Please use this identifier to cite or link to this item: http://hdl.handle.net/11455/16922
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dc.contributor張啟光zh_TW
dc.contributorChi-Kwong Changen_US
dc.contributor.advisorChen-Yu Yehen_US
dc.contributor.advisor葉鎮宇zh_TW
dc.contributor.author王綸鴻zh_TW
dc.contributor.authorWang, Lun-Hongen_US
dc.contributor.other中興大學zh_TW
dc.date2012zh_TW
dc.date.accessioned2014-06-06T06:56:40Z-
dc.date.available2014-06-06T06:56:40Z-
dc.identifierU0005-2807201115514200zh_TW
dc.identifier.citation第一章 參考資料 1.Flak, J. -E., Ed. Porphyrins and Metalloporphyrins, Elsevier: Amsterdam, 1964. 2.Dolphin D., Ed. The Porphyrins, Academic Press: New York, 1978. 3.Kadish, K.-M.; Smith, K. M.; Guilard, R. Ed. The Porphyrin Handbook, 2000, 1. 4.Boudif, A.; Momenteau, M. J. Chem. Soc., Chem. Commun. 1994, 2096. 5.Plater, M.-J.; Aiken, S.; Bourhill, G. Tetrahedron 2002, 58, 2405. 6.Chio, M. S.; Yamazaki, T.; Yammazaki, I.; Aida, T. Angew. Chem. Int.Ed. 2004, 43, 150. (b) Holten, D.; Bocian, D. F.; Lindsey, J. S. Acc. Chem. Res. 2002, 35, 57. (c) Loewe, R. S.; Lammi, R. K.; Dier, J. R.; Kirmaier, C.; Holten, D.; Lindsey, J. S. J. Mater. Chem. 2002, 12, 1530. 7.(a) Anderson, H.-L. Chem. Commun. 1999, 2323. (b) Furutsu, D.; Satake, A.; Kobuke, Y. Inorg. Chem. 2005, 44, 4460. (c) Osuka, A.; Tsuda, A. Science, 2001, 293, 79. (d) Imahori, H. J. Phys. Chem.. B. 2004, 108, 6130. 8.Lee, C. -H.; Yoon, H.; Jang, W. -D. Chem. Eur. J. 2009, 15, 9972. 9.(a) Colluman, J. -P. J. Am. Chem. Soc. 1999, 121, 460. (b) Colluman, J. -P. J. Am. Chem. Soc. 1995, 117, 692. 10.(a) Beljonne D.; O’Keefe G. E.; Hamer P. J.; Friend R. H.; Anderson H. L.; Br’edas J. L. J. Chem. Phys. 1997, 106, 9439. 11.Kessel, D.; Dougherty, T. J.; Chang, C. K. Photochem. Photobiol. 1991, 53, 475. 12.(a) Imahori, H.; Tamkki, K.; Araki, Y.; Sekiguchi, Y. ; Ito, O.; Sakata, Y.; Fukuzumi, S. J. Am. Chem. Soc. 2002, 124, 5165. (b) Hasobe, T.; Imahori, H.; Kamat, P. V.; Ahn, T. K.; Kim, S. K.; Kim, D.; Fujiimoto, A.; Hirakawa, T.; Fukuzumi, S. J. Am. Chem. Soc. 2005, 127, 1216. 13.駱立揚,九十五學年度國立交通大學研究所博士論文,2006. 14.Simpson, W. T. J. Chem. Phys. 1949, 17, 1218. 15.Gouterman, M., J. Mol. Spectroscopy 1961, 6, 138. 16.Dorough, G. D.; Miller, J. R.; Huennekens, F. M. J. Am. Chem. Soc. 1951, 73, 4315. 17.Schmid, D.; Ruckh, M.; Grunwald, F.; Schock, H. W. Appl. Phys. Lett. 1993, 73, 2903. 18.Pankove, J. I., Ed. Optical Processes in Semiconductors, Dover, 1971. 19.Chapin, D. M.; Fuller, C. S.; Pearson, G. L. 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K.; Penchy, P.; Grätzel, M. Chem. Commum. 1997, 1705. 31.Nazeeruddin, M. K.; Zakeeruddin, S. M.; Humphrey-Baker, R.; Jirousek, M.; Liska, P.; Vlachopoulos, N.; Shklover, V.; Fischer, C.-H.; Grätzel, M. Inorg. Chem. 1999, 38, 6298. 32.Grätzel, M. Journal of Photochemistry and Photobiology C-Phhotochemistry Reviews. 2003, 4, 145. 33.(a) Wu, C.-G.; Ho, K.-C.; Angew. Chem. 2008, 7342. (b) Chen, C.-Y.; Pootrakulchote, N.; Wu, S.-J.; Wang, M.; Li, J.-Y.; Tsai, J.-H.; Wu, C.