Electron-acceptor-dependent light absorption and charge-transfer dynamics in N-annulated perylene dye-sensitized solar cells

Journal of Physical Chemistry C

Volumn 119, Issue 2, 2015, Pages 980-988

  Yang, Lin ^a,b   Ren, Yameng ^a,b   Yao, Zhaoyang ^a,b   Yan, Cancan ^a,b   Ma, Wentao ^a   Wang, Peng ^a  

^a CHANGCHUN INSTITUTE OF APPLIED CHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIC ACID; CHARGE TRANSFER; DENSITY FUNCTIONAL THEORY; DYES; ELECTROMAGNETIC WAVE ABSORPTION; ELECTRON INJECTION; ELECTRONS; HETEROJUNCTIONS; LIGHT ABSORPTION; MOLECULAR ORBITALS; POLYCYCLIC AROMATIC HYDROCARBONS; TITANIUM DIOXIDE;

BENZOTHIADIAZOLES; CHARGE-TRANSFER DYNAMICS; ELECTRON ACCEPTOR; FEMTOSECOND TRANSIENT ABSORPTION; LOWEST UNOCCUPIED MOLECULAR ORBITAL; OPEN-CIRCUIT PHOTOVOLTAGE; PHOTOPHYSICAL MEASUREMENTS; TIME-DEPENDENT DFT;

SOLAR CELLS;

EID: 84949115171     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp511687e     Document Type: Article

References (62)

