Table of Contents Author Guidelines Submit a Manuscript
International Journal of Photoenergy
Volume 2017 (2017), Article ID 7594869, 14 pages
https://doi.org/10.1155/2017/7594869
Research Article

Organic Dyes Containing Coplanar Dihexyl-Substituted Dithienosilole Groups for Efficient Dye-Sensitised Solar Cells

1SFI Strategic Research Cluster in Solar Energy Conversion, UCD School of Chemical and Bioprocess Engineering, University College Dublin, Dublin 4, Ireland
2SFI Strategic Research Cluster in Solar Energy Conversion, Department of Chemical Sciences and Bernal Institute, University of Limerick, Limerick, Ireland
3Laboratoire de Photonique et Interfaces (LPI), Ecole Polytechnique Fédérale de Lausanne, 1015 Lausanne, Switzerland

Correspondence should be addressed to Edmond Magner, Niall J. English, and K. Ravindranathan Thampi

Received 20 October 2016; Accepted 20 February 2017; Published 4 May 2017

Academic Editor: Bill Pandit

Copyright © 2017 Ciaran Lyons et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. B. O'Regan and M. Grätzel, “A low-cost, high-efficiency solar cell based on dye-sensitized,” Nature, vol. 353, no. 6346, pp. 737–740, 1991. View at Publisher · View at Google Scholar
  2. R. Komiya, A. Fukui, N. Murofushi, N. Koide, R. Yamanaka, and H. Katayama, in Technical Digest, 21st International Photovoltaic Science and Engineering Conference, Fukuoka, November 2011, 2 C-5O-08.
  3. M. A. Green, K. Emery, Y. Hishikawa, W. Warta, and E. D. Dunlop, “Solar cell efficiency tables (version 45),” Progress in Photovoltaics, vol. 23, no. 1, pp. 1–9, 2015. View at Publisher · View at Google Scholar · View at Scopus
  4. H. Imahori, T. Umeyama, and S. Ito, “Large π-aromatic molecules as potential sensitizers for highly efficient dye-sensitized solar cells,” Accounts of Chemical Research, vol. 42, no. 11, pp. 1809–1818, 2009. View at Publisher · View at Google Scholar · View at Scopus
  5. A. Yella, H. W. Lee, H. N. Tsao et al., “Porphyrin-sensitized solar cells with cobalt (II/III)–based redox electrolyte exceed 12 percent efficiency,” Science, vol. 334, no. 6056, pp. 629–634, 2011. View at Publisher · View at Google Scholar · View at Scopus
  6. S. Mathew, A. Yella, P. Gao et al., “Dye-sensitized solar cells with 13% efficiency achieved through the molecular engineering of porphyrin sensitizers,” Nature Chemistry, vol. 6, no. 3, pp. 242–247, 2014. View at Publisher · View at Google Scholar · View at Scopus
  7. K. Kakiage, Y. Aoyama, T. Yano, K. Oya, J. Fujisawa, and M. Hanaya, “Highly-efficient dye-sensitized solar cells with collaborative sensitization by silyl-anchor and carboxy-anchor dyes,” Chemical Communications, vol. 51, no. 88, pp. 15894–15897, 2015. View at Publisher · View at Google Scholar · View at Scopus
  8. J. N. Clifford, G. Yahioglu, L. R. Milgrom, and J. R. Durrant, “Molecular control of recombination dynamics in dye sensitised nanocrystalline TiO 2 films,” Chemical Communications, no. 12, pp. 1260–1261, 2002. View at Publisher · View at Google Scholar
  9. T. Bessho, S. M. Zakeeruddin, C. Y. Yeh, E. W. G. Diau, and M. Grätzel, “Highly efficient mesoscopic dye-sensitized solar cells based on donor-acceptor-substituted porphyrins,” Angewandte Chemie, International Edition, vol. 49, no. 37, pp. 6646–6649, 2010. View at Publisher · View at Google Scholar · View at Scopus
  10. S. M. Feldt, E. A. Gibson, E. Gabrielsson, L. Sun, G. Boschloo, and A. Hagfeldt, “Design of organic dyes and cobalt polypyridine redox mediators for high-efficiency dye-sensitized solar cells,” Journal of the American Chemical Society, vol. 132, no. 46, pp. 16714–16724, 2010. View at Publisher · View at Google Scholar · View at Scopus
