Design and characterization of novel porphyrins with oligo(phenylethylnyl) links of varied length for dye-sensitized solar cells: Synthesis and optical, electrochemical, and photovoltaic investigation

Journal of Physical Chemistry C

Volumn 113, Issue 2, 2009, Pages 755-764

  Lin, Ching Yao ^a   Lo, Chen Fu ^a   Luo, Liyang ^b,c   Lu, Hsueh Pei ^b   Hung, Chen Shiung ^c   Diau, Eric Wei Guang ^b  

^a NATIONAL CHI NAN UNIVERSITY   (Taiwan)

^b NATIONAL CHIAO TUNG UNIVERSITY   (Taiwan)

^c INSTITUTE OF CHEMISTRY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIC VOLTAMMOGRAMS; DENSITY-FUNCTIONAL THEORIES; DYE-SENSITIZED SOLAR CELLS; ELECTROCHEMICAL POTENTIALS; ELECTRON TRANSFERS; FEMTOSECOND FLUORESCENCES; PHOTOVOLTAIC PERFORMANCE; PORPHYRIN CATIONS; POWER CONVERSIONS; SOLUTION SAMPLES; TETRAHYDROFURAN; UP CONVERSIONS; UV-VISIBLE SPECTRUM; ZINC PORPHYRINS;

DENSITY FUNCTIONAL THEORY; EMISSION SPECTROSCOPY; PHOTODEGRADATION; PHOTOELECTROCHEMICAL CELLS; PHOTOVOLTAIC CELLS; PORPHYRINS; SOLAR ENERGY; SOLAR POWER GENERATION; SYNTHESIS (CHEMICAL); ZINC;

SOLAR CELLS;

EID: 61649093298     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp806777r     Document Type: Article

References (76)

