Skip to main content
Log in

Photovoltaic properties of three new cyanine dyes for dye-sensitized solar cells

  • Paper
  • Published:
Photochemical & Photobiological Sciences Aims and scope Submit manuscript

Abstract

Three carboxylated cyanine dyes, 2-[(1-butyl-3,3-dimethyl-5-carboxylindoline-2-ylidene)propenyl]-[1-butyl-3,3-dimethyl-7-(1-ethyl-1 H-1,2,3-triazole-4-yl]-1 H-benz[e]indolium iodide (Cy1), 2-[(1-butyl-3,3-dimethyl-5-carboxyl-indoline-2-ylidene)propenyl]-{1-butyl-3,3-dimethyl-7-[(4-piperidine- N-ethyl-1,8-naphthalimide)-1 H-1,2,3-triazole-4-yl]}-1 H-benz[e]indolium iodide (Cy2) and 2-[(1-butyl-3,3-dimethyl-5-carboxyl-indoline-2-ylidene)propenyl)-[1-butyl-3,3-dimethyl-7-{(4-piperidine- N-butyl-1,8-naphthalimide)-1 H-1,2,3-triazole-4-yl}]-1 H-benz[e]indolium iodide (Cy3), have been synthesized and characterized with regard to their structures and electrochemical properties. Upon adsorption onto a TiO2 electrode, the absorption spectra of the three cyanine dyes are all broadened to both red and blue sides compared with their respective spectra in an acetonitrile and ethanol mixture. Cy2 and Cy3, containing a naphthalimide group, have stronger absorption intensities and broader absorption spectra than Cy1, which consequently leads to better light-to-electricity conversion properties. Among the three cyanine dyes, Cy3 generated the highest photoelectric conversion yield of 4.80% (Jsc = 14.5 mA cm-2, Voc = 500 mV, FF = 0.49) under illumination with 75 mW cm-2 white light from a Xe lamp.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. M. K. Nazeeruddin, A. Kay, I. Rodicio, R. Humphry-Baker, E. Müller, P. Liska, N. V. Lachopoulos, M. Grätzel, Conversion of Light to Electricity by cis-X2Bis(2,2’-bipyridyl-4,4’-dicarboxylate) ruthenium(ii) Charge-Transfer Sensitizers (X = C1-, Br-, I-, CN-, and SCN-) on Nanocrystalline TiO2 Electrodes, J. Am. Chem. Soc., 1993, 115, 6382–6390.

    Article  CAS  Google Scholar 

  2. P. Wang, C. Klein, R. H. Baker, S. M. Zakeeruddin, M. Grätzel, A High Molar Extinction Coefficient Sensitizer for Stable Dye-Sensitized Solar Cells, J. Am. Chem. Soc., 2005, 127, 808–809.

    Article  CAS  Google Scholar 

  3. T. Horiuchi, H. Miura, S. Uchida, Highly-efficient metal-free organic dyes for dye-sensitized solar cells, Chem. Commun., 2003, 3036–3037.

    Google Scholar 

  4. D. P. Hagberg, T. Edvinsson, T. Marinado, G. Boschloo, A. Hagfeldt, L. Sun, A Novel Organic Chromophore for Dye-Sensitized Nanostructured Solar Cell, Chem. Commun., 2006, 2245–2247.

    Google Scholar 

  5. K. Hara, Z. Wang, T. Sato, A. Furube, R. Katoh, H. Sugihara, Y. Dan-oh, C. Kasada, A. Shinpo, S. Suga, Oligothiophene-Containing Coumarin Dyes for Efficient Dye-Sensitized Solar Cells, J. Phys. Chem. B, 2005, 109, 15476–15482.

    Article  CAS  Google Scholar 

  6. S. Ito, S. M. Zakeeruddin, R. Humphry-Baker, P. Liska, R. Charvet, P. Comte, M. K. Nazeeruddin, M. Takata, H. Miura, S. Uchida, M. Grätzel, High-Efficiency Organic-Dye-Sensitized Solar Cells Controlled by Nanocrystalline-TiO2 Electrode Thickness, Adv. Mater., 2006, 18, 1202–1205.

    Article  CAS  Google Scholar 

  7. K. Hara, M. Kurashige, Y. Dan-oh, C. Kasada, A. Shinpo, S. Suga, K. Sayama, H. Arakawa, Design of New Coumarin Dyes Having Thiophene Moieties for Highly Efficient Organic-Dye-Sensitized Solar Cells, New J. Chem., 2003, 27, 783–785.

