, S.; Kim, D.; Sumi, H. ; Osuka, A. J. Am. Chem. Soc. 2003, 125, 9668-9681 14. Ogawa, K.; Zhang, T.; Yoshihara, K.; Kobuke, Y. J. Am. Chem. Soc. 2002, 124, 22-23 15. Sessler, J. L.; Wangt, B.; Harriman, A. J. Am. Chem. Soc. 1995,117, 704-714 16. Priyadarshy, S.;Therien, M. D.; Beratan, D. N. J. Am. Chem. Soc. 1996, 118, 1504-1510 17. Arnold, D. P.; Hartnell, R. D.; Heath, G.A.; Newbya, L.; Webster, R.D. Chem. Comm., 2002, 754–755 18. (a) Choi, M. S.; Yamazaki, T.; Yamazaki, I.; Aida, T. Angew. Chem. 2004, 43, 150 –158 (b) Yu, L.; Lindsey, J. S. Tetrahedron, 2001, 57, 9285-9298 19. Ambroise, A.; Wagner, R. W.; Rao, P. D.; Riggs, J. A.; Hascoat, P.; Diers, J. R.; Seth, J.; Lammi, R. K.; Bocian, D. F.; Holten, D.; Lindsey,J. S. Chem. Mater. 2001, 13, 1023-1034 20. Susumu, K.; Therien, M. J. J. Am. Chem. Soc. 2002, 124, 8550-8552, and references 21. Priyadarshy, S.; Therien, M. J.; Beratan, D. N. J. Am. Chem. Soc. 1996, 118, 1054. 22. LeCours, S. T.; Guan, H. W.; DiMagno, S. G.; Wang, C. H.; Therin, M. J. J. Am. Chem. Soc. 1996, 118, 1497-1503. 23. Hasselman, G. M.; Watson, D. F.; Stromberg, J. R.; Bocian, D. F.; Holten, D.; Lindsey, J. S.; Meyer, G. J. J. Phys. Chem. B. 2006, 110, 25430-25440 24. Tomizaki, K. Y.; Loewe, R, S.; Kirmaier, C.; Schwartz, J. K.; Retsek, J. L.; Bocian, D. F.; Holten, D; Lindsey, J. S. J. Org. Chem. 2002, 67, 6519-6534 25. Ka, J. W.; Lee, C. H. Ttrahedron Letter, 2000, 41, 4609. 26. Plater, M. J.; Aiken, S.; Bourhill, G. Ttrahedron, 2002, 58, 2405 27. Plater, M. J.; Aiken, S.; Bourhill, G. Ttrahedron, 2002, 58, 2415 28. Li, F.;Yang, K.;Tyhonas, J. S.; Maccrum, K. A.;Lindsey, J. S. Ttrahedron, 1997, 53, 12339 29. Monnereau, C.;Blert, E.; Montembault, V.; Fontaine, L.; Odobel, F. Ttrahedron, 2005, 61, 10113 30. Susumu, K.; Frail, P. R.; Angiolillo, P. J.; Therien, M. J. J. Am. Chem. Soc. 2006, 128, 8380-8381, and references 31. Ray, P. C.; Bonifassi, P.; Leszczynski, J. J. Phys. Chem. A. 2008, 112, 2870- 2879 32. Tomizaki, K. Y; Thamyongkit, P.; Loewe, R. S.; Lindsey, J. S. Tetrahedron, 2003, 59, 1191-1207 33. Gosztola, D.; Niemczyk, M. P.; Wasielewski , M. R. J. Am. Chem. Soc. 1998, 120, 5118-5119, and reference

我們合成了一系列Donar-acceptor具推拉電子的紫質非線性分子,紫質在D和A之間扮演著能提供強的電子偶合的橋基。有機分子若是具有強的電子推拉電子基以及大的π- 共軛系統的結構,都會表現出高的β值,所以這裡我們利用三鍵的乙炔基來擴大系統的π- 共軛性。這些樣品的製備是利用Sonogashira cross-coupling。

另外我們也合成一系列紫質染料應用於太陽能電池的研究。我們可以藉由觀測紫外-可見光光譜以及螢光光譜來探討紫質和perylene之間能量傳遞的關係。我們相信紫質- perylene系統在太陽能電池領域中,可以有不錯的表現。


A series of zinc porphyrins with both electron donor and acceptor groups were synthesized for use as NLO chromophores in optoelectronic materials and devices.The porphyrin bridge connecting D and A groups should provide a pathway for strong electronic coupling between D and A. Organic molecules with strong electron donor and electron aceptor groups that are connected by a large conjugated π- electron system usually show high β values, so we utilized a ethynyl unit to extendπ- conjugation of the systems. The preparation of porphyrins with ethyne-linked functional groups can be achieved by the
sonogashira cross-coupling method.

Light - harvesting arrays that consist of porphyrin and perylene units were synthesized. These arrays show broad absorption in the visible region. The energy transfer between porphyrin and perylene pigments was investigated by fluorescence spectroscopy. We except that porphyrin - perylene systems have high energy conversion efficiency in
solar cells.
其他識別: U0005-2208200813044300
Appears in Collections:化學系所

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