1. O'Regan, B.; Grätzel, M. Nature 1991, 353, 737.
2. Nazeeruddin, M. K.; Kay, A.; Rodicio, I.; Humphry-Baker, R.; Muller, E.; Liska, P.; Vlachopoulos, N.; Grätzel, M. J. Am. Chem. Soc. 1993, 115, 6382.
3. (a) Wang, Q.; Ito, S.; Grätzel, M.; Fabregat-Santiago, F.; Mora- Seró, I.; Bisquert, J.; Bessho, T.; Imai, H. J. Phys. Chem. B 2006, 110, 764 J. Phys. Chem. C, Vol. 113, No. 2, 2009 Lin et al. 25210.
4. (b) Wei, M.; Konishi, Y.; Zhou, H.; Yanagida, M.; Sugihara, H.; Arakawa, H. J. Mater. Chem. 2006, 16, 1287.
5. (c) Koide, N.; Islam, A.; Chiba, Y.; Han, L. J. Photochem. Photobiol. A 2006, 182, 296.
6. (a) Nazeeruddin, M. K.; Humphry-Baker, R.; Officer, D. L.; Campbell, W. M.; Burrell, A. K.; Grätzel, M. Langmuir 2004, 20, 6514.
7. (b) Campbell, W. M.; Burrell, A. K.; Officer, D. L.; Jolley, K. W. Coord. Chem. Rev. 2004, 248, 1363.
8. (c) 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.
9. (d) Campbell, W. M.; Jolley, K. W.; Wagner, P.; Wagner, K.; Walsh, P. J.; Gordon, K.; Schmidt-Mende, L.; Nazeeruddin, M. K.; Wang, Q.; Pechy, P.; Renouard, T.; Zakeeruddin, S. M.; Grätzel, M.; Officer, D. J. Phys. Chem. C 2007, 111, 11760.
10. Odobel, F.; Blart, E.; Lagree, M.; Villieras, M.; Boujtita, H.; Murr, N. E.; Caramori, S.; Bignozzi, C. A. J. Mater. Chem. 2003, 13, 502.
11. Bignozzi, C. A.; Argazzi, R.; Kleverlaan, C. J. Chem. Soc. Rev. 2000, 29, 87.
12. Cid, J.-J.; Yum, J.-H.; Jang, S.-R.; Nazeeruddin, M. K.; Martínez- Ferrero, E.; Palomares, E.; Ko, J.; Grätzel, M.; Torres, T. Angew. Chem., Int. Ed. 2007, 46, 8358.
13. (a) Luo, L.; Lo, C.-F.; Lin, C.-Y.; Chang, I.-J.; Diau, E. W.-G. J. Phys. Chem. B 2006, 110, 410.
14. (b) Lo, C.-F.; Luo, L.; Diau, E. W.-G.; Chang, I.-J.; Lin, C.-Y. Chem. Commun. 2006, 1430.
15. (a) Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632.
16. (b) Bunz, U. H. F. Chem. Rev. 2000, 100, 1605.
17. (c) Yang, S. I.; Prathapan, S.; Miller, M. A.; Seth, J.; Bocian, D. F.; Lindsey, J. S.; Holten, D. J. Phys. Chem. B 2001, 105, 8249.
18. (a) Kim, D.; Osuka, A. J. Phys. Chem. A 2003, 107, 8791.
19. (b) Holten, D.; Bocian, D. F.; Lindsey, J. S. Acc. Chem. Res. 2002, 35, 57, and references therein.
20. (c) Loewe, R. S.; Lammi, R. K.; Diers, J. R.; Kirmaier, C.; Bocian, D. F.; Holten, D.; Lindsey, J. S. J. Mater. Chem. 2002, 12, 1530.
21. (d) Wojaczynski, J.; Latos-Grazynski, L. Coord. Chem. Rev. 2000, 204, 113.
22. (e) Rubtsov, I. V.; Susumu, K.; Rubtsov, G. I.; Therien, M. J. J. Am. Chem. Soc. 2003, 125, 2687.
23. (f) Susumu, K.; Therien, M. J. J. Am. Chem. Soc. 2002, 124, 8550.
24. (g) Screen, T. E. O.; Lawton, K. B.; Wilson, G. S.; Dolney, N.; Ispasoiu, R.; Goodson, T., III.; Martin, S. J.; Bradley, D. D. C.; Anderson, H. L. J. Mater. Chem. 2001, 11, 312.
25. (a) Piotrowiak, P.; Galoppini, E.; Wei, Q.; Meyer, G. J.; Wiewior, P. J. Am. Chem. Soc. 2003, 125, 5278.
26. (b) Hoertz, P. G.; Carlisle, R. A.; Meyer, G. J.; Wang, D.; Piotrowiak, P.; Galoppini, E. Nano Lett. 2003, 3, 325.
27. (c) Galoppini, E.; Guo, W.; Zhang, W.; Hoertz, P. G.; Qu, P.; Meyer, G. J. J. Am. Chem. Soc. 2002, 124, 7801.
28. (d) Galoppini, E. Coord. Chem. Rev. 2004, 248, 1283.
29. (e) Myahkostupov, M.; Piotrowiak, P.; Wang, D.; Galoppini, E. J. Phys. Chem. C 2007, 111, 2827.
30. (f) Rochford, J.; Chu, D.; Hagfeldt, A.; Galoppini, E. J. Am. Chem. Soc. 2007, 129, 4655.
31. (g) Rochford, J.; Galoppini, E. Langmuir 2008, 24, 5366.
32. Sazanovich, I. V.; Kirmaier, C.; Hindin, E.; Yu, L.; Bocian, D. F.; Lindsey, J. S.; Holten, D. J. Am. Chem. Soc. 2004, 126, 2664.
33. (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tet. Lett. 1975, 4467.
34. (b) Takahashi, S.; Kuroyama, Y.; Sonogashira, K. Synthesis 1980, 627.
35. (a) Zhang, T.-G.; Zhao, Y.; Asselberghs, I.; Persoons, A.; Clays, K.; Therien, M. J. J. Am. Chem. Soc. 2005, 127, 9710.
36. (b) Susumu, K.; Duncan, T. V.; Therien, M. J. J. Am. Chem. Soc. 2005, 127, 5186.
37. (c) Liu, Z.; Schmidt, I.; Thamyongkit, P.; Loewe, R. S.; Syomin, D.; Diers, J. R.; Zhao, Q.; Misra, V.; Lindsey, J. S.; Bocian, D. F. Chem. Mater. 2005, 17, 3728.
