Organic dyes incorporating a thiophene or furan moiety for efficient dye-sensitized solar cells

Dyes and Pigments

Volumn 104, Issue , 2014, Pages 75-82

  He, Jinxiang ^a   Hua, Jianli ^a   Hu, Guangxia ^b   Yin, Xi Jiang ^c   Gong, Hao ^b   Li, Chunxiang ^c  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^c SINGAPORE POLYTECHNIC   (Singapore)

Author keywords

Alkyl functionalized carbazole; Dye sensitized solar cell; Furan; Organic dye; Photovoltaic; Thiophene

Indexed keywords

DYE-SENSITIZED SOLAR CELL; FUNCTIONALIZED; FURAN; ORGANIC DYE; PHOTOVOLTAIC;

CONVERSION EFFICIENCY; ORGANIC POLLUTANTS; ORGANIC POLYMERS; PHOTOELECTROCHEMICAL CELLS; POLYCYCLIC AROMATIC HYDROCARBONS; THIOPHENE; TITANIUM DIOXIDE;

SOLAR CELLS;

EID: 84892745808     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2013.12.025     Document Type: Article

References (69)

1. 2 films Nature 353 1991 737 740
2. F. Gao, Y. Wang, J. Zhang, D. Shi, M. Wang, and R. Humphry-Baker et al. A new heteroleptic ruthenium sensitizer enhances the absorptivity of mesoporous titania film for a high efficiency dye-sensitized solar cell Chem Commun 44 2008 2635 2637
3. J.-H. Yum, I. Jung, C. Baik, J. Ko, M.K. Nazeeruddin, and M. Gratzel High efficient donor-acceptor ruthenium complex for dye-sensitized solar cell applications Energ Environ Sci 2 2009 100 102
4. P. Wang, S.M. Zakeeruddin, J.E. Moser, M.K. Nazeeruddin, T. Sekiguchi, and M. Gratzel A stable quasi-solid-state dye-sensitized solar cell with an amphiphilic ruthenium sensitizer and polymer gel electrolyte Nat Mater 2 2003 402 407
5. G. Zhang, H. Bala, Y. Cheng, D. Shi, X. Lv, and Q. Yu et al. High efficiency and stable dye-sensitized solar cells with an organic chromophore featuring a binary [small pi]-conjugated spacer Chem Commun 45 2009 2198 2200
6. S. Qu, W. Wu, J. Hua, C. Kong, Y. Long, and H. Tian New diketopyrrolopyrrole (DPP) dyes for efficient dye-sensitized solar cells J Phys Chem C 114 2009 1343 1349
7. D. Kim, J.K. Lee, S.O. Kang, and J. Ko Molecular engineering of organic dyes containing N-aryl carbazole moiety for solar cell Tetrahedron 63 2007 1913 1922
8. H. Tian, X. Yang, R. Chen, Y. Pan, L. Li, and A. Hagfeldt et al. Phenothiazine derivatives for efficient organic dye-sensitized solar cells Chem Commun 43 2007 3741 3743
9. Z. Iqbal, W.-Q. Wu, D.-B. Kuang, L. Wang, H. Meier, and D. Cao Phenothiazine-based dyes with bilateral extension of π-conjugation for efficient dye-sensitized solar cells Dyes Pigm 96 2013 722 731
10. W. Wu, J. Yang, J. Hua, J. Tang, L. Zhang, and Y. Long et al. Efficient and stable dye-sensitized solar cells based on phenothiazine sensitizers with thiophene units J Mater Chem 20 2010 1772 1779
11. X. Ma, J. Hua, W. Wu, Y. Jin, F. Meng, and W. Zhan et al. A high-efficiency cyanine dye for dye-sensitized solar cells Tetrahedron 64 2008 345 350
12. K. Funabiki, H. Mase, A. Hibino, N. Tanaka, N. Mizuhata, and Y. Sakuragi et al. Synthesis of a novel heptamethine-cyanine dye for use in near-infrared active dye-sensitized solar cells with porous zinc oxide prepared at low temperature Energ Environ Sci 4 2011 2186 2192
13. K. Sayama, K. Hara, Y. Ohga, A. Shinpou, S. Suga, and H. Arakawa Significant effects of the distance between the cyanine dye skeleton and the semiconductor surface on the photoelectrochemical properties of dye-sensitized porous semiconductor electrodes New J Chem 25 2001 200 202
14. J. Tang, W. Wu, J. Hua, J. Li, X. Li, and H. Tian Starburst triphenylamine-based cyanine dye for efficient quasi-solid-state dye-sensitized solar cells Energ Environ Sci 2 2009 982 990
