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Phthalocyanines: colorful macroheterocyclic sensitizers for dye-sensitized solar cells

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Abstract

Dye-sensitized solar cells (DSSCs) have gained great attention as lower-cost alternatives to conventional photovoltaic devices. One way to improve the excellent efficiencies (ca. 11%) exhibited by DSSCs based on ruthenium polypyridyl dyes would consist in using sensitizers with enhanced light-harvesting properties in the red region of the spectrum. Phthalocyanines (Pcs) are very robust molecules which present extraordinary high extinction coefficients in the 600- to 700-nm spectral region. Intensive research has been focused on reducing the undesired aggregation phenomena of Pcs on the metal oxide surface, while keeping a good electronic coupling between the LUMO of the Pcs and the TiO2 conduction band, and a good solubility of the dye in organic solvents. Recently, unsymmetrically substituted “push–pull” Pcs have emerged as efficient red-absorbing dyes, reaching power conversion efficiencies of up to 4.7%, when used as single sensitizers.

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References

  1. Grätzel M (2005) Inorg Chem 44:6841

    Article  Google Scholar 

  2. O′Regan BC, Durrant JR (2009) Acc Chem Res 42:1799

    Article  Google Scholar 

  3. Hagfeldt A, Grätzel M (2000) Acc Chem Res 33:269

    Article  CAS  Google Scholar 

  4. Grätzel M (2003) J Photochem Photobiol C 4:145

    Article  Google Scholar 

  5. Grätzel M (2004) J Photochem Photobiol A 164:3

    Article  Google Scholar 

  6. Snaith HJ, Schmidt-Mende L (2007) Adv Mater 19:3187

    Article  CAS  Google Scholar 

  7. Snaith HJ, Humphry-Baker R, Chen P, Cesar I, Zakeeruddin SM, Grätzel M (2008) Nanotechnology 19:424003

    Article  Google Scholar 

  8. Ding IK, Tetreault N, Brillet J, Hardin BE, Smith EH, Rosenthal SJ, Sauvage F, Gratzel M, McGehee MD (2009) Adv Funct Mater 19:2431

    Article  CAS  Google Scholar 

  9. Luo Y, Li D, Meng Q (2009) Adv Mater 21:4647

    Article  CAS  Google Scholar 

  10. Nazeeruddin MK, De Angelis F, Fantacci S, Selloni A, Viscardi G, Liska P, Ito S, Takeru B, Grätzel M (2005) J Am Chem Soc 127:16835

    Article  CAS  Google Scholar 

  11. Wang P, Zakeeruddin SM, Moser JE, Nazeeruddin MK, Sekiguchi T, Grätzel M (2003) Nat Mater 2:402

    Article  CAS  Google Scholar 

  12. Bai Y, Lao Y, Zhang J, Wang M, Li R, Wang P, Zakeeruddin SM, Grätzel M (2008) Nat Mater 7:626

    Article  CAS  Google Scholar 

  13. Ooyama Y, Harima Y (2009) Eur J Org Chem 18:2903

    Article  Google Scholar 

  14. Robertson N (2006) Angew Chem Int Ed 45:2338

    Article  CAS  Google Scholar 

  15. Mishra A, Fischer MKR, Bäuerle P (2009) Angew Chem Int Ed 48:2474

    Article  CAS  Google Scholar 

  16. Himahori H, Umeyama T, Ito S (2009) Acc Chem Res 42:1809

    Article  Google Scholar 

  17. Campbell WM, Burrell AK, Officer DL, Jolley KW (2004) Coord Chem Rev 248:1363

    Article  CAS  Google Scholar 

  18. Kay A, Grätzel M (1993) J Phys Chem 97:6272

    Article  CAS  Google Scholar 

  19. Bessho T, Zakeeruddin SM, Yeh CY, Diau EWG, Grätzel M (2010) Angew Chem Int Ed 49:6646

    Article  CAS  Google Scholar 

  20. Campbell WM, Jolley KW, Wagner P, Wagner K, Walsh PJ, Gordon KC, Schmidt-Mende L, Nazeeruddin MK, Wang Q, Grätzel M, Officer DL (2007) J Phys Chem C 111:11760