  11. H. N. Tsao, C. Yi, T. Moehl et al., “Cyclopentadithiophene bridged donor-acceptor dyes achieve high power conversion efficiencies in dye-sensitized solar cells based on the tris-cobalt bipyridine redox couple,” ChemSusChem, vol. 4, no. 5, pp. 591–594, 2011. View at Publisher · View at Google Scholar · View at Scopus
  12. L. Liao, A. Cirpan, Q. Chu, F. E. Karasz, and Y. Pang, “Synthesis and optical properties of light‐emitting π‐conjugated polymers containing biphenyl and dithienosilole,” Journal of Polymer Science Part A: Polymer Chemistry, vol. 45, no. 10, pp. 2048–2058, 2007. View at Google Scholar
  13. T.-Y. Chu, J. Lu, S. Beaupré et al., “Effects of the molecular weight and the side‐chain length on the photovoltaic performance of dithienosilole/thienopyrrolodione copolymers,” Advanced Functional Materials, vol. 22, no. 11, pp. 2345–2351, 2012. View at Publisher · View at Google Scholar · View at Scopus
  14. S. Ko, H. Choi, M.-S. Kang et al., “Silole-spaced triarylamine derivatives as highly efficient organic sensitizers in dye-sensitized solar cells (DSSCs),” Journal of Materials Chemistry, vol. 20, no. 12, pp. 2391–2399, 2010. View at Publisher · View at Google Scholar · View at Scopus
  15. L.-Y. Lin, C.-H. Tsai, K.-T. Wong et al., “Organic dyes containing coplanar diphenyl-substituted dithienosilole core for efficient dye-sensitized solar cells,” The Journal of Organic Chemistry, vol. 75, no. 14, pp. 4778–4785, 2010. View at Publisher · View at Google Scholar · View at Scopus
  16. M. J. Ross and K. R. William, Impedance spectroscopy, Wiley, New York, 1987.
  17. J. Bisquert, “Theory of the impedance of charge transfer via surface states in dye-sensitized solar cells,” Journal of Electroanalytical Chemistry, vol. 646, no. 1-2, pp. 43–51, 2010. View at Publisher · View at Google Scholar · View at Scopus
  18. L. Andrade, R. Cruz, H. Ribeiro, and A. Mendes, “Impedance characterization of dye-sensitized solar cells in a tandem arrangement for hydrogen production by water splitting,” International Journal of Hydrogen Energy, vol. 35, no. 17, pp. 8876–8883, 2010. View at Publisher · View at Google Scholar · View at Scopus
  19. F. Fabregat-Santiago, J. Bisquert, E. Palomares et al., “Correlation between photovoltaic performance and impedance spectroscopy of dye-sensitized solar cells based on ionic liquids,” Journal of Physical Chemistry C, vol. 111, no. 17, pp. 6550–6560, 2007. View at Google Scholar
  20. R. Kern, R. Sastrawan, J. Ferber, R. Stangl, and J. Luther, “Modeling and interpretation of electrical impedance spectra of dye solar cells operated under open-circuit conditions,” Electrochimica Acta, vol. 47, no. 26, pp. 4213–4225, 2002. View at Publisher · View at Google Scholar · View at Scopus
  21. S. Ito, T. N. Murakami, P. Comte et al., “Fabrication of thin film dye sensitized solar cells with solar to electric power conversion efficiency over 10%,” Thin Solid Films, vol. 516, no. 14, pp. 4613–4619, 2008. View at Publisher · View at Google Scholar · View at Scopus
  22. S. Ito, P. Chen, P. Comte et al., “Fabrication of screen‐printing pastes from TiO2 powders for dye‐sensitised solar cells,” Progress in Photovoltaics Research and Applications, vol. 15, no. 7, pp. 603–612, 2007. View at Publisher · View at Google Scholar · View at Scopus
  23. G. Lu, H. Usta, C. Risko et al., “Synthesis, characterization, and transistor response of semiconducting silole polymers with substantial hole mobility and air stability. Experiment and theory,” Journal of the American Chemical Society, vol. 130, no. 24, pp. 7670–7685, 2008. View at Publisher · View at Google Scholar · View at Scopus
  24. J. M. Kroon, N. J. Bakker, H. J. P. Smit et al., “Nanocrystalline dye‐sensitized solar cells having maximum performance,” Progress in Photovoltaics Research and Applications, vol. 15, no. 1, pp. 1–18, 2007. View at Publisher · View at Google Scholar · View at Scopus
