Theoretical Investigation of Carbazole-Based
D-D-π-A Organic Dyes for Efficient
Dye-Sensitized Solar Cell
In this paper, four carbazole-based D-D-π-A organic
dyes code as CCT2A, CCT3A, CCT1PA and CCT2PA were reported.
A series of these organic dyes containing identical donor and
acceptor group but different π-system. The effect of replacing of
thiophene by phenyl thiophene as π-system on the physical
properties has been focused. The structural, energetic properties and
absorption spectra were theoretically investigated by means of
Density Functional Theory (DFT) and Time-Dependent Density
Functional Theory (TD-DFT). The results show that nonplanar
conformation due to steric hindrance in donor part (cabazolecarbazole
unit) of dye molecule can prevent unfavorable dye
aggregation. By means of the TD-DFT method, the absorption
spectra were calculated by B3LYP and BHandHLYP to study the
affect of hybrid functional on the excitation energy (Eg). The results
revealed the increasing of thiophene units not only resulted in
decreasing of Eg, but also found the shifting of absorption spectra to
higher wavelength. TD-DFT/BHandHLYP calculated results are
more strongly agreed with the experimental data than B3LYP
functions. Furthermore, the adsorptions of CCT2A and CCT3A on the
TiO2 anatase (101) surface were carried out by mean of the chemical
periodic calculation. The result exhibit the strong adsorption energy.
The calculated results provide our new organic dyes can be
effectively used as dye for Dye Sensitized Solar Cell (DSC).
[1] D. Kim, M. Kang, K. Song, S. Kang, J. Ko, "Molecular engineering of
organic sensitizers containing indole moiety for dye-sensitized solar
cells" Tetrahedron, vol. 64, 2008, pp. 10417-10424.
[2] R. Ma, P. Guo, H. Cui, X. Zhang, M.K. Nazeeruddin, M. J. Grätzel,
"Substituent Effect on the Meso-Substituted Porphyrins: Theoretical
Screening of Sensitizer Candidates for Dye-Sensitized Solar Cells"
Phys. Chem. A, vol. 113, 2009, pp. 10119-10124.
[3] M. Grätzel, "Photoelectrochemical cells" Nature, vol. 414, 2001, pp.
338-344.
[4] M.P. Balanay, D. H. Kim, "DFT/TD-DFT molecular design of porphyrin
analogues for use in dye-sensitized solar cells" Phys. Chem. Chem.
Phys., vol. 10, 2008, pp. 5121-5127.
[5] M. Grätzel, "Dye-sensitized solar cells" J. Photochem. Photobiol. C, vol.
4, 2003, pp. 145-153.
[6] K. Hara, Z.S. Wang, T. Sato, A. Furube, R. Katho, K. Sugihara, Y. Danoh,
C. Kasada, A. Shinpo, S. Suga, "Oligothiophene-Containing
Coumarin Dyes for Efficient Dye-Sensitized Solar Cells" J. Phys. Chem. B, vol. 109, 2005, pp. 15476-15482.
[7] T. Horiuchi, H. Miura, K. Sumioka, S. Ushida, "High Efficiency of Dye-Sensitized Solar Cells Based on Metal-Free Indoline Dyes" J. Am.
Chem. Soc., vol. 126, 2004, pp. 12218-12219.
[8] G. Li, K.J. Jiang, Y.F. Li, S.L. Li, L.M. Yang, "Efficient Structural
Modification of Triphenylamine-Based Organic Dyes for Dye-Sensitized Solar Cells" J. Phys. Chem. C, vol. 112, 2008, pp. 11591-11599.
[9] Y. Shibano, T. Umeyama, Y. Matano, H. Imahori, "Electron-Donating
Perylene Tetracarboxylic Acids for Dye-Sensitized Solar Cells" Org. Lett., vol. 9, 2007, pp. 1971-1974.
[10] Z.S. Wang, F.Y. Li, C.H. Huang, "Highly efficient sensitization of
nanocrystalline TiO2 films with styryl benzothiazolium propylsulfonate"
Chem. Comm., 2000, pp. 2063-2064.
