Variation in optoelectronic properties of Azo dye-sensitized TiO 2 semiconductor interfaces with different adsorption anchors: Carboxylate, sulfonate, hydroxyl and pyridyl groups

ACS Applied Materials and Interfaces

Volumn 6, Issue 10, 2014, Pages 7535-7546

  Zhang, Lei ^a   Cole, Jacqueline M ^a,b   Dai, Chencheng ^c  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b ARGONNE NATIONAL LABORATORY   (United States)

^c UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

anchor; azo; carboxylate; DFT; dye sensitized solar cell; first principles; hydroxyl; nanoparticles; pyridyl; sulfonate; TDDFT

Indexed keywords

ADSORPTION; ANCHORS; AZO DYES; CALCULATIONS; CARBOXYLATION; CYCLIC VOLTAMMETRY; NANOCOMPOSITES; NANOPARTICLES; PHOTOELECTROCHEMICAL CELLS; SOLAR CELLS; TITANIUM DIOXIDE; TWO DIMENSIONAL;

AZO; CARBOXYLATE; DFT; DYE-SENSITIZED SOLAR CELL; FIRST-PRINCIPLES; HYDROXYL; PYRIDYL; SULFONATE; TDDFT;

DYE-SENSITIZED SOLAR CELLS;

EID: 84961980448     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/am502186k     Document Type: Article

References (95)

