Effects of π-elongation and the fused position of quinoxaline-fused porphyrins as sensitizers in dye-sensitized solar cells on optical, electrochemical, and photovoltaic properties

Journal of Physical Chemistry C

Volumn 114, Issue 25, 2010, Pages 11293-11304

  Kira, Aiko ^a   Matsubara, Yusuke ^a   Iijima, Hiroaki ^a   Umeyama, Tomokazu ^a   Matano, Yoshihiro ^a   Ito, Seigo ^b   Niemi, Marja ^c   Tkachenko, Nikolai V ^c   Lemmetyinen, Helge ^c   Imahori, Hiroshi ^a,d,e  

^a KYOTO UNIVERSITY   (Japan)

^b UNIVERSITY OF HYOGO   (Japan)

^c TAMPERE UNIVERSITY OF TECHNOLOGY   (Finland)

^d KYOTO UNIVERSITY   (Japan)

^e KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BLUE-SHIFTED; CHARGE RECOMBINATIONS; DENSITY FUNCTIONAL THEORY CALCULATIONS; DEVICE STRUCTURES; DOUBLE LAYERS; DYE-SENSITIZED SOLAR CELL; ELECTRONIC COUPLING; EXCITED SINGLET STATE; FLUORESCENCE LIFETIMES; HIGH POWER CONVERSION; HOMO-LUMO GAPS; INCIDENT PHOTON-TO-CURRENT EFFICIENCIES; INJECTED ELECTRONS; OPEN CIRCUIT POTENTIAL; OPTIMIZED CONDITIONS; PHOTOVOLTAIC PROPERTY; Q-BANDS; QUINOXALINES; RED-SHIFTED; SORET BANDS; TIME-SCALES; TIO;

CARBOXYLIC ACIDS; CELLS; CONVERSION EFFICIENCY; DENSITY FUNCTIONAL THEORY; ELECTROCHEMICAL PROPERTIES; ELECTRON INJECTION; ELECTRON MOBILITY; OPTICAL PROPERTIES; OPTIMIZATION; ORGANIC ACIDS; PORPHYRINS; SOLAR CELLS; SOLAR POWER GENERATION;

CYTOLOGY;

EID: 77954061540     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp1004049     Document Type: Article

References (133)

