染料敏化太阳能电池新型联吡啶钌染料的合成与应用
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摘要
染料敏化太阳能电池(DSSC)因其无污染、低成本、高光电转化效率以及稳定性好等特点成为最有发展前景的太阳能电池之一。染料敏化剂作为它的重要组成部分对其光电转化效率有着重要的影响,因此新型染料敏化剂的研究是该领域的前沿课题。
本文以联吡啶为原料,经过氧化、硝化、还原以及酰化合成了4,4’-二苯甲酰氨基-2,2’-联吡啶(配体A)和4,4’-二乙酰氨基-2,2’-联吡啶(配体B),收率分别为59.5%和80.4%。用红外吸收光谱、氢核磁共振谱以及质谱等进行了化合物的结构表征。得到了各步产物的优化合成条件。
以硫氰酸铵,4,4’-二羧基-2,2’-联吡啶,4,4’-二苯甲酰氨基-2,2’-联吡啶和4,4’-二乙酰氨基-2,2’-联吡啶为配体,采用一锅法与RuCl3反应制备了染料敏化太阳能电池的敏化染料—顺-二硫氰根-(4,4’-二苯甲酰氨基-2,2’-联吡啶)(4,4’-二羧基-2,2’-联吡啶)钌(Ⅱ)(Dye-A)和顺-二硫氰根-(4,4’-二乙酰氨基-2,2’-联吡啶)(4,4’-二羧基-2,2’-联吡啶)钌(Ⅱ)(Dye-B)。Dye-A和Dye-B在甲醇中最大吸收波长分别是531nm和518nm,其摩尔消光系数分别为0.99×104M-1cm-1和0.75×104M-1cm-1。Dye-A和Dye-B的LUMO能级分别为-3.758eV和-3.717eV,均高于TiO2的导带能级。组装成电池的性能分别是Dye-A:开路电压Voc=0.663V,短路电流密度Isc=6.48 mA·cm~(-2),填充因子FF=0.670,能量转换效率η=2.88%;Dye-B:开路电压Voc=0.665V,短路电流密度Isc=5.76mA·cm~(-2),填充因子FF=0.687,能量转换效率η=2.63%。
Because of its clean, low-cost, high photoelectric conversion efficiency and good stability, dye-sensitized solar cell (DSSC) is one of the most promising solar cells. Dye sensitizer, as an important component of DSSC, impacts on its photoelectric conversion efficiency, so the study on new dye sensitizer is a focus in this field.
In this paper, 4,4’-dibenzoylamino-2,2’-bipyridine(ligand A) and 4,4’-diacetyl- amino-2,2’-bipyridine (ligand B) were synthesized using bipyridine as raw material , through oxidation, nitration, reduction, and N-acylation reaction, whose yields were 59.5% and 80.4% , respectively. The synthesized compounds were characterized by IR, 1H NMR and MS. At the same time, synthesis conditions for the each step reaction have been optimized.
Using―one-pot‖synthetic procedure, dye sensitizers-cis-dithiocyanato- (4,4’-di- benzoylamino-2,2’-bipyridine)-(4,4’-dicarboxy-2,2’-bipyridine) ruthenium(Ⅱ) (Dye- A) and cis-dithiocyanato-(4,4’-diacetyl-2,2’-bipyridine)-(4,4’-dicarboxy-2,2’-bipyri- dine) ruthenium (Ⅱ) (Dye-B) were prepared by a complex reaction of 4,4’-dicarboxy- 2,2’-bipyridine, ligand A(or ligand B) and ammonium thiocyanate with RuCl3. The maximum absorption wavelength of Dye-A and Dye-B is 531nm and 518nm, and their molar extinction coefficient is 0.99×104M-1cm-1 and 0.75×104M-1cm-1 in methanol solution, respectively. The LUMO energy of Dye-A is -3.758eV, and Dye-B is -3.717Ev, both of which were higher than TiO2 conduction band energy level. The performances of the DSSC assembled with Dye-A are thatηis 2.88%, Voc is 0.663V, Isc is 6.48 mA·cm~(-2) and FF is 0.670. The performances of the DSSC assembled with Dye-B are thatηis 2.63%,Voc is 0.665V, Isc is 5.76 mA·cm~(-2) and FF=0.687.