  25. M. Frisch, G. Trucks, H. Schlegel et al., “Semiempirical GGA-type density functional constructed with a long-range dispersion correction,” Journal of Computational Chemistry, vol. 27, no. 15, pp. 1787–1799, 2006. View at Google Scholar
  26. M. J. G. Peach, P. Benfield, T. Helgaker, and D. J. Tozer, “Excitation energies in density functional theory: an evaluation and a diagnostic test,” The Journal of Chemical Physics, vol. 128, no. 4, p. 044118, 2008. View at Publisher · View at Google Scholar · View at Scopus
  27. P. Dev, S. Agrawal, and N. J. English, “Determining the appropriate exchange-correlation functional for time-dependent density functional theory studies of charge-transfer excitations in organic dyes,” The Journal of Chemical Physics, vol. 136, no. 22, p. 224301, 2012. View at Publisher · View at Google Scholar · View at Scopus
  28. A. D. Becke, “Density‐functional thermochemistry. III. The role of exact exchange,” The Journal of Chemical Physics, vol. 98, no. 7, pp. 5648–5652, 1993. View at Publisher · View at Google Scholar
  29. R. Kavathekar, P. Dev, N. J. English, and J. M. D. MacElroy, “Molecular dynamics study of water in contact with TiO2 rutile-110, 100, 101, 001 and anatase-101, 001 surfaces,” Molecular Physics, vol. 109, no. 13, pp. 1649–1656, 2011. View at Publisher · View at Google Scholar · View at Scopus
  30. P. J. Stephens, F. J. Devlin, C. S. Ashvar, C. F. Chabalowski, and M. J. Frisch, “Theoretical calculation of vibrational circular dichroism spectra,” Faraday Discussions, vol. 99, pp. 103–119, 1994. View at Google Scholar
  31. T. Yanai, D. P. Tew, and N. C. Handy, “A new hybrid exchange–correlation functional using the Coulomb-attenuating method (CAM-B3LYP),” Chemical Physics Letters, vol. 393, no. 1–3, pp. 51–57, 2004. View at Publisher · View at Google Scholar · View at Scopus
  32. M. Cossi, N. Rega, G. Scalmani, and V. Barone, “Energies, structures, and electronic properties of molecules in solution with the C‐PCM solvation model,” Journal of Computational Chemistry, vol. 24, no. 6, pp. 669–681, 2003. View at Publisher · View at Google Scholar · View at Scopus
  33. P. Persson, R. Bergström, and S. Lunell, “Quantum chemical study of photoinjection processes in dye-sensitized TiO2 nanoparticles,” The Journal of Physical Chemistry. B, vol. 104, no. 44, pp. 10348–10351, 2000. View at Publisher · View at Google Scholar
  34. F. De Angelis, A. Tilocca, and A. Selloni, “Time-dependent DFT study of [Fe (CN) 6] 4-sensitization of TiO2 nanoparticles,” Journal of the American Chemical Society, vol. 126, no. 46, pp. 15024–15025, 2004. View at Publisher · View at Google Scholar · View at Scopus
  35. F. De Angelis, “Direct vs. indirect injection mechanisms in perylene dye-sensitized solar cells: a DFT/TDDFT investigation,” Chemical Physics Letters, vol. 493, no. 4–6, pp. 323–327, 2010. View at Google Scholar
  36. S. Agrawal, P. Dev, N. J. English, K. R. Thampi, and J. MacElroy, “First-principles study of the excited-state properties of coumarin-derived dyes in dye-sensitized solar cells,” Journal of Materials Chemistry, vol. 21, no. 30, pp. 11101–11108, 2011. View at Google Scholar
  37. S. Agrawal, P. Dev, N. J. English, K. R. Thampi, and J. MacElroy, “A TD-DFT study of the effects of structural variations on the photochemistry of polyene dyes,” Chemical Science, vol. 3, no. 2, pp. 416–424, 2012. View at Publisher · View at Google Scholar · View at Scopus
  38. T. A. Halgren, “Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94,” Journal of Computational Chemistry, vol. 17, no. 5-6, pp. 490–519, 1996. View at Publisher · View at Google Scholar
  39. MOE, The Molecular Operating Environment from Chemical Computing Group Inc., 1010 Sherbrooke St. W., Suite 910, Montréal, Québec, Canada H3A 2R7.