1. O'Regan, B.; Grätzel, M. Nature 1991, 353, 737
2. Nazeeruddin, M. K.; Kay, A.; Rodicio, I.; Humphry-Baker, R.; Müller, E.; Liska, P.; Vlachopoulos, N.; Grätzel, M. J. Am. Chem. Soc. 1993, 115, 6382
3. Grätzel, M. Acc. Chem. Res. 2009, 42, 1788
4. Nazeeruddin, M. K.; Angelis, F. D.; Fantacci, S.; Selloni, A.; Viscardi, G.; Liska, P.; Ito, S.; Takeru, B.; Grätzel, M. J. Am. Chem. Soc. 2005, 127, 16835
5. Gao, F.; Wang, Y.; Shi, D.; Zhang, J.; Wang, M.; Jing, X.; Humphry-Baker, R.; Wang, P.; Zakeeruddin, S. M.; Grätzel, M. J. Am. Chem. Soc. 2008, 130, 10720
6. Chen, C.-Y.; Wang, M.; Li, J.-Y.; Pootrakulchote, N.; Alibabaei, L.; Ngoc-le, C.; Decoppet, J.-D.; Tsai, J.-H.; Grätzel, C.; Wu, C.-G.; Zakeeruddin, S. M.; Grätzel, M. ACS Nano 2009, 3, 3103
7. Chiba, Y.; Islam, A.; Watanabe, Y.; Komiya, R.; Koide, N.; Han, L. Jpn. J. Appl. Phys. 2006, 45, L638
8. Mishra, A.; Fischer, M. K. R.; Bäuerle, P. Angew. Chem., Int. Ed. 2009, 48, 2474
9. Ooyama, Y.; Harima, Y. Eur. J. Org. Chem. 2009, 2903
10. Imahori, H.; Umeyama, T.; Ito, S. Acc. Chem. Res. 2009, 42, 1809
11. Hara, K.; Sayama, K.; Ohga, Y.; Shinpo, A.; Suga, S.; Arakawa, H. Chem. Commun. 2001, 569
12. Hara, K.; Kurashige, M.; Danoh, Y.; Kasada, C.; Shinpo, A.; Suga, S.; Arakawa, H. New. J. Chem. 2003, 27, 783
13. Wang, Z.-S.; Cui, Y.; Dan-oh, Y.; Kasada, C.; Shinpo, A.; Hara, K. J. Phys. Chem. C 2007, 111, 7224
14. Wang, Z.-S.; Cui, Y.; Dan-oh, Y.; Kasada, C.; Shinpo, A.; Hara, K. J. Phys. Chem. C 2008, 112, 17011
15. Horiuchi, T.; Miura, H.; Uchida, S. Chem. Commun. 2003, 3036
16. Horiuchi, T.; Miura, H.; Sumioka, K.; Uchida, S. J. Am. Chem. Soc. 2004, 126, 12218
17. Ito, S.; Zakeeruddin, S. M.; Humphry-Baker, R.; Liska, P.; Charvet, R.; Comte, P.; Nazeeruddin, M. K.; Péchy, P.; Takata, M.; Miura, H.; Uchida, S..; Grätzel, M. Adv. Mater. 2006, 18, 1202
18. Ito, S.; Miura, H.; Uchida, S.; Takata, M.; Sumioka, K.; Liska, P.; Comte, P.; Péchy, P.; Grätzel, M. Chem. Commun. 2008, 5194
19. Hara, K.; Kurashige, M.; Ito, S.; Shinpo, A.; Suga, S.; Sayama, K.; Arakawa, H. Chem. Commun. 2003, 252
20. Kitamura, T.; Ikeda, M.; Shigaki, K.; Inoue, T.; Anderson, N. A.; Ai, X.; Lian, T.; Yanagida, S. Chem. Mater. 2004, 16, 1806
21. Hwang, S.; Lee, J. H.; Park, C.; Lee, H.; Kim, C.; Park, C.; Lee, M.-H.; Lee, W.; Park, J.; Kim, K.; Park, N.-G.; Kim, C. Chem. Commun. 2007, 4887
22. Kim, C.; Choi, H.; Kim, S.; Baik, C.; Song, K.; Kang, M.-S.; Kang, S. O.; Ko, J. J. Org. Chem. 2008, 73, 7072
23. Im, H.; Kim, S.; Park, C.; Jang, S.-H.; Kim, C.-J.; Kim, K.; Park, N.-G.; Kim, C. Chem. Commun., 2010, 1335.
24. Tan, S.; Zhai, J.; Fang, H.; Jiu, T.; Ge, J.; Li, Y.; Jiang, L.; Zhu, D. Chem.-Eur. J. 2005, 11, 6272
25. 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, 5152
