Abstract
2-(Thiophen-2-yl)thiazole was introduced as a π-bridge into diethylamino coumarin and novel coumarin sensitizers were synthesized with cyanoacrylic acid or rhodanine acetic acid as electron acceptor. Their light-harvesting capabilities and photovoltaic performance were investigated and compared with those of a similar sensitizer bearing a phenylthiophene bridge. Replacement of benzene in the π-bridge with a thiazole ring contributes to the improvement of the light-harvesting capability and hence superior JSC. 7-Diethylamino coumarin dye with a 2-(thiophen-2-yl)thiazole bridge and cyanoacrylic acid acceptor shows the most efficient photoelectricity conversion efficiency which has the maximum value of 4.78% (VOC = 690 mV, JSC = 9.79 mA cm−2, and ff = 0.71) under simulated AM 1.5 G irradiation (100 mW cm−2).
Similar content being viewed by others
References
R. W. Miles, K. M. Hynes, I. Forbes, Photovoltaic solar cells: An overview of state-of-the-art cell development and environmental issues, Prog. Cryst. Growth Charact. Mater., 2005, 51, 1–42.
C. Strümpel, M. McCann, G. Beaucarne, V. Arkhipoc, A. Slaoui, V. Švrček, C. del Canizo, I. Tobias, Modifying the solar spectrum to enhance silicon solar cell efficiency–An overview of available materials, Sol. Energy Mater. Sol. Cells, 2007, 91, 238–249.
M. Grätzel, Recent advances in sensitized mesoscopic solar cells, Acc. Chem. Res., 2009, 42, 1788–1798.
Y. Wang, K. Liu, P. Mukherjee, D. A. Hines, P. Santra, H. Y. Shen, P. Kamat, D. H. Waldeck, Driving charge separation for hybrid solar cells: photo-induced hole transfer in conjugated copolymer and semiconductor nanoparticle assemblies, Phys. Chem. Chem. Phys., 2014, 16, 5066–5070.
A. Hafeldt, G. Boschloo, L. C. Sun, L. Kloo, H. Pettersson, Dye-sensitized solar cells, Chem. Rev., 2010, 110, 6595–6663.
B.-G. Kim, K. Chung, J. Kim, Molecular design principle of all-organic dyes for dye-sensitized solar cells, Chem.–Eur. J., 2013, 19, 5220–5230.
Y. Z. Wu, W. H. Zhu, Organic sensitizers from D–π-A to D–A–π-A: effect of the internal electron-withdrawing units on molecular absorption, energy levels and photovoltaic performances, Chem. Soc. Rev., 2013, 42, 2039–2058.
J. N. Clifford, E. Nartinez-Ferrero, A. Viterisi, E. Palomares, Sensitizer molecular structure-device efficiency relationship in dye sensitized solar cells, Chem. Soc. Rev., 2011, 40, 1635–1646.
H. Ozawa, Y. Okuyama, H. Arakawa, Dependence of the efficiency improvement of black-dye-based dye-sensitized solar cells on alkyl chain length of quaternary ammonium cations in electrolyte solutions, ChemPhysChem, 2014, 15, 1201–1206.
C. F. Chi, S. C. Su, I. P. Liu, C. W. Lai, Y. L. Lee, Charge transfer and performance enhancement of dye-sensitized solar cells by utilization of a tandem structure, J. Phys. Chem. C, 2014, 118, 17446–17451.
A. Mishra, M. K. R. Fischer, P. Bäuerle, Metal-free organic dyes for dye-sensitized solar cells: from structure: property relationships to design rules, Angew. Chem., Int. Ed., 2009, 48, 2474–2499.
A. Baheti, K. R. J. Thomas, C. P. Lee, C. T. Li, K. C. Ho, Organic dyes containing fluoren-9-ylidene chromophores for efficient dye-sensitized solar cells, J. Mater. Chem. A, 2014, 2, 5766–5779.
X. G. Liu, J. M. Cole, P. G. Waddel, T. C. Lin, J. Radia, Z. Zeidler, Molecular origins of optoelectronic properties in coumarin dyes: toward designer solar cell and laser applications, J. Phys. Chem. A, 2012, 116, 727–737.
B. Liu, B. Wang, R. Wang, L. Gao, S. H. Huo, Q. B. Liu, X. Y. Li, W. H. Zhu, Influence of conjugated π-linker in D–D–π-A indoline dyes: towards long-term stable and efficient dye-sensitized solar cells with high photovoltage, J. Mater. Chem. A, 2014, 2, 804–812.
