Acid azo dyes for efficient molecular photovoltaic: study of dye-sensitized solar cells performance


Journal: Vol.9, No.1, Winter 2016 - Article 7   Pages :  61 Until 70



Article Code:
PCCC-2016-07-20-330

Authors:
M. Hosseinnezhad: Institute of Color Science and Technology - Department for Organic Colorants
S. Moradian: Amirkabir University of Technology - Faculty of Polymer and Color Engineering
K. Gharanjig: Institute for Color Science and Technology - Department of Organic Colorants


Article's abstract:

In this paper we sensitized three free-metal azo days Dye 1, Dye 2 and Dye 3 based on 1,8-naphthalimide with n-propyl as the electron donor group. We used sulfonic acid and hydroxyl substituents as the electron acceptor anchoring group in synthesized dyes. The proposed dyes were sensitized from acenaphthene as the starting material by standard reactions and characterized by different techniques such as melting point, FTIR, 1HNMR, elemental analysis and UV-Visible spectroscopy after purification. Spectrophotometric measurements of the azo dyes in solution and on a TiO2 substrate were carried out in order to assess changes in the status of the dyes. The wavelength of maximum absorption for Dye 1, Dye 2 and Dye 3 in solution are 530 nm, 568 nm and 550 nm and on TiO2 films are 552 nm, 591 nm and 575 nm, respectively. Finally, the proposed dyes used as sensitizer in a dye solar cell structure and their photovoltaic properties investigated. The Conversion efficiency for Dye 1, Dye 2 and Dye 3 are 2.11 and 2.32 and 2.17, respectively.


Keywords:
Dye-sensitized solar cells; Azo dyes; Photovoltaic materials; Power conversion efficiencies; 1,8-naphthalimide.