    Article  CAS  Google Scholar 

  8. F. A. Castro, A. Faes, T. Geiger, C. F. O. Graeff, M. Nagel, F. Nüesch, R. Hany, On the Use of Cyanine Dyes as Low-Bandgap Materials in Bulk Heterojunction Photovoltaic Devices, Synth. Met., 2006, 156, 973–978.

    Article  CAS  Google Scholar 

  9. H. A. Shindy, M. A. El-Maghraby, F. M. Eissa, Synthesis, Photosensitization and Antimicrobial Activity of Certain Oxadiazine Cyanine Dyes, Dyes Pigm., 2006, 70, 110–116.

    Article  CAS  Google Scholar 

  10. M. Guo, P. Diao, Y. J. Ren, F. S. Meng, H. Tian, S. M. Cai, Photoelectrochemical Studies of Nanocrystalline TiO2 Co-Sensitized by Novel Cyanine Dyes, Sol. Energy Mater. Sol. Cells, 2005, 88, 23–35.

    Article  CAS  Google Scholar 

  11. K. Sayama, S. Tsukagoshi, K. Hara, Y. Ohga, A. Shinpou, Y. Abe, S. Suga, H. Arakawa, Photoelectrochemical Properties of J Aggregates of Benzothiazole Merocyanine Dyes on a Nanostructured TiO2 Film, J. Phys. Chem. B, 2002, 106, 1363–1371.

    Article  CAS  Google Scholar 

  12. X. Y. Chen, J. H. Guo, X. J. Peng, M. Guo, Y. Q. Xu, L. Shi, C. L. Liang, L. Wang, Y. L. Gao, S. G. Sun, S. M. Cai, Novel Cyanine Dyes with Different Methine Chains as Sensitizers for Nanocrystalline Solar Cell, J. Photochem. Photobiol., A, 2005, 171, 231–236.

    Article  CAS  Google Scholar 

  13. Z. S. Wang, Y. Cui, K. Hara, Y. Dan-oh, C. Kasada, A. Shinpo, A High-Light-Harvesting-Efficiency Coumarin Dye for Stable Dye-Sensitized Solar Cells, Adv. Mater., 2007, 19, 1138–111.

    Article  CAS  Google Scholar 

  14. Q. H. Yao, F. S. Meng, F. L. Li, H. Tian, C. H. Huang, Photoelectric Conversion Properties of Four Novel Carboxylated Hemicyanine Dyes on TiO2 Electrode, J. Mater. Chem., 2003, 13, 1048–1053.

    Article  CAS  Google Scholar 

  15. F. S. Meng, Q. H. Yao, J. G. Shen, F. L. Li, C. H. Huang, K. C. Chen, H. Tian, Novel Cyanine Dyes with Multi-carboxyl Groups and their Sensitization on Nanocrystalline TiO2 Electrode, Synth. Met., 2003, 137, 1543–1544.

    Article  CAS  Google Scholar 

  16. W. H. Zhan, W. J. Wu, J. L. Hua, Y. H. Jing, F. S. Meng, H. Tian, Photovoltaic properties of new cyanine-naphthalimide dyads synthesized by ‘Click’ chemistry, Tetrahedron Lett., 2007, 48, 2461–2465.

    Article  CAS  Google Scholar 

  17. S. Ito, T. Kitamura, Y. Wada, S. Yanagida, Facile Fabrication of Mesoporous TiO2 Electrodes for Dye Solar Cells: Chemical Modification And Repetitive Coating, Sol. Energy Mater. Sol. Cells, 2003, 76, 3–13.

    Article  CAS  Google Scholar 

  18. Hagfeldt, M. Grätzel, Light-Induced Redox Reaction in Nanocrystalline Systems, Chem. Rev., 1995, 95, 49–68.

    Article  Google Scholar 

  19. N. Koumura, Z. S. Wang, S. Mori, M. Miyashita, E. Suzuki, K. Hara, Alkyl-Functionalized Organic Dyes for Efficient Molecular Photovoltaics, J. Am. Chem. Soc., 2006, 128, 14256–14257.

    Article  CAS  Google Scholar 

  20. C. J. Barbè, F. Arendse, P. Comte, M. Jirousek, F. Lenzmann, V. Shklover, M. Grätzel, Nanocrystalline Titanium Oxide Electrode for Photovoltaic Application, J. Am. Ceram. Soc., 1997, 80, 3157–3171.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to He Tian.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Wu, W., Hua, J., Jin, Y. et al. Photovoltaic properties of three new cyanine dyes for dye-sensitized solar cells. Photochem Photobiol Sci 7, 63–68 (2008). https://doi.org/10.1039/b712439b

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1039/b712439b

Navigation