Monatshefte für Chemie - Chemical Monthly

, Volume 142, Issue 1, pp 45–52 | Cite as

Density functional theory as a guide for the design of pyran dyes for dye-sensitized solar cells

  • Christopher Johnson
  • Seth B. Darling
  • Youngjae You
Original Paper


Using density functional theory and hybrids, we examined several derivatives of the dye 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran, with the objective of identifying modifications which would improve the properties of dyes for dye-sensitized solar cells. We calculated the electronic structure of numerous derivatives at the HOMO and LUMO energy levels, with the hypothesis that directing the flow of excited electrons to the point of the dye at which the molecule attaches to TiO2 would increase the energy conversion efficiency of the cell. We also examined the UV–visible absorption spectra of the dyes, with the objective of capturing the maximum amount of solar light. By use of the derivatives we compared the use of two electron-donating groups instead of one, extension of the conjugated chain leading to the attachment point of the dye, use of oxygen versus sulfur or selenium in the dye, and the use of different electron-donating groups. We identified several promising donating groups and determined that the other modifications to the dye are likely to increase solar cell efficiency.

Graphical Abstract


Absorption spectra Computational chemistry Dyes Electronic structure Orbitals 


  1. 1.
    O’Regan B, Graetzel M (1991) Nature 353:737CrossRefGoogle Scholar
  2. 2.
    Grätzel M (2004) J Photochem Photobiol A 164:3CrossRefGoogle Scholar
  3. 3.
    Hara K, Arakawa H (2003) Dye-sensitized solar cells. In: Luque A, Hegedus S (eds) Handbook of photovoltaic science and engineering. Wiley, New YorkGoogle Scholar
  4. 4.
    Kroon JM, Bakker NJ, Smit HJP, Liska P, Thampi KR, Wang P, Zakeeruddin SM, Grätzel M, Hinsch A, Hore S, Würfel U, Sastrawan R, Durrant JR, Palomares E, Pettersson H, Gruszecki T, Walter J, Skupien K, Tulloch GE (2007) Prog Photovolt Res Appl 15:1CrossRefGoogle Scholar
  5. 5.
    Xie P, Guo F (2007) Curr Org Chem 11:1272CrossRefGoogle Scholar
  6. 6.
    Chen Z, Li F, Huang C (2007) Curr Org Chem 11:1241CrossRefGoogle Scholar
  7. 7.
    Wang ZS, Hara K, Danoh Y, Kasada C, Shinpo A, Suga S, Arakawa H, Sugihara H (2005) J Phys Chem B 109:3907CrossRefGoogle Scholar
  8. 8.
    Wang ZS, Cui Y, Hara K, Dan-oh Y, Kasada C, Shinpo A (2007) Adv Mater 19:1138CrossRefGoogle Scholar
  9. 9.
    Alex S, Santhosh U, Das S (2005) J Photochem Photobiol A 172:63CrossRefGoogle Scholar
  10. 10.
    Burke A, Schmidt-Mende L, Ito S, Gratzel M (2007) Chem Commun 234Google Scholar
  11. 11.
    Howie WH, Claeyssens F, Miura H, Peter Laurence M (2008) J Am Chem Soc 130:1367CrossRefGoogle Scholar
  12. 12.
    Horiuchi T, Miura H, Sumioka K, Uchida S (2004) J Am Chem Soc 126:12218CrossRefGoogle Scholar
  13. 13.
    Campbell WM, Burrell AK, Officer DL, Jolley KW (2004) Coord Chem Rev 248:1363CrossRefGoogle Scholar
  14. 14.
    Walsh PJ, Gordon KC, Officer DL, Campbell WM (2006) J Mol Struct (THEOCHEM) 759:17Google Scholar
  15. 15.
    Vyas S, Hadad CM, Modarelli DA (2008) J Phys Chem A 112:6533CrossRefGoogle Scholar
  16. 16.
    Balanay MP, Kim DH (2008) Phys Chem Chem Phys 10:5121CrossRefGoogle Scholar
  17. 17.
    Liu T, Zhang HX, Zhou X, Xia BH (2008) Eur J Inorg Chem 2008:1268CrossRefGoogle Scholar
  18. 18.
    Liu Z (2008) J Mol Struct (THEOCHEM) 862:44CrossRefGoogle Scholar
  19. 19.
    Balanay MP, Kim DH (2009) J Mol Struct (THEOCHEM) 910:20CrossRefGoogle Scholar
  20. 20.
    Mann JR, Gannon MK, Fitzgibbons TC, Detty MR, Watson DF (2008) J Phys Chem C 112:13057CrossRefGoogle Scholar
  21. 21.
    Nueesch F, Zuppiroli L, Berner D, Ma C, Wang X, Cao Y, Zhang B (2004) Res Chem Intermed 30:495CrossRefGoogle Scholar
  22. 22.
    Detty MR, Merkel PB (1990) J Am Chem Soc 112:3845CrossRefGoogle Scholar
  23. 23.
    Mautner HG, Clayton EM (1959) J Am Chem Soc 81:6270CrossRefGoogle Scholar
  24. 24.
    Ohulchanskyy TY, Donnelly DJ, Detty MR, Prasad PN (2004) J Phys Chem B 108:8668CrossRefGoogle Scholar
  25. 25.
    Darling SB (2008) J Phys Chem B 112:8891CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 2010

Authors and Affiliations

  • Christopher Johnson
    • 1
  • Seth B. Darling
    • 2
  • Youngjae You
    • 1
  1. 1.Department of Chemistry and BiochemistrySouth Dakota State UniversityBrookingsUSA
  2. 2.Argonne National LaboratoryCenter for Nanoscale MaterialsArgonneUSA

Personalised recommendations