[11] L. Zhang, Y. Liu, Z. Wang, M. Liang, Z. Sun, S. Xue, "Synthesis of
sensitizers containing donor cascade of triarylamine and dimethylaryl -
amine moieties for dye-sensitized solar cells" Tetrahedron, vol. 66,
2010, pp. 3318-3325.
[12] R. Ma, P. Guo, L. Yang, L. Guo, Q. Zeng, G. Lui, X. J. Zhang, "A theoretical interpretation and screening of porphyrin sensitizer
candidates with anticipated good photo-to-electric conversion performances for dye-sensitized solar cells" Mol. Str. (Theochem), vol.
942, 2010, pp. 131-136.
[13] S.E. Ela, M. Marszalek, S. Tekoglu, M. Can, S. Icli, "Synthesis, characterization and photovoltaic properties of novel molecules based on
triarylamine dyes" Curr. Appl. Phys., vol. 10, 2010, pp. 749-756.
[14] Y. Tachinaba, S.A. Haque, I.P. Mercer, J.R. Durrant, D.R. Klug,
"Electron Injection and Recombination in Dye Sensitized Nanocrystalline Titanium Dioxide Films: A Comparison of Ruthenium
Bipyridyl and Porphyrin Sensitizer Dyes" J. Phys. Chem. B, vol. 104,
2000, pp. 1198-1205
[15] K. Srinivas, K. Yesudas, K. Bhanuprakash, V.J. Roa, L. Giribabu, "A
Combined Experimental and Computational Investigation of Anthracene
Based Sensitizers for DSSC: Comparison of Cyanoacrylic and Malonic Acid Electron Withdrawing Groups Binding onto the TiO2 Anatase (101) Surface" J. Phys. Chem. C, vol. 113, 2009, pp. 20117-20126.
[1] D. Kim, M. Kang, K. Song, S. Kang, J. Ko, "Molecular engineering of
organic sensitizers containing indole moiety for dye-sensitized solar
cells" Tetrahedron, vol. 64, 2008, pp. 10417-10424.
[2] R. Ma, P. Guo, H. Cui, X. Zhang, M.K. Nazeeruddin, M. J. Grätzel,
"Substituent Effect on the Meso-Substituted Porphyrins: Theoretical
Screening of Sensitizer Candidates for Dye-Sensitized Solar Cells"
Phys. Chem. A, vol. 113, 2009, pp. 10119-10124.
[3] M. Grätzel, "Photoelectrochemical cells" Nature, vol. 414, 2001, pp.
338-344.
[4] M.P. Balanay, D. H. Kim, "DFT/TD-DFT molecular design of porphyrin
analogues for use in dye-sensitized solar cells" Phys. Chem. Chem.
Phys., vol. 10, 2008, pp. 5121-5127.
[5] M. Grätzel, "Dye-sensitized solar cells" J. Photochem. Photobiol. C, vol.
4, 2003, pp. 145-153.
[6] K. Hara, Z.S. Wang, T. Sato, A. Furube, R. Katho, K. Sugihara, Y. Danoh,
C. Kasada, A. Shinpo, S. Suga, "Oligothiophene-Containing
Coumarin Dyes for Efficient Dye-Sensitized Solar Cells" J. Phys. Chem. B, vol. 109, 2005, pp. 15476-15482.
[7] T. Horiuchi, H. Miura, K. Sumioka, S. Ushida, "High Efficiency of Dye-Sensitized Solar Cells Based on Metal-Free Indoline Dyes" J. Am.
Chem. Soc., vol. 126, 2004, pp. 12218-12219.
[8] G. Li, K.J. Jiang, Y.F. Li, S.L. Li, L.M. Yang, "Efficient Structural
Modification of Triphenylamine-Based Organic Dyes for Dye-Sensitized Solar Cells" J. Phys. Chem. C, vol. 112, 2008, pp. 11591-11599.
[9] Y. Shibano, T. Umeyama, Y. Matano, H. Imahori, "Electron-Donating
Perylene Tetracarboxylic Acids for Dye-Sensitized Solar Cells" Org. Lett., vol. 9, 2007, pp. 1971-1974.
