Copyright (c) 2014 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Novel Donor p-Acceptor Conjugates-Functionalized Zinc Phthalocyanines Application in Dye-Sensitized Solar Cells
Corresponding Author(s) : Xuejun Zhang
Asian Journal of Chemistry,
Vol. 26 No. 8 (2014): Vol 26 Issue 8
Abstract
New zinc phthalocyanines [2-(N,N-bisacetic acid amino)-9,16,23-(N,N-bisethylamino)zinc phthalocyanine (SPC), 2-(N,N-bisacetic acid amino)-9,16,23-(N,N-bispropyl-amino)zinc phthalocyanine (TPC), 2-(N,N-bisacetic acid amino)-9,16,23-(N,N-bisbutylamino)zinc phthalocyanine (FPC)], functionalized with donor-p-acceptor conjugates were synthesized, The new compounds were characterized using FTIR, UV-visible, 1H NMR, cyclic voltammetry, differential pulse voltammetry and elemental analysis. From the reduction and oxidation behaviour, it is proved that SPC, TPC, FPC have negative LUMO levels and positive HOMO levels, satisfying the energy gap rule, they can be employed as sensitizers for dye-sensitized solar cells and their optical, electrochemical and photovoltaic properties were also studied. They exhibited broad absorption adsorbed onto a 6 μm thick TiO films. The photovoltaic devices produced short circuit current densities of 1.53, 2.07, 1.89 mA/cm2, the open circuit voltage of 0.48, 0.55, 0.56 V and power conversion efficiency of 1.42, 1.67, 1.64 % respectively under AM1.5G illumination.
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T.M. Pappenfus, M.W. Burand, D.E. Janzen and K.R. Mann, Org. Lett., 5, 1535 (2003); doi:10.1021/ol034317q.
P. Suresh, P. Balraju, G.D. Sharma, J.A. Mikroyannidis and M.M. Stylianakis, ACS Appl. Mater., 1, 1370 (2009); doi:10.1021/am900244y.
M.-S. An, S.-W. Kim and J.-D. Hong, Bull. Korean Chem. Soc., 31, 3272 (2010); doi:10.5012/bkcs.2010.31.11.3272.
X. Li, A. Liu, S. Xun, W. Qiao, X. Wan and Z.Y. Wang, Org. Lett., 10, 3785 (2008); doi:10.1021/ol801345r.
G. Qian, Z. Zhong, M. Luo, D. Yu, Z. Zhang, Z.Y. Wang and D. Ma, Adv. Mater., 21, 111 (2009); doi:10.1002/adma.200801918.
F. Zhang, W. Mammo, L.M. Andersson, S. Admassie, M.R. Andersson and O. Inganäs, Adv. Mater., 18, 2169 (2006); doi:10.1002/adma.200600124.
S.-G. Yim and T.S. Jones, Bull. Korean Chem. Soc., 31, 2247 (2010); doi:10.5012/bkcs.2010.31.8.2247.
N. Blouin, A. Michaud and M. Leclerc, Adv. Mater., 19, 2295 (2007); doi:10.1002/adma.200602496.
G.-S. Park, I.-S. Heo, I.-H. Ryu and S.-G. Yim, Bull. Korean Chem. Soc., 32, 943 (2011); doi:10.5012/bkcs.2011.32.3.943.
I. Kim, H.M. Haverinen, Z. Wang, S. Madakuni, Y. Kim, J. Li and G.E. Jabbour, Chem. Mater., 21, 4256 (2009); doi:10.1021/cm901320p.
C. Yoon, J.-H. Choi and J.-P. Kim, Bull. Korean Chem. Soc., 32, 1033 (2011); doi:10.5012/bkcs.2011.32.3.1033.
J. Xue, B.P. Rand, S. Uchida and S.R. Forrest, Adv. Mater., 17, 66 (2005); doi:10.1002/adma.200400617.
D. Wohrle and D. Meissner, Adv. Mater., 3, 129 (1991); doi:10.1002/adma.19910030303.
K.J. Hwang, S.J. Yoo, S.H. Jung, D.W. Park, S.I. Kim and J.W. Lee, Bull. Korean Chem. Soc., 30, 172 (2009); doi:10.5012/bkcs.2009.30.1.172.
