Organic dyes containing a triple bond spacer for dye sensitized solar cells: A combined experimental and theoretical investigation

Current Organic Chemistry

Volumn 15, Issue 19, 2011, Pages 3535-3543

  Scrascia, Angela ^a   Pastore, Mariachiara ^a,b   Yin, Lunxiang ^c   Picca, Rosaria Anna ^a   Manca, Michele ^d   Guo, Ying Cen ^e   de Angelis, Filippo ^b   della Sala, Fabio ^d,e   Cingolani, Roberto ^d   Gigli, Giuseppe ^a,d,e   Ciccarella, Giuseppe ^a,e  

^a UNIVERSITY OF SALENTO   (Italy)

^b UNIVERSITY OF PERUGIA   (Italy)

^c DALIAN UNIVERSITY OF TECHNOLOGY   (China)

^d ISTITUTO ITALIANO DI TECNOLOGIA   (Italy)

^e NATIONAL NANOTECHNOLOGY LABORATORY   (Italy)

Author keywords

DSSC; Metal free sensitizer; Organic dye

Indexed keywords

CONVERSION EFFICIENCY; DENSITY FUNCTIONAL THEORY; DICHLOROMETHANE; PHOTOSENSITIZERS; ULTRAVIOLET SPECTROSCOPY;

DSSC; DYE- SENSITIZED SOLAR CELLS; EXPERIMENTAL INVESTIGATIONS; METAL-FREE SENSITIZERS; ORGANIC DYE; SYNTHESISED; THEORETICAL INVESTIGATIONS; TRIPHENYLAMINES; TRIPLE BONDS; Π-ACCEPTORS;

DYE-SENSITIZED SOLAR CELLS;

EID: 80053514095     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527211797374742     Document Type: Article

References (52)