26. Choi, H.; Baik, C.; Kang, S. O.; Ko, J.; Kang, M.-S.; Nazeeruddin, M. K.; Grätzel, M. Angew. Chem., Int. Ed. 2008, 47, 327
27. Wang, Z.-S.; Koumura, N.; Cui, Y.; Takahashi, M.; Sekiguchi, H.; Mori, A.; Kubo, T.; Furube, A.; Hara, K. Chem. Mater. 2008, 20, 3993
28. Zhang, G.; Bala, H.; Cheng, Y.; Shi, D.; Lv, X.; Yu, Q.; Wang, P. Chem. Commun. 2009, 2198
29. Ehret, A.; Stuhl, L.; Spitler, M. T. Electrochim. Acta 2000, 45, 4553
30. Wu, W.; Hua, J.; Jin, Y.; Zhan, W.; Tian, H. Photochem. Photobiol. Sci. 2008, 7, 63
31. Wang, Z.-S.; Li, F.-Y.; Huang, C.-H.; Wang, L.; Wei, M.; Jin, L.-P.; Li, N.-Q. J. Phys. Chem. B 2000, 104, 9676
32. Yao, Q.-H.; Shan, L.; Li, F.-Y.; Yin, D.-D.; Huang, C.-H. New J. Chem. 2003, 27, 1277
33. Chen, Y.-S.; Li, C.; Zeng, Z.-H.; Wang, W.-B.; Wang, X.-S.; Zhang, B.-W. J. Mater. Chem. 2005, 15, 1654
34. Chen, Y.; Zeng, Z.; Li, C.; Wang, W.; Wang, X.; Zhang, B. New J. Chem. 2005, 29, 773
35. Yum, J.-H.; Walter, P.; Huber, S.; Rentsch, D.; Geiger, T.; Nüesch, F.; Angelis, F. D.; Grätzel, M.; Nazeeruddin, M. K. J. Am. Chem. Soc. 2007, 129, 10320
36. Reddy, P. Y.; Giribabu, L.; Lyness, C.; Snaith, H. J.; Vijaykumar, C.; Chandrasekharam, M.; Lakshmikantam, M.; Yum, J.-H.; Kalyanasundaram, K.; Grätzel, M.; Nazeeruddin, M. K. Angew. Chem., Int. Ed. 2007, 46, 373
37. Cid, J.-J.; Yum, J.-H.; Jang, S.-R.; Nazeeruddin, M. K.; Martínez-Ferrero, E.; Palomares, E. J.; Ko, J.; Grätzel, M.; Torres, T. Angew. Chem., Int. Ed. 2007, 46, 8358
38. Eu, S.; Katoh, T.; Umeyama, T.; Matano, Y.; Imahori, H. Dalton Trans. 2008, 5476
39. Cid, J.-J.; García-Iglesias, M.; Yum, J.-M.; Forneli, A.; Albero, J.; Martínez-Ferrero, E.; Vázquez, P.; Grätzel, M.; Nazeeruddin, M. K.; Palomares, E.; Torres, T. Chem.-Eur. J. 2009, 15, 5130
40. Ferrere, S.; Zaban, A.; Gregg, B. A. J. Phys. Chem. B 1997, 101, 4490
41. Shibano, Y.; Umeyama, T.; Matano, Y.; Imahori, H. Org. Lett. 2007, 9, 1971
42. Li, C.; Yum, J.-H.; Moon, S.-J.; Herrmann, A.; Eickemeyer, F.; Pschirer, N. G.; Erk, P.; Schöneboom, J.; Müllen, K.; Grätzel, M.; Nazeeruddin, M. K. ChemSusChem. 2008, 1, 615
43. Kay, A.; Grätzel, M. J. Phys. Chem. 1993, 97, 6272
44. Ma, T.; Inoue, K.; Noma, H.; Yao, K.; Abe, E. J. Photochem. Photobiol. A 2002, 152, 207
45. Nazeeruddin, M. K.; Humphry-Baker, R.; Officer, D. L.; Campbell, W. M.; Burrell, A. K.; Grätzel, M. Langmuir 2004, 20, 6514
46. Schmidt-Mende, L.; Campbell, W. M.; Wang, Q.; Jolley, K. W.; Officer, D. L.; Nazeeruddin, M. K.; Grätzel, M. ChemPhysChem 2005, 6, 1253
47. Mozer, A. J.; Griffith, M. J.; Tsekouras, G.; Wagner, P.; Wallace, G. G.; Mori, S.; Sunahara, K.; Miyashita, M.; Earles, J. C.; Gordon, K. C.; Du, L.; Katoh, R.; Furube, A.; Officer, D. L. J. Am. Chem. Soc. 2009, 131, 15621
48. Park, J. K.; Lee, H. R.; Chen, J.; Shinokubo, H.; Osuka, A.; Kim, D. J. Phys. Chem. C 2008, 112, 16691
