Please use this identifier to cite or link to this item: http://hdl.handle.net/11455/14496
標題: 應用於染料敏化太陽能電池具多樣化推、拉電子基之紫質合成
Synthesis of Porphyrins with Various Push-Pull Units for Dye-Sensitized Solar Cells
作者: 李旋維
Lee, Hsuan-Wei
關鍵字: 染料敏化太陽能電池
Porphyrin
推、拉電子基
紫質
Push-Pull Units
Dye-Sensitized Solar Cells
YD2-o-C8
DSSC
出版社: 化學系所
引用: 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. J. Appl. Phys. 1954, 51, 676. 20.Meyers, P.; V Albright, S. P. Prog. Photovolt. Res. Appl. 2000, 8, 161. 21.Schock, H. W.; Noufi, R. Prog. Photovolt. Res. Appl. 2000, 8, 151. 22.(a) Beaumont, N. ; Hancox, I. ; Sullivan, P. ; Hatton, R. A. ; Jones, T. S., Energy Environ. Sci. 2011, 4, 1708. (b) Dou, L. ; Gao, J. ; Richard, E. ; You, J. ; Chen, C.-C. ; Cha, K.C. ;He, Y. ; Li, G. ; Yang, Y., J. Am. Chem. Soc. 2012, 134 23.Gratzel, M., Acc. Chem. Res. 2009, 42, 1288. 24.Regan, B. O.; Gratzel, M. Nature 1991, 353, 737. 25.Matsumura, M.; Matsudaira, S.; Takata, M.; Yanagida, H.; Tsubomura, H. Ind. Eng. Chem. Prod. Res. Dev. 1980, 19, 415. 26.(a) Clifford, J. N.; Palomares, E.; Nazeeruddin, M. K.; Gratzel, M.; Nelson, J.; Li, X.; Long, N. J.; Durrant, J. R. J. Am. Chem. Soc. 2004, 126, 5225. (b) A. Yella, H.-W. Lee, H.N. Tsao, C. Yi, A.K. Chandiran, M.K. Nazeeruddin, E.W. Diau, C.-Y. Yeh, S.M. Zakeeruddin, M. Gratzel, Science, 2011, 334, 629-634. 27.(a) Robertson, N. Angew. Chem. Int. Ed. 2006, 45, 2338. Gratzel, M., J. Am. Chem. Soc. 1993, 115,6382-6390. (b) Gratzel, M. Journal of Photochemistry and Photobiology C-Phhotochemistry Reviews 2003, 4, 145. 28.Kalyanasundaram, K.; Gratzel, M. Coord. Chem. Rev. 1998, 177, 347. 29.Tsubomura, H.; Matsumura, M.; Nomura, Y.; Amamiya, T. Nature(London), 1976, 261, 402. 30.Nazeeruddin, M. K.; Penchy, P.; Gratzel, 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.; Gratzel, M. Inorg. Chem. 1999, 38, 6298. 32.Gratzel, 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.; Gratzel, M. J. Phys. Chem. C., 2009, 20752. 34.(a) Choi, H.; Baik, C.; Kang, S. O.; Ko, J.; Kang, M. S.; Nazeeruddin, Md. K.; Gratzel, M. Angew. Chem. Int. Ed,. 2008, 47, 327. (b) Wang, Z.-S.; Cui, Y.; Dan- oh, Y.; Kasada, C.; Shinpo, A.; Hara, K., J. Phys. Chem. C, 2007, 111, 7224. (c) Liu, W.-H.; Wu, I.-C.; Lai, C.-H.; Lai, C.-H.; Chou, P.-T.; Li, Y.-T.; Chen, C.-L.; Hsu, Y.-Y.; Chi, Y., Chem Commun., 2008, 41, 5152-4 (d) Zeng, W.-D.; Cao, Y.-M.; Bai, Y.; Wang, Y.-H.; Shi, Y.-S.; Zhang, M.; Wang, F.-F.; Pan, C.-Y.; Wang, P.; Chem. Mater., 2010, 22, 1915-1925 (e) Edvinsson, T.; Li, C.; Pschirer, N.; Schoneboom, J.; Eickemeyer, F.; Sens, R.;Boschloo, G.; Herrmann, A.; Mullen, K.; Hagfeldt, A., J. Phys. Chem. C, 2007, 111, 15137–15140. 