1. Hardin, B. E.; Snaith, H. J.; McGehee, M. D. The Renaissance of Dye-Sensitized Solar Cells Nat. Photonics 2012, 6, 162-169
2. Grätzel, M. Photoelectrochemical Cells Nature 2001, 414, 338-344
3. Zou, W.; Visser, C.; Maduro, J. A.; Pshenichnikov, M. S.; Hummelen, J. C. Broadband Dye-Sensitized Upconversion of near-Infrared Light Nat. Photonics 2012, 6, 560-564
4. 2 Films Nature 1991, 353, 737-740
5. Xie, Z.; Jin, X.; Chen, G.; Xu, J.; Chen, D.; Shen, G. Integrated Smart Electrochromic Windows for Energy Saving and Storage Applications Chem. Commun. 2014, 50, 608-610
6. Bechinger, C.; Ferrere, S.; Zaban, A.; Sprague, J.; Gregg, B. A. Photoelectrochromic Windows and Displays Nature 1996, 383, 608-610
7. Ahn, K.-S.; Yoo, S. J.; Kang, M.-S.; Lee, J.-W.; Sung, Y.-E. Tandem Dye-Sensitized Solar Cell-Powered Electrochromic Devices for the Photovoltaic-Powered Smart Window J. Power Sources 2007, 168, 533-536
8. Hardin, B. E.; Hoke, E. T.; Armstrong, P. B.; Yum, J.-H.; Comte, P.; Torres, T.; Fréchet, J. M. J.; Nazeeruddin, M. K.; Grätzel, M.; McGehee, M. D. Increased Light Harvesting in Dye-Sensitized Solar Cells with Energy Relay Dyes Nat. Photonics 2009, 3, 406-411
9. Anthonysamy, A.; Lee, Y.; Karunagaran, B.; Ganapathy, V.; Rhee, S.-W.; Karthikeyan, S.; Kim, K. S.; Ko, M. J.; Park, N.-G.; Ju, M.-J. Molecular Design and Synthesis of ruthenium(II) Sensitizers for Highly Efficient Dye-Sensitized Solar Cells J. Mater. Chem. 2011, 21, 12389-12397
10. 2 Solar Cells with a High Solar-Energy-Conversion Efficiency Adv. Funct. Mater. 2007, 17, 2964-2974
11. 2 Films: Free Energy vs Distance Dependence J. Am. Chem. Soc. 2004, 126, 5225-5233
12. 2-Based Solar Cells J. Am. Chem. Soc. 2001, 123, 1613-1624
13. Burschka, J.; Pellet, N.; Moon, S.-J.; Humphry-Baker, R.; Gao, P.; Nazeeruddin, M. K.; Grätzel, M. Sequential Deposition as a Route to High-Performance Perovskite-Sensitized Solar Cells Nature 2013, 499, 316-319
14. Alibabaei, L.; Kim, J.-H.; Wang, M.; Pootrakulchote, N.; Teuscher, J.; Di Censo, D.; Humphry-Baker, R.; Moser, J.-E.; Yu, Y.-J.; Kay, K.-Y. Molecular Design of Metal-Free D-π-A Substituted Sensitizers for Dye-Sensitized Solar Cells Energy Environ. Sci. 2010, 3, 1757
15. Fischer, M. K. R.; Wenger, S.; Wang, M.; Mishra, A.; Zakeeruddin, S. M.; Grätzel, M.; Bäuerle, P. D-Π-A Sensitizers for Dye-Sensitized Solar Cells: Linear vs Branched Oligothiophenes Chem. Mater. 2010, 22, 1836-1845
16. Clifford, J. N.; Martínez-Ferrero, E.; Viterisi, A.; Palomares, E. Sensitizer Molecular Structure-Device Efficiency Relationship in Dye Sensitized Solar Cells Chem. Soc. Rev. 2011, 40, 1635-1646
17. Mishra, A.; Fischer, M. K. R.; 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
18. Ooyama, Y.; Inoue, S.; Nagano, T.; Kushimoto, K.; Ohshita, J.; Imae, I.; Komaguchi, K.; Harima, Y. Dye-Sensitized Solar Cells Based on Donor-Acceptor Π-Conjugated Fluorescent Dyes with a Pyridine Ring as an Electron-Withdrawing Anchoring Group Angew. Chem., Int. Ed. 2011, 123, 7567-7571
19. Brewster, T. P.; Konezny, S. J.; Sheehan, S. W.; Martini, L. A.; Schmuttenmaer, C. A.; Batista, V. S.; Crabtree, R. H. Hydroxamate Anchors for Improved Photoconversion in Dye-Sensitized Solar Cells Inorg. Chem. 2013, 52, 6752-6764
