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Dye-sensitized solar cells based on functionalized truxene structure

Fei Wu ,  Jian-Lin Liu ,  Lawrence Tien Lin Lee ,  Tao Chen ,  Min Wang ,  Lin-Na Zhu

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Citation:  Fei Wu, Jian-Lin Liu, Lawrence Tien Lin Lee, Tao Chen, Min Wang, Lin-Na Zhu. Dye-sensitized solar cells based on functionalized truxene structure[J]. Chinese Chemical Letters, 2015, 26(8): 955-962. doi: 10.1016/j.cclet.2015.03.008 shu

Dye-sensitized solar cells based on functionalized truxene structure

    • 通讯作者: Lin-Na Zhu,
摘要: 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.

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    1. [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.[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. [2] M. Grä tzel, Recent advances in sensitized mesoscopic solar cells, Acc. Chem. Res. 42 (2009) 1788-1798.[2] M. Grä tzel, Recent advances in sensitized mesoscopic solar cells, Acc. Chem. Res. 42 (2009) 1788-1798.

    3. [3] A. Hagfeldt, G. Boschloo, L. Sun, L. Kloo, H. Pettersson, Dye-sensitized solar cells, Chem. Rev. 110 (2010) 6595-6663.[3] A. Hagfeldt, G. Boschloo, L. Sun, L. Kloo, H. Pettersson, Dye-sensitized solar cells, Chem. Rev. 110 (2010) 6595-6663.

    4. [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.[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. [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.[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. [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.[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. [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.[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. [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.[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. [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.[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. [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.[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. [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.[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. [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.[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. [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.[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. [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.[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. [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.[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. [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.[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. [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.[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. [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.[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. [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.[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. [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.[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. [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.[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. [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.[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. [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.[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. [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.[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. [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.[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. [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.[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. [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.[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. [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.[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. [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.[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. [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.[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. [31] M.J. Frisch, G.W. Trucks, H.B. Schlegel, et al., Gaussian 09, Revision A.1, Gaussian, Inc., Wallingford, 2009.[31] M.J. Frisch, G.W. Trucks, H.B. Schlegel, et al., Gaussian 09, Revision A.1, Gaussian, Inc., Wallingford, 2009.

    32. [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.[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. [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.[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. [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.[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.

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  • 发布日期:  2015-03-19
  • 收稿日期:  2015-01-09
  • 网络出版日期:  2015-02-27
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