本文以联吡啶为原料,经过氧化、硝化、还原以及酰化合成了4,4’-二苯甲酰氨基-2,2’-联吡啶(配体A)和4,4’-二乙酰氨基-2,2’-联吡啶(配体B),收率分别为59.5%和80.4%。用红外吸收光谱、氢核磁共振谱以及质谱等进行了化合物的结构表征。得到了各步产物的优化合成条件。
以硫氰酸铵,4,4’-二羧基-2,2’-联吡啶,4,4’-二苯甲酰氨基-2,2’-联吡啶和4,4’-二乙酰氨基-2,2’-联吡啶为配体,采用一锅法与RuCl3反应制备了染料敏化太阳能电池的敏化染料—顺-二硫氰根-(4,4’-二苯甲酰氨基-2,2’-联吡啶)(4,4’-二羧基-2,2’-联吡啶)钌(Ⅱ)(Dye-A)和顺-二硫氰根-(4,4’-二乙酰氨基-2,2’-联吡啶)(4,4’-二羧基-2,2’-联吡啶)钌(Ⅱ)(Dye-B)。Dye-A和Dye-B在甲醇中最大吸收波长分别是531nm和518nm,其摩尔消光系数分别为0.99×104M-1cm-1和0.75×104M-1cm-1。Dye-A和Dye-B的LUMO能级分别为-3.758eV和-3.717eV,均高于TiO2的导带能级。组装成电池的性能分别是Dye-A:开路电压Voc=0.663V,短路电流密度Isc=6.48 mA·cm~(-2),填充因子FF=0.670,能量转换效率η=2.88%;Dye-B:开路电压Voc=0.665V,短路电流密度Isc=5.76mA·cm~(-2),填充因子FF=0.687,能量转换效率η=2.63%。
Because of its clean, low-cost, high photoelectric conversion efficiency and good stability, dye-sensitized solar cell (DSSC) is one of the most promising solar cells. Dye sensitizer, as an important component of DSSC, impacts on its photoelectric conversion efficiency, so the study on new dye sensitizer is a focus in this field.
In this paper, 4,4’-dibenzoylamino-2,2’-bipyridine(ligand A) and 4,4’-diacetyl- amino-2,2’-bipyridine (ligand B) were synthesized using bipyridine as raw material , through oxidation, nitration, reduction, and N-acylation reaction, whose yields were 59.5% and 80.4% , respectively. The synthesized compounds were characterized by IR, 1H NMR and MS. At the same time, synthesis conditions for the each step reaction have been optimized.
Using―one-pot‖synthetic procedure, dye sensitizers-cis-dithiocyanato- (4,4’-di- benzoylamino-2,2’-bipyridine)-(4,4’-dicarboxy-2,2’-bipyridine) ruthenium(Ⅱ) (Dye- A) and cis-dithiocyanato-(4,4’-diacetyl-2,2’-bipyridine)-(4,4’-dicarboxy-2,2’-bipyri- dine) ruthenium (Ⅱ) (Dye-B) were prepared by a complex reaction of 4,4’-dicarboxy- 2,2’-bipyridine, ligand A(or ligand B) and ammonium thiocyanate with RuCl3. The maximum absorption wavelength of Dye-A and Dye-B is 531nm and 518nm, and their molar extinction coefficient is 0.99×104M-1cm-1 and 0.75×104M-1cm-1 in methanol solution, respectively. The LUMO energy of Dye-A is -3.758eV, and Dye-B is -3.717Ev, both of which were higher than TiO2 conduction band energy level. The performances of the DSSC assembled with Dye-A are thatηis 2.88%, Voc is 0.663V, Isc is 6.48 mA·cm~(-2) and FF is 0.670. The performances of the DSSC assembled with Dye-B are thatηis 2.63%,Voc is 0.665V, Isc is 5.76 mA·cm~(-2) and FF=0.687.
引文
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[5]高建华,钱伟君,吴伟等.染料敏化太阳能电池TiO2薄膜的制备方法,2008,8(44):431-442.
[6]孙振范,郭飞燕,陈淑贞.二氧化钛纳米薄膜材料及应用.中山大学出版社,2009,第1、3章.