49. Cherian, S.; Wamser, C. C. J. Phys. Chem. B 2000, 104, 3624
50. Watson, D. F.; Marton, A.; Stux, A. M.; Meyer, G. J. J. Phys. Chem. B 2003, 107, 10971
51. Watson, D. F.; Marton, A.; Stux, A. M.; Meyer, G. J. J. Phys. Chem. B 2004, 108, 11680
52. Rochford, J.; Chu, D.; Hagfeldt, A.; Galoppini, E. J. Am. Chem. Soc. 2007, 129, 4655
53. Rochford, J.; Galoppini, E. Langmuir 2008, 24, 5366
54. Boschloo, G. K.; Goossens, A. J. Phys. Chem. 1996, 100, 19489
55. Koehorst, R. B. M.; Boschloo, G. K.; Savenije, T. J.; Goossens, A.; Schaafsma, T. J. J. Phys. Chem. B 2000, 104, 2371
56. Clifford, J. N.; Yahioglu, G.; Milgrom, L. R.; Durrant, J. R. Chem. Commun. 2002, 1260
57. Odobel, F.; Blart, E.; Lagrée, M.; Villieras, M.; Boujtita, H.; El Murr, N.; Caramori, S.; Bignozzi, C. A. J. Mater. Chem. 2003, 13, 502
58. Jasieniak, J.; Johnston, M.; Waclawik, E. R. J. Phys. Chem. B 2004, 108, 12962
59. Imahori, H.; Hayashi, S.; Umeyama, T.; Eu, S.; Oguro, A.; Kang, S.; Matano, Y.; Shishido, T.; Ngamsinlapasathian, S.; Yoshikawa, S. Langmuir 2006, 22, 11405
60. Eu, S.; Hayashi, S.; Umeyama, T.; Oguro, A.; Kawasaki, M.; Kadota, N.; Matano, Y.; Imahori, H. J. Phys. Chem. C 2007, 111, 3528
61. Tanaka, M.; Hayashi, S.; Eu, S.; Umeyama, T.; Matano, Y.; Imahori, H. Chem. Commun. 2007, 2069
62. Hayashi, S.; Matsubara, Y.; Eu, S.; Hayashi, H.; Umeyama, T.; Matano, Y.; Imahori, H. Chem. Lett. 2008, 37, 846
63. Eu, S.; Hayashi, S.; Umeyama, T.; Matano, Y.; Araki, Y.; Imahori, H. J. Phys. Chem. C 2008, 112, 4396
64. Hayashi, S.; Tanaka, M.; Hayashi, H.; Eu, S.; Umeyama, T.; Matano, Y.; Araki, Y.; Imahori, H. J. Phys. Chem. C 2008, 112, 15576
65. Imahori, H.; Hayashi, S.; Hayashi, H.; Oguro, A.; Eu, S.; Umeyama, T.; Matano, Y. J. Phys. Chem. C 2009, 113, 18406
66. Kira, A.; Tanaka, M.; Umeyama, T.; Matano, Y.; Yoshimoto, N.; Zhang, Y.; Ye, S.; Lehtivuori, H.; Tkachenko, N. V.; Lemmetyinen, H.; Imahori, H. J. Phys. Chem. C 2007, 111, 13618
67. Imahori, H.; Umeyama, T. J. Phys. Chem. C 2009, 113, 9029
68. Imahori, H.; Matsubara, Y.; Iijima, H.; Umeyama, T.; Matano, Y.; Ito, S.; Niemi, M.; Tkachenko, N. V.; Lemmetyinen, H. J. Phys. Chem. C, DOI: 10.1021/jp102486b.
69. Amao, Y.; Yamada, Y. Langmuir 2005, 21, 3008
70. Stromberg, J. R.; Marton, A.; Kee, H. L.; Kirmaier, C.; Diers, J. R.; Muthiah, C.; Taniguchi, M.; Lindsey, J. S.; Bocian, D. F.; Meyer, G. J.; Holten, D. J. Phys. Chem. C 2007, 111, 15464
71. Wang, X.-F.; Kitao, O.; Zhou, H.; Tamiaki, H.; Sasaki, S. J. Phys. Chem. C 2009, 113, 7954
72. Tachibana, Y.; Haque, S. A.; Mercer, I. P.; Durrant, J. R.; Klug, D. R. J. Phys. Chem. B 2000, 104, 1198
73. Lee, C.-W.; Lu, H.-P.; Lan, C.-M.; Huag, Y.-L.; Liang, Y.-R.; Yen, W.-N.; Liu, Y.-C.; Lin, Y.-S.; Diau, E. W.-G.; Yeh, C.-Y. Chem.-Eur. J. 2009, 15, 1403