  40. N. J. English and J. M. D. MacElroy, “Atomistic simulations of liquid water using Lekner electrostatics,” Molecular Physics, vol. 100, no. 23, pp. 3753–3769, 2002. View at Publisher · View at Google Scholar · View at Scopus
  41. N. J. English, “Effect of electrostatics techniques on the estimation of thermal conductivity via equilibrium molecular dynamics simulation: application to methane hydrate,” Molecular Physics, vol. 106, no. 15, pp. 1887–1898, 2008. View at Publisher · View at Google Scholar · View at Scopus
  42. M. Xu, S. Wenger, H. Bala et al., “Tuning the energy level of organic sensitizers for high-performance dye-sensitized solar cells,” Journal of Physical Chemistry C, vol. 113, no. 7, pp. 2966–2973, 2009. View at Google Scholar
  43. M. P. Allen and D. J. Tildesley, Molecular Simulation of Liquids, Clarendon, Oxford, 1987.
  44. S. Roquet, A. Cravino, P. Leriche, O. Alévêque, P. Frère, and J. Roncali, “Triphenylamine−thienylenevinylene hybrid systems with internal charge transfer as donor materials for heterojunction solar cells,” Journal of the American Chemical Society, vol. 128, no. 10, pp. 3459–3466, 2006. View at Publisher · View at Google Scholar · View at Scopus
  45. J. H. Yum, D. P. Hagberg, S. J. Moon et al., “A light‐resistant organic sensitizer for solar‐cell applications,” Angewandte Chemie (International Edition in English), vol. 48, no. 9, pp. 1576–1580, 2009. View at Publisher · View at Google Scholar · View at Scopus
  46. A. Hagfeldt and M. Gratzel, “Light-induced redox reactions in nanocrystalline systems,” Chemical Reviews, vol. 95, no. 1, pp. 49–68, 1995. View at Publisher · View at Google Scholar
  47. C. Klein, M. K. Nazeeruddin, P. Liska et al., “Engineering of a novel ruthenium sensitizer and its application in dye-sensitized solar cells for conversion of sunlight into electricity,” Inorganic Chemistry, vol. 44, no. 2, pp. 178–180, 2004. View at Publisher · View at Google Scholar · View at Scopus
  48. C. Teng, X. Yang, C. Yang et al., “Influence of triple bonds as π-spacer units in metal-free organic dyes for dye-sensitized solar cells,” Journal of Physical Chemistry C, vol. 114, no. 25, pp. 11305–11313.