1. 2 Films. Nature 1991, 353, 737-740.
2. Bai, Y.; Mora-Seró, I.; De Angelis, F.; Bisquert, J.; Wang, P. Titanium Dioxide Nanomaterials for Photovoltaic Application. Chem. Rev. 2014, 114, 10095-10130.
3. Wang, P.; Zakeeruddin, S. M.; Moser, J.-E.; Nazeeruddin, M. K.; Sekiguchi, T.; Grätzel, M. A Stable Quasi-Solid-State Dye-Sensitized Solar Cell with an Amphiphilic Ruthenium Sensitizer and Polymer Gel Electrolyte. Nat. Mater. 2003, 2, 402-407.
4. Yu, Q.; Zhou, D.; Shi, Y.; Si, X.; Wang, Y.; Wang, P. Stable and Efficient Dye-Sensitized Solar Cells: Photophysical and Electrical Characterizations. Energy Environ. Sci. 2010, 3, 1722-1725.
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. Mathew, S.; Yella, A.; Gao, P.; Humphry-Baker, R.; Curchod, B. F. E.; Ashari-Astani, N.; Tavernelli, I.; Rothlisberger, U.; Nazeeruddin, M. K.; Grätzel, M. Dye-Sensitized Solar Cells with 13% Efficiency Achieved through the Molecular Engineering of Porphyrin Sensitizers. Nat. Chem. 2014, 6, 242-247.
7. 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.
8. Imahori, H.; Umeyama, T.; Ito, S. Large π-Aromatic Molecules as Potential Sensitizers for Highly Efficient Dye-Sensitized Solar Cells. Acc. Chem. Res. 2009, 42, 1809-1818.
9. Yen, Y.-S.; Chou, H.-H.; Chen, Y.-C.; Hsu, C.-Y.; Lin, J. T. Recent Developments in Molecule-Based Organic Materials for Dye-Sensitized Solar Cells. J. Mater. Chem. 2012, 22, 8734-8747.
10. Wu, Y.; Zhu, W. Organic Sensitizers from D-π-A to D-A-π-A: Effect of the Internal Electron-Withdrawing Units on Molecular Absorption, Energy Levels and Photovoltaic Performances. Chem. Soc. Rev. 2013, 42, 2039-2058.
11. Hara, K.; Kurashige, M.; Dan-oh, Y.; Kasada, C.; Shinpo, A.; Suga, S.; Sayama, K.; Arakawa, H. Design of New Coumarin Dyes Having Thiophene Moieties for Highly Efficient Organic-Dye-Sensitized Solar Cells. New J. Chem. 2003, 27, 783-785.
12. Velusamy, M.; Justin Thomas, K. R.; Lin, J. T.; Hsu, Y.-C.; Ho, K.-C. Organic Dyes Incorporating Low-Band-Gap Chromophores for Dye-Sensitized Solar Cells. Org. Lett. 2005, 7, 1899-1902.
13. Koumura, N.; Wang, Z.-S.; Mori, S.; Miyashita, M.; Suzuki, E.; Hara, K. Alkyl-Functionalized Organic Dyes for Efficient Molecular Photovoltaics. J. Am. Chem. Soc. 2006, 128, 14256-14257.
14. 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.
15. 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. Adv. Mater. 2007, 19, 1138-1141.
16. 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.
17. 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.
18. 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, 211-215.
19. 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.
20. Wu, Y.; Marszalek, M.; Zakeeruddin, S. M.; Zhang, Q.; Tian, H.; Grätzel, M.; Zhu, W. High-Conversion-Efficiency Organic Dye-Sensitized Solar Cells: Molecular Engineering on D-A-π-A Featured Organic Indoline Dyes. Energy Environ. Sci. 2012, 5, 8261-8272.
21. Lin, R. Y.-Y.; Lin, H.-W.; Yen, Y.-S.; Chang, C.-H.; Chou, H.-H.; Chen, P.-W.; Hsu, C.-Y.; Chen, Y.-C.; Lin, J. T.; Ho, K.-C. 2,6-Conjugated Anthracene Sensitizers for High-Performance Dye-Sensitized Solar Cells. Energy Environ. Sci. 2013, 6, 2477-2486.
22. Zhang, M.; Wang, Y.; Xu, M.; Ma, W.; Li, R.; Wang, P. Design of High-Efficiency Organic Dyes for Titania Solar Cells Based on the Chromophoric Core of Cyclopentadithiophene-Benzothiadiazole. Energy Environ. Sci. 2013, 6, 2944-2949.
23. Kakiage, K.; Aoyama, Y.; Yano, T.; Otsuka, T.; Kyomen, T.; Unno, M.; Hanaya, M. An Achievement of Over 12% Efficiency in an Organic Dye-Sensitized Solar Cell. Chem. Commun. 2014, 50, 6379-6381.