-G.; Zakeeruddin, S. M.; Grätzel, M. J. Phys. Chem. C. 2009, 20752. 34.(a) Choi, H.; Baik, C.; Kang, S. O.; Ko, J.; Kang, M. S.; Nazeeruddin, Md. K.; Grätzel, M. Angew. Chem. Int. Ed. 2008, 47, 327. (b) Hwang, S.; Lee, J. H.; Park, C.; Lee, H.; Kim, C.; Lee, M.-H.; Lee, W.; Park, J.; Kim, K.; Park, N.-G.; Kim, C.; Chem. Commun. 2007, 4887. (c) Ito, S.; Miura, H.; Uchida, S.; Takata, M.; Sumioka, K.; Liska, P.; Comte, P.; Pechy, P.; M. Grätzel, Chem. Commun. 2008, 5194. (d) Wang, Z. S.; Cui, Y.; Dan-oh, Y.; Kasada, C.; Shinpo, A.; Hara, K.; J. Phys. Chem. C 2007, 111, 7224. 35.Clifford, J. N.; Yahioglu,G.; Milgrom,L. R.; Durran, J. R. Chem. Commum. 2002, 1260. 36.Nazeeruddin, M. K.; Humphry-Baker, R.; Officer, D. L.; Campbell, W. M.; Burrell, A. K.; Grätzel, M. Langmuir 2004, 20, 6514. 37.Wang, Q.; Campbell, W. M.; Bonfantani, E. E.; Jolley, K. W.; Officer, D. L.; Walsh, P. J.; Gordon, K.; Humphry-Baker, R.; Nazeeruddin, M. J.; Grätzel, M . J. Phys. Chem. B 2005, 109, 15397. 38.Schmidt-Mende, L.; Campbell, W. M.; Wang Q.; Jolley, K. W.; Officer, D. L.; Nazeeruddin, M. J.; Grätzel, M. Chem. Phys. Chem. 2005, 6, 1253. 39.Eu, S.; Hayashi, S.; Umeyama, T.; Oguro, A.; Kawasaki, M.; Kadota, N.; Matano, Y.; Imahori, H. J. Phys. Chem. C 2007, 111, 3528. 40.Takana, M.; Hayashi, S.; Eu, S.; Umeyama, T.; Matano, Y.; Imahori, H. Chem.Commun. 2007, 2069. 41.Eu, S.; Hayashi, S.; Umeyama, T.; Matano, Y.; Araki, Y.; Imahori, H. J. Phys. Chem. C 2008, 112, 4396. 42.Hayashi, S.; Takana, M.; Hayashi, H.; Eu, S.; Umeyama, T.; Matano, Y.; Araki, Y.; Imahori, H. J. Phys. Chem. C. 2008, 112, 15576. 43.Lee, C.-W.; Lu, H.-P.; Lan, C.-M.; Huang, Y.-L.; Liang, Y.-R.; Yen, W.-N.; Liu, Y.-C.; Lin, Y.-S.; Eric Diau, W.-G.; Yeh, C.-Y. Chem. Eur. J. 2009, 15, 1403. 44.Lu, H.-P.; Mai, C.-L.; Tsia, C.-Y.; Hsu, D.-J.; Hsieh, C.-P.; Chiu, C.-L.; Yeh, C.-Y.; Eric Diau, W.-G. Phys. Chem. Chem. Phys. 2009, 11, 10270. 45.Wang, C.-L.; Chang, Y.-C.; Lan, C.-M.; Lo, C.-F.; Eric Diau, W.-G.; Lin, C.-Y. Energy Environ. Sci. 2011, 4, 1788. 46.Hsieh, C.-P.; Lu, H.-P.; Chiu, C.-L.; Lee, C.-W.; Chuang, S.-H.; Mai, C.-L.; Yen, W.-N.; Hsu, S.-J.; Eric Diau, W.-G.; Yeh, C.-Y. J. Mater. Chem., 2010, 6, 1127. 47.Bessho, T.; Zakeeruddin, S. M.; Yeh, C.-Y. ; Eric Diau, W.-G.; Grätzel, M. Angew. Chem. Int.Ed. 2010, 49, 1. 第二章 參考資料 1.Ka, J. W.; Lee, C. H. Tetrahedron Lett. 2000, 41, 4609. 2.Plater, M. J.; Aiken, S.; Bourhill, G. Tetrahedron 2002, 58, 2405. 3.Lee, C. Y. ; Hupp, J. T. Langmuir 2010, 26, 3760. 4.Odom, S. A.; Lancaster, K.; Beverina, L.; Lefler, K. M.; Thompson, N.J.; Coropceanu, V.; Marder, S. R.; Barlow, S. Chem. Eur. J. 2007, 13,9367. 5.Li, F.; Yang, K.; Tyhonas, J. S.; Maccrum, K. A.; Lindsey, J. S. Tetrahedron 1997, 53, 12339. 6.Susumu, K.; Therien, M. J. J. Am. Chem. Soc. 2002, 124, 8550. 7.Susumu, K.; Frail, P. R.; Angiolillo, P. J.; Therien, M. J. J. Am. Chem.Soc. 2006, 128, 8380. 8.Chen, Y.; Zhang, X. P. J. Org. Chem. 2003, 68, 4432. 9.Sasaki, T.; Morin, J.-F.; Lu, M.; Tour, J. M. Tetrahedron Lett. 2007, 48, 5817. 