Optical properties and aggregation of phenothiazine-based dye-sensitizers for solar cells applications: A combined experimental and computational investigation

Journal of Physical Chemistry C

Volumn 117, Issue 19, 2013, Pages 9613-9622

  Agrawal, Saurabh ^a   Pastore, Mariachiara ^a   Marotta, Gabriele ^a   Reddy, Marri Anil ^b   Chandrasekharam, Malapaka ^b   De Angelis, Filippo ^a  

^a CNR   (Italy)

^b INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTATIONAL INVESTIGATION; COMPUTATIONAL MODELING; DYE-SENSITIZED SOLAR CELL; METAL OXIDE SURFACES; MOLECULAR ENGINEERING; PHOTOELECTROCHEMICAL PROPERTIES; SPECTROSCOPIC SIGNALS; UV-VIS ABSORPTION SPECTRA;

CHARGE TRANSFER; INSECTICIDES; OPTICAL PROPERTIES; SOLAR CELLS; SOLVATION; ULTRAVIOLET SPECTROSCOPY;

AGGLOMERATION;

EID: 84878072118     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp4026305     Document Type: Article

References (92)

1. Hagfeldt, A.; Peter, L. Dye-Sensitized Solar Cells: EPFL Press: Lausanne, 2010; pp 323-403.
2. 2 Films Nature 1991, 353, 737-740 (Pubitemid 21912607)
3. Nazeeruddin, M. K.; De Angelis, F.; Fantacci, S.; Selloni, A.; Viscardi, G.; Liska, P.; Ito, S.; Takeru, B.; Grätzel, M. Combined Experimental and DFT-TDDFT Computational Study of Photoelectrochemical Cell Ruthenium Sensitizers J. Am. Chem. Soc. 2005, 127, 16835-16847 (Pubitemid 41772844)
4. Grätzel, M. Conversion of Sunlight to Electric Power by Nanocrystalline Dye-Sensitized Solar Cells J. Photochem. Photobiol. A 2004, 164, 3-14
5. Yella, A.; Lee, H.-W.; Tsao, H. N.; Yi, C.; Chandiran, A. K.; Nazeeruddin, M. K.; Diau, E. W.-G.; Yeh, C.-Y.; Zakeeruddin, S. M.; Grätzel, M. Porphyrin-Sensitized Solar Cells with Cobalt (II/III) Based Redox Electrolyte Exceed 12% Efficiency Science 2011, 334, 629-634
6. 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 J. Org. Chem. 2007, 72, 9550-9556 (Pubitemid 350231800)
7. Daeneke, T.; Kwon, T.-H.; Holmes, A. B.; Duffy, N. W.; Bach, U.; Spiccia, L. High-Efficiency Dye-Sensitized Solar Cells with Ferrocene-based Electrolytes Nat. Chem. 2011, 3, 213-217
8. Feldt, S. M.; Gibson, E. A.; Gabrielsson, E.; Sun, L.; Boschloo, G.; Hagfeldt, A. Design of Organic Dyes and Cobalt Polypyridine Redox Mediators for High-Efficiency Dye-Sensitized Solar Cells J. Am. Chem. Soc. 2010, 132, 16714-16724
9. Feldt, S. M.; Cappel, U. B.; Johansson, E. M. J.; Boschloo, G.; Hagfeldt, A. Characterization of Surface Passivation by Poly(methylsiloxane) for Dye-Sensitized Solar Cells Employing the Ferrocene Redox Couple J. Phys. Chem. C 2010, 114, 10551-10558
10. Bai, Y.; Zhang, J.; Zhou, D.; Wang, Y.; Zhang, M.; Wang, P. Engineering Organic Sensitizers for Iodine-Free Dye-Sensitized Solar Cells: Red-Shifted Current Response Concomitant with Attenuated Charge Recombination J. Am. Chem. Soc. 2011, 133, 11442-11445
11. 2 Redox Couple as a Mediator for Dye-Sensitized Nanocrystalline Solar Cells Coord. Chem. Rev. 2004, 248, 1447-1453
12. Hara, K.; Sato, T.; Katoh, R.; Furube, A.; Yoshihara, T.; Murai, M.; Kurashige, M.; Ito, S.; Shinpo, A.; Suga, S. Novel Conjugated Organic Dyes for Efficient Dye-Sensitized Solar Cells Adv. Funct. Mater. 2005, 15, 246-252 (Pubitemid 40384676)
13. Hara, K.; Kurashige, M.; Ito, S.; Shinpo, A.; Suga, S.; Sayama, K.; Arakawa, H. Novel Polyene Dyes for Highly Efficient Dye-Sensitized Solar Cells Chem. Commun. 2003, 252-253 (Pubitemid 36132045)