20. Hirva, P.; Haukka, M. Effect of Different Anchoring Groups on the Adsorption of Photoactive Compounds on the Anatase (101) Surface Langmuir 2010, 26, 17075-17081
21. Baik, C.; Kim, D.; Kang, M.-S.; Kang, S. O.; Ko, J.; Nazeeruddin, M. K.; Grätzel, M. Organic Dyes with a Novel Anchoring Group for Dye-Sensitized Solar Cell Applications J. Photochem. Photobiol., A 2009, 201, 168-174
22. Mao, J.; He, N.; Ning, Z.; Zhang, Q.; Guo, F.; Chen, L.; Wu, W.; Hua, J.; Tian, H. Stable Dyes Containing Double Acceptors without COOH as Anchors for Highly Efficient Dye-Sensitized Solar Cells Angew. Chem. Int. Ed. 2012, 51, 9873-9876
23. Ambrosio, F.; Martsinovich, N.; Troisi, A. What Is the Best Anchoring Group for a Dye in a Dye-Sensitized Solar Cell? J. Phys. Chem. Lett. 2012, 3, 1531-1535
24. Wiberg, J.; Marinado, T.; Hagberg, D. P.; Sun, L.; Hagfeldt, A.; Albinsson, B. Effect of Anchoring Group on Electron Injection and Recombination Dynamics in Organic Dye-Sensitized Solar Cells J. Phys. Chem. C 2009, 113, 3881-3886
25. Galoppini, E. Linkers for Anchoring Sensitizers to Semiconductor Nanoparticles Coord. Chem. Rev. 2004, 248, 1283-1297
26. 2 Electrodes: Carboxylate versus Phosphonate Linkages J. Phys. Chem. B 2006, 110, 8740-8749
27. 2 on Hydrogen Production under Visible Light J. Phys. Chem. B 2006, 110, 14792-14799
28. Ambrosio, F.; Martsinovich, N.; Troisi, A. Effect of the Anchoring Group on Electron Injection: Theoretical Study of Phosphonated Dyes for Dye-Sensitized Solar Cells J. Phys. Chem. C 2012, 116, 2622-2629
29. 2 Films for Dye-Sensitized Solar Cells Appl. Surf. Sci. 2012, 258, 7833-7838
30. 2 Anatase (101) Surface Determined by a First-Principles Study Langmuir 2010, 26, 4813-4821
31. 2 Anatase (101) and Rutile (110) Surfaces J. Phys. Chem. C 2009, 113, 5730-5740
32. Grätzel, M. Recent Advances in Sensitized Mesoscopic Solar Cells Acc. Chem. Res. 2009, 42, 1788-1798
33. Zhang, L.; Cole, J. M.; Waddell, P. G.; Low, K. S.; Liu, X. Relating Electron Donor and Carboxylic Acid Anchoring Substitution Effects in Azo Dyes to Dye-Sensitized Solar Cell Performance ACS Sustain. Chem. Eng. 2013, 1, 1440-1452
34. Almeida, M. R.; Stephani, R.; Dos Santos, H. F.; Oliveira, L. F. C. De Spectroscopic and Theoretical Study of the "Azo"-Dye E124 in Condensate Phase: Evidence of a Dominant Hydrazo Form J. Phys. Chem. A 2010, 114, 526-534
35. Charlton, M. H.; Docherty, R.; McGeein, D. J.; Morley, J. O. Theoretical Investigation of the Structure and Spectra of Donor-Acceptor Azobenzenes Faraday Trans. 1993, 89, 1671-1675
36. Olmsted, J.; Lawrence, J.; Yee, G. G. Photochemical Storage Potential of Azobenzenes Sol. Energy 1983, 30, 271-274
37. Jono, R.; Fujisawa, J.; Segawa, H.; Yamashita, K. Theoretical Study of the Surface Complex between TiO 2 and TCNQ Showing Interfacial Charge-Transfer Transitions J. Phys. Chem. Lett. 2011, 2, 1167-1170
38. 2 Conduction Band in Dye-Sensitized Solar Cells: Disentangling Charge Transfer and Electrostatic Effects Energy Environ. Sci. 2013, 6, 183
39. Pastore, M.; Angelis, F. De First-Principles Computational Modeling of Fluorescence Resonance Energy Transfer in Co-Sensitized Dye Solar Cells J. Phys. Chem. Lett. 2012, 3, 2146-2153