    Article  CAS  Google Scholar 

  21. de la Torre G, Claessens CG, Torres T (2007) Chem Commun 20:2000

  22. Claessens CG, Hahn U, Torres T (2008) Chem Rec 8:75

    Article  CAS  Google Scholar 

  23. Rio Y, Rodríguez-Morgade MS, Torres T (2008) Org Biomol Chem 6:1877

    Article  CAS  Google Scholar 

  24. He J, Benkö G, Korodi F, Polivka T, Lomoth R, Åkermark B, Sun L, Hagfeldt A, Sundstrom V (2002) J Am Chem Soc 124:4922

    Article  CAS  Google Scholar 

  25. Nazeeruddin MK, Humphry-Baker R, Grätzel M, Wöhrle D, Schnurpfeil G, Schneider G, Hirth A, Trombach N (1999) J Porphyr Phthalocyanines 3:230

    Article  CAS  Google Scholar 

  26. Nazeeruddin MK, Humphry-Baker R, Grätzel M, Murrer BA (1998) Chem Commun 6:719

    Article  Google Scholar 

  27. Yanagisawa M, Korodi F, He J, Sun L, Sundstrom V, Åkermark B (2002) J Porphyr Phthalocyanines 6:217

    Article  CAS  Google Scholar 

  28. Yanagisawa M, Korodi F, Bergquist J, Holmberg A, Hagfeldt A, Åkermark B, Sun L (2004) J Porphyr Phthalocyanines 8:1128

    Article  Google Scholar 

  29. Morandeira A, López-Duarte I, Martínez-Díaz MV, O’Regan B, Shuttle C, Haji-Zainulabidin NA, Torres T, Palomares E, Durrant JR (2007) J Am Chem Soc 129:9250

    Article  CAS  Google Scholar 

  30. Palomares E, Martínez-Díaz MV, Haque AS, Torres T, Durrant JR (2004) Chem Commun 18:2112

    Article  Google Scholar 

  31. Macor L, Fungo F, Tempesti T, Durantini EM, Otero L, Barea EM, Fabregat-Santiago F, Bisquert J (2009) Energy Environ Sci 2:529

    Article  CAS  Google Scholar 

  32. Martínez-Díaz MV, Quintiliani M, Torres T (2008) Synlett 20:1

    Article  Google Scholar 

  33. Reddy Y, Giribabu L, Lyness C, Snaith H, Vijaykumar C, Chandrasekharam M, Lakshmikantam M, Yum JH, Kalyanasundaram K, Grätzel M, Nazeeruddin MK (2007) Angew Chem Int Ed 46:373

    Article  CAS  Google Scholar 

  34. Cid JJ, Yum JH, Jang SR, Nazeeruddin MK, Martínez-Ferrero E, Palomares E, Ko J, Grätzel M, Torres T (2007) Angew Chem Int Ed 46:8358

    Article  CAS  Google Scholar 

  35. Kusama H, Arakawa H (2004) Sol Energy Mater Sol Cells 81:87

    Article  CAS  Google Scholar 

  36. Yum JH, Jang SR, Humphry-Baker R, Grätzel M, Cid JJ, Torres T, Nazeeruddin MK (2008) Langmuir 24:5636

    Article  CAS  Google Scholar 

  37. Morandeira A, López-Duarte I, O’Regan B, Martínez-Díaz MV, Forneli A, Palomares E, Torres T, Durrant JR (2009) J Mater Chem 19:5016

    Article  CAS  Google Scholar 

  38. Cid JJ, García-Iglesias M, Yum JH, Forneli A, Albero J, Martínez-Ferrero E, Vázquez P, Grätzel M, Nazeeruddin MK, Palomares E, Torres T (2009) Chem Eur J 15:5130

    Article  CAS  Google Scholar 

  39. Silvestri F, García-Iglesias M, Yum JH, Vázquez P, Martínez-Díaz MV, Grätzel M, Nazeeruddin MK, Torres T (2009) J Porphyr Phthalocyanines 13:369