14. Hara, K.; Kurashige, M.; Dan-oh, Y.; Kasada, C.; Shinpo, A.; Suga, S.; Sayama, K.; Arakawa, K. Design of New Coumarin Dyes Having Thiophene Moieties for Highly Efficient Organic-Dye-Sensitized Solar Cells New. J. Chem. 2003, 27, 783-785 (Pubitemid 36623430)
15. 2 Solar Cell Having a High Solar-Energy Conversion Efficiency up to 5.6% Chem. Commun. 2001, 0, 569-570 (Pubitemid 32250701)
16. 2 Solar Cells Based on Novel Coumarin Dyes Sol. Energy Mater. Sol. Cells 2003, 77, 89-103
17. Hara, K.; Wang, Z.-S.; Sato, T.; Furube, A.; Katoh, R.; Sugihara, H.; Dan-oh, Y.; Kasada, C.; Shinpo, A.; Suga, S. Oligothiophene-Containing Coumarin Dyes for Efficient Dye-Sensitized Solar Cells J. Phys. Chem. B 2005, 15476-15482
18. 2 Electrodes J. Phys. Chem. B 2005, 109, 23776-23778 (Pubitemid 43081425)
19. 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 J. Phys. Chem. B 2003, 107, 597-606
20. Wang, Z.-S.; Cui, Y.; Dan-oh, Y.; Kasada, C.; Shinpo, A.; Hara, K. Thiophene-Functionalized Coumarin Dye for Efficient Dye-Sensitized Solar Cells: Electron Lifetime Improved by Coadsorption of Deoxycholic Acid J. Phys. Chem. C 2007, 111, 7224-7230 (Pubitemid 46854589)
21. Chen, R.; Yang, X.; Tian, H.; Sun, L. Tetrahydroquinoline Dyes With Different Spacers for Organic Dye-Sensitized Solar Cells J. Photochem. Photobiol. A 2007, 189, 295-300
22. 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 Chem. Mater. 2007, 19, 4007-4015 (Pubitemid 47266094)
23. Campbell, W. M.; Jolley, K. W.; Wagner, P.; Wagner, K.; Walsh, P. J.; Gordon, K. C.; Schmidt-Mende, L.; Nazeeruddin, M. K.; Wang, Q.; Grätzel, M. Highly Efficient Porphyrin Sensitizers for Dye-Sensitized Solar Cells J. Phys. Chem. C 2007, 111, 11760-11762 (Pubitemid 47325747)
24. Wang, Z. S.; Cui, Y.; Dan-Oh, Y.; Kasada, C.; Shinpo, A.; Hara, K. Molecular Design of Coumarin Dyes for Stable and Efficient Organic Dye-Sensitized Solar Cells J. Phys. Chem. C 2008, 112, 17011-17017
25. Thomas, K. R. J.; Lin, J. T.; Hsu, Y.-C.; Ho, K.-C. Organic Dyes Containing Thienylfluorene Conjugation for Solar Cells Chem. Commun. 2005, 0, 4098-4100 (Pubitemid 41206298)
26. Hwang, S.; Lee, J. H.; Park, C.; Lee, H.; Kim, C.; Park, C.; Lee, M. H.; Lee, W.; Park, J.; Kim, K. A Highly Efficient Organic Sensitizer for Dye-Sensitized Solar Cells Chem. Commun. 2007, 4887-4889
27. Xu, W.; Peng, B.; Chen, J.; Liang, M.; Cai, F. New Triphenylamine-Based Dyes for Dye-Sensitized Solar Cells J. Phys. Chem. C 2008, 112, 874-880 (Pubitemid 351206064)
28. 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. Simple Organic Molecules Bearing a 3,4-Ethylenedioxythiophene Linker for Efficient Dye-Sensitized Solar Cells Chem. Commun. 2008, 5152-5154
29. Tian, H.; Yang, X.; Chen, R.; Pan, Y.; Li, L.; Hagfeldt, A.; Sun, L. Phenothiazine Derivatives for Efficient Organic Dye-Sensitized Solar Cells Chem. Commun. 2007, 0, 3741-3743 (Pubitemid 47404178)
30. Tan, S.; Zhai, J.; Fang, H.; Jiu, T.; Ge, J.; Li, Y.; Jiang, L.; Zhu, D. Novel Carboxylated Oligothiophenes as Sensitizers in Photoelectric Conversion Systems Chem.-Eur. J. 2005, 11, 6272-6276 (Pubitemid 41527793)
31. 2 Solar Cells Chem. Lett. 2006, 35, 592-593 (Pubitemid 44306339)