74. Lin, C.-Y.; Lo, C.-F.; Luo, L.; Lu, H.-P.; Hung, C.-S.; Diau, E. W.-G. J. Phys. Chem. C 2009, 113, 755
75. Lu, H.-P.; Tsai, C.-Y.; Yen, W.-N.; Hsieh, C.-P.; Lee, C.-W.; Yeh, C.-Y.; Diau, E. W.-G. J. Phys. Chem. C 2009, 113, 20990
76. Lu, H.-P.; Mai, C.-L.; Tsia, C.-Y.; Hsu, S.-J.; Hsieh, C.-P.; Chiu, C.-L.; Yeh, C.-Y.; Diau, E. W.-G. Phys. Chem. Chem. Phys. 2009, 11, 10270
77. Lin, C.-Y.; Wang, Y.-C.; Hsu, S.-J.; Lo, C.-F.; Diau, E. W.-G. J. Phys. Chem. C 2010, 114, 687
78. Chen, C.-T.; Yeh, H.-C.; Zhang, X.; Yu, J. Org. Lett. 1999, 1, 1767
79. Wang, Q.; Campbell, W. M.; Bonfantani, E. E.; Jolley, K. W.; Officer, D. L.; Walsh, P. J.; Gordon, K.; Humphry-Baker, R.; Nazeeruddin, M. K.; Grätzel, M. J. Phys. Chem. B 2005, 109, 15397
80. Campbell, W. M.; Jolley, K. W.; Wagner, P.; Wagner, K.; Walsh, P. J.; Gordon, K. C.; Schmidt-Mende, L.; Nazeeruddin, Md. K.; Wang, Q.; Grätzel, M.; Officer, D. L. J. Phys. Chem. C 2007, 111, 11760
81. Ito, S.; Murakami, T. N.; Comte, P.; Liska, P.; Grätzel, C.; Nazeeruddin, M. K.; Grätzel, M. Thin Solid Films 2008, 516, 4613
82. Zhang, W.; Wicks, M. N.; Burn, P. L. Org. Biomol. Chem. 2008, 6, 879
83. Zhao, S.; Neves, M. G. P. M. S.; Tomé, A. C.; Silva, A. M. S.; Cavaleiro, J. A. S.; Domingues, M. R. M.; Correia, A. J. F. Tetrahedron Lett. 2005, 46, 2189
84. Maligaspe, E.; Tkachenko, N. V.; Subbaiyan, N. K.; Chitta, R.; Zandler, M. E.; Lemmetyinen, H.; D'Souza, F. J. Phys. Chem. A 2009, 113, 8478
85. Tkachenko, N. V.; Rantala, L.; Tauber, A. Y.; Helaja, J.; Hynninen, P. H.; Lemmetyinen, H. J. Am. Chem. Soc. 1999, 121, 9378
86. Vehmanen, V.; Tkachenko, N. V.; Imahori, H.; Fukuzumi, S.; Lemmetyinen, H. Spectrochim. Acta. A 2001, 57, 2229
87. Isosomppi, M.; Tkachenko, N. V.; Efimov, A.; Lemmetyinen, H. J. Phys. Chem. A 2005, 109, 4881
88. Binkley, J. S.; Pople, J. A.; Hehre, W. J. J. Am. Chem. Soc. 1980, 102, 939
89. Frisch, M. J.;; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; 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.; Yazyev, 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; Gaussian, Inc.: Wallingford, CT, 2004.
90. We have shown that porphyrin carboxylic acids exhibit high cell performance after sensitization in protic solvents. (16g) Specifically, the cell performance is in the order MeOH > EtOH. Unfortunately, ZnBQA was found to be insoluble in MeOH. Thus, the cell performance of ZnBQA was evaluated after sensitization in EtOH.
91. -2).
92. Stuart, D. R.; Bertrand-Laperle, M.; Burgess, K. M. N.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 16474
93. Buckles, R. E.; Bellis, M. P. In Organic Syntheses Collective; Kamm, O.; Rabjohn, N., Eds.; Wiley: New York, 1963; Vol. 4, p 722.
94. Aguirre, G.; Boiani, L.; Cerecetto, H.; Maio, R. D.; González, M.; Porcal, W.; Denicola, A.; Möller, M.; Thomson, L.; Tórtora, V. Bioorg. Med. Chem. 2005, 13, 6324