10.Ragoussis, N. Tetrahedron Lett. 1987, 28, 93. 11.Morriello, G. J.; David, R. J.; Moyes, C. R. HETEROCYCLYL-SUBSTITUTED ANTI-HYPERCHOLESTEROLEMIC COMPOUNDS: WO 2008/057336. 2008-05-15. 12.Song, A.; Wang, X.; Lam, K. S. Tetrahedron Lett. 2003, 44, 1755. 13.Krebs, F. C.; Jensen, T. J. Fluorine Chem. 2003, 120, 77. 14.Leroy, J. et al. J. Fluorine Chem. 2004, 125,1379. 15.M. Hunsen, Synthesis 2005, 2487. 16.Guha, S. K.; Obora, Y.; Ishihara, D.; Matsubara, H.;Ryu, I.; Ishii, Y. Adv.Synth.Catal. 2008, 350, 1323. 17.Bessho, T.; Zakeeruddin, S. M.; Yeh, C. Y.; Eric Diau, W. G.; Gratzel, M. Angew. Chem. Int. Ed. 2010, 49, 1. 18.Boomgaarden, W.; Vögtle, F.; Nieger, M.; Hupfer, H. Chem. Eur. J. 1999, 5, 345. 第三章參考資料 1.Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R. ; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yaztev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision C.02; Gaussian, Inc.:Wallingford, CT, 2004. 第六章參考資料 1.Ka, J. W.; Lee, C. H. Tetrahedron Lett. 2000, 41, 4609. 2.Plater, M. J.; Aiken, S.; Bourhill, G. Tetrahedron, 2002, 58, 2405. 3.Lee, C. Y. ; Hupp, J. T. Langmuir, 2010, 26, 3760. 4.Odom, S. A.; Lancaster, K.; Beverina, L.; Lefler, K. M.; Thompson, N. J.; Coropceanu, V.; Marder, S. R.; Barlow, S. Chem. Eur. J. 2007, 13, 9367. 5.Li, F.; Yang, K.; Tyhonas, J. S.; Maccrum, K. A.; Lindsey, J. S. Tetrahedron, 1997, 53, 12339. 6.Susumu, K.; Therien, M. J. J. Am. Chem. Soc. 2002, 124, 8550. 7.Susumu, K.; Frail, P. R.; Angiolillo, P. J.; Therien, M. J. J. Am. Chem.Soc. 2006, 128, 8380. 8.Chen, Y.; Zhang, X. P. J. Org. Chem. 2003, 68, 4432. 9.Sasaki, T.; Morin, J.-F.; Lu, M.; Tour, J. M. Tetrahedron Lett. 2007, 48, 5817. 10.Ragoussis, N. Tetrahedron Lett. 1987, 28, 93. 11.Morriello, G. J.; David, R. J.; Moyes, C. R. HETEROCYCLYL-SUBSTITUTED ANTI-HYPERCHOLESTEROLEMIC COMPOUNDS: WO 2008/057336. 2008-05-15. 12.Song, A.; Wang, X.; Lam, K. S. Tetrahedron Lett. 2003, 44, 1755. 13.Krebs, F. C.; Jensen, T. J. Fluorine Chem. 2003, 120, 77. 14.Leroy, J. et al. J. Fluorine Chem. 2004, 125,1379. 15.M. Hunsen, Synthesis, 2005, 2487. 16.Guha, S. K.; Obora, Y.; Ishihara, D.; Matsubara, H.;Ryu, I.; Ishii, Y. Adv.Synth.Catal. 2008, 350, 1323.zh_TW
dc.identifier.urihttp://hdl.handle.net/11455/16922-
dc.description.abstract我們成功的利用簡單的合成步驟合成出一系列具有不同拉電子單元的鋅紫質染料,並進一步應用在染料敏化太陽能電池上。由於此類的紫質染料受到拉電子單元的影響,使其UV-Vis吸收光譜均比YD2有變寬及紅位移的現象,但是由UV-Vis吸收光譜與emission計算結果HOMO-LUMO能階差卻沒有明顯的減小,而由DFT理論計算結果顯示,在LUMO時電子密度主要集中在拉電子單元,預期可以增加電子注入TiO2的效率,結果光電轉換率最佳的紫質染料為(27) ,僅有10.14%,無法有效的超越YD2(11%)。 由於以YD2為基本架構改良拉電子單元的紫質染料在光電轉換率上的表現不如預期,於是我們又另外設計並合成出一系列引入具有長的烷氧鏈的鋅紫質染料,其目的是用來減少染料分子間的堆疊,以及減少電解液進入紫質染料分子間,進而提升光電轉換率,我們相信若繼續修飾上不同的拉電子單元將對光電轉換率的提升有所幫助。zh_TW