32. 2 Films by an Unsymmetrical Squaraine Dye J. Am. Chem. Soc. 2007, 129, 10320-10321 (Pubitemid 47330234)
33. 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 Adv. Mater. 2005, 17, 813-815 (Pubitemid 40527538)
34. Horiuchi, T.; Miura, H.; Uchida, S. Highly-Efficient Metal-Free Organic Dyes for Dye-Sensitized Solar Cells Chem. Commun. 2003, 3036-3037 (Pubitemid 38019261)
35. Horiuchi, T.; Miura, H.; Sumioka, K.; Uchida, S. High Efficiency of Dye-Sensitized Solar Cells Based on Metal-Free Indoline Dyes J. Am. Chem. Soc. 2004, 126, 12218-12219 (Pubitemid 39304876)
36. Mishra, A.; Fischer, M.; Bäuerle, P. Metal-Free Organic Dyes for Dye-Sensitized Solar Cells: From Structure: Property Relationships to Design Rules Angew. Chem., Int. Ed. 2009, 48, 2474-2499
37. Tatay, S.; Haque, S. A.; O'Regan, B.; Durrant, J. R.; Verhees, W. J. H.; Kroon, J. M.; Vidal-Ferran, A.; Gavina, P.; Palomares, E. Kinetic Competition in Liquid Electrolyte and Solid-State Cyanine Dye Sensitized Solar Cells J. Mater. Chem. 2007, 17, 3037-3044 (Pubitemid 47118856)
38. 2 Film J. Phys. Chem. B 2002, 106, 1363-1371 (Pubitemid 35276101)
39. Burfeindt, B.; Hannappel, T.; Storck, W.; Willig, F. Measurement of Temperature-Independent Femtosecond Interfacial Electron Transfer from an Anchored Molecular Electron Donor to a Semiconductor as Acceptor J. Phys. Chem. 1996, 100, 16463-16465 (Pubitemid 126787983)
40. 2 Nanocrystallites with Cresyl Violet Aggregates J. Phys. Chem. B 1997, 101, 2583-2590 (Pubitemid 127581052)
41. Tian, H.; Yang, X.; Chen, R.; Zhang, R.; Hagfeldt, A.; Sun, L. Effect of Different Dye Baths and Dye-Structures on the Performance of Dye-Sensitized Solar Cells Based on Triphenylamine Dyes J. Phys. Chem. C 2008, 112, 11023-11033
42. 2 Nanocrystalline Electrodes with Aggregated Cyanine Dyes J. Phys. Chem. B 2001, 105, 9960-9965 (Pubitemid 35338606)
43. Bujdák, J.; Iyi, N. Molecular Orientation of Rhodamine Dyes on Surfaces of Layered Silicates J. Phys. Chem. B 2005, 109, 4608-4615 (Pubitemid 40429322)
44. 2 Langmuir 2012, 28, 7071-7082
45. Würthner, F.; Kaiser, T. E.; Saha-Möller, C. R. J-Aggregates: From Serendipitous Discovery to Supramolecular Engineering of Functional Dye Materials Angew. Chem., Int. Ed. 2011, 50, 3376-3410
46. 2 in Dye-Sensitized Solar Cells Models: An Ab Initio Investigation ACS nano 2010, 4, 556-562
47. Kawasaki, M.; Aoyama, S. High Efficiency Photocurrent Generation by Two-Dimensional Mixed J-Aggregates of Cyanine Dyes Chem. Commun. 2004, 988-989 (Pubitemid 38624715)
48. 2 Films. An Organized Assembly Approach for Enhancing the Efficiency of Photosensitization J. Phys. Chem. B 1999, 103, 4693-4700 (Pubitemid 129702635)
49. 2 Nanocrystals J. Phys. Chem. B 2003, 107, 14336-14341
50. 2 Junctions by Surface Adsorbed Phosphinate Amphiphiles Enhances the Photovoltaic Performance of Dye Sensitized Solar Cells Dalton Trans. 2009, 45, 10015-10020
51. Han, L.; Islam, A.; Chen, H.; Malapaka, C.; Chiranjeevi, B.; Zhang, S.; Yang, X.; Yanagida, M. High-Efficiency Dye-Sensitized Solar Cell with a Novel Co-Adsorbent Energy Environ. Sci. 2012, 5, 6057-6060
52. 2 Films J. Phys Chem. B 2005, 109, 15397-15409
53. Lee, C.-W.; Lu, H.-P.; Lan, C.-M.; Huang, Y.-L.; Liang, Y.-R.; Yen, W.-N.; Liu, Y.-C.; Lin, Y.-S.; Diau, E. W.-G.; Yeh, C.-Y. Novel Zinc Porphyrin Sensitizers for Dye-Sensitized Solar Cells: Synthesis and Spectral, Electrochemical, and Photovoltaic Properties Chem.-Eur. J. 2009, 15, 1403-1412
