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http://dx.doi.org/10.5012/bkcs.2013.34.4.1081

Donor-π-Acceptor Type Diphenylaminothiophenyl Anthracene-mediated Organic Photosensitizers for Dye-sensitized Solar Cells  

Heo, Dong Uk (Department of Chemistry, Research Institute for Natural Sciences, Korea University)
Kim, Sun Jae (Department of Chemistry, Research Institute for Natural Sciences, Korea University)
Yoo, Beom Jin (Department of Chemistry, Research Institute for Natural Sciences, Korea University)
Kim, Boeun (Photo-electronic Hybrids Research Center, Korea Institute of Science and Technology (KIST))
Ko, Min Jae (Photo-electronic Hybrids Research Center, Korea Institute of Science and Technology (KIST))
Cho, Min Ju (Department of Chemistry, Research Institute for Natural Sciences, Korea University)
Choi, Dong Hoon (Department of Chemistry, Research Institute for Natural Sciences, Korea University)
Publication Information
Bulletin of the Korean Chemical Society / v.34, no.4, 2013 , pp. 1081-1088 More about this Journal
Abstract
Two new metal-free organic dyes bridged by anthracene-mediated ${\pi}$-conjugated moieties were successfully synthesized for use in a dye-sensitized solar cell (DSSC). A N,N-diphenylthiophen-2-amine unit in these dyes acts as an electron donor, while a (E)-2-cyano-3-(thiophen-2-yl)acrylic acid group acts as an electron acceptor and an anchoring group to the $TiO_2$ electrode. The photovoltaic properties of (E)-2-cyano-3-(5-((10-(5-(diphenylamino)thiophen-2-yl)anthracen-9-yl)ethynyl)thiophen-2-yl)acrylic acid (DPATAT) and (E)-2-cyano-3-(5'-((10-(5-(diphenylamino)thiophen-2-yl)anthracen-9-yl)ethynyl)-2,2'-bithiophen-5-yl)acrylic acid (DPATABT) were investigated to identify the effect of conjugation length between electron donor and acceptor on the DSSC performance. By introducing an anthracene moiety into the dye structure, together with a triple bond and thiophene moieties for fine-tuning of molecular configurations and for broadening the absorption spectra, the short-circuit photocurrent densities ($J_{sc}$), and open-circuit photovoltages ($V_{oc}$) of DSSCs were improved. The improvement of $J_{sc}$ in DSSC made of DPATABT might be attributed to much broader absorption spectrum and higher molecular extinction coefficient (${\varepsilon}$) in the visible wavelength range. The DPATABT-based DSSC showed the highest power conversion efficiency (PCE) of 3.34% (${\eta}_{max}$ = 3.70%) under AM 1.5 illumination ($100mWcm^{-2}$) in a photoactive area of $0.41cm^2$, with the $J_{sc}$ of $7.89mAcm^{-2}$, the $V_{oc}$ of 0.59 V, and the fill factor (FF) of 72%. In brief, the solar cell performance with DPATABT was found to be better than that of DPATAT-based DSSC.
Keywords
Dyes-sensitized solar cells; Anthracene; N,N-Diphenylthiophen-2-amine; Conjugation length; Power conversion efficiency;
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1 Gao, F.; Wang, Y.; Zhang, J.; Shi, D.; Wang, M.; Humphry-Baker, R.; Wang, P.; Zakeeruddin, S. M.; Gratzel, M. Chem. Commun. 2008, 2635.
2 Horiuchi, T.; Miura, H.; Sumioka, K.; Uchida, S. J. Am. Chem. Soc. 2004, 126, 12218.   DOI   ScienceOn
3 Wang, Z.-S.; Cui, Y.; Hara, K.; Dan-oh, Y.; Kasada, C.; Shinpo, A. Adv. Mater. 2007, 19, 1138.   DOI   ScienceOn
4 Hara, K.; Wang, Z.-S.; Sato, T.; Furube, A.; Katoh, R.; Sugihara, H.; Dan-oh, Y.; Kasada, C.; Shinpo, A.; Suga, S. J. Phys. Chem. B 2005, 109, 15476.   DOI   ScienceOn