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.; Gratzel, 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.; Gratzel, 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.; Gratzel, M., Chem. Phys. Chem., 2005, 6, 1253. 39.Ishida, M. I., Park, S.-W.; Hwang, D.; Koo, Y.-B.; Sessler, J. L.; Kim, D.-Y.; Kim, D.-H., J. Phys. Chem. C., 2011, 114, 10656–10665. 40.Eu, S.; Hayashi, S.; Umeyama, T.; Oguro, A.; Kawasaki, M.; Kadota, N.; Matano, Y.; Imahori, H., J. Phys. Chem. C., 2007, 111, 3528. 41.Takana, M.; Hayashi, S.; Eu, S.; Umeyama, T.; Matano, Y.; Imahori, H., Chem.Commun., 2007, 2069. 42.Eu, S.; Hayashi, S.; Umeyama, T.; Matano, Y.; Araki, Y.; Imahori, H., J. Phys. Chem. C., 2008, 112, 4396. 43.Hayashi, S.; Takana, M.; Hayashi, H.; Eu, S.; Umeyama, T.; Matano, Y.; Araki, Y.; Imahori, H., J. Phys. Chem. C., 2008, 112, 15576. 44.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. 45.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. 46.Chen, H.-Y.; Lu, H.-P.; Lee, C.-W.; Chuang, S.-W.; Eric Diau, W.-G.; Yeh, C.-Y., J. Chin. Chem. Soc., 2010, 57, 1141-1146. 47.Hsieh, C.-P.; Lu, H.-P.; C S. Yanagida, Y.-H. Yu, K. Manseki, Acc. Chem. Res., 2009, 42, 1827-1838. 48.Nusbaumer, H.; Moser, J. E.; Zakeeruddin, S. M.; Nazeeruddin, M. K.; Gratzel, M., J. Phys. Chem. B, 2001, 105, 10461–10464. 49.Hamann, T. W., Dalton Trans., 2012, 41, 3111. 50.Hsieh, C.-P.; Mia, 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. 51.Bessho, T.; Zakeeruddin, S. M.; Yeh, C.-Y. ; Eric Diau, W.-G.; Gratzel, M. Angew. Chem. Int.Ed. 2010, 49, 1. 52.(a).McGehee, M. D., Science, 2011, 334, 607. (b).Yella, A.; Lee, H.-W.; Tsao, H. N. ; Yi, C.;Chandiran, A. K.; Nazeeruddin, M. K.; Diau, E.W.; Yeh, C.-Y.; Zakeeruddin, S. M.; Gratzel, M., Science, 2011, 334, 629-634. 53.Wu, S.-L.; Lu, H.-P.; Yu, H.-T.; Chuang, S.-H.; Chiu, C.-L.; Lee, C.-W.; Eric Diau, W.-G.; Yeh, C.-Y., Energy Environ. Sci., 2010, 3, 949-955. 54.Lee, C.-W.; Lu, H.-P.; Reddy, N.M.; Lee, H.-W.; Diau, E.W.-G.; Yeh, C.-Y., Dyes and Pigments, 2011, 91, 317-323. 55.Mathew, S.; Iijima, H.;Toude, Y.; Umeyama, T.; Matano, Y.; Ito, S.; Tkachenko, N.V.; Lemmetyinen, H.; Imahori, H., J. Phys. Chem. C, 2011, 115,14415-14424. 56.王綸鴻,一百學年度國立中興大學研究所碩士論文,2011. 57.Graetzel, M., J. Phys. Chem., 1993, 97, 6272–6277. 58.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. 第二章 參考資料 1.Ka, J. W.; Lee, C. H., Tetrahedron Lett., 2000, 41, 4609. 2.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. 3.B. Mohr, V. Enkelmann, G. Wegner, J. Org. Chem., 1994, 59, 635. 4.(a) Splan, K. E.; Hupp, J. T., Langmuir, 2004, 20, 10560. (b) Lee, C. Y. ; Hupp, J. T. Langmuir 2010, 26, 3760. 