15. K. Sayama, K. Hara, N. Mori, M. Satsuki, S. Suga, and S. Tsukagoshi et al. Photosensitization of a porous TiO electrode with merocyanine dyes containing a carboxyl group and a long alkyl chain Chem Commun 36 2000 1173 1174
16. 2 films with cyanine and merocyanine organic dyes Sol Energ Mat Sol C 80 2003 47 71
17. K. Hara, T. Sato, R. Katoh, A. Furube, Y. Ohga, and A. Shinpo et al. Molecular design of coumarin dyes for efficient dye-sensitized solar cells J Phys Chem B 107 2002 597 606
18. K. Hara, Z.-S. Wang, T. Sato, A. Furube, R. Katoh, and H. Sugihara et al. Oligothiophene-containing coumarin dyes for efficient dye-sensitized solar cells J Phys Chem B 109 2005 15476 15482
19. Z.S. Wang, Y. Cui, K. Hara, Y. Dan-oh, C. Kasada, and A. Shinpo A high-light-harvesting-efficiency coumarin dye for stable dye-sensitized solar cells Adv Mater 19 2007 1138 1141
20. X. Cheng, S. Sun, M. Liang, Y. Shi, Z. Sun, and S. Xue Organic dyes incorporating the cyclopentadithiophene moiety for efficient dye-sensitized solar cells Dyes Pigm 92 2012 1292 1299
21. W.H. Howie, F. Claeyssens, H. Miura, and L.M. Peter Characterization of solid-state dye-sensitized solar cells utilizing high absorption coefficient metal-free organic dyes J Am Chem Soc 130 2008 1367 1375
22. D. Kuang, S. Uchida, R. Humphry-Baker, S.M. Zakeeruddin, and M. Grätzel Organic dye-sensitized ionic liquid based solar cells: remarkable enhancement in performance through molecular design of indoline sensitizers Angew Chem Int Ed 47 2008 1923 1927
23. T. Dentani, Y. Kubota, K. Funabiki, J. Jin, T. Yoshida, and H. Minoura et al. Novel thiophene-conjugated indoline dyes for zinc oxide solar cells New J Chem 33 2009 93 101
24. W. Zhu, Y. Wu, S. Wang, W. Li, X. Li, and J. Chen et al. Organic D-A-π-A solar cell sensitizers with improved stability and spectral response Adv Funct Mater 21 2011 756 763
25. B. Liu, W. Zhu, Q. Zhang, W. Wu, M. Xu, and Z. Ning et al. Conveniently synthesized isophorone dyes for high efficiency dye-sensitized solar cells: tuning photovoltaic performance by structural modification of donor group in donor-[small pi]-acceptor system Chem Commun 45 2009 1766 1768
26. B. Liu, W. Wu, X. Li, L. Li, S. Guo, and X. Wei et al. Molecular engineering and theoretical investigation of organic sensitizers based on indoline dyes for quasi-solid state dye-sensitized solar cells Phys Chem Chem Phys 13 2011 8985 8992
27. Z.-S. Wang, F.-Y. Li, and C.-H. Huang Highly efficient sensitization of nanocrystalline TiO films with styryl benzothiazolium propylsulfonate Chem Commun 36 2000 2063 2064
28. E. Stathatos, P. Lianos, A. Laschewsky, O. Ouari, and P. Van Cleuvenbergen Synthesis of a hemicyanine dye bearing two carboxylic groups and its use as a photosensitizer in dye-sensitized photoelectrochemical cells Chem Mater 13 2001 3888 3892
29. Y. Cui, Y. Wu, X. Lu, X. Zhang, G. Zhou, and F.B. Miapeh et al. Incorporating benzotriazole moiety to construct D-A-π-A organic sensitizers for solar cells: significant enhancement of open-circuit photovoltage with long alkyl group Chem Mater 23 2011 4394 4401
30. H. Tian, X. Yang, R. Chen, A. Hagfeldt, and L. Sun A metal-free "black dye" for panchromatic dye-sensitized solar cells Energ Environ Sci 2 2009 674 677
31. Gupta KSV, Suresh T, Singh SP, Islam A, Han L, Chandrasekharam M. Carbazole based A-π-D-π-A dyes with double electron acceptor for dye-sensitized solar cell. Organic Electronics.
32. L.-L. Tan, L.-J. Xie, Y. Shen, J.-M. Liu, L.-M. Xiao, and D.-B. Kuang et al. Novel organic dyes incorporating a carbazole or dendritic 3,6-diiodocarbazole unit for efficient dye-sensitized solar cells Dyes Pigm 100 2014 269 277
