The Synthesis of D-π-D Derivate Phthalocyanines for Dye-Sensitized Solar Cell, Investigation of Spectroscopic and Electrical Properties

Abstract

We report on photovoltaic cell devices based on metallo phthalocyanine structures, such as zinc and nickel phthalocyanines (ZnPc and NiPc), which are formed by 4-(Diphenylamino) benzaldehyde containing substituents D-π-D features were synthesized and used for dye-sensitized solar cells (DSSCs). These novel compounds were characterized by using FTIR, UV-vis, MS spectroscopic data and elemental analysis. Furthermore, the relationship between ZnPc and NiPc morphology and photovoltaic properties are discussed. Among ZnPc and NiPc, the ZnPc-DSSC exhibited significantly excellent photovoltaic activities under radiation of visible light. In this case, photovoltaic cell efficiencies are up to 1.139% for ZnPc, compared to an average of 0.427% for NiPc. Moreover, the ZnPc device prepared at room temperature exhibits relatively higher photovoltaic cell efficiency (PCE) because of the significant improvements in short-circuit photocurrent (J_sc) and open-circuit voltage (V_oc). However, a DSSC assembled with NiPc material due to metallic behavior of nickel in the structures electrochemical reactions run at the interface between NiPc and back contact, which causes electrochemical corrosion of metal. Thus NiPc-DSSC shows lower photovoltaic properties than ZnPc-DSSC.

Keywords

• Phthalocyanine; Triphenylamine; DSSC; Fluorescence

References

1. [1] B. O’Regan, M. Gratzel, “A low-cost, high-efficiency solar cell based on dyesensitised colloidal TiO2 films”, Nature, 353 (1991), 737-740.
2. [2] M. Gratzel, “Dye-sensitized solar cells”, Journal of Photochemistry and Photobiology C: Photochemistry Reviews, 4 (2003), 145-153.
3. [3] R.K. Kanaparthi, J. Kandhadi, L. Giribabu “Metal-free organic dyes for dye-sensitized solar cells” Tetrahedron, 68 (2012), 8383-8393
4. [4] G. Wu, F. Kong, J. Li, W. Chen, X. Fang, C. Zhang, Q. Chen, X. Zhang, S. Dai, “Influence of different acceptor groups in julolidine-based organic dye-sensitized solar cells”, Dyes and Pigments, 99 (2013), 653-660.
5. [5] A. Kay, M. Graetzel, “Photosensitisation of TiO2 solarcells with chlorophyll derivatives and related natural porphyrins” J.Phys. Chem., 97(23) (1993).6272-6277.
6. [6] H. Tributsch, "Dye sensitization solar cells: a critical assessment of the learning curve", Coordination Chemistry Reviews, 248(13) (2004), 1511-1530.
7. [7] L. Wang, M. Liang, Y. Zhang, F. Cheng, X. Wang, Z. Sun, S. Xue, “Influence of donor and bridge structure in D-A-π-A indoline dyes on the photovoltaic properties of dye-sensitized solar cells employing iodine/cobalt electrolyte”, Dyes and Pigments, 101 (2014), 270-279.
8. [8] Hwang S, Lee J.H., Park C., Lee H., Kim C., Park C., Lee M.H., Lee W., Park J., Kim K., Park N.G., Kim C., “A highly efficient organic sensitizer for dye-sensitized solar cells” Chem.Commun., 14(46) (2007) 4887-4889.