W. H. Zhu, Y. Z. Wu, S. T. Wang, W. Q. Li, X. Li, J. Chen, Z. S. Wang, H. Tian, Organic D–A–π -A solar cell sensitizers with improved stability and spectral response, Adv. Funct. Mater., 2011, 21, 756–763.
L. Han, X. Y. Zu, Y. H. Cui, H. B. Wu, Q. Ye, J. R. Gao, Novel D–A–π-A carbazole dyes containing benzothiadiazole chromophores for dye-sensitized solar cells, Org. Electron., 2014, 15, 1536–1544.
Y. Hua, S. Chang, J. He, C. S. Zhang, J. Z. Zhao, T. Chen, W. Y. Wong, W. K. Wong, X. J. Zhu, Molecular engineering of simple phenothiazine-based dyes to modulate dye aggregation, charge recombination, and dye regeneration in highly efficient dye-sensitized solar cells, Chem.–Eur. J., 2014, 20, 6300–6308.
H. J. Tan, C. Y. Pan, G. Wang, Y. Y. Wu, Y. P. Zhang, Y. P. Zou, G. P. Yu, M. Zhang, Phenoxazine-based organic dyes with different chromophores for dye-sensitized solar cells, Org. Electron., 2013, 14, 2795–2801.
Z. S. Wang, Y. Cui, Y. Dan-oh, C. Kasada, A. Shinpo, K. Hara, Thiophene-functionalized coumarin dye for efficient dye-sensitized solar cells: electron lifetime improved by coadsorption of deoxycholic acid, J. Phys. Chem. C, 2007, 111, 7224–7230.
K. D. Seo, I. T. Choi, Y. G. Park, S. Kang, J. Y. Lee, H. K. Kim, Novel D-A-π-A coumarin dyes containing low band-gap chromophores for dye-sensitised solar cells, Dyes Pigm., 2012, 94, 469–474.
B. Liu, R. Wang, W. Mi, X. Li, H. Yu, Novel branched coumarin dyes for dye-sensitized solar cells: significant improvement in photovoltaic performance by simple structure modification, J. Mater. Chem., 2012, 22, 15379–15387.
L. Han, X. Zhou, Q. Ye, Y. J. Li, J. R. Gao, Synthesis and photoelectric properties of coumarin type sensitizing dyes, Chin. J. Org. Chem., 2013, 33, 1000–1004.
L. Han, H. B. Wu, Y. H. Cui, X. Y. Zu, Q. Ye, J. R. Gao, Synthesis and density functional theory study of novel coumarin-typedyes for dye sensitized solar cells, J. Photochem. Photobiol., A, 2014, 290, 54–62.
Y. Wang, Z. Xie, G. Gotesman, L. Wang, B. P. Bloom, T. Z. Markus, D. Oron, R. Naaman, D. H. Waldeck, Determination of the electronic energetics of CdTe nanoparticle assemblies on Au electrodes by photoemission, electrochemical, and photocurrent studies, J. Phys. Chem. C, 2012, 116, 17464–17472.
B. Liu, W. Q. Li, B. Wang, X. Y. Li, Q. B. Liu, Y. Naruta, W. H. Zhu, Influence of different anchoring groups in indoline dyes for dye-sensitized solar cells: Electron injection, impedance and charge recombination, J. Power Sources, 2013, 234, 139–146.
J. Wiberg, T. Marinado, D. P. Hagberg, L. C. Sun, A. Hagfeldt, B. Albinsson, J. Phys. Chem. C, 2009, 113, 3881–3886.
Q. Wang, J. E. Moser, M. Grätzel, Electrochemical impedance spectroscopic analysis of dye-sensitized solar cells, J. Phys. Chem. B, 2005, 109, 14945–14953.
K. Pan, Y. Z. Dong, C. G. Tian, W. Zhou, G. H. Tian, B. F. Zhao, H. G. Fu, TiO2-B narrow nanobelt/TiO2 nanoparticle composite photoelectrode for dye-sensitized solar cells, Electrochim. Acta, 2009, 54, 7350–7356.
Author information
Authors and Affiliations
Corresponding author
Additional information
Electronic supplementary information (ESI) available. See DOI: 10.1039/c5pp00216h
Rights and permissions
About this article
Cite this article
Han, L., Kang, R., Zu, X. et al. Novel coumarin sensitizers based on 2-(thiophen-2-yl)thiazole π-bridge for dye-sensitized solar cells. Photochem Photobiol Sci 14, 2046–2053 (2015). https://doi.org/10.1039/c5pp00216h
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1039/c5pp00216h