1. O'Regan, B.; Gratzel, M., A low-cost, high-efficiency solar cell based on dye-sensitized colloidal TiO2 films. Nature 1991, 353 (6346), 737-740.
2. Islam, A.; Watanabe, Y.; AKomiya, R.; Koide, N.; Han, L., Dye-Sensitized Solar Cells with Conversion Efficiency of 11.1%. Japanese Journal of Applied Physics 2006, 45 (25), L638.
3. Nazeeruddin, M. K.; De Angelis, F.; Fantacci, S.; Selloni, A.; Viscardi, G.; Liska, P.; Ito, S.; Takeru, B.; Gratzel, M., Combined Experimental and DFT-TDDFT Computational Study of Photoelectrochemical Cell Ruthenium Sensitizers. Journal of the American Chemical Society 2005, 127 (48), 16835-16847.
4. Hara, K.; Sato, T.; Katoh, R.; Furube, A.; Ohga, Y.; Shinpo, A.; Suga, S.; Sayama, K.; Sugihara, H.; Arakawa, H., Molecular design of coumarin dyes for efficient dye-sensitized solar cells. Journal of Physical Chemistry B 2003, 107 (2), 597-606.
5. Wang, Z. S.; Cui, Y.; Hara, K.; Dan-Oh, Y.; Kasada, C.; Shinpo, A., A high-light-harvesting-efficiency coumarin dye for stable dye-sensitized solar cells. Advanced Materials 2007, 19 (8), 1138-1141.
6. Sayama, K.; Hara, K.; Mori, N.; Satsuki, M.; Suga, S.; Tsukagoshi, S.; Abe, Y.; Sugihara, H.; Arakawa, H., Photosensitization of a porous TiO2 electrode with merocyanine dyes containing a carboxyl group and a long alkyl chain. Chemical Communications 2000, (13), 1173-1174.
7. Sayama, K.; Tsukagoshi, S.; Hara, K.; Ohga, Y.; Shinpou, A.; Abe, Y.; Suga, S.; Arakawa, H., Photoelectrochemical properties of J aggregates of benzothiazole merocyanine dyes on a nanostructured TiO2 film. Journal of Physical Chemistry B 2002, 106 (6), 1363-1371.
8. Ma, X. M.; Hua, J. L.; Wu, W. J.; Jin, Y. H.; Meng, F. S.; Zhan, W. H.; Tian, H., A high-efficiency cyanine dye for dye-sensitized solar cells. Tetrahedron 2008, 64 (2), 345-350.
9. Zhan, W. H.; Wu, W. J.; Hua, J. L.; Jing, Y. H.; Meng, F. S.; Tian, H., Photovoltaic properties of new cyanine-naphthalimide dyads synthesized by 'Click' chemistry. Tetrahedron Letters 2007, 48 (14), 2461-2465.
10. Wang, Z. S.; Li, F. Y.; Huang, C. H., Photocurrent enhancement of hemicyanine dyes containing RSO3- group through treating TiO2 films with hydrochloric acid. Journal of Physical Chemistry B 2001, 105 (38), 9210-9217.
11. Chen, Y. S.; Li, C.; Zeng, Z. H.; Wang, W. B.; Wang, X. S.; Zhang, B. W., Efficient electron injection due to a special adsorbing group's combination of carboxyl and hydroxyl: dye-sensitized solar cells based on new hemicyanine dyes. Journal of Materials Chemistry 2005, 15 (16), 1654-1661.
12. Kim, S.; Lee, J. K.; Kang, S. O.; Ko, J.; Yum, J. H.; Fantacci, S.; De Angelis, F.; Di Censo, D.; Nazeeruddin, M. K.; Gratzel, M., Molecular engineering of organic sensitizers for solar cell applications. Journal of the American Chemical Society 2006, 128 (51), 16701-16707.
13. Choi, H.; Baik, C.; Kang, S. O.; Ko, J.; Kang, M. S.; Nazeeruddin, M. K.; Gratzel, M., Highly efficient and thermally stable organic sensitizers for solvent-free dye-sensitized solar cells. Angewandte Chemie-International Edition 2008, 47 (2), 327-330.
14. Koumura, N.; Wang, Z.-S.; Mori, S.; Miyashita, M.; Suzuki, E.; Hara, K., Alkyl-Functionalized Organic Dyes for Efficient Molecular Photovoltaics. Journal of the American Chemical Society 2006, 128 (44), 14256-14257.
15. Kim, D.; Lee, J. K.; Kang, S. O.; Ko, J., Molecular engineering of organic dyes containing N-aryl carbazole moiety for solar cell. Tetrahedron 2007, 63 (9), 1913-1922.
16. Li, S. L.; Jiang, K. J.; Shao, K. F.; Yang, L. M., Novel organic dyes for efficient dye-sensitized solar cells. Chemical Communications 2006, (26), 2792-2794.
17. Hara, K.; Sato, T.; Katoh, R.; Furube, A.; Yoshihara, T.; Murai, M.; Kurashige, M.; Ito, S.; Shinpo, A.; Suga, S.; Arakawa, H., Novel conjugated organic dyes for efficient dye-sensitized solar cells. Advanced Functional Materials 2005, 15 (2), 246-252.