[10] Z.S. Wang, F.Y. Li, C.H. Huang, "Highly efficient sensitization of
nanocrystalline TiO2 films with styryl benzothiazolium propylsulfonate"
Chem. Comm., 2000, pp. 2063-2064.
[11] L. Zhang, Y. Liu, Z. Wang, M. Liang, Z. Sun, S. Xue, "Synthesis of
sensitizers containing donor cascade of triarylamine and dimethylaryl -
amine moieties for dye-sensitized solar cells" Tetrahedron, vol. 66,
2010, pp. 3318-3325.
[12] R. Ma, P. Guo, L. Yang, L. Guo, Q. Zeng, G. Lui, X. J. Zhang, "A theoretical interpretation and screening of porphyrin sensitizer
candidates with anticipated good photo-to-electric conversion performances for dye-sensitized solar cells" Mol. Str. (Theochem), vol.
942, 2010, pp. 131-136.
[13] S.E. Ela, M. Marszalek, S. Tekoglu, M. Can, S. Icli, "Synthesis, characterization and photovoltaic properties of novel molecules based on
triarylamine dyes" Curr. Appl. Phys., vol. 10, 2010, pp. 749-756.
[14] Y. Tachinaba, S.A. Haque, I.P. Mercer, J.R. Durrant, D.R. Klug,
"Electron Injection and Recombination in Dye Sensitized Nanocrystalline Titanium Dioxide Films: A Comparison of Ruthenium
Bipyridyl and Porphyrin Sensitizer Dyes" J. Phys. Chem. B, vol. 104,
2000, pp. 1198-1205
[15] K. Srinivas, K. Yesudas, K. Bhanuprakash, V.J. Roa, L. Giribabu, "A
Combined Experimental and Computational Investigation of Anthracene
Based Sensitizers for DSSC: Comparison of Cyanoacrylic and Malonic Acid Electron Withdrawing Groups Binding onto the TiO2 Anatase (101) Surface" J. Phys. Chem. C, vol. 113, 2009, pp. 20117-20126.
@article{"International Journal of Chemical, Materials and Biomolecular Sciences:61000", author = "S. Jungsuttiwong and R. Tarsang and S. Pansay and T. Yakhantip and V. Promarak and T. Sudyoadsuk and T. Kaewin and S. Saengsuwan and S. Namuangrak", title = "Theoretical Investigation of Carbazole-Based
D-D-π-A Organic Dyes for Efficient
Dye-Sensitized Solar Cell", abstract = "In this paper, four carbazole-based D-D-π-A organic
dyes code as CCT2A, CCT3A, CCT1PA and CCT2PA were reported.
A series of these organic dyes containing identical donor and
acceptor group but different π-system. The effect of replacing of
thiophene by phenyl thiophene as π-system on the physical
properties has been focused. The structural, energetic properties and
absorption spectra were theoretically investigated by means of
Density Functional Theory (DFT) and Time-Dependent Density
Functional Theory (TD-DFT). The results show that nonplanar
conformation due to steric hindrance in donor part (cabazolecarbazole
unit) of dye molecule can prevent unfavorable dye
aggregation. By means of the TD-DFT method, the absorption
spectra were calculated by B3LYP and BHandHLYP to study the
affect of hybrid functional on the excitation energy (Eg). The results
revealed the increasing of thiophene units not only resulted in
decreasing of Eg, but also found the shifting of absorption spectra to
higher wavelength. TD-DFT/BHandHLYP calculated results are
more strongly agreed with the experimental data than B3LYP
functions. Furthermore, the adsorptions of CCT2A and CCT3A on the
TiO2 anatase (101) surface were carried out by mean of the chemical
periodic calculation. The result exhibit the strong adsorption energy.
The calculated results provide our new organic dyes can be
effectively used as dye for Dye Sensitized Solar Cell (DSC).", keywords = "Dye-Sensitized Solar cell, Carbarzole, TD-DFT,
D-D-π-A organic dye", volume = "5", number = "5", pages = "439-7", }