5 Park, S. S.; Won, Y. S.; Choi, Y. C.; Kim, J. H. Energy & Fuels 2009, 23, 3732.   DOI   ScienceOn
6 Tian, H.; Yang, X.; Cong, J.; Chen, R.; Liu, J.; Hao, Y.; Hagfeldt, A.; Sun, L. Chem. Comm. 2009, 6288.
7 Tang, J.; Wu, W.; Hua, J.; Li, J.; Li, X.; Tian, H. Chem. Comm. 2009, 982.
8 Khazraji, A. C.; Hotchandani, S.; Das, S.; Kamat, P. V. J. Phys. Chem. B 1997, 103, 4693.
9 Liang, M.; Xu, W.; Cai, F.; Chen, P.; Peng, B.; Chen, J.; Li, Z. J. Phys. Chem. C 2007, 111, 4465.   DOI   ScienceOn
10 Hagberg, D. P.; Edvinsson, T.; Marinado, T.; Boschloo, G.; Hagfeldt, A.; Sun, L. Chem. Commun. 2006, 2245.
11 Thomas, K. R. J.; Lin, J. T.; Hsu, Y.-C.; Ho, K.-C. Chem. Comm. 2005, 4098.
12 Velusamy, M.; Thomas, K. R. J.; Lin, J. T.; Hsu, Y.-C.; Ho, K.-C. Org. Lett. 2005, 7, 1899.   DOI   ScienceOn
13 Koumura, N.; Wang, Z.-S.; Mori, S.; Miyashita, M.; Suzuki, E.; Hara, K. J. Am. Chem. Soc. 2006, 128, 14256.   DOI   ScienceOn
14 Kim, S.; Lee, J. K.; Kang, S. O.; Ko, J.; Yum, J.-H.; Fantacci, S.; de Angelis, F.; Censo, D. D.; Nazeeruddin, M. K.; Gratzel, M. J. Am. Chem. Soc. 2006, 128, 16701.   DOI   ScienceOn
15 Sun, S.; Gao, L.; Liu, Y. Appl. Phys. Lett. 2010, 96, 083113.   DOI   ScienceOn
16 Kern, R.; Sastrawan, R.; Ferber, J.; Stangl, R.; Luther, J. Electrochim. Acta 2002, 47, 4213.   DOI   ScienceOn
17 Kozma, E.; Concina, I.; Braga, A.; Borgese, L.; Depero, L. E.; Vomiero, A.; Sberveglieri, G.; Catellani, M. J. Mater. Chem. 2011, 21, 13785.   DOI   ScienceOn
18 Chen, C.-Y.; Wu, S.-J.; Wu, C.-G.; Chen, J.-G.; Ho, K.-C. Angew. Chem. Int. Ed. 2006, 45, 5822.   DOI   ScienceOn
19 Qin, P.; Yang, X.; Chen, R.; Sun, L.; Marinado, T.; Edvinsson, T.; Boschloo, G.; Hagfeldt, A. J. Phys. Chem. C. 2007, 111, 1853.   DOI   ScienceOn
20 Fischer, M. K.; Wenger, S.; Wang, M.; Mishra, A.; Zakeeruddin, S. M.; Gratzel, M.; Bauerle, P. Chem. Mater. 2010, 22, 1836.   DOI   ScienceOn
21 Tao, S.; Zhou, Y.; Lee, C. S.; Lee, S. T.; Huang, D.; Zhang, X. J. Phys. Chem. C 2008, 112, 14603.   DOI   ScienceOn
22 Li, Z. H.; Wong, M. S.; Tao, Y.; Fukutani, H. Org. Lett. 2007, 9, 3659.   DOI   ScienceOn
23 Liao, Y.-L.; Lin, C.-Y.; Wong, K.-T.; Hou, T.-H.; Hung, W.-Y. Org. Lett. 2007, 9, 4511.   DOI   ScienceOn
24 Huang, T.-H.; Lin, J. T.; Chen, L.-Y.; Lin, Y.-T.; Wu, C.-C. Adv. Mater. 2006, 18, 602.   DOI   ScienceOn
25 Xia, Z.-Y.; Zhang, Z.-Y.; Su, J.-H.; Zhang, Q.; Fung, K.-M.; Lam, M.-K.; Li, K.-F.; Wong, W.-Y.; Cheah, K.-W.; Tian, H.; Chen, C. H. J. Mater. Chem. 2010, 20, 3768.   DOI   ScienceOn
26 Reddy, M. A.; Thomas, A.; Srinivas, K.; Rao, V. J.; Bhanuprakash,K.; Sridhar, B.; Kumar, A.; Kamalasanan, M. N.; Srivastava, R. J.Mater. Chem. 2009, 19, 6172.   DOI   ScienceOn