33. N. Koumura, Z.-S. Wang, S. Mori, M. Miyashita, E. Suzuki, and K. Hara Alkyl-functionalized organic dyes for efficient molecular photovoltaics J Am Chem Soc 128 2006 14256 14257
34. Z.-S. Wang, N. Koumura, Y. Cui, M. Takahashi, H. Sekiguchi, and A. Mori et al. Hexylthiophene-functionalized carbazole dyes for efficient molecular photovoltaics: tuning of solar-cell performance by structural modification Chem Mater 20 2008 3993 4003
35. L.-F. Lai, C. Qin, C.-H. Chui, A. Islam, L. Han, and C.-L. Ho et al. New fluorenone-containing organic photosensitizers for dye-sensitized solar cells Dyes Pigm 98 2013 428 436
36. 2 films and quasi-solid state solar cells sensitized with a dipolar fluorene organic dye J Photochem Photobiology Chem 251 2013 18 24
37. P. Singh, A. Baheti, K.R.J. Thomas, C.-P. Lee, and K.-C. Ho Fluorene-based organic dyes containing acetylene linkage for dye-sensitized solar cells Dyes Pigm 95 2012 523 533
38. W. Zeng, Y. Cao, Y. Bai, Y. Wang, Y. Shi, and M. Zhang et al. Efficient dye-sensitized solar cells with an organic photosensitizer featuring orderly conjugated ethylenedioxythiophene and dithienosilole blocks Chem Mater 22 2010 1915 1925
39. L. Li, Y. Hao, X. Yang, J. Zhao, H. Tian, and C. Teng et al. A Double-band tandem organic dye-sensitized solar cell with an efficiency of 11.5 % ChemSusChem 4 2011 609 612
40. A. Yella, H.-W. Lee, H.N. Tsao, C. Yi, A.K. Chandiran, and M.K. Nazeeruddin et al. Porphyrin-sensitized solar cells with cobalt (II/III)-based redox electrolyte exceed 12 percent efficiency Science 334 2011 629 634
41. T.-Y. Wu, M.-H. Tsao, F.-L. Chen, S.-G. Su, C.-W. Chang, and H.-P. Wang et al. Synthesis and characterization of organic dyes containing various donors and acceptors Int J Mol Sci 11 2010 329 353
42. Y. Bai, Q. Yu, N. Cai, Y. Wang, M. Zhang, and P. Wang High-efficiency organic dye-sensitized mesoscopic solar cells with a copper redox shuttle Chem Commun 47 2011 4376 4378
43. Y. Numata, I. Ashraful, Y. Shirai, and L. Han Preparation of donor-acceptor type organic dyes bearing various electron-withdrawing groups for dye-sensitized solar cell application Chem Commun 47 2011 6159 6161
44. R. Chen, X. Yang, H. Tian, and L. Sun Tetrahydroquinoline dyes with different spacers for organic dye-sensitized solar cells J Photochem Photobiol A 189 2007 295 300
45. R. Chen, X. Yang, H. Tian, X. Wang, A. Hagfeldt, and L. Sun Effect of tetrahydroquinoline dyes structure on the performance of organic dye-sensitized solar cells Chem Mater 19 2007 4007 4015
46. A. Baheti, P. Singh, C.-P. Lee, K.R.J. Thomas, and K.-C. Ho 2,7-diaminofluorene-based organic dyes for dye-sensitized solar cells: effect of auxiliary donor on optical and electrochemical properties J Org Chem 76 2011 4910 4920
47. M. Liang, Z.-Y. Wang, L. Zhang, H.-Y. Han, Z. Sun, and S. Xue New organic photosensitizers incorporating carbazole and dimethylarylamine moieties for dye-sensitized solar cells Renew Energ 36 2011 2711 2716
48. Z. Ning, Q. Zhang, W. Wu, H. Pei, B. Liu, and H. Tian Starburst triarylamine based dyes for efficient dye-sensitized solar cells J Org Chem 73 2008 3791 3797
49. H. Tian, X. Yang, J. Pan, R. Chen, M. Liu, and Q. Zhang et al. A triphenylamine dye model for the study of intramolecular energy transfer and charge transfer in dye-sensitized solar cells Adv Funct Mater 18 2008 3461 3468
50. G. Li, Y.-F. Zhou, X.-B. Cao, P. Bao, K.-J. Jiang, and Y. Lin et al. Novel TPD-based organic D-[small pi]-A dyes for dye-sensitized solar cells Chem Commun 45 2009 2201 2203
51. J. Zhuang, W. Su, W. Li, Y. Zhou, Q. Shen, and M. Zhou Configuration effect of novel bipolar triazole/carbazole-based host materials on the performance of phosphorescent OLED devices Org Electron 13 2012 2210 2219
