|
|
|
| Dye-sensitized solar cells based on functionalized truxene structure |
| Fei Wua, Jian-Lin Liua, Lawrence Tien Lin Leeb, Tao Chenb, Min Wanga, Lin-Na Zhua |
a Faculty of Materials and Energy, Southwest University, Chongqing 400715, China;
b Department of Physics, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China |
|
|
|
|
Abstract Three new metal-free organic dyes (TX1, TX2 and TX3) based on truxene core structure, with triphenylamine as the electron donor, thiophene as the p spacers, and cyanoacetic acid or rhodanine-3-acetic acid as the electron acceptor are designed and synthesized. Their UV-vis absorption spectra, electrochemical and photovoltaic properties were investigated. The cyanoacrylic acid is verified to be a better acceptor unit (meanwhile the anchoring group) compared to the rhodanine-3-acetic acid. And also, two anchoring groups in TX2 could provide stronger adsorption ability on the TiO2 surface. In addition, the EIS results indicate a slower charge recombination processes for TX2. As a result, dye TX2 bearing two cyanoacetic acid outperforms the other two dyes, exhibiting the photo-conversion efficiency of 2.64%, with Jsc = 5.09 mA cm-2, Voc = 729 mV, FF = 71.1.
|
|
Received: 09 January 2015
Published: 19 March 2015
|
| Fund:This work is supported by "Fundamental Research Funds for the Central Universities" (Nos. XDJK2014C145 and XDJK2014C052), and the Starting Foundation of Southwest University (Nos. SWU113076 and SWU113078). L. Zhu thanks the financial support from National Natural Science Foundation of China (No. 51203046). |
|
Corresponding Authors:
Lin-Na Zhu
E-mail: lnzhu@swu.edu.cn
|
|
|
|
| [1] |
B. O'Regan, M. Grä tzel, A low-cost, high-efficiency solar cell based on dye-sensitized colloidal TiO2 films, Nature 353 (1991) 737-740.
|
| [2] |
M. Grä tzel, Recent advances in sensitized mesoscopic solar cells, Acc. Chem. Res. 42 (2009) 1788-1798.
|
| [3] |
A. Hagfeldt, G. Boschloo, L. Sun, L. Kloo, H. Pettersson, Dye-sensitized solar cells, Chem. Rev. 110 (2010) 6595-6663.
|
| [4] |
C.Y. Chen, M.K. Wang, J.Y. Li, et al., Highly efficient light-harvesting ruthenium sensitizer for thin-film dye-sensitized solar cells, ACS Nano 3 (2009) 3103-3109.
|
| [5] |
M.K. Nazeeruddin, F. De Angelis, S. Fantacci, et al., Combined experimental and DFT-TDDFT computational study of photoelectrochemical cell ruthenium sensitizers, J. Am. Chem. Soc. 127 (2005) 16835-16847.
|
| [6] |
A. Yella, H.W. Lee, H.N. Tsao, et al., Porphyrin-sensitized solar cells with cobalt (II/ III)-based redox electrolyte exceed 12 percent efficiency, Science 334 (2011) 629-634.
|
| [7] |
H. Li, T.M. Koh, A. Hagfeldt, et al., New donor-π-acceptor sensitizers containing 5H-［1,2,5］thiadiazolo ［3,4-f］isoindole-5, 7(6H)-dione and 6H-pyrrolo［3,4-g］quinoxaline-6, 8(7H)-dione units, Chem. Commun. 49 (2013) 2409-2411.
|
| [8] |
Y. Bai, J. Zhang, D. Zhou, et al., Engineering organic sensitizers for iodine-free dyesensitized solar cells: red-shifted current response concomitant with attenuated charge recombination, J. Am. Chem. Soc. 133 (2011) 11442-11445.
|
| [9] |
W. Hung, Y.Y. Liao, T.H. Lee, et al., Eugenic metal-free sensitizers with double anchors for high performance dye-sensitized solar cells, Chem. Commun. 51 (2015) 2152-2155.
|
| [10] |
Y.R. Gao, L.L. Chu, W. Guo, T.L. Ma, Synthesis and photoelectric properties of an organic dye containing benzo［1,2-b: 4, 5-b'］dithiophene for dye-sensitized solar cells, Chin. Chem. Lett. 24 (2013) 149-152.
|
| [11] |
Y. Hua, S. Chang, D.D. Huang, et al., Significant improvement of dye-sensitized solar cell performance using simple phenothiazine-based dyes, Chem. Mater. 25 (2013) 2146-2153.
|
| [12] |
M.W. Lee, J.Y. Kim, D.H. Lee, M.J. Ko, Novel D-π-A organic dyes with thieno［3,2-b］thiophene-3, 4-ethylenedioxythiophene unit as a π-bridge for highly efficient dye-sensitized solar cells with long-term stability, ACS Appl. Mater. Inter. 6 (2014) 4102-4108.
|
| [13] |
Y.Y. Gao, C.J. You, J.P. Chen, et al., Synthesis of a polymer-bound sensitizer and its application in the photoisomerization of trans-vitamin D3 to cis-vitamin D3, Chin. Chem. Lett. 13 (2002) 1158-1161.
|
| [14] |
Z.J. Ning, Q. Zhang, H.C. Pei, et al., Photovoltage improvement for dye-sensitized solar cells via cone-shaped structural design, J. Phys. Chem. C 113 (2009) 10307-10313.