40. Pastore, M.; Mosconi, E.; Angelis, F. De Computational Investigation of Dye-Iodine Interactions in Organic Dye-Sensitized Solar Cells J. Phys. Chem. C 2012, 116, 5965-5973
41. 2 Sensitized Solar Cells Energy Environ. Sci. 2011, 4, 1820
42. 2 Surfaces in Dye-Sensitized Solar Cells: Interplay of Theory and Experiment Phys. Chem. Chem. Phys. 2012, 14, 15963-15974
43. 2 Surfaces Exposing the (001) or (101) Faces: A First-Principles Investigation J. Phys. Chem. C 2012, 116, 18124-18131
44. 2 Nanoclusters J. Chem. Theory Comput. 2010, 6, 2856-2865
45. Sánchez-de-Armas, R.; San Miguel, M. á.; Oviedo, J.; Sanz, J. F. Coumarin Derivatives for Dye Sensitized Solar Cells: A TD-DFT Study Phys. Chem. Chem. Phys. 2012, 14, 225-233
46. 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.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenb, D. J. Gaussian 09, Revision B 01 2009.
47. Agrawal, S.; Pastore, M.; Marotta, G.; Reddy, M. A.; Chandrasekharam, M.; Angelis, F. De Optical Properties and Aggregation of Phenothiazine-Based Dye-Sensitizers for Solar Cells Applications: A Combined Experimental and Computational Investigation J. Phys. Chem. C 2013, 117, 9613-9622
48. Pastore, M.; Angelis, F. De Aggregation of Organic Dyes on TiO2 in Dye-Sensitized Solar Cells Models: An Ab Initio Investigation ACS Nano 2010, 4, 556-562
49. Becke, A. D. Density-Functional Thermochemistry. III. The Role of Exact Exchange J. Chem. Phys. 1993, 7, 5648-5652
50. Rassolov, V. A.; Ratner, M. A.; Pople, J. A.; Redfern, P. C.; Curtiss, L. A. 6-31G* Basis Set for Third-Row Atoms J. Comput. Chem. 2001, 22, 976-984
51. Miertuš, S.; Scrocco, E.; Tomasi, J. Electrostatic Interaction of a Solute with a Continuum. A Direct Utilizaion of Ab Initio Molecular Potentials for the Prevision of Solvent Effects Chem. Phys. 1981, 55, 117-129
52. Dennington, R.; Keith, T.; Millam, J. GaussView, version 5; Semichem: Shawnee Mission, KS, 2009.
53. Turro, N. J. Modern Molecular Photochemistry; University Science Books: Sausalito, CA, 1991; p 87.
54. 2 Anatase (101) Surfaces by DFT Calculations J. Phys. Chem. B 2000, 104, 1300-1306
55. 2 Semiconductor: Insight from First Principles Calculations Phys. Chem. Chem. Phys. 2013, 15, 13844-13851
56. Segall, M. D.; Lindan, P. J. D.; Probert, M. J.; Pickard, C. J.; Hasnip, P. J.; Clark, S. J.; Payne, M. C. First-Principles Simulation: Ideas, Illustrations and the CASTEP Code J. Phys. Condens. Matter 2002, 14, 2717-2744
57. Hagfeldt, A.; Boschloo, G.; Sun, L.; Kloo, L.; Pettersson, H. Dye-Sensitized Solar Cells Chem. Rev. 2010, 110, 6595-6663
58. 2 Annu. Rev. Phys. Chem. 2007, 58, 143-184
59. Fantacci, S.; Angelis, F. De A Computational Approach to the Electronic and Optical Properties of Ru(II) and Ir(III) Polypyridyl Complexes: Applications to DSC, OLED and NLO Coord. Chem. Rev. 2011, 255, 2704-2726
60. Martsinovich, N.; Troisi, A. Theoretical Studies of Dye-Sensitised Solar Cells: From Electronic Structure to Elementary Processes Energy Environ. Sci. 2011, 4, 4473
61. Martsinovich, N.; Troisi, A. Theoretical Studies of Dye-Sensitised Solar Cells: From Electronic Structure to Elementary Processes Energy Environ. Sci. 2011, 4, 4473