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[13] Durr M, Schmid A, Obermaier M, et al. Low-temperature fabrication of dye-sensitized solar cells by transfer of composite porous layers [J]. Nature Materials, 2005, 4(8): 607-611.
[14] Srikanth K, Rahman M D M, Tanaka H, et al. Investigation of the effect of sol processing parameters on the photoelectrical properties of dye-sensitized TiO2 solar cells[J]. Solar Energy Materials Solar Cells, 2001, 65(1/4):171-177.
[15] Takenaka S, Machara Y, Imai H, et al. Layer-by-layer self-assembly replication technique: Application to photoelectrode of dye–sensitized solar cell[J]. Thin Solid Films, 2003, 438-439: 346-351.
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[23]秦国旭,袁希梅,李祥飞.染料敏化太阳能电池的染料敏化剂的研究进展.巢湖学院学报,2009,11(3):89-97.
[24] Palomares E, Clifford J N, Haque S A. , et al. Control of Charge Recombination Dynamics in Dye Sensitized Solar Cells by the Use of Conformally Deposited Metal Oxide Blocking Layers[J]. Journal of the American Chemical Society, 2003, 125: 475.
[25] Nazeeruddin M K, Angelis F D, Fantacci S, et al. Combined experimental and DFT- TDDFT computational study of photoelectrochemical cell ruthenium sensitizers[J]. Journal of the American Chemical Society,2005,127:16835-16847.
[26] K Sayama, S Tsukagoshi, et al. Photoelectrochemical properties of J aggregates of benzothiazole merocyanine dyes on a nanostructured TiO2 film[J]. Journal of Physical Chemistry B, 2002,106:1363.
[27] P Wang, S M Zakeeruddin, R Humphry-Baker, et al. Molecular-scale inferface engineering of TiO2 nanocrystals : Improving the efficiency and stability of dye-sensitized solar cells[J]. Advanced Materials,2003,15(24):2101-2104.
[28] P Wang, S M Zakeeruddin, J E Moser et al. Stable new sensitizer with improved light harvesting for nanocrystalline dye-sensitized solar cells[J]. Advanced Materials,2004,16(20):1806-1811.
[29] S M Zakeeruddin, M K Kalyanasundaram, P Pechy ea al. Molecular Engineering of Photosensitizers for Nanocrystalline Solar Cells: Synthesis and Characterization of Ru Dye Based on Phosphonated Terpyridies[J]. Inorganic Chemistry,1997,36(25):5937-5946.
[30] C R Rice, M D Ward, M K Zakeeruddin et al. Catechol as an efficient anchoring group for attachment of ruthenium-polypridine photosensitisers to solar cells based on nanocrystalline TiO2 films[J]. New Journal of Chemistry,2000,24(9):651-652.
[31] R Amadelli, R Argazzi, C A Bignozzi et al. Design of Antenna-Sensitizer Polynuclear Complexes Sensitization of Titanium Dioxide with [Ru(bpy)2(CN)2]2Ru(bpy(COO)2)22-[J]. Journal of the American Chemical Society,1990,112(20):7099-7103.
[32] K Hara, H Horiuchi, R Katoh et al. Effect of the ligand structure on the efficiency of electron injection from excited Ru-phenanthroline complexes to nanocrystalline TiO2 films[J]. Journal of Physical Chemistry B,2002,106(2):374-379.
[33] Gr(a|¨)tzel M. Mesoporous oxide junctions and nanostructured solar cells[J]. Current Opinion in Colloid & interface Science,1999,4:314.
[34] Y C Shen, L Wang, Z H Lu et al. Fabrication,characterization and photovoltaic study of a TiO2 microporous electrode[J]. Thin Solid Films,1995,572(1):144-146.
[35] K Hara, M Kurashige, Y Darroh et al. Design of new coumarin dyes having thiophene moieties for highly efficient organic-dye-sensitized solar cells. Chemical Communications,2003,27(5):783-785.
[36] S Ferrere, B A Gregg. New Perylenes for dye sensitization of TiO2. New Journal of Chemistry,2002,26(9):1155-1160.