    Article  CAS  Google Scholar 

  40. García-Iglesias M, Cid JJ, Yum JH, Forneli A, Vázquez P, Nazeeruddin MK, Palomares E, Grätzel M, Torres T (2010) Energ Environ Sci (in press)

  41. Wang Q, Campbell WM, Bonfantani EE, Jolley KW, Officer DL, Walsh PJ, Gordon K, Humphry-Baker R, Nazeeruddin MK, Grätzel M (2005) J Phys Chem B 109:15397

    Article  CAS  Google Scholar 

  42. Qin H, Wenger S, Xu M, Gao F, Jing X, Wang P, Zakkeruddin SM, Grätzel M (2008) J Am Chem Soc 130:9202

    Article  CAS  Google Scholar 

  43. Giribabu L, Kumar CHV, Reddy PY, Yum JH, Grätzel M, Nazeeruddin MK (2009) J Chem Sci 121:75

    Article  CAS  Google Scholar 

  44. Giribabu L, Vijaykumar C, Reddy VG, Reddy PY, Rao CS, Jang SR, Yum JH, Nazeeruddin MK, Grätzel M (2007) Sol Energy Mater Sol Cells 91:1611

    Article  CAS  Google Scholar 

  45. Eu S, Katoh T, Umeyama T, Matano Y, Imahori H (2008) Dalton Trans 40:5476

    Article  Google Scholar 

  46. Mori S, Nagata M, Nakahata Y, Yasuta K, Goto R, Kimura M, Taya M (2010) J Am Chem Soc 132:4054

    Article  CAS  Google Scholar 

  47. O′Regan BC, López-Duarte I, Martínez-Díaz MV, Forneli A, Albero J, Morandeira A, Palomares E, Torres T, Durrant JR (2008) J Am Chem Soc 130:2906

    Article  Google Scholar 

  48. Hardin BW, Hoke ET, Armstrong PB, Yum JH, Comte P, Torres T, Frechet JM, Nazeeruddin MK, Grätzel M, McGehee MD (2009) Nat Photonics 3:406

    Article  CAS  Google Scholar 

  49. Hardin BE, Yum JH, Hoke ET, Jun YC, Pechy P, Torres T, Brongersma ML, Nazeeruddin MK, Grätzel M, McGehee MD (2010) Nano Lett 10:3077

    Article  CAS  Google Scholar 

  50. Shankar K, Feng X, Grimes CA (2009) ACS Nano 3:788

    Article  CAS  Google Scholar 

  51. Lee HJ, Leventis HC, Moon SJ, Chen P, Ito S, Haque SA, Torres T, Nueesch F, Geiger T, Zakeeruddin SM, Graetzel M, Nazeeruddin MK (2009) Adv Funct Mater 19:2735

    Article  CAS  Google Scholar 

  52. Lee HJ, Leventis HC, Haque SA, Torres T, Grätzel M, Nazeeruddin MK (2011) J Power Sour 196:596

    Article  CAS  Google Scholar 

  53. Driscoll K, Fang J, Humphry-Baker N, Torres T, Huck WTS, Snaith HJ, Friend RH (2010) Nano Lett (in press)

Download references

Acknowledgments

Financial support by the MEC, Spain (CTQ2008-00418/BQU, CONSOLIDER-INGENIO 2010 CDS 2007-00010, PLE2009-0070), and CAM (MADRISOLAR-2, S2009/PPQ/1533), is gratefully acknowledged. This work has been also supported by the EU projects SOLAR n-TYPE, MRTN CT-2006-035533 and ROBUST DSC, FP7-Energy-2007-1-RTD, No 212792. MI thanks the EU for a YR contract within the Marie Curie Project MRTN CT-2006-035533.

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Correspondence to M. Victoria Martínez-Díaz or Tomás Torres.

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Martínez-Díaz, M.V., Ince, M. & Torres, T. Phthalocyanines: colorful macroheterocyclic sensitizers for dye-sensitized solar cells. Monatsh Chem 142, 699–707 (2011). https://doi.org/10.1007/s00706-010-0431-0

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