References:
1. B. O'Regan, M. Grätzel, A low cost, high efficiency solar cell based on dye-sensitized colloidal TiO2 films, Nature, 353 (1991), 737-40. 2. N. Yin, L. Wang, Y. Ma, Y. Lin, J. Wu, Q. Luo, H. Yang, C. Ma, X. Zhao, 4,8-Bis(thienyl_-benzo[1,2-b:4,5-b']dithiophene based A-π-D-π-A typed conjugated small molecules with mono-thiophene as the π-bridge: synthesis, properties and photovoltaic performance, Dyes Pigment, 120 (2015), 299-306. 3. Z. Wang, Y. Cui, K. Hara, Y. Danoh, C. Kasada, A. Shinpo, A High Light Harvesting Efficiency Coumarin Dye for Stable Dye-Sensitized Solar Cells, Adv. Mater., 19 (2007), 1138-41. 4. X. Qian, X. Wang, L. Shao, H. Li, R. Yan, L. Hou, Molecular engineering of D-D-π-A type organic dyes incorporating indoloquinoline and phenothiazine for highly efficient dye-sensitized solar cells, J. Power Source, 326 (2016) 129-136. 5. E. V. Verbitskiy, E. M. Cheprakova, J. O. Subbotina, A. V. Schepochkin, P. A. Slepukhin, G. L. Rusinov, v. N. Chaarushin, O. N. Chupakhin, N. I. Makarava, A. V. Metalitsa, V. I. Minkin, Synthesis, spectral and electrochemical properties of pyrimidine-containing dyes as photosensitizers for dye-sensitized solar Cells, Dyes Pigment, 100 (2014), 201-214. 6. Z. Wang, N. Koumura, Y. Cui, M. Takahashi, H. Sekiguchi, A. Mori, T. Kubo, A. Furube, K. Hara, Hexylthiophene Functionalized Carbazole Dyes for Efficient Molecular Photovoltaics: Tuning of Solar-Cell Performance by Structural Modification, Chem Mater, 20 (2008), 3993-4003. 7. S. Ito, H. Miura, S. Uchida, M. Takata, K. Sumioka, P. Liska, P. Comte, P. Péchy, M. Grätzel, High-conversion-efficiency organic dye-sensitized solar cells with a novel indoline dye, Chem Commun, 2008, 5194-6. 8. A. Khazaji, S. Hotchandani, S. Das, P. Kamat, Controlling Dye (Merocyanine-540) Aggregation on Nanostructured TiO2 Films: an Organized Assembly Approach for Enhancing the Efficiency of Photosensitization, J Phys Chem B, 103 (1999), 4693-4700. 9. T. Kanti Pradhan, A. De, J. Mortier, Application of directed metalation in synthesis. Part 8: Interesting example of chemoselectivity in the synthesis of thioaurones and hydroxy ketones and a novel anionic ortho-Fries rearrangement used as a tool in the synthesis of thienopyranones and thiafluorenones, Tetrahedron, 6 (2005), 9007–17. 10. M. Matsui, T. Fujita, Y. Kubota, K. Funabiki, J. Jin, T. Yoshida, H. Miura, The use of indoline dyes in a zinc oxide dye-sensitized solar cell, Dyes Pigmen, 80 (2009), 233-8. 11. S. Zhu, Z. An, X. Sun, Z. Wu, X. Chen, P. Chen, Synthesis and evaluation of simple molecules as a co-adsorbent dye for highly efficient co-sensitized solar cells, Dyes Pigment, 120 (2015) 85-92. 12. A. Mahmood, M. Hussain Tahir, A. Irfan, A.G. Al-Sehemi, M.S. Al-Assiri, Heterocyclic azo dyes for dye sensitized solar cells: A quantum chemical study, Comput. Theor. Chem., 1066 (2015) 94-99. 13. M. L. G. Vieria, V. M. Esquerdo, L. R. Nobre, G. L. Dotto, L. A. A. Pinto, Glass beads coated with chitosan for the food azo dyes adsorption in a fixed bed column, J. Ind. Eng. Chem., 20 (2014) 3387-3393. 14. S. Rouhani, S. Haghgoo, A novel fluorescence nanosensor based on 1,8-naphthalimide thiophene doped silica nanoparticles, and its application to the determination of methamphetamine, Sens. Actu. B. Chem., 209 (2014) 957-965. 15. S. Rouhani, A Novel Electrochemical Sensor for Sunset Yellow based on a Platinum Wire Coated Electrode, Anal. Lett., 42 (2009) 141-153. 16. A. Khosravi, S. Moradian, K. Gharanjig, F. Afshar Taromi, Synthesis and spectroscopic studies of some naphthalimide based disperse azo dyestuffs for the dyeing of polyester fibers, Dyes Pigment, 69 (2006) 79-92. 17. M. Hosseinnezhad, S. Moradian, K. Gharanjig, Investigation of effect of anti-aggregation agent on the performance of nanostructure dye-sensitized solar cells, Opto-Electron. Rev., 23 (2015) 126-130. 