  49. D. Shi, Y. Cao, N. Pootrakulchote et al., “New organic sensitizer for stable dye-sensitized solar cells with solvent-free ionic liquid electrolytes,” Journal of Physical Chemistry C, vol. 112, no. 44, pp. 17478–17485, 2008. View at Publisher · View at Google Scholar · View at Scopus
  50. R. M. Silverstein, G. C. Bassler, and T. C. Morrill, Spectrometric identification of organic compounds, 1974. View at Publisher · View at Google Scholar
  51. M. K. Nazeeruddin, R. Humphry-Baker, D. L. Officer, W. M. Campbell, A. K. Burrell, and M. Gratzel, “Application of metalloporphyrins in nanocrystalline dye-sensitized solar cells for conversion of sunlight into electricity,” Langmuir, vol. 20, no. 15, pp. 6514–6517, 2004. View at Publisher · View at Google Scholar · View at Scopus
  52. G. B. Deacon and R. J. Phillips, “Relationships between the carbon-oxygen stretching frequencies of carboxylato complexes and the type of carboxylate coordination,” Coordination Chemistry Reviews, vol. 33, no. 3, pp. 227–250, 1980. View at Publisher · View at Google Scholar
  53. A. Vittadini, A. Selloni, F. P. Rotzinger, and M. Gratzel, “Formic acid adsorption on dry and hydrated TiO2 anatase (101) surfaces by DFT calculations,” The Journal of Physical Chemistry. B, vol. 104, no. 6, pp. 1300–1306, 2000. View at Publisher · View at Google Scholar
  54. J. Bisquert, F. Fabregat-Santiago, I. Mora-Sero, G. Garcia-Belmonte, and S. Giménez, “Electron lifetime in dye-sensitized solar cells: theory and interpretation of measurements,” Journal of Physical Chemistry C, vol. 113, no. 40, pp. 17278–17290, 2009. View at Google Scholar
  55. Q. Wang, J.-E. Moser, and M. Grätzel, “Electrochemical impedance spectroscopic analysis of dye-sensitized solar cells,” The Journal of Physical Chemistry B, vol. 109, no. 31, pp. 14945–14953, 2005. View at Publisher · View at Google Scholar · View at Scopus
  56. L. Han, N. Koide, Y. Chiba, and T. Mitate, “Modeling of an equivalent circuit for dye-sensitized solar cells,” Applied Physics Letters, vol. 84, no. 13, pp. 2433–2435, 2004. View at Publisher · View at Google Scholar · View at Scopus
  57. J. Halme, P. Vahermaa, K. Miettunen, and P. Lund, “Device physics of dye solar cells,” Advanced Materials, vol. 22, no. 35, pp. 22–E234, 2010. View at Publisher · View at Google Scholar · View at Scopus
  58. L.-L. Li, Y.-C. Chang, H.-P. Wu, and E. W.-G. Diau, “Characterisation of electron transport and charge recombination using temporally resolved and frequency-domain techniques for dye-sensitised solar cells,” International Reviews in Physical Chemistry, vol. 31, no. 3, pp. 420–467, 2012. View at Publisher · View at Google Scholar · View at Scopus
  59. N. J. English and D. G. Carroll, “Prediction of Henry’s Law constants by a Quantitative Structure Property Relationship and neural networks,” Journal of Chemical Information and Computer Sciences, vol. 41, no. 5, pp. 1150–1161, 2001. View at Google Scholar
  60. M. Adachi, M. Sakamoto, J. Jiu, Y. Ogata, and S. Isoda, “Determination of parameters of electron transport in dye-sensitized solar cells using electrochemical impedance spectroscopy,” The Journal of Physical Chemistry. B, vol. 110, no. 28, pp. 13872–13880, 2006. View at Publisher · View at Google Scholar · View at Scopus
  61. P. Dev, S. Agrawal, and N. J. English, “Functional assessment for predicting charge-transfer excitations of dyes in complexed state: a study of triphenylamine-donor dyes on titania for dye-sensitized solar cells,” The Journal of Physical Chemistry. A, vol. 117, no. 10, pp. 2114–2124, 2013. View at Publisher · View at Google Scholar · View at Scopus
  62. A. Singh, N. J. English, and K. M. Ryan, “Highly ordered nanorod assemblies extending over device scale areas and in controlled multilayers by electrophoretic deposition,” The Journal of Physical Chemistry. B, vol. 117, no. 6, pp. 1608–1615, 2013. View at Publisher · View at Google Scholar · View at Scopus
  63. M. Pazoki, P. W. Lohse, N. Taghavinia, A. Hagfeldt, and G. Boschloo, “The effect of dye coverage on the performance of dye-sensitized solar cells with a cobalt-based electrolyte,” Physical Chemistry Chemical Physics, vol. 16, no. 18, pp. 8503–8508, 2014. View at Publisher · View at Google Scholar · View at Scopus