18. Hagberg, D. P.; Marinado, T.; Karlsson, K. M.; Nonomura, K.; Qin, P.; Boschloo, G.; Brinck, T.; Hagfeldt, A.; Sun, L., Tuning the HOMO and LUMO energy levels of organic chromophores for dye sensitized solar cells. Journal of Organic Chemistry 2007, 72 (25), 9550-9556.
19. Hagberg, D. P.; Edvinsson, T.; Marinado, T.; Boschloo, G.; Hagfeldt, A.; Sun, L. C., A novel organic chromophore for dye-sensitized nanostructured solar cells. Chemical Communications 2006, (21), 2245-2247.
20. Velusamy, M.; Thomas, K. R. J.; Lin, J. T.; Hsu, Y. C.; Ho, K. C., Organic dyes incorporating low-band-gap chromophores for dye-sensitized solar cells. Organic Letters 2005, 7 (10), 1899-1902.
21. Erten-Ela, S.; Marszalek, M.; Tekoglu, S.; Can, M.; Icli, S., Synthesis, characterization and photovoltaic properties of novel molecules based on triarylamine dyes. Current Applied Physics 10 (3), 749-756.
22. Tian, H.; Yang, X.; Chen, R.; Pan, Y.; Li, L.; Hagfeldt, A.; Sun, L., Phenothiazine derivatives for efficient organic dye-sensitized solar cells. Chemical Communications 2007, (36), 3741-3743.
23. Chen, R.; Yang, X.; Tian, H.; Wang, X.; Hagfeldt, A.; Sun, L., Effect of Tetrahydroquinoline Dyes Structure on the Performance of Organic Dye-Sensitized Solar Cells. Chemistry of Materials 2007, 19 (16), 4007-4015.
24. Horiuchi, T.; Miura, H.; Sumioka, K.; Uchida, S., High Efficiency of Dye-Sensitized Solar Cells Based on Metal-Free Indoline Dyes. Journal of the American Chemical Society 2004, 126 (39), 12218-12219.
25. Schmidt-Mende, L.; Bach, U.; Humphry-Baker, R.; Horiuchi, T.; Miura, H.; Ito, S.; Uchida, S.; Grätzel, M., Organic Dye for Highly Efficient Solid-State Dye-Sensitized Solar Cells. Advanced Materials 2005, 17 (7), 813-815.
26. Song, J.; Zhang, F.; Li, C.; Liu, W.; Li, B.; Huang, Y.; Bo, Z., Phenylethyne-Bridged Dyes for Dye-Sensitized Solar Cells. The Journal of Physical Chemistry C 2009, 113 (30), 13391-13397.
27. Hsieh, C.-P.; Lu, H.-P.; Chiu, C.-L.; Lee, C.-W.; Chuang, S.-H.; Mai, C.-L.; Yen, W.-N.; Hsu, S.-J.; Diau, E. W.-G.; Yeh, C.-Y., Synthesis and characterization of porphyrin sensitizers with various electron-donating substituents for highly efficient dye-sensitized solar cells. Journal of Materials Chemistry 2010, 20 (6), 1127-1134.
28. Chang, Y. J.; Chow, T. J., Dye-sensitized solar cell utilizing organic dyads containing triarylene conjugates. Tetrahedron 2009, 65 (24), 4726-4734.
29. Baheti, A.; Tyagi, P.; Thomas, K. R. J.; Hsu, Y. C.; Lin, J. T., Simple Triarylamine-Based Dyes Containing Fluorene and Biphenyl Linkers for Efficient Dye-Sensitized Solar Cells. Journal of Physical Chemistry C 2009, 113 (20), 8541-8547.
30. Boschloo, G.; Hagfeldt, A., Characteristics of the Iodide/Triiodide Redox Mediator in Dye-Sensitized Solar Cells. Accounts of Chemical Research 2009, 42 (11), 1819-1826.
31. Wenger, S.; Bouit, P.-A.; Chen, Q.; Teuscher, J. L.; Censo, D. D.; Humphry-Baker, R.; Moser, J.-E.; Delgado, J. L.; Martín, N.; Zakeeruddin, S. M.; Gratzel, M., Efficient Electron Transfer and Sensitizer Regeneration in Stable π-Extended Tetrathiafulvalene-Sensitized Solar Cells. Journal of the American Chemical Society 2010, 132 (14), 5164-5169.
32. Dreuw, A.; Weisman, J. L.; Head-Gordon, M., Long-range charge-transfer excited states in time-dependent density functional theory require non-local exchange. Journal of Chemical Physics 2003, 119 (6), 2943-2946.
33. Tozer, D. J., Relationship between long-range charge-transfer excitation energy error and integer discontinuity in Kohn-Sham theory. Journal of Chemical Physics 2003, 119 (24), 12697-12699.
34. Jacquemin, D.; Perpete, E. A.; Scuseria, G. E.; Ciofini, I.; Adamo, C., TD-DFT Performance for the Visible Absorption Spectra of Organic Dyes: Conventional versus Long-Range Hybrids. Journal of Chemical Theory and Computation 2007, 4 (1), 123-135.