54. Li, J.; Wu, W.; Yang, J.; Tang, J.; Long, Y.; Hua, J. Effect of Chenodeoxycholic Acid (CDCA) Additive on Phenothiazine Dyes Sensitized Photovoltaic Performance Sci. China Chem. 2011, 54, 699-706
55. 2 Sensitized Solar Cells Energy Environ. Sci. 2011, 4, 1820-1829
56. 2 Heterointerfaces J. Phys. Chem. Lett. 2011, 2, 1261-1267
57. Yang, C.-J.; Chang, Y. J.; Watanabe, M.; Hon, Y.-S.; Chow, T. J. Phenothiazine Derivatives as Organic Sensitizers for Highly Efficient Dye-Sensitized Solar Cells J. Mater. Chem. 2012, 22, 4040-4049
58. Marszalek, M.; Nagane, S.; Ichake, A.; Humphry-Baker, R.; Paul, V.; Zakeeruddin, S. M.; Grätzell, M. Tuning Spectral Properties of Phenothiazine Based Donor-π-Acceptor Dyes for Efficient Dye-Sensitized Solar Cells J. Mater. Chem. 2012, 22, 889-894
59. Park, S. S.; Won, Y. S.; Choi, Y. C.; Kim, J. H. Molecular Design of Organic Dyes with Double Electron Acceptor for Dye-Sensitized Solar Cell Energy Fuels 2009, 23, 3732-3736
60. Meyer, T.; Ogermann, D.; Pankrath, A.; Kleinermanns, K.; Müller, T. J. J. Phenothiazinyl Rhodanylidene Merocyanines for Dye-Sensitized Solar Cells J. Org. Chem. 2012, 77, 3704-3715
61. Tsao, M.-H.; Wu, T.-Y.; Wang, H.-P.; Sun, I. W.; Su, S.-G.; Lin, Y.-C.; Chang, C.-W. An Efficient Metal-Free Sensitizer for Dye-Sensitized Solar Cells Mater. Lett. 2011, 65, 583-586
62. Tian, H.; Yang, X.; Chen, R.; Hagfeldt, A.; Sun, L. A Metal-Free "Black Dye" for Panchromatic Dye-Sensitized Solar Cells Energy Environ. Sci. 2009, 2, 674-677
63. Xie, Z.; Midya, A.; Loh, K. P.; Adams, S.; Blackwood, D. J.; Wang, J.; Zhang, X.; Chen, Z. Highly Efficient Dye-Sensitized Solar Cells Using Phenothiazine Derivative organic dyes Progr. Photovoltaics 2010, 18, 573-581
64. Kim, S. H.; Kim, H. W.; Sakong, C.; Namgoong, J.; Park, S. W.; Ko, M. J.; Lee, C. H.; Lee, W. I.; Kim, J. P. Effect of Five-Membered Heteroaromatic Linkers to the Performance of Phenothiazine-Based Dye-Sensitized Solar Cells Org. Lett. 2011, 13, 5784-5787
65. Wan, Z.; Jia, C.; Duan, Y.; Zhou, L.; Lin, Y.; Shi, Y. Phenothiazine-triphenylamine Based Organic Dyes Containing Various Conjugated Linkers for Efficient Dye-Sensitized Solar Cells J. Mater. Chem. 2012, 22, 25140-25147
66. Wu, W.; Yang, J.; Hua, J.; Tang, J.; Zhang, L.; Long, Y.; Tian, H. Efficient and Stable Dye-Sensitized Solar Cells Based on Phenothiazine Sensitizers with Thiophene Units J. Mater. Chem. 2010, 20, 1772-1779
67. Yin, J.-F.; Chen, J.-G.; Lin, J.-T. s.; Bhattacharya, D.; Hsu, Y.-C.; Lin, H.-C.; Ho, K.-C.; Lu, K.-L. Enhanced Light-Harvesting Capability by Phenothiazine in Ruthenium Sensitizers with Superior Photovoltaic Performance J. Mater. Chem. 2012, 22, 130-139
68. Cao, D.; Peng, J.; Hong, Y.; Fang, X.; Wang, L.; Meier, H. Enhanced Performance of the Dye-Sensitized Solar Cells with Phenothiazine-Based Dyes Containing Double D-A Branches Org. Lett. 2011, 13, 1610-1613
69. 2 Nanoparticles J. Am. Chem. Soc. 2004, 126, 15024-15025 (Pubitemid 39557251)
70. 2 Nanoparticles J. Phys. Chem. B 2000, 104, 10348-10351
71. 2 Surfaces and Effect of Molecular Adsorbates Using Different DFT Implementations J. Phys. Chem. C 2010, 114, 22659-22670