18. M. Nazeeruddin, A. Kay, I. Rodicio, R. Humpbry-Baker, E. Miiller, P. Liska, N. Vlachopoulos, M. Grätzel, Conversion of light to electricity by cis-X2bis(2,2'-bipyridyl-4,4'-dicarboxylate) ruthenium(II) charge-transfer sensitizers (X = Cl-, Br-, I-, CN-, and SCN-) on nanocrystalline titanium dioxide electrodes, J Am Chem Soc, 115 (1993), 6382-90. 19. P. Sommeling, B. Oregan, R. Haswell, H. Smit, N. Bakker, T. Smits, J. Kroon, J. Roosmalen, Influence of a TiCl4 Post-Treatment on Nanocrystalline TiO2 Films in Dye-Sensitized Solar Cells, J Phys Chem B, 110 (2006), 19191-7. 20. M. Hosseinnezhad, S. Moradian, K. Gharanjig, Synthesis and application of two organic dyes for dye-sensitized solar cells, Prog. Color. Colorants, 6 (2013) 109-117. 21. M. Hoseinnezhad, A. Khosravi, K. Gharanjig, S. Moradian, Synthesis of some monoazo acid dyes based on naphthalimides, Asian J. Chem., 21 (2009) 4812-4820. 22. D. Xu, Z. Li, Y. Peng, J. Geng, H. Qian, W. Hung, Post modification of 2-formylthiophene based heterocyclic azo dyes, Dyes Pigment, 133 (2016) 143-152. 23. H. Yousefpour Navid, K. Gharanjig, M. Arami, Synthesis, characterization and textile application of novel disperse dyes, Prog. Color. Colorants, 7 (2014) 155-163 24. 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), 4465-72. 25. J. Sworakowski, J. Linpinski, K. Janus, On the reliability of determination of energies oh HOMO and LUMO levels in organic semiconductors from electrochemical measurements: A simple picture based on the electrostatic model, Org. Electron., 33 (2016) 300-310. 26. S. Kim, J. Lee, S. Kang, J. Ko, J. Yung, S. Fantacci, F. DeAngelis, M. DiCenco, K. Nazeeruddin, M. Gratzel, Molecular Engineering of Organic Sensitizers for Solar Cell Applications, J. Am. Chem. Soc., 128 (2006), 16701-16707. 27. L. Schmidt Mende, U. Bach, R. Baker, T. Horiuchi, H. Miura, S. Ito, S. Uchida, M. Gratzel, Organic Dyes for Highly Efficient Solid-State Dye-Sensitized Solar Cells, Adv. Mater., 17 (2005), 813-815. 28. D. Hagberg, J. Yum, H. Lee, F. Angelis, T. Marinado, K. Karlsson, R. Humphry Baker, L. Sun, A. Hagfedt, M. Gratzel, M. Nazeeruddin, Molecular Engineering of Organic Sensitizers for Dye-Sensitized Solar Cell Applications, J. Am. Chem. Soc., 130 (2008), 6259-66. 29. S. Park, Y. Won, Y. Choi, J. Kim, Molecular Design of Organic Dyes with Double Electron Acceptor for Dye-Sensitized Solar Cell, Energy Fuel, 23 (2009), 3732-3736. 30. M. Rani, S. K. Tripathi, Electron transfer properties of organic dye-sensitized ZnO and ZnO/TiO2 photoanode for dye-sensitized solar cells, Renew. Sust. Energy Rev., 61 (2016), 97-107. 31. M. Matsui, T. Fujita, Y. Kubota, K. Funabiki, J. Jin, T. Yoshida, H. Miura, Substituent effects in a double rhodanine indoline dye on performance of zinc oxide dye-sensitized solar cell, Dyes Pigmen, 86 (2010), 143-8. 32. M. Tabatabaee, H. Bagheri, M. Shahvazian, Application of Thionine dye for highly sensitive and selective catalytic kinetic determination of Osmium, Prog. Color. Colorants. Coat, 3 (2010), 33-40. 33. A. Khosravi, K. Gharanjig, S. Moradian, M. Hosseinnezhad, A Kinetic study on the dissolution of tqwo naphthalimide based synthesized disperse dyestuffs in the presence of dispersing agent, Prog. Color. Colorants, Coat., 4 (2011), 107-112. 34. K. Hara, T. Sato, R. Katoh, A. Furube, Y. Ohga, A. Shinpo, Molecular Design of Coumarin Dyes for Efficient Dye-Sensitized Solar Cells, J Phys Chem B, 107 (2003), 597-606. 35. F. Dolatzadeh, S. Moradian, M. M. Jalili, Effect of nano silica on moisture absorption of polyurethane clear coat as studied by EIS and Gravimetric methods, Prog. Color. Colorants. Coat. 3 (2010), 92-100.


Article's file
Page view: 1579
Article's download quantity : 35


Article System Login
Introduction

Manager-in-Chief:
Prof. Zahra Ranjbar
Editor-in-Chief:
Dr. Farahnaz Nourmohammadian
Assistant Editor:
Dr. Mozhgan Hosseinnezhad
ISSN:
2008-2134
ISSN (online):
2383-1790
Publisher:
Institute for Color Science and Technology (ICST)

Quick Access
Publications
E-Vote
What is your opinion about the manuscript subscription system of PCCC website?
Excellent
Good
Fair
Poor
Website Statistics
Page view:1,580
Online Visitors:14