35. Pastore, M.; Mosconi, E.; De Angelis, F.; Gra tzel, M., A Computational Investigation of Organic Dyes for Dye-Sensitized Solar Cells: Benchmark, Strategies, and Open Issues. The Journal of Physical Chemistry C 2010, 114 (15), 7205-7212.
36. Kim, J. J.; Choi, H.; Lee, J. W.; Kang, M. S.; Song, K.; Kang, S. O.; Ko, J., A polymer gel electrolyte to achieve >= 6% power conversion efficiency with a novel organic dye incorporating a low-band-gap chromophore. Journal of Materials Chemistry 2008, 18 (43), 5223-5229.
37. Yen, Y. S.; Hsu, Y. C.; Lin, J. T.; Chang, C. W.; Hsu, C. P.; Yin, D. J., Pyrrole-based organic dyes for dye-sensitized solar cells. Journal of Physical Chemistry C 2008, 112 (32), 12557-12567.
38. Li, R. Z.; Lv, X. J.; Shi, D.; Zhou, D. F.; Cheng, Y. M.; Zhang, G. L.; Wang, P., Dye-Sensitized Solar Cells Based on Organic Sensitizers with Different Conjugated Linkers: Furan, Bifuran, Thiophene, Bithiophene, Selenophene, and Biselenophene. Journal of Physical Chemistry C 2009, 113 (17), 7469-7479.
39. Seo, E. T.; Nelson, R. F.; Fritsch, J. M.; Marcoux, L. S.; Leedy, D. W.; Adams, R. N., Anodic Oxidation Pathways of Aromatic Amines. Electrochemical and Electron Paramagnetic Resonance Studies. Journal of the American Chemical Society 1966, 88 (15), 3498-3503.
40. Nelson, R. R.; Adams, R. N., Anodic oxidation pathways of substituted triphenylamines. II. Quantitative studies of benzidine formation. Journal of the American Chemical Society 1968, 90 (15), 3925-3930.
41. Li, G.; Jiang, K.-J.; Li, Y.-F.; Li, S.-L.; Yang, L.-M., Efficient Structural Modification of Triphenylamine-Based Organic Dyes for Dye-Sensitized Solar Cells. The Journal of Physical Chemistry C 2008, 112 (30), 11591-11599.
42. Ooyama, Y.; Ishii, A.; Kagawa, Y.; Imae, I.; Harima, Y., Dye-sensitized solar cells based on novel donor-acceptor [small pi]-conjugated benzofuro[2,3-c]oxazolo[4,5-a]carbazole-type fluorescent dyes exhibiting solid-state fluorescence. New Journal of Chemistry 2007, 31 (12), 2076-2082.
43. De Marco, L.; Manca, M.; Giannuzzi, R.; Malara, F.; Melcarne, G.; Ciccarella, G.; Zama, I.; Cingolani, R.; Gigli, G., Novel Preparation Method of TiO2-Nanorod-Based Photoelectrodes for Dye-Sensitized Solar Cells with Improved Light-Harvesting Efficiency. The Journal of Physical Chemistry C 2010, 114 (9), 4228-4236.
44. Melcarne, G.; De Marco, L.; Carlino, E.; Martina, F.; Manca, M.; Cingolani, R.; Gigli, G.; Ciccarella, G., Surfactant-free synthesis of pure anatase TiO2 nanorods suitable for dye-sensitized solar cells. Journal of Materials Chemistry 2010, 20 (34), 7248-7254.
45. Fritsch, M. J. E. A., Gaussian 03, Revision B05; Gaussian Inc.: Pittsburgh PA, 2003. 2003
46. Becke, A. D., A NEW MIXING OF HARTREE-FOCK AND LOCAL DENSITY-FUNCTIONAL THEORIES. Journal of Chemical Physics 1993, 98 (2), 1372-1377.
47. Cossi, M.; Barone, V., Time-dependent density functional theory for molecules in liquid solutions. Journal of Chemical Physics 2001, 115 (10), 4708-4717.
48. Schafer, A.; Horn, H.; Ahlrichs, R., FULLY OPTIMIZED CONTRACTED GAUSSIAN-BASIS SETS FOR ATOMS LI TO KR. Journal of Chemical Physics 1992, 97 (4), 2571-2577.
49. Schafer, A.; Huber, C.; Ahlrichs, R., Fully optimized contracted gaussian-basis sets of triple zeta valence quality for atoms LI TO KR. Journal of Chemical Physics 1994, 100 (8), 5829-5835.
50. TURBOMOLE v. 5.10 2009, a development of University of Karlsruhe and Forschungszentrum Karlsruhe GmbH 1989-2007; TURBOMOLE GmbH, 2007.
51. Hattig, C.; Weigend, F., CC2 excitation energy calculations on large molecules using the resolution of the identity approximation. Journal of Chemical Physics 2000, 113 (13), 5154-5161.
52. Hattig, C.; Hellweg, A.; Kohn, A., Distributed memory parallel implementation of energies and gradients for second-order Moller-Plesset perturbation theory with the resolution-of-the-identity approximation. Physical Chemistry Chemical Physics 2006, 8 (10), 1159-1169.