72. Agrawal, S.; Dev, P.; English, N. J.; Thampi, K. R.; MacElroy, J. M. D. A TD-DFT Study of the Effects of Structural Variations on the Photochemistry of Polyene Dyes Chem. Sci. 2012, 3, 416-424
73. Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. Structures, and Electronic Properties of Molecules in Solution with the C-PCM Solvation Model J. Comput. Chem. 2003, 24, 669-681
74. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A., Gaussian 09, Revision A.1; Gaussian, Inc.: Wallingford, CT, 2009.
75. Pastore, M.; Fantacci, S.; De Angelis, F. Modeling Excited States and Alignment of Energy Levels in Dye-Sensitized Solar Cells: Successes, Failures, and Challenges J. Phys Chem. C 2013, 117, 3685-3700
76. Pastore, M.; Mosconi, E.; De Angelis, F.; Grätzel, M. A Computational Investigation of Organic Dyes for Dye-Sensitized Solar Cells: Benchmark, Strategies, and Open Issues J. Phys. Chem. C 2010, 114, 7205-7212
77. Agrawal, S.; Dev, P.; English, N. J.; Thampi, K. R.; MacElroy, J. M. D. First-Principles Study of the Excited-State Properties of Coumarin-Derived Dyes in Dye-Sensitized Solar Cells J. Mater. Chem. 2011, 21, 11101-11108
78. Dev, P.; Agrawal, S.; English, N. J. Determining the Appropriate Exchange-Correlation Functional for Time-Dependent Density Functional Theory Studies of Charge-Transfer Excitations in Organic Dyes J. Chem. Phys. 2012, 136, 224301-11
79. Yanai, T.; Tew, D. P.; Handy, N. C. A New Hybrid Exchange-Correlation Functional Using the Coulomb-Attenuating Method (CAM-B3LYP) Chem. Phys. Lett. 2004, 393, 51-57
80. Kalyanasundaram, K.; Grätzel, M. Applications of Functionalized Transition Metal Complexes in Photonic and Optoelectronic Devices Coord. Chem. Rev. 1998, 177, 347
81. Falaras, P. Synergetic Effect of Carboxylic Acid Functional Groups and Fractal Surface Characteristics for Efficient Dye Sensitization of Titanium Oxide Sol. Energy Mater. Sol. Cells 1998, 53, 163-175 (Pubitemid 128413808)
82. Finnie, K. S.; Bartlett, J. R.; Woolfrey, J. L. Vibrational Spectroscopic Study of the Coordination of (2,2′-Bipyridyl-4,4′-dicarboxylic acid)ruthenium(II) Complexes to the Surface of Nanocrystalline Titania Langmuir 1998, 14, 2744-2749
83. 2 Anatase (101) Surface J. Phys. Chem. C 2009, 113, 20117-20126
84. 2 Surfaces Chem. Asian J. 2010, 5, 852-858
85. 2 Solar Cell J. Phys. Chem. B 2003, 107, 8981-8987
86. 2 Films for DSSC Applications Using Vibrational Spectroscopy and Confocal Raman Imaging Langmuir 2010, 26, 9575-9583
87. 2 Films with UV-Vis, Raman, and FTIR Spectroscopies J. Phys. Chem. B 2006, 110, 8723-8730 (Pubitemid 43798577)
88. 2 Surfaces Sensitized by Organic Dyes With Different Anchoring Groups: Adsorption modes, Electronic Structure and Implication for Electron Injection/Recombination Phys. Chem. Chem. Phys. 2012, 14, 920-928
89. 2 Surfaces in Dye-Sensitized Solar Cells: Interplay of Theory and Experiment Phys. Chem. Chem. Phys. 2012, 14, 15963-15974
90. 3-: Origin of Non-Single-Exponential and Particle Size Independent Dynamics J. Phys Chem. B 2000, 104, 93-104
91. 2 Nanoparticles: A Study of Direct Charge Injection by Electroabsorption Spectroscopy J. Am. Chem. Soc. 2003, 125, 4637-4642 (Pubitemid 36418709)
92. Pastore, M.; De Angelis, F. Intermolecular Interactions in Dye-Sensitized Solar Cells: A Computational Modeling Perspective J. Phys. Chem. Lett. 2013, 956-974