|
| [15] |
J.L. Wang, Z.M. Tang, Q. Xiao, Y. Ma, J. Pei, Star-shaped D-π-A conjugated molecules: synthesis and broad absorption bands, Org. Lett. 11 (2009) 863-866.
|
| [16] |
X.Y. Cao, X.H. Zhou, H. Zi, J. Pei, Novel blue-light-emitting truxene-containing hyperbranched and zigzag type copolymers: synthesis, optical properties, and investigation of thermal spectral stability, Macromolecules 37 (2004) 8874-8882.
|
| [17] |
Z.F. Yang, B. Xu, J.T. He, et al., Solution-processable and thermal-stable triphenylamine-based dendrimers with truxene cores as hole-transporting materials for organic light-emitting devices, Org. Elect. 10 (2009) 954-959.
|
| [18] |
W.Y. Lai, R.D. Xia, Q.Y. He, et al., Enhanced solid-state luminescence and lowthreshold lasing from starburst macromolecular materials, Adv. Mater. 21 (2009) 355-360.
|
| [19] |
Y.M. Sun, K. Xiao, Y.Q. Liu, et al., Oligothiophene-functionalized truxene: starshaped compounds for organic field-effect transistors, Adv. Funct. Mater. 15 (2005) 818-822.
|
| [20] |
X.Y. Yang, Q.D. Zheng, C.Q. Tang, et al., Star-shaped chromophores based on a benzodithiophene fused truxene core for solution processed organic solar cells, Dyes Pigments 99 (2013) 366-373.
|
| [21] |
Y.J. Hao, M. Liang, Z.H. Wang, et al., Synthesis of new truxene based organic sensitizers for iodine-free dye-sensitized solar cells, Tetrahedron 69 (2013) 10573-10580.
|
| [22] |
X.P. Zong, M. Liang, T. Chen, et al., Efficient iodine-free dye-sensitized solar cells employing truxene-based organic dyes, Chem. Commun. 48 (2012) 6645-6647.
|
| [23] |
C.B. Nielsen, E. Voroshazi, S. Holliday, et al., Electron-deficient truxenone derivatives and their use in organic photovoltaics, J. Mater. Chem. A 2 (2014) 12348-12354.
|
| [24] |
S.H. Lin, Y.C. Hsu, J.T. Lin, C.K. Lin, J.S. Yang, Isotruxene-derived cone-shaped organic dyes for dye-sensitized solar cells, J. Org. Chem. 75 (2010) 7877-7886.
|
| [25] |
L.N. Zhu, H.B. Yang, C. Zhong, C.M. Li, Modified triphenylamine-dicyanovinylbased donor-acceptor dyes with enhanced power conversion efficiency of p-type dye-sensitized solar cells, Chem. Asian J. 7 (2012) 2791-2795.
|
| [26] |
M.S. Yuan, Q. Fang, Z.Q. Liu, et al., Acceptor or donor (diaryl B or N) substituted octupolar truxene: synthesis, structure, and charge-transfer-enhanced fluorescence, J. Org. Chem. 71 (2006) 7858-7861.
|
| [27] |
A.L. Kanibolotsky, R. Berridge, P.J. Skabara, et al., Synthesis and properties of monodisperse oligofluorene-functionalized truxenes: highly fluorescent starshaped architectures, J. Am. Chem. Soc. 126 (2004) 13695-13702.
|
| [28] |
W.H. Liu, I.C. Wu, C.H. Lai, et al., Simple organic molecules bearing a 3,4-ethylenedioxythiophene linker for efficient dye-sensitized solar cells, Chem. Commun. (2008) 5152-5154.
|
| [29] |
J.K. Zhao, Y.G. Wang, A facile and efficient synthesis of N,N-dimethylarylamines from aryl bromides, Chin. Chem. Lett. 13 (2002) 1149-1151.
|
| [30] |
Z.Q. Wan, L.L. Zhou, C.Y. Jia, et al., Comparative study on photovoltaic properties of imidazole-based dyes containing varying electron acceptors in dye-sensitized solar cells, Synth. Met. 196 (2014) 193-198.
|
| [31] |
M.J. Frisch, G.W. Trucks, H.B. Schlegel, et al., Gaussian 09, Revision A.1, Gaussian, Inc., Wallingford, 2009.
|
| [32] |
J.J. He, G. Benkö , F. Korodi, et al., Modified phthalocyanines for efficient near-IR sensitization of nanostructured TiO2 electrode, J. Am. Chem. Soc. 124 (2002) 4922-4932.
|
| [33] |
X. Qian, Y.Z. Zhu, J. Song, X.P. Gao, J.Y. Zheng, New donor-π-acceptor type triazatruxene derivatives for highly efficient dye-sensitized solar cells, Org. Lett. 15 (2013) 6034-6037.
|
| [34] |
J. van de Lagemaat, N.G. Park, A.J. Frank, Influence of electrical potential distribution, charge transport, and recombination on the photopotential and photocurrent conversion efficiency of dye-sensitized nanocrystalline TiO2 solar cells: a study by electrical impedance and optical modulation techniques, J. Phys. Chem. B 104 (2000) 2044-2052.
|
|
|
|