95. Baldwin, J. E.; Crossley, M. J.; Debernardis, J. Tetrahedron 1982, 38, 685
96. Gierschner, J.; Cornil, J.; Egelhaaf, H.-J. Adv. Mater. 2007, 19, 173
97. The fluorescence decay of ZnQCA could not be measured in dichloromethane because of the degradation of the sample during the measurement. Thus, the fluorescence lifetime measurement for ZnQCA was carried out in benzonitrile.
98. At the present, the reason for the short lifetime is unclear, but it has been reported that the fused benzene ring at β positions of porphyrins decreases the lifetime of the excited singlet state. See
99. Rogers, J. E.; Nguyen, K. A.; Hufnagle, D. C.; McLean, D. G.; Su, W.; Gossett, K. M.; Burke, A. R.; Vinogradov, S. A.; Pachter, R.; Fleitz, P. A. J. Phys. Chem. A 2003, 107, 11331
100. Thus, we postulate that the short lifetime of ZnQCA derives from the fused benzene ring at the β positions. On the other hand, the pyrazine rings are fused to the β positions in ZnBQA and ZnQMA, which shows a rather longer lifetime than that of ZnQCA. Therefore, we attribute the shorter lifetime of ZnQCA to the benzene ring fused directly at the β positions.
101. Rehm, J. M.; McLendon, G. L.; Nagasawa, Y.; Yoshihara, K.; Moser, J.; Grätzel, M. J. Phys. Chem. 1996, 100, 9577
102. Burfeindt, B.; Hannappel, T.; Storck, W.; Willig, F. J. Phys. Chem. 1996, 100, 16463
103. Hilgendorff, M.; Sundström, V. J. Phys. Chem. B. 1998, 102, 10505
104. Asbury, J. B.; Hao, E.; Wang, Y.; Ghosh, H. N.; Lian, T. J. Phys. Chem. B 2001, 105, 4545
105. Kadish, K. M.; Wenbo, E; Sintic, P. J.; Ou, Z.; Shao, J.; Ohkubo, K.; Fukuzumi, S.; Govenlock, L. J.; McDonald, J. A.; Try, A. C.; Cai, Z.-L.; Reimers, J. R.; Crossley, M. J J. Phys. Chem. B 2007, 111, 8762
106. Kamat, P. V.; Haria, M.; Hotchandani, S. J. Phys. Chem. B 2004, 108, 5166
107. Foresman, J. B.; Frisch, A. Exploring Chemistry with Electronic Structure Methods; Gaussian Inc.: Pittsburgh, 1995.
108. DFT calculations reveal that the electron density of the porphyrin core in the LUMO of ZnQCA is significantly smaller than those in the LUMOs of ZnBQA and ZnQMA, whereas that in the HOMO of ZnQCA is slightly smaller than those in the HOMOs of ZnBQA and ZnQMA. This is consistent with the electrochemical results that ZnQCA is considerably easier to be reduced than ZnBQA and ZnQMA but is slightly more difficult to be oxidized. This rationalizes the small HOMO-LUMO gap of ZnQCA relative to ZnBQA and ZnQMA.
109. Hagberg, D. P.; Edvinsson, T.; Marinado, T.; Boschloo, G.; Hagfeldt, A.; Sun, L. Chem. Commun. 2006, 2245
110. Vallée, A.; Humblot, V.; Méthivier, C.; Pradier, C.-M. J. Phys. Chem. C 2009, 113, 9336
111. Johansson, E. M. J.; Hedlund, M.; Siegbahn, H.; Rensmo, H. J. Phys. Chem. B 2005, 109, 22256