62. Abbott, L. C.; Batchelor, S. N.; Oakes, J.; Gilbert, B. C.; Whitwood, A. C.; Lindsay Smith, J. R.; Moore, J. N. Experimental and Computational Studies of Structure and Bonding in Parent and Reduced Forms of the Azo Dye Orange II J. Phys. Chem. A 2005, 109, 2894-2905
63. Liu, X.; Cole, J. M.; Waddell, P. G.; Lin, T.-C.; Radia, J.; Zeidler, A. Molecular Origins of Optoelectronic Properties in Coumarin Dyes: Toward Designer Solar Cell and Laser Applications J. Phys. Chem. A 2012, 116, 727-737
64. Dean, J. A. Lange's Handbook of Chemistry, 15 th ed.; McGraw-Hill, Inc.: New York, 1999; pp 91-98.
65. Zhang, L.; Cole, J. M.; Liu, X. Tuning Solvatochromism of Azo Dyes with Intramolecular Hydrogen Bonding in Solution and on Titanium Dioxide Nanoparticles J. Phys. Chem. C 2013, 117, 26316-26323
66. Liu, X.; Cole, J. M.; Low, K. S. Molecular Origins of Dye Aggregation and Complex Formation Effects in Coumarin 343 J. Phys. Chem. C 2013, 117, 14723-14730
67. 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
68. Zeng, W.; Cao, Y.; Bai, Y.; Wang, Y.; Shi, Y.; Zhang, M.; Wang, F.; Pan, C.; Wang, P. Efficient Dye-Sensitized Solar Cells with an Organic Photosensitizer Featuring Orderly Conjugated Ethylenedioxythiophene and Dithienosilole Blocks Chem. Mater. 2010, 22, 1915-1925
69. Kalyanasundaram, K. Dye-Sensitized Solar Cells; EPFL Press: Lausanne, Switzerland, 2010; pp 10-50.
70. Macrae, C. F.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Shields, G. P.; Taylor, R.; Towler, M.; Streek, J. van de Mercury: Visualization and Analysis of Crystal Structures J. Appl. Crystallogr. 2006, 39, 453-457
71. Gou, F.; Jiang, X.; Li, B.; Jing, H.; Zhu, Z. Salicylic Acid as a Tridentate Anchoring Group for Azo-Bridged Zinc Porphyrin in Dye-Sensitized Solar Cells ACS Appl. Mater. Interfaces 2013, 5, 12631-12637
72. 2(001): Geometries, Energetics, and Effects of Coverage, Hydration, and Reconstruction J. Phys. Chem. B 2006, 110, 2804-2811
73. Liu, X.; Cole, J. M.; Low, K. S. Molecular Origins of Dye Aggregation and Complex Formation Effects in Coumarin 343 J. Phys. Chem. C 2013, 117, 14723-14730
74. El-Zohry, A.; Orthaber, A.; Zietz, B. Isomerization and Aggregation of the Solar Cell Dye D149 J. Phys. Chem. C 2012, 116, 26144-26153
75. Agrawal, S.; Pastore, M.; Marotta, G.; Reddy, M. A.; Chandrasekharam, M.; Angelis, F. De Optical Properties and Aggregation of Phenothiazine-Based Dye-Sensitizers for Solar Cells Applications: A Combined Experimental and Computational Investigation J. Phys. Chem. C 2013, 117, 9613-9622
76. 2 in Dye-Sensitized Solar Cells Models: An Ab Initio Investigation ACS Nano 2010, 4, 556-562
77. Rochford, J.; Chu, D.; Hagfeldt, A.; Galoppini, E. Tetrachelate Porphyrin Chromophores for Metal Oxide Semiconductor Sensitization: Effect of the Spacer Length and Anchoring Group Position J. Am. Chem. Soc. 2007, 129, 4655-4665
78. Sánchez-de-Armas, R.; San-Miguel, M. A.; Oviedo, J.; Sanz, J. F. Molecular Modification of Coumarin Dyes for More Efficient Dye Sensitized Solar Cells J. Chem. Phys. 2012, 136, 194702
79. Ozawa, H.; Awa, M.; Ono, T.; Arakawa, H. Effects of Dye-Adsorption Solvent on the Performances of the Dye-Sensitized Solar Cells Based on Black Dye Chem.-Asian J. 2012, 7, 156-162