52. N. Agarwal, P.K. Nayak, F. Ali, M.P. Patankar, K.L. Narasimhan, and N. Periasamy Tuning of HOMO levels of carbazole derivatives: new molecules for blue OLED Synth Met 161 2011 466 473
53. N. Koumura, Z.-S. Wang, S. Mori, M. Miyashita, E. Suzuki, and K. Hara Alkyl-functionalized organic dyes for efficient molecular photovoltaics [J Am Chem Soc 2006, 128, 14256-14257] J Am Chem Soc 130 2008 4202 4203
54. Z. Ning, and H. Tian Triarylamine: a promising core unit for efficient photovoltaic materials Chem Commun 45 2009 5483 5495
55. C.-H. Yang, S.-H. Liao, Y.-K. Sun, Y.-Y. Chuang, T.-L. Wang, and Y.-T. Shieh et al. Optimization of multiple electron donor and acceptor in carbazole-triphenylamine-based molecules for application of dye-sensitized solar cells J Phys Chem C 114 2010 21786 21794
56. N. Koumura, Z.-S. Wang, M. Miyashita, Y. Uemura, H. Sekiguchi, and Y. Cui et al. Substituted carbazole dyes for efficient molecular photovoltaics: long electron lifetime and high open circuit voltage performance J Mater Chem 19 2009 4829 4836
57. J.T. Lin, P.-C. Chen, Y.-S. Yen, Y.-C. Hsu, H.-H. Chou, and M.-C.P. Yeh Organic dyes containing furan moiety for high-performance dye-sensitized solar cells Org Lett 11 2008 97 100
58. T. Kumchoo, V. Promarak, T. Sudyoadsuk, M. Sukwattanasinitt, and P. Rashatasakhon Dipyrenylcarbazole derivatives for blue organic light-emitting diodes Chem Asian J 5 2010 2162 2167
59. P. Bonhôte, A.-P. Dias, N. Papageorgiou, K. Kalyanasundaram, and M. Grätzel Hydrophobic, highly conductive ambient-temperature molten salts Inorg Chem 35 1996 1168 1178
60. J. He, W. Wu, J. Hua, Y. Jiang, S. Qu, and J. Li et al. Bithiazole-bridged dyes for dye-sensitized solar cells with high open circuit voltage performance J Mater Chem 21 2011 6054 6062
61. S. Ito, T.N. Murakami, P. Comte, P. Liska, C. Grätzel, and M.K. Nazeeruddin et al. Fabrication of thin film dye sensitized solar cells with solar to electric power conversion efficiency over 10% Thin Solid Films 516 2008 4613 4619
62. Z. Ning, Y. Fu, and H. Tian Improvement of dye-sensitized solar cells: what we know and what we need to know Energ Environ Sci 3 2010 1170 1181
63. P. Shen, X. Liu, S. Jiang, Y. Huang, L. Yi, and B. Zhao et al. Effects of aromatic π-conjugated bridges on optical and photovoltaic properties of N,N-diphenylhydrazone-based metal-free organic dyes Org Electron 12 2011 1992 2002
64. K. Kinashi, K.-P. Lee, S. Matsumoto, K. Ishida, and Y. Ueda Alkyl substituent effects on J- or H-aggregate formation of bisazomethine dyes Dyes Pigm 92 2012 783 788
65. L.-Y. Lin, C.-H. Tsai, K.-T. Wong, T.-W. Huang, L. Hsieh, and S.-H. Liu et al. Organic dyes containing coplanar diphenyl-substituted dithienosilole core for efficient dye-sensitized solar cells J Org Chem 75 2010 4778 4785
66. A. Hagfeldt, and M. Graetzel Light-induced redox reactions in nanocrystalline systems Chem Rev 95 1995 49 68
67. C. Teng, X. Yang, C. Yang, H. Tian, S. Li, and X. Wang et al. Influence of triple bonds as π-spacer units in metal-free organic dyes for dye-sensitized solar cells J Phys Chem C 114 2010 11305 11313
68. S. Qu, B. Wang, F. Guo, J. Li, W. Wu, and C. Kong et al. New diketo-pyrrolo-pyrrole (DPP) sensitizer containing a furan moiety for efficient and stable dye-sensitized solar cells Dyes Pigm 92 2012 1384 1393
69. S.H. Kim, H.W. Kim, C. Sakong, J. Namgoong, S.W. Park, and M.J. Ko et al. Effect of five-membered heteroaromatic linkers to the performance of phenothiazine-based dye-sensitized solar cells Org Lett 13 2011 5784 5787