112. Patthey, L.; Rensmo, H.; Persson, P.; Westermark, K.; Vayssieres, L.; Stashans, A.; Petersson, Å.; Bruhwiler, P. A.; Siegbahn, H.; Lunell, S.; Martensson, N. J. Chem. Phys. 1999, 110, 5913
113. Polzonetti, G.; Ferri, A.; Russo, M. V.; Iucci, G.; Licoccia, S.; Paolesse, R. J. Vac. Sci. Technol. A 1999, 17, 832
114. Sarno, D. M.; Matienzo, L. J.; Jones, W. E., Jr. Inorg. Chem. 2001, 40, 6308
115. Lu, M.; Chen, B.; He, T.; Li, Y.; Tour, J. M. Chem. Mater. 2007, 19, 4447
116. Vilmercati, P.; Castellarin-Cudia, C.; Gebauer, R.; Ghosh, P.; Lizzit, S.; Petaccia, L.; Cepek, C.; Larciprete, R.; Verdini, A.; Floreano, L.; Morgante, A.; Goldoni, A. J. Am. Chem. Soc. 2009, 131, 644
117. Condorelli, G. G.; Motta, A.; Favazza, M.; Fragalà, I. L.; Busi, M.; Menozzi, E.; Dalcanale, E.; Cristofolini, L. Langmuir 2006, 22, 11126
118. Shen, C.; Haryono, M.; Grohmann, A.; Buck, M.; Weidner, T.; Ballav, N.; Zharnikov, M. Langmuir 2008, 24, 12883
119. Yu, S.; Ahmadi, S.; Palmgren, P.; Hennies, F.; Zuleta, M.; Göthelid, M. J. Phys. Chem. C 2009, 113, 13765
120. Bhargava, G.; Ramanarayanan, T. A.; Bernasek, S. L. Langmuir 2010, 26, 215
121. He, Q.; Liu, Z.; Xiao, P.; Liang, R.; He, N.; Lu, Z. Langmuir 2003, 19, 6982
122. Higo, M.; Futagawa, T.; Mitsushio, M.; Yoshidome, T.; Ozono, Y. J. Phys. Chem. B 2003, 107, 5871
123. Ameur, S.; Bureau, C.; Charlier, J.; Palacin, S. J. Phys. Chem. B 2004, 108, 13042
124. Yoshida, H.; Sato, N. J. Phys. Chem. B 2006, 110, 4232
125. Palma, R. D.; Peeters, S.; Van Bael, M. J.; Van den Rul, H.; Bonroy, K.; Laureyn, W.; Mullens, J.; Borghs, G.; Maes, G. Chem. Mater. 2007, 19, 1821
126. Olivares-Xometl, O.; Likhanova, N. V.; Domínguez-Aguilar, M. A.; Hallen, J. M.; Zamudio, L. S.; Arce, E. Appl. Surf. Sci. 2006, 252, 2139
127. Jones, F; Farrow, J. N.; van Bronswilk, W. Langmuir 1998, 14, 6512
128. 2 films at the Q bands are 50-90% due to the low molar absorption coefficients at the Q bands relative to the Soret band, although the scattering layers in the actual cells may enhance the light-harvesting efficiencies. Taking into account the intense solar energy distribution at 400-700 nm, we can improve the IPCE values of the porphyrin-sensitized cells by increasing the molar absorption coefficients of the porphyrins at the Q bands.
129. sc and IPCE, may be at least partially attributed to the short lifetime. Similar deterioration of photovoltaic properties due to short lifetime has been reported for cyanine dyes. See
130. Cherepy, N. J.; Smestad, G. P.; Grätzel, M.; Zhang, J. Z. J. Phys. Chem. B 1997, 101, 9342.
131. Kusama, H.; Orita, H.; Sugihara, H. Langmuir 2008, 24, 4411
132. Hara, K.; Miyamoto, K.; Abe, Y.; Yanagida, M. J. Phys. Chem. B 2005, 109, 23776
133. Chen, R.; Yang, X.; Tian, H.; Wang, X.; Hagfeldt, A.; Sun, L. Chem. Mater. 2007, 19, 4007