24. Würther, F. Perylene Bisimide Dyes as Versatile Building Blocks for Functional Supramolecular Architectures. Chem. Commun. 2004, 1564-1579.
25. Herbst, W.; Hunger, K. Industrial Organic Pigments, 3rd ed.; Wiley: Weinhein, Germany, 2006.
26. Ferrere, S.; Zaban, A.; Gregg, B. A. Dye Sensitization of Nanocrystalline Tin Oxide by Perylene Derivatives. J. Phys. Chem. B 1997, 101, 4490-4493.
27. Li, C.; Wonneberger, H. Perylene Imides for Organic Photovoltaics: Yesterday, Today, and Tomorrow. Adv. Mater. 2012, 24, 613-636.
28. Mathew, S.; Imahori, H. Tunable, Strongly-Donating Perylene Photosensitizers for Dye-Sensitized Solar Cells. J. Mater. Chem. 2011, 21, 7166-7174.
29. 2. New J. Chem. 2002, 26, 1155-1160.
30. Shibano, Y.; Umeyama, T.; Matano, Y.; Imahori, H. Electron-Donating Perylene Tetracarboxylic Acids for Dye-Sensitized Solar Cells. Org. Lett. 2007, 9, 1971-1974.
31. Zafer, C.; Kus, M.; Turkmen, G.; Dincalp, H.; Demic, S.; Kuban, B.; Teoman, Y.; Icli, S. New Perylene Derivative Dyes for Dye-Sensitized Solar Cells. Sol. Energy Mater. Sol. Cells 2007, 91, 427-431.
32. Edvinsson, T.; Li, C.; Pschirer, N.; Schöneboom, J.; Eickemeyer, F.; Sens, R.; Boschloo, G.; Herrmann, A.; Müllen, K.; Hagfeldt, A. Intramolecular Charge-Transfer Tuning of Perylenes: Spectroscopic Features and Performance in Dye-Sensitized Solar Cells. J. Phys. Chem. C 2007, 111, 15137-15140.
33. 2 Dye-Sensitized Solar Cells. J. Photochem. Photobiol. A 2008, 197, 156-169.
34. Jin, Y.; Hua, J.; Wu, W.; Ma, X.; Meng, F. Synthesis, Characterization and Photovoltaic Properties of Two Novel Near-Infrared Absorbing Perylene Dyes Containing Benzo[e]indole for Dye-Sensitized Solar Cells. Synth. Met. 2008, 158, 64-71.
35. 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. An Improved Perylene Sensitizer for Solar Cell Applications. ChemSusChem 2008, 1, 615-618.
36. Cappel, U. B.; Karlsson, M. H.; Pschirer, N. G.; Eickemeyer, F.; Schöneboom, J.; Erk, P.; Boschloo, G.; Hagfeldt, A. A Broadly Absorbing Perylene Dye for Solid-State Dye-Sensitized Solar Cells. J. Phys. Chem. C 2009, 113, 14595-14597.
37. Li, C.; Liu, Z.; Schöneboom, J.; Eickemeyer, F.; Pschirer, N. G.; Erk, P.; Herrmann, A.; Müllen, K. Perylenes as Sensitizers in Hybrid Solar Cells: How Molecular Size Influences Performance. J. Mater. Chem. 2009, 19, 5405-5415.
38. Pleux, L. L.; Smeigh, A. L.; Gibson, E.; Pellegrin, Y.; Blart, E.; Boschloo, G.; Hagfeldt, A.; Hammarström, L.; Odobe, F. Synthesis, Photophysical and Photovoltaic Investigations of Acceptor-Functionalized Perylene Monoimide Dyes for Nickel Oxide p-Type Dye-Sensitized Solar Cells. Energy Environ. Sci. 2011, 4, 2075-2084.
39. Keerthi, A.; Liu, Y.; Wang, Q.; Valiyaveettil, S. Synthesis of Perylene Dyes with Multiple Triphenylamine Substituents. Chem. - Eur. J. 2012, 18, 11669-11676.
40. Langhals, H.; Christian, S.; Hofer, A. Substitution of Aromatics by Amines at Room Temperature with Negative Energy of Activation: Amino peri-Arylenes as Metal-Free Components for Dye-Sensitized Solar Cells. J. Org. Chem. 2013, 78, 9883-9891.
41. Yao, Z.; Yan, C.; Zhang, M.; Li, R.; Cai, Y.; Wang, P. N-Annulated Perylene as a Coplanar π-Linker Alternative to Benzene as a Low Energy-Gap, Metal-Free Dye in Sensitized Solar Cells. Adv. Energy Mater. 2014, 4, 1400244.
42. Yan, C.; Ma, W.; Ren, Y.; Zhang, M.; Wang, P. Efficient Triarylamine-Perylene Dye Sensitized Solar Cells: Influence of Triple-Bond Insertion on Charge Recombination. ACS Appl. Mater. Interfaces 2015, 7, 10.1021/am507261j.
43. Zhang, M.; Yao, Z.; Yan, C.; Cai, Y.; Ren, Y.; Zhang, J.; Wang, P. Unraveling the Pivotal Impacts of Electron-Acceptor on Light Absorption and Carrier Photogeneration in Perylene Dye Sensitized Solar Cells. ACS Photonics 2014, 1, 710-717.
44. Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. Energies, Structures, and Electronic Properties of Molecules in Solution with the C-PCM Solvation Model. J. Comput. Chem. 2003, 24, 669-681.
45. Becke, A. D. A New Mixing of Hartree-Fock and Local Density-Functional Theories. J. Chem. Phys. 1993, 98, 1372-1377.
46. Lynch, B. J.; Fast, P. L.; Harris, M.; Truhlar, D. G. Adiabatic Connection for Kinetics. J. Phys. Chem. A 2000, 104, 4811-4815.
47. Pastore, M.; Mosconi, E.; De Angelis, F.; Gätzel, 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.
48. 2 Nanocrystals. J. Phys. Chem. B 2003, 107, 14336-14341.
49. Duffy, N. W.; Peter, L. M.; Rajapakse, R. M. G.; Wijayant, K. G. U. A Novel Charge Extraction Method for the Study of Electron Transport and Interfacial Transfer in Dye Sensitised Nanocrystalline Solar Cells. Electrochem. Commun. 2000, 2, 658-662.
50. 2/Dye/CuSCN Photovoltaic Cells Explored by Recombination and DOS Characterization Using Transient Photovoltage Measurements. J. Phys. Chem. B 2005, 109, 4616-4623.
51. Liu, J.; Li, R.; Si, X.; Zhou, D.; Shi, Y.; Wang, Y.; Wang, P. Oligothiophene Dye-Sensitized Solar Cells. Energy Environ. Sci. 2010, 3, 1924-1928.
52. Cai, N.; Wang, Y.; Xu, M.; Fan, Y.; Li, R.; Zhang, M.; Wang, P. Engineering of Push-Pull Thiophene Dyes to Enhance Light Absorption and Modulate Charge Recombination in Mesoscopic Solar Cells. Adv. Funct. Mater. 2013, 23, 1846-1854.
53. Wang, Y.; Yang, L.; Zhang, J.; Li, R.; Zhang, M.; Wang, P. Altering the Self-Organization of Dyes on Titania with Dyeing Solvents to Tune the Charge-Transfer Dynamics of Sensitized Solar Cells. ChemPhysChem 2014, 15, 1037-1042.
54. Snellenburg, J. J.; Laptenok, S. P.; Seger, R.; Mullen, K. M.; van Stokkum, I. H. M. Glotaran: A Java-Based Graphical User Interface for the R Package TIMP. J. Stat. Software 2012, 49, 1-22.
55. Glasbeek, M.; Zhang, H. Femtosecond Studies of Solvation and Intramolecular Configurational Dynamics of Fluorophores in Liquid Solution. Chem. Rev. 2004, 104, 1929-1954.
56. Amdursky, N.; Erez, Y.; Huppert, D. Molecular Rotors: What Lies Behind the High Sensitivity of the Thioflavin-T Fluorescent Marker. Acc. Chem. Res. 2012, 45, 1548-1557.
57. Nelson, T.; Fernandez-Alberti, S.; Roitberg, A. E.; Tretiak, S. Nonadiabatic Excited-State Molecular Dynamics: Modeling Photophysics in Organic Conjugated Materials. Acc. Chem. Res. 2014, 47, 1155-1164.
58. Oliver, T. A. A.; Lewis, N. H. C.; Fleming, G. R. Correlating the Motion of Electrons and Nuclei with Two-Dimensional Electronic-Vibrational Spectroscopy. Proc. Natl. Acad. Sci. U.S.A. 2014, 111, 10061-10066.
59. van Stokkum, I. H. M.; Larsen, D. S.; van Grondelle, R. Global and Target Analysis of Time-Resolved Spectra. Biochim. Biophys. Acta 2004, 1657, 82-104.
60. Berera, R.; Herrero, C.; van Stokkum, I. H. M.; Vengris, M.; Kodis, G.; Palacios, R. E.; van Amerongen, H.; van Grondelle, R.; Gust, D.; Moore, T. A.; Moore, A. L.; Kennis, J. T. M. A Simple Artificial Light-Harvesting Dyad as a Model for Excess Energy Dissipation in Oxygenic Photosynthesis. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 5343-5348.
61. Ruban, A. V.; Berera, R.; Ilioaia, C.; van Stokkum, I. H. M.; Kennis, J. T. M.; Pascal, A. A.; van Amerongen, H.; Robert, B.; Horton, P.; van Grondelle, R. Identification of a Mechanism of Photoprotective Energy Dissipation in Higher Plants. Nature 2007, 450, 575-578.
62. Daillant, J.; Gihaud, A. X-ray and Neutron Reflectivity: Principles and Applications; Springer-Verlag: Berlin, 2009.