38. (d) Yasseri, A. A.; Syomin, D.; Malinovskii, V. L.; Loewe, R. S.; Lindsey, J. S.; Zaera, F.; Bocian, D. F. J. Am. Chem. Soc. 2004, 126, 11944.
39. (e) Screen, T. E. O.; Thorne, J. R. G.; Denning, R. G.; Bucknall, D. G.; Anderson, H. L. J. Am. Chem. Soc. 2002, 124, 9712.
40. (f) Blake, I. M.; Rees, L. H.; Claridge, T. D. W.; Anderson, H. L. Angew. Chem., Int. Ed. 2000, 39, 1818.
41. (g) Wilson, G. J.; Arnold, D. P. J. Phys. Chem. A 2005, 109, 6104.
42. (h) Webb, S. J.; Sanders, J. K. M. Inorg. Chem. 2000, 39, 5912.
43. (a) Lin, C.-Y.; Chuang, L.-C.; Lin, Y.-C.; Lin, C.-L. Dalton Trans. 2004, 4006.
44. (b) Lin, C.-Y.; Chuang, L.-C.; Yang, Y.-F.; Lin, C.-L.; Kao, H.-C.; Wang, W.-J. Dalton Trans. 2004, 456.
45. (c) Blake, I. M.; Rees, L. H.; Claridge, T. D. W.; Anderson, H. L. Angew. Chem., Int. Ed. 2000, 39, 1818.
46. (d) Taylor, P. N.; Wylie, A. P.; Huuskonen, J.; Anderson, H. L. Angew. Chem., Int. Ed. 1998, 37, 986.
47. (e) LeCours, S. M.; Philips, C. M.; de Paula, J. C.; Therien, M. J. J. Am. Chem. Soc. 1997, 119, 12578.
48. (f) LeCours, S. M.; Guan, H. W.; DiMagno, S. G.; Wang, C. H.; Therien, M. J. J. Am. Chem. Soc. 1996, 118, 1497.
49. Gouterman, M. J. Mol. Spectrosc. 1961, 6, 138.
50. Nielsen, K. T.; Spanggaard, H.; Krebs, F. C. Macromolecules 2005, 38, 1180.
51. Gurzadyan, G. G.; Tran-Thi, T.-H.; Gustavsson, T. J. Chem. Phys. 1998, 108, 385.
52. Mataga, N.; Shibata, Y.; Chosrowjan, H.; Yoshida, N.; Osuka, A. J. Phys. Chem. B 2000, 104, 4001.
53. Yu, H.; Baskin, J. S.; Zewail, A. H. J. Phys. Chem. A 2002, 106, 9845.
54. (a) Kadish, K. M.; Caemelbecke, E. V.; Royal, G. In The Porphyrin Handbook ; Kadish, K. M.; Smith, K. M.; Guilard, G., Eds.;Academic Press: New York, 2000; Vol. 8, pp 1-97.
55. (b) Kadish, K. M.; Royal, G.; Caemelbecke, E. V.; Gueletti, L. In The Porphyrin Handbook ; Kadish, K. M.; Smith, K. M.; Guilard, G., Eds.; Academic Press: New York, 2000; Vol. 9.
56. We observed ill-defined reduction waves before the porphyrin first ring-reductions; these reduction waves are similar to the reduction waves of the substituents under the same experimental conditions, e.g., 4-iodo- benzoic acid, 4-ethynylbenzoic acid, 4-(trimethylsilylethynyl)benzoic acid, and 4-(4-ethynylphenylethynyl)benzoic acid.
57. (a) Thomas, K. R. J.; Lin, J. T.; Tao, Y.-T.; Ko, C.-W. J. Am. Chem. Soc. 2001, 123, 9404.
58. (b) Koene, B. E.; Loy, D. E.; Thompson, M. E. Chem. Mater. 1998, 10, 2235.
59. (c) Thelakkat, M.; Schmidt, H.-W. Adv. Mater. 1998, 10, 219.
60. (d) Janietz, S.; Bradley, D. D. C.; Grell, M.; Giebeler, C.; Inbasekaran, M.; Woo, E. P. Appl. Phys. Lett. 1998, 73, 2453.
61. (a) Hagfeldt, A.; Grätzel, M. Chem. Rev. 1995, 95, 49.
62. (b) Pommerehne, J.; Vestweber, H.; Guss, W.; Mahrt, R. F.; Bassler, H.; Porsch, M.; Daub, J. Adv. Mater. 1995, 7, 551.
63. 2 surfaces in monomeric form with a less extent of aggregation.
64. (a) Donker, H.; Koehorst, R. B. M.; Schaafsma, T. J. J. Phys. Chem. B 2005, 109, 17031.
65. (b) Donker, H.; Hoek, A.; Schaik, W.; Koehorst, R. B. M.; Yatskou, M. M.; Schaafsma, T. J. J. Phys. Chem. B 2005, 109, 17038.
66. (c) Schaafsma, T.; Dag, I.; Sitters, R.; Glasbeek, M.; Lifshitz, E. J. Phys. Chem. B 2005, 109, 17047.
67. Kasha, M. Radiat. Res. 1963, 20, 55.
68. Maiti, N. C.; Mazumdar, S.; Periasamy, N. J. Phys. Chem. B 1998, 102, 1528.
69. (a) Chowdhury, A.; Wachsmann-Hogiu, S.; Bangal, P. R.; Raheen, I.; Peteanu, L. A. J. Phys. Chem. B 2001, 105, 12196.
70. (b) Wang, M.; Silva, G. L.; Armitage, B. A. J. Am. Chem. Soc. 2000, 122, 9977.
71. Lu, Y.-C.; Chang, C.-W.; Diau, E. W.-G. J. Chin. Chem. Soc. 2002, 49, 693.
72. Gundlach, L.; Ernstorfer, R.; Willig, F. J. Phy. Chem. C 2007, 111, 13586.
73. Clark, C. C.; Meyer, G. J.; Wei, Q.; Galoppini, E. J. Phy. Chem. B 2006, 110, 11044.
74. Perrin, D. D.; Armarego, W. L. F. Purification of laboratory chemicals, 3rd ed.; Pergamon Press: Oxford, 1988.
75. Lu, Y. C.; Diau, E. W.-G.; Rau, H. J. Phys. Chem. A 2005, 109, 2090.
76. Ito, S.; Matsui, H.; Okada, K.; Kusano, S.; Kitamura, T.; Wada, Y.; Yanagida, S. Sol. Energy Mater. Sol. Cells 2004, 82, 421.