80. Kim, S.; Lee, J. K.; Kang, S. O.; Ko, J.; Yum, J.-H.; Fantacci, S.; De Angelis, F.; Di Censo, D.; Nazeeruddin, M. K.; Grätzel, M. Molecular Engineering of Organic Sensitizers for Solar Cell Applications J. Am. Chem. Soc. 2006, 128, 16701-16707
81. 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
82. Miguel, G. de; Ziółek, M.; Zitnan, M.; Organero, J. A.; Pandey, S. S.; Hayase, S.; Douhal, A. Photophysics of H-and J-Aggregates of Indole-Based Squaraines in Solid State J. Phys. Chem. C 2012, 116, 9379-9389
83. Ooyama, Y.; Harima, Y. Molecular Designs and Syntheses of Organic Dyes for Dye-Sensitized Solar Cells European J. Org. Chem. 2009, 2009, 2903-2934
84. Li, S.-F.; Yang, X.-C.; Cheng, M.; Zhao, J.-H.; Wang, Y.; Sun, L.-C. Novel D-π-A Type II Organic Sensitizers for Dye Sensitized Solar Cells Tetrahedron Lett. 2012, 53, 3425-3428
85. He, H.; Gurung, A.; Si, L. 8-Hydroxylquinoline as a Strong Alternative Anchoring Group for Porphyrin-Sensitized Solar Cells Chem. Commun. 2012, 48, 5910-5912
86. An, B.-K.; Hu, W.; Burn, P. L.; Meredith, P. New Type II Catechol-Thiophene Sensitizers for Dye-Sensitized Solar Cells J. Phys. Chem. C 2010, 114, 17964-17974
87. Yan, Z.; Guang, S.; Su, X.; Xu, H. Near-Infrared Absorbing Squaraine Dyes for Solar Cells: Relationship between Architecture and Performance J. Phys. Chem. C 2012, 116, 8894-8900
88. Ooyama, Y.; Nagano, T.; Inoue, S.; Imae, I.; Komaguchi, K.; Ohshita, J.; Harima, Y. Dye-Sensitized Solar Cells Based on Donor-Π-Acceptor Fluorescent Dyes with a Pyridine Ring as an Electron-Withdrawing-Injecting Anchoring Group Chem.-Eur. J. 2011, 17, 14837-14843
89. Ooyama, Y.; Inoue, S.; Asada, R.; Ito, G.; Kushimoto, K.; Komaguchi, K.; Imae, I.; Harima, Y. Dye-Sensitized Solar Cells Based on a Novel Fluorescent Dye with a Pyridine Ring and a Pyridinium Dye with the Pyridinium Ring Forming Strong Interactions with Nanocrystalline TiO2 Films Eur. J. Org. Chem. 2010, 2010, 92-100
90. Ooyama, Y.; Yamaguchi, N.; Imae, I.; Komaguchi, K.; Ohshita, J.; Harima, Y. Dye-Sensitized Solar Cells Based on D-π-A Fluorescent Dyes with Two Pyridyl Groups as an Electron-Withdrawing-Injecting Anchoring Group Chem. Commun. 2013, 49, 2548-2550
91. Daphnomili, D.; Landrou, G.; Prakash Singh, S.; Thomas, A.; Yesudas, K.; K, B.; Sharma, G. D.; Coutsolelos, A. G. Photophysical, Electrochemical and Photovoltaic Properties of Dye Sensitized Solar Cells Using a Series of Pyridyl Functionalized Porphyrin Dyes RSC Adv. 2012, 2, 12899
92. Zhang, M.-D.; Xie, H.-X.; Ju, X.-H.; Qin, L.; Yang, Q.-X.; Zheng, H.-G.; Zhou, X.-F. D-D-Π-A Organic Dyes Containing 4,4′-di(2-Thienyl) triphenylamine Moiety for Efficient Dye-Sensitized Solar Cells Phys. Chem. Chem. Phys. 2013, 15, 634-641
93. Daphnomili, D.; Sharma, G. D.; Biswas, S.; Justin Thomas, K. R.; Coutsolelos, A. G. A New Porphyrin Bearing a Pyridinylethynyl Group as Sensitizer for Dye Sensitized Solar Cells J. Photochem. Photobiol. A Chem. 2013, 253, 88-96
94. Lu, J.; Xu, X.; Li, Z.; Cao, K.; Cui, J.; Zhang, Y.; Shen, Y.; Li, Y.; Zhu, J.; Dai, S. Zinc Porphyrins with a Pyridine-Ring-Anchoring Group for Dye-Sensitized Solar Cells Chem.-Asian J. 2013, 8, 956-962
95. 2 Surface for Adsorption of Organic Dye Having Pyridyl Group as Anchoring Unit J. Phys. Chem. C 2013, 117, 16364-16370