M.K. Nazeeruddin, R. Humphry-Baker, M. Grätzel and B.A. Murrer, Chem. Commun., 719 (1998); doi:10.1039/a708834e.
M.S. An, S.J. Kim and D. Hong, Bull. Korean Chem. Soc., 31, 3272 (2010); doi:10.5012/bkcs.2010.31.11.3272.
M.J. Cook, J. Mater. Chem., 6, 677 (1996); doi:10.1039/jm9960600677.
S. Vagin and M. Hanack, Eur. J. Org. Chem., 2003, 2661 (2003); doi:10.1002/ejoc.200300062.
Y.S. Ko, M.H. Kim and Y.U. Kwon, Bull. Korean Chem. Soc., 29, 463 (2008); doi:10.5012/bkcs.2008.29.2.463.
C.J. Barbe, F. Arendse, P. Comte, M. Jirousek, F. Lenzmann, V. Shklover and M.J. Grätzel, Am. Chem. Soc., 80, 3157 (1997).
P. Wang, S.M. Zakeeruddin, P. Comte, R. Charvet, R. Humphry-Baker and M. Grätzel, J. Phys. Chem. B, 107, 14336 (2003); doi:10.1021/jp0365965.
M.K. Nazeeruddin, F. De Angelis, S. Fantacci, A. Selloni, G. Viscardi, P. Liska, S. Ito, B. Takeru and M. Grätzel, Am. Chem. Soc., 127, 16835 (2005); doi:10.1021/ja052467l.
Z.S. Wang, K. Hara, Y. Dan-oh, C. Kasada, A. Shinpo, S. Suga, H. Arakawa and H.J. Sugihara, Phys. Chem. B, 109, 3907 (2005); doi:10.1021/jp044851v.
D. Zhang, X.J. Zhang, L. Zhang and L.J. Mao, Bull. Korean Chem. Soc., 33, 1225 (2012); doi:10.5012/bkcs.2012.33.4.1225.
M. Özçeşmeci, I. Özçeşmeci and E. Hamuryudan, Polyhedron, 29, 2710 (2010); doi:10.1016/j.poly.2010.06.023.
M. Kandaz, M.N.U. Yaraşir, A. Koca and Ö. Bekaroglu, Polyhedron, 21, 255 (2002); doi:10.1016/S0277-5387(01)00982-2.
A. Hagfeldt and M. Graetzel, Chem. Rev., 95, 49 (1995); doi:10.1021/cr00033a003.
C.Y. Li, X.C. Yang, R.K. Chen, J.X. Pan, H.N. Tian, H.J. Zhu, X.N. Wang, A. Hagfeldt and L.C. Sun, Sol. Energy Mater. Sol. Cells, 91, 1863 (2007); doi:10.1016/j.solmat.2007.07.002.
M.K. Nazeeruddin, R. Humphry-Baker, M. Grätzel, D. Wohrle, G. Schnurpfeil, G. Schneider, A. Hirth and N.J. Trombach, Porphyrins Phthalocyanines., 3, 230 (1999); doi:10.1002/(SICI)1099-1409(199903)3:3<230::AID-JPP127>3.0.CO;2-L.
H.H. Deng, H.F. Mao, H. Zhang, Z.H. Lu and H.J.J. Xu, Porphyrins Phthalocyanines, 2, 171 (1998); doi:10.1002/(SICI)1099-1409(199803/04)2:2<171::AID-JPP59>3.0.CO;2-8.
X.J. Zhang, L.J. Mao, D. Zhang and L.J. Zhang, Mol. Struct., 1022, 153 (2012); doi:10.1016/j.molstruc.2012.04.046.