dc.description.abstractA series of porphyrin dyes with various pull-units have been designed and synthesized for use as sensitizers in dye-sensitized solar cells (DSSC). Because of the pull-units, UV-vis absorption spectra of porphyrin show broadened and red-shifted Soret and Q bands with respect to those of reference porphyrin YD2. But the HOMO-LUMO gaps of porphyrins decrease insignificantly even the π conjugated system was extended. Quantum-chemical (DFT) calculations demonstrate electronic distribution of the LUMO mainly located on the pull-units, and that results in efficient electron injection. However, in this series, the best power conversion efficiency is 10.14% for (27) which still not effective beyond YD2(11%). Since the power conversion efficiency of modified porphyrin dyes which based on YD2 was not so high as we excepted, we designed and synthesized another series of porphyrin dyes. By modification of the long alkoxyl chains to prevent the porphyrin molecules from dye aggregation for an efficient electron injection and to form a blocking layer on TiO2 surface for a retarded charge recombination. We also hope to have better results by modification of various pull-units in this series.en_US
dc.description.tableofcontents第一章 緒論..............................................1 1-1 紫質簡介.............................................1 1-2 紫質吸收光譜原理.....................................4 1-3 太陽能電池的起源與發展...............................8 1-4 染料敏化型太陽能電池的起源..........................12 1-5 染料敏化太陽能電池之組成與工作原理..................13 1-6 染料敏化太陽能電池相關文獻回顧......................18 1-7 研究動機與方向......................................35 第一章 參考資料.........................................38 第二章 紫質合成.........................................41 2-1 紫質及其衍生物的合成................................41 2-2 拉電子單元的合成....................................46 2-3 鋅紫質染料的合成....................................49 第二章 參考資料.........................................56 第三章 結果與討論.......................................57 3-1 UV-vis光譜比較......................................57 3-2 電化學..............................................60 3-3 分子及軌域計算模型..................................65 3-4染料敏化太陽能電池之結果與討論.......................67 第三章參考資料..........................................70 第四章 結論.............................................71 第五章 未來展望.........................................73 第六章 實驗步驟.........................................74 6-1 藥品與儀器..........................................74 6-2 實驗步驟............................................77 第六章參考資料.........................................102 附錄...................................................104zh_TW
dc.language.isoen_USzh_TW
dc.publisher化學系所zh_TW
dc.relation.urihttp://www.airitilibrary.com/Publication/alDetailedMesh1?DocID=U0005-2807201115514200en_US
dc.subjectDye-Sensitized Solar Cellsen_US
dc.subject染料敏化太陽能電池zh_TW
dc.subjectPorphyrinsen_US
dc.subjectpull-unitsen_US
dc.subject紫質zh_TW
dc.subject拉電子單元zh_TW
dc.titleSynthesis of Porphyrins with Various Pull Units for Dye-Sensitized Solar Cellsen_US
dc.title應用於染料敏化太陽能電池具多樣化拉電子單元之紫質合成zh_TW
dc.typeThesis and Dissertationzh_TW
item.fulltextno fulltext-
item.languageiso639-1en_US-
item.openairetypeThesis and Dissertation-
item.cerifentitytypePublications-
item.openairecristypehttp://purl.org/coar/resource_type/c_18cf-
item.grantfulltextnone-
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