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.(a) Boomgaarden, W.; Vogtle, F.; Nieger, M.; Hupfer, H. Chem. Eur. J. 1999, 5, 345. (b) A. Yella, H.-W. Lee, H. N. Tsao, C. Yi, A. K. Chandiran, M. K. Nazeeruddin, E.W. Diau, C.-Y. Yeh, S.M. Zakeeruddin, M. Gratzel, Science, 2011, 334, 629-634. 10.Bessho, T.; Zakeeruddin, S. M.; Yeh, C.-Y. ; Eric Diau, W.-G.; Gratzel, M. Angew. Chem. Int.Ed. 2010, 49, 1. 11.A. Yella, H.-W. Lee, H.N. Tsao, C. Yi, A.K. Chandiran, M.K. Nazeeruddin, E.W. Diau, C.-Y. Yeh, S.M. Zakeeruddin, M. Gratzel, Science, 2011, 334, 629-634. 12.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.; 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. 13.Tsao, H. N., ChemSusChem , 2011, 4, 591. 14.Hardin, B. E.; Sellinger, A.; Moehl, T.; Robin H. B.; Moser, J.-E.; Wang, P.; Zakeeruddin, S. M.; Gratzel, M.; McGehee M. D., J. Am. Chem. Soc. 2011, 133, 10662–10667. 15.Liu, Y.-H.; Lin, H.; Dy, J. T.; Tamaki, K.; Nakazaki, J.; Nakayama, D.; Uchida, S.; Kuboa, T.; Segawa, H., Chem. Commun., 2011, 47, 4010–4012. 16.Michinobu, T.; Inui, J.; Nishide, H., Polymer Journal, 2010, 42, 575-582. 17.Jeong, M.J.; Park, J.-H.; Lee, C.-J.; Chang, J.-Y., Org. Lett., 2006, 8, 2221–2224. 18.Eggers, F.; Luning, U., Eur. J. Org. Chem., 2009, 2328–2341. 19.Thomas, G.; Ruediger, S.; Sophia, E., Bibliographic data: WO2009141288, 2009-11-26. 20.Lee, C.-W.; Lu, H.-P.; Reddy, N.M.; Lee, H.-W.; Diau, E.W.-G.; Yeh, C.-Y., Dyes and Pigments, 2011, 91, 317-323. 21.Kawai, K.; Kawabata, K.; Tojo, S.; Majima, S., Bioorganic & Medicinal Chemistry Letters, 2002, 12, 2363–2366. 22.Tomizaki, K. Y; Thamyongkit, P.; Loewe, R. S.; Lindsey, J. S., Tetrahedron, 2003, 59, 1191-1207. 23.Gosztola, D.; Niemczyk, M. P.; Wasielewski , M. R., J. Am. Chem. Soc. 1998, 120, 5118-5119. 24.Edvinsson, T.; Li, C.; Pschirer, N.; Schoneboom, J.; Eickemeyer, F.; Sens, R.;Boschloo, G.; Herrmann, A.; Mullen, K.; Hagfeldt, A., J. Phys. Chem. C, 2007, 111, 15137–15140. 25.Fulop, A.; Arian, D.; Lysenko, A.; Mokhir, A., Bioorganic & Medicinal Chemistry Letters, 2009, 19, 3104–3107. 26.Ma, L.; Jiao, P.;Zhang, Q.; Xu, J.,Tetrahedron Asymmetry, 2005, 16, 3718–3734. 27.Pacchioni, M.; Cornia, A.; Fabretti, A. C.; Zobbi, L.; Bonacchi, D.; Caneschi, A.; Chastanet, G.; Gatteschib, D.; Sessoli, R.,Chem. Commun., 2004, 2604-2605. 28.Kim, H.-S.; Bae, C.-O.; Kwon, J.-Y.; Kim, S.-K.; Choi, M.; Yoon, J., Bull. Korean Chem. Soc., 2001, 22, 929. 29.Lu, G.; Usta, H.; Risko, C.; Wang, L.; Facchetti, A.; Ratner, M. A.; Marks, T. J., J. Am. Chem. Soc., 2008, 130, 7670–7685. 