9. [9] P.C. Kao, S.Y. Chu, S.J. Liu, Z.X. You, C.A.Chuang, “Improved Performance of Organic Light-Emitting Diodes Using a Metal-Phthalocyanine Hole-Injection Layer”, Journal of the Electrochemical Society, 153(6) (2006) 122-126.
10. [10] M. Yanagisawa, F. Korodi, J. Bergquist, A. Holmberg, A. Hagfeldt, B. Akermark, L.C.Sun, “Synthesis of Phthalocyanines with two Carboxylic Acid Groups and Their Utilization in Solar Cells Based on Nanostructured TiO2”, Journal of Porphyrins and Phthalocyanines, 8(10) (2004) 1228-1235.
11. [11] S. Kim, D. Kim, H. Choi, M.S. Kang, K. Song, S. O. Kang and J. Ko, “Enhanced photovoltaic performance and long-term stability of quasi-solid-state dye-sensitized solar cells via molecular engineering”, Chem. Commun., (2008) 4951-4953.
12. [12] Z. Ji, K. Yu-He, L. Hai-Bin, G. Yun, W. Yong, S. Zhong-Min, “How to design proper p-spacer order of the D-π-A dyes for DSSCs, A density functional response”, Dyes and Pigments, 95(2012) 313-321.
13. [13] Y. Wu, W. Zhu “Organic sensitizers from D–π–A to D–A–π–A: effect of the internal electron-withdrawing units on molecular absorption, energy levels and photovoltaic performances” Chem Soc Rev, 42 (2013) 2039-2058.
14. [14] W. Ling, S. Ping, C. Zhencai, L. Xinping, H. Yuanshuai, L. Chunyan, C. Pan, Z. Bin, TT. Songting, “Effects of the acceptors in triphenylamine-based D-π-A-π-A dyes on photophysical, electrochemical, and photovoltaic properties”, Journal of Power Sources, 246 (2014) 831-839.
15. [15] J.L. Song, P. Amaladass, S.H. Wen, K.K. Pasunooti, A. Li, Y.L. Yu, et al. “Aryl/hetero-arylethyne bridged dyes: the effect of planar π-bridge on the performance of dye sensitized solar cells” New J Chem, 35 (2011) 127-136.
16. [16] S. Ping, L. Xinping, J. Shenghui, W. Ling, Y. Ling, Y. Dandan, Z. Bin, T. Songting, “Synthesis of new N, N-diphenylhydrazone dyes for solar cells: Effects of thiophene-derived π-conjugated bridge”, Dyes and Pigments, 92 (2012) 1042-1051.
17. [17] A. Erdogmus, Nyokong T., “Synthesis of zinc phthalocyanine derivatives with improved photophysicochemical properties in aqueous media”, Journal of Moleculer Structure, 977 (2010) 26-38.
18. [18] A. Erdogmus, Nyokong T., “New soluble methylendioxy-phenoxy-substituted zinc phthalocyanine derivatives: Synthesis, photophysical and photochemical studies” Polyhedron, 28(14) (2009) 2855-2862.
19. [19] L. Hu, S. Dai, J. Weng, S. Xiao, Y. Sui, Y. Huang, “Microstructure design of nanoporous TiO2 photoelectrodes for dye-sensitized solar cell modules” J. Phys. Chem. B 111 (2006) 358-362.
20. [20] G.P. Smestad, “Education and solar conversion: demonstrating electron transfer” Solar Energy Materials and Solar Cells 55 (1998) 157-168.
21. [21] J.B. Yuan, M.L. Louis, M. Gong, Tetrahedron Letters 45 (2004) 6361
22. [22] Z. Ying et al., “Controlled growth of ZnPc thin films for photovoltaic appplications” Physics Procedia 14 (2011) 221-252.
23. [23] J. G. van Dijken, M. D. Fleischauer, and M. J. Brett, “Solvent effects on ZnPc thin films and their role in fabrication of nanostructured organic solar cells,” Organic Electronics, 12(12) (2011) 2111-2119.
24. [24] R. Zhou, F. Josse, W. Göpel, Z.Z Öztürk and Ö. Bekaroğlu, “Phthalocyanines as sensitive materials for chemical sensors” Appl. Organometallic Chem. 10(8) (1996) 557-577.
25. [25] M. Liang, W. Xu, F. Cai, P. Chen, B. Peng, J. Chen, Z. Li, “New Triphenylamine-Based Organic Dyes for Efficient Dye-Sensitized Solar Cells”, J., Phys. Chem. C.111(2007) 4465-4472.
26. [26] A. Erdogmus, M. Sharon, L. Christian, T. Nyokong, "Photophysical properties of newly synthesized fluorinated zinc phthalocyanines in the presence of CdTe quantum dots and the accompanying energy transfer processes", Journal of Photochemistry and Photobiology A: Chemistry, 210 (2010) 200-208.
27. [27] A. Erdogmus, T. Nyokong, “Synthesis, photophysical and photochemical properties of novel soluble tetra[4-(thiophen-3yl)-phenoxy]phthalocyaninato zinc(II) and Ti(IV)O complexes” Inorganica Chimica Acta, 362 (2009) 4875-4883.