27 Lyu, Y. Y.; Kwak, J.; Kwon, O.; Lee, S. H.; Kim, D.; Lee, C.;Char, K. Adv. Mater. 2008, 20, 2820.
28 Silvestri, F.; Marrocchi, A.; Seri, M.; Kim, C.; Marks, T. J.;Facchetti, A.; Taicchi, A. J. Am. Chem. Soc. 2010, 132, 6108.   DOI   ScienceOn
29 Jung, K. H.; Bae, S. Y.; Kim, K. H.; Cho, M. J.; Lee, K.; Kim, Z.H.; Choi, D. H. Chem. Commun. 2009, 5290.
30 Chung, D. S.; Park, J. W.; Park, J.-H.; Moon, D.; Kim, G. H.; Lee,H.-S.; Lee, D. H.; Shim, H.-K.; Kwon, S.-K.; Park, C. E. J. Mater.Chem. 2010, 20, 524.   DOI   ScienceOn
31 Marrocchi, A.; Silvestri, F.; Seri, M.; Facchetti, A.; Taticchi, A.;Marks, T. J. Chem. Commun. 2009, 1380.
32 Teng, C.; Yang, X. C.; Yang, C.; Li, S. F.; Cheng, M.; Hagfeldt,A.; Sun, L. J. Phys. Chem. C 2010, 114, 9101.   DOI   ScienceOn
33 Srinivas, K.; Yesudas, K.; Bhanuprakash, K.; Rao, V. J.; Giribabu,L. J. Phys. Chem. C 2009, 113, 20117.   DOI
34 Thomas, K. R. J.; Singh, P.; Baheti, A.; Hsu, Y.-C.; Ho, K.-C.;Lin, J. T. Dyes. Pigments 2011, 91, 33.   DOI   ScienceOn
35 Kuang, D.; Ito, S.; Wenger, B.; Klein, C.; Moser, J. E.; Humphry-Baker, R.; Zakeerudddin, S. M.; Gratzel, M. J. Am.Chem. Soc. 2006, 128, 4146.   DOI   ScienceOn
36 Kuang, D.; Wang, P.; Ito, S.; Zakeeruddin, S. M.; Gratzel, M. J. Am. Chem. Soc. 2006, 128,7732.   DOI   ScienceOn
37 Bisquert, J. J. Phys. Chem. B 2002, 106, 325.   DOI   ScienceOn
38 Bisquert,J.; Zaban, A.; Greenshtein, M.; Mora-Sero, I. J. Am. Chem. Soc.2004, 126, 13550.   DOI   ScienceOn
39 Lee, K. M.; Suryanarayananb, V.; Ho, K. C. J. Power Sources 2009, 188, 635.   DOI   ScienceOn
40 O'Regan, B.; Gratzel, M. Nature 1991, 353, 737.   DOI
41 Gratzel, M. Nature 2001, 414, 338.   DOI   ScienceOn
42 Nazeeruddin, M. K.; de Angelis, F.; Fantacci, S.; Selloni, A.;Viscardi, G.; Liska, P.; Ito, S.; Takeru, B.; Gratzel, M. J. Am. Chem. Soc. 2005, 127, 16835.   DOI   ScienceOn
43 Yum, J.-H.; Jung, I.; Baik, C.; Ko, J.; Nazeeruddin, M. K.; Gratzel, M. Energ. Environ. Sci. 2009, 2, 100.   DOI   ScienceOn