30.Zeng, W.; Cao, Y.; Bai, Y.; Wang, Y.; Shi, Y.; Zhang, M.; Wang, F.; Pan, C.; Wang, P., Chem. Mater., 2010, 22, 1915-1925. 31.Liu, W.-H.; Wu, I.-C.; Lai, C.-H.; Lai, C.-H.; Chou, P.-T.; Li, Y.-T.; Chen, C.-L.; Hsub, Y.-Y.; Chi, Y., Chem. Commun., 2008, 5152–5154. 32.Mohanakrishnan, A. K.; Hucke, A.; Lyon, M. A.; Lakshmikantham, M. V.; Cava, M. P., Tetrahedron, 1999, 55, 11745. 33.Raimundo, J. M.; Blanchard, P.;Nuria, G. P.; Mercier, N.; Isabelle, L. R.; Hierle, R.; Roncali, J., J. Org. Chem. 2002, 67, 205-218. 34.Campbell, W. M.; Burrell, A. K.; Officer, D. L.; Jolley, K. W., Coord.Chem. Rev. 2004, 248, 1363 35.王綸鴻,一百學年度國立中興大學研究所碩士論文,2011. 36.Mathew, S.; Iijima, H.;Toude, Y.; Umeyama, T.; Matano, Y.; Ito, S.; Tkachenko, N.V.; Lemmetyinen, H.; Imahori, H., J. Phys. Chem. C, 2011, 115,14415-14424. 37.Tachibana, Y.; Haque, S. A.; Mercer, I. P.; Durrant, J. R.; Klug, D. R., J. Phys. Chem. B, 2000, 104, 1198-1205. 38.Oguro, K.; Hirai, Y., Japanese Patent, JP2009, 137894. 39.Hori, H.; Nagasawa, H.; Ishibashi, M.; Uto, Y.; Hirata, A.; Saijo, K.; Ohkura, K.; Kirk, K. L.; Uehara, Y. Bioorg. Med. Chem, 2002, 10, 3257-3265. 40.Rabai, J.; Szabo, D.; Borbas, E. K.; Kovesi, I.; Kovesdi, I.; Csampai, A.; Gomory, A.; Pashinnik, V. E.; Shermolovich, Y. G., Journal of Fluorine Chemistry, 2002, 114, 199–207. 41.Shetonde, O.-M.; Wendimagegn, M.; Merhatibeb, B.; Kerstin, A. M.; Berhanu, M. A., Bioorganic & Medicinal Chemistry, 2010, 18, 2464–2473. 42.Dube, H.; Kasumaj, B.; Calle, C.; Felber, B.; Saito, M.; Jeschke, G.; Diederich, F., Chem. Eur. J. 2009, 15, 125-135. 43.Borbas, K. E.; Chandrashaker, V.; Muthiah, C.; Kee, H. L.; Holten, D.; Lindsey, J. S., J. Org. Chem. 2008, 73, 3145-3158. 第五章 參考資料 1.Ka, J. W.; Lee, C. H., Tetrahedron Lett., 2000, 41, 4609. 2.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. 3.B. Mohr, V. Enkelmann, G. Wegner, J. Org. Chem., 1994, 59, 635. 4.(a) Splan, K. E.; Hupp, J. T., Langmuir, 2004, 20, 10560. (b) Lee, C. Y. ; Hupp, J. T. Langmuir 2010, 26, 3760. 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.(a) Boomgaarden, W.; Vögtle, F.; Nieger, M.; Hupfer, H. Chem. Eur. J. 1999, 5, 345. (b) A. Yella, H.-W. Lee, H. N. Tsao, C. Yi, A. K. Chandiran, M. K. Nazeeruddin, E.W. Diau, C.-Y. Yeh, S.M. Zakeeruddin, M. Grätzel, Science, 2011, 334, 629-634. 10.Liu, Y.-H.; Lin, H.; Dy, J. T.; Tamaki, K.; Nakazaki, J.; Nakayama, D.; Uchida, S.; Kuboa, T.; Segawa, H., Chem. Commun., 2011, 47, 4010–4012. 11.Michinobu, T.; Inui, J.; Nishide, H., Polymer Journal, 2010, 42, 575-582. 12.Jeong, M.J.; Park, J.-H.; Lee, C.-J.; Chang, J.-Y., Org. Lett., 2006, 8, 2221–2224. 13.Eggers, F.; Lüning, U., Eur. J. Org. Chem., 2009, 2328–2341. 14.Thomas, G.; Ruediger, S.; Sophia, E., Bibliographic data: WO2009141288, 2009-11-26. 15.Lee, C.-W.; Lu, H.-P.; Reddy, N.M.; Lee, H.-W.; Diau, E.W.-G.; Yeh, C.-Y., Dyes and Pigments, 2011, 91, 317-323. 16.Kawai, K.; Kawabata, K.; Tojo, S.; Majima, S., Bioorganic & Medicinal Chemistry Letters, 2002, 12, 2363–2366. 17.Tomizaki, K. Y; Thamyongkit, P.; Loewe, R. S.; Lindsey, J. S., Tetrahedron, 2003, 59, 1191-1207. 18.Gosztola, D.; Niemczyk, M. P.; Wasielewski , M. R., J. Am. Chem. Soc. 1998, 120, 5118-5119. 19.Edvinsson, T.; Li, C.; Pschirer, N.; Schoneboom, J.; Eickemeyer, F.; Sens, R.;Boschloo, G.; Herrmann, A.; Mullen, K.; Hagfeldt, A., J. Phys. Chem. C, 2007, 111, 15137–15140. 20.Fulop, A.; Arian, D.; Lysenko, A.; Mokhir, A., Bioorganic & Medicinal Chemistry Letters, 2009, 19, 3104–3107. 21.Ma, L.; Jiao, P.;Zhang, Q.; Xu, J.,Tetrahedron Asymmetry, 2005, 16, 3718–3734. 22.Pacchioni, M.; Cornia, A.; Fabretti, A. C.; Zobbi, L.; Bonacchi, D.; Caneschi, A.; Chastanet, G.; Gatteschib, D.; Sessoli, R.,Chem. Commun., 2004, 2604-2605. 23.Kim, H.-S.; Bae, C.-O.; Kwon, J.-Y.; Kim, S.-K.; Choi, M.; Yoon, J., Bull. Korean Chem. Soc., 2001, 22, 929. 24.Lu, G.; Usta, H.; Risko, C.; Wang, L.; Facchetti, A.; Ratner, M. A.; Marks, T. J., J. Am. Chem. Soc., 2008, 130, 7670–7685. 25.Zeng, W.; Cao, Y.; Bai, Y.; Wang, Y.; Shi, Y.; Zhang, M.; Wang, F.; Pan, C.; Wang, P., Chem. Mater., 2010, 22, 1915-1925. 26.Liu, W.-H.; Wu, I.-C.; Lai, C.-H.; Lai, C.-H.; Chou, P.-T.; Li, Y.-T.; Chen, C.-L.; Hsub, Y.-Y.; Chi, Y., Chem. Commun., 2008, 5152–5154. 27.Mohanakrishnan, A. K.; Hucke, A.; Lyon, M. A.; Lakshmikantham, M. V.; Cava, M. P., Tetrahedron, 1999, 55, 11745. 28.Raimundo, J. M.; Blanchard, P.;Nuria, G. P.; Mercier, N.; Isabelle, L. R.; Hierle, R.; Roncali, J., J. Org. Chem. 2002, 67, 205-218. 29.王綸鴻,一百學年度國立中興大學研究所碩士論文,2011. 30.Oguro, K.; Hirai, Y., Japanese Patent, JP2009, 137894. 31.Hori, H.; Nagasawa, H.; Ishibashi, M.; Uto, Y.; Hirata, A.; Saijo, K.; Ohkura, K.; Kirk, K. L.; Uehara, Y. Bioorg. Med. Chem, 2002, 10, 3257-3265. 32.Rabai, J.; Szabo, D.; Borbas, E. K.; Kovesi, I.; Kovesdi, I.; Csampai, A.; Gomory, A.; Pashinnik, V. E.; Shermolovich, Y. G., Journal of Fluorine Chemistry, 2002, 114, 199–207. 33.Shetonde, O.-M.; Wendimagegn, M.; Merhatibeb, B.; Kerstin, A. M.; Berhanu, M. A., Bioorganic & Medicinal Chemistry, 2010, 18, 2464–2473. 34.Dube, H.; Kasumaj, B.; Calle, C.; Felber, B.; Saito, M.; Jeschke, G.; Diederich, F., Chem. Eur. J. 2009, 15, 125-135. 35.Borbas, K. E.; Chandrashaker, V.; Muthiah, C.; Kee, H. L.; Holten, D.; Lindsey, J. S., J. Org. Chem. 2008, 73, 3145-3158.
摘要: 先前本實驗室已成功合成出紫質主體苯環上的meta-位置為t-butyl,且具有推、拉電子基的的鋅紫質染料,並進一步應用在於染料敏化太陽能電池(DSSC)上,最具代表之化合物為YD2,光電轉換率為11%。我們將苯環上改成ortho-位置並加入較長的烷氧鏈,目的是用來減少染料分子間的堆疊及減少電解液進入紫質染料分子間,而YD2-o-C8經由瑞士Michael Gratzel教授之團隊利用鈷(Co)錯合物當電解質,大幅提升Voc,所測得其光電轉換率在50%模擬光照下為破世界紀錄的12.7% (全太陽光照射強度的效率為11.9%)。 我們以YD2-o-C8為主體,在meso-位置改變不同推電子基的染料,比較在diarylamine上碳鏈的長短及推電子基強度與光電轉換率的關係,預期推電子強度越強可以增加電子注入TiO2的效率,不過光電轉換率並無法有效的超越YD2-o-C8。同樣的,在meso-位置改變不同拉電子基的染料經由π共軛系統的延伸,其吸收光譜已有明顯變寬和紅位移的現象,且由UV-Vis吸收與放射光譜計算結果HOMO-LUMO能階差有明顯的減小,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基,預期可以增加電子注入TiO2的效率,但光電轉換率也無法有效的超越YD2-o-C8。
Previously, a serious of the push-pull zinc porphyrin dyes, which contain tert-butyl groups in the meta positions of each meso-phenyl ring have been designed and synthesized in our laboratory. We applied these dyes in the dye-sensitized solar cells (DSSCs), and YD2 has achieved a PCE of 11% with iodide / triiodide redox electrolyte. To reduce dye aggregation and lower charge recombination, YD2-o-C8 with two octyloxy groups at the ortho positions of meso-phenyls has been synthesized. YD2-o-C8 shows efficient electron injection and the hydrophobic alkoxyl chains form a blocking layer on TiO2 surface for a retarded charge recombination. Under optimized conditions performed by the team of Professor Michael Gratzel, the YD2-o-C8 devices with Co(II/III)tris(bipyridyl)–based redox electrolyte can enhance the Voc to achieve high PCE values 12.7% of the world record under the 50% simulated sunlight and an efficiency of 11.9% under full sunlight intensity. We modified porphyrin dyes based on YD2-o-C8 with various push units on the meso-position, i.e. the diarylamines having different length of alky-chains and electron-donating ability. It was expected that the stronger push units can increase efficient electron injection on TiO2. However, the PCE of these modified porphyrin dyes is lower than that of YD2-o-C8. In addition, we extended π conjugated systems via the various pull units, so the UV-vis absorption spectra of porphyrins show broadened and red-shifted Soret and Q bands with respect to those of reference YD2-o-C8. The HOMO-LUMO gaps of porphyrins decreased obviously with the extended π conjugated system. Quantum-chemical (DFT) calculations demonstrate electronic distribution of the LUMO mainly located on the pull-units, resulting in efficient photocurrent density and electron injection.
URI: http://hdl.handle.net/11455/14496
其他識別: U0005-2407201209325700
文章連結: http://www.airitilibrary.com/Publication/alDetailedMesh1?DocID=U0005-2407201209325700
Appears in Collections:化學系所

文件中的檔案:

取得全文請前往華藝線上圖書館



Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.