[37] Horiaehi T, Miura H, Sumioka K, et a1. High Efficient of Dye-Sensitized. Solar Cells Based on Metal- Free Indoline Dyes[J]. Journal of the American Chemical Society, 2004, 126:12218- 12219.
[38] Ito S, Zakeemddin S M, Humphry- Baker R, et a1. High- efficiency organic-dye-sensitized solar cells controlled by canocrystalline- TiO2 electrode thickness[J]. Advanced . Material., 2006,18:1202- 1205.
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[2]王紫兰.染料敏化太阳能电池技术概述.Technologh Forum,2009,5:43-46.
[3]杨术明.染料敏化纳米晶太阳能电池.郑州.郑州大学出版社,2007,第1-2章.
[4]梁茂,陶占良,陈军.染料敏化太阳能电池中的敏化剂.化学通报,2005,12:889-896.
[5]高建华,钱伟君,吴伟等.染料敏化太阳能电池TiO2薄膜的制备方法,2008,8(44):431-442.
[6]孙振范,郭飞燕,陈淑贞.二氧化钛纳米薄膜材料及应用.中山大学出版社,2009,第1、3章.
[7] Kalyanasundaram K, Gratzel M. Artificial photosynthesis : efficient dye-sensitized photoelect rochemical cells for the direct conversion of sunlight to electricity [J ] . Curr Science , 1994, 66 :706 - 715.
[8] Fotsa Ngaffo F ,Caricato A P , Fernandez M , et al .Structural properties of single and multilayer ITO and TiO2 films deposited by reactive pulsed laser ablation deposition techniques [J ] . Applied Surface Science , 2007 ,253 : 6508 - 6511.
[9] Lindstrom Henrik , Holmberg Anna , Magnusson Eva , et al . A new method to make dye-sensitized nanocrystalline solar cells at room temperature [J]. Journal of photochemistry and photobiology A : Chemistry , 2001,145:107-112.
[10] Thlakkat M, Schmitz C, Schmidt H W. Full vaper-deposited thin-layer titanium dioxide solar cells[J]. Advanced Materials, 2002, 14(8): 577-581.
[11] Jiu J T, Wang F M, Sakamoto M, et al. Preparation of nanocrystalline TiO2 with mixed template and its application for dye -sensitized solar cells[J]. Journal of the Electrochemical Society, 2004, 151(10): A1653-A1658.
[12] Gomez M M, Lu J, Solis J L, et al. Dye-sensitized nanocrystalline Titanium-Oxide-Based solar cells prepared by sputtering: influence of the substrate temperature during deposition [J]. Journal of Physical Chemistry B, 2000, 104(36): 8712-8718.
[13] Durr M, Schmid A, Obermaier M, et al. Low-temperature fabrication of dye-sensitized solar cells by transfer of composite porous layers [J]. Nature Materials, 2005, 4(8): 607-611.
[14] Srikanth K, Rahman M D M, Tanaka H, et al. Investigation of the effect of sol processing parameters on the photoelectrical properties of dye-sensitized TiO2 solar cells[J]. Solar Energy Materials Solar Cells, 2001, 65(1/4):171-177.
[15] Takenaka S, Machara Y, Imai H, et al. Layer-by-layer self-assembly replication technique: Application to photoelectrode of dye–sensitized solar cell[J]. Thin Solid Films, 2003, 438-439: 346-351.
[16] Kay A , Gr?tzel M. Low cost photovoltaic modules based on dye sensitized nanocrystalline titanium dioxide and carbon power[J].Solar Energy Materials and Solar Cells,1996,44:99- 117.
[17] Barbe C J, Arendse F, Comte P,et al. Nanocrystalline titanium oxide electrodes for photovoltaic applications[J ].Journal of the American Ceramic Society , 1997,80:3157-3171.
[18] Wang Z S , Kawaycgu H , Kashima T , et al . Significant influence of TiO2 photoelectrode morphology on the energy conversion effiency of N719 dye-sensitized solar cells[J] . Coordination Chemistry Reviews,2004,248:1381-1389.
[19]张力,孙岳明.染料敏化太阳能电池的研究进展.化工时刊,2008,22(10):59-63.
[20]于哲勋,李冬梅,秦达等.染料敏化太阳能电池的研究与发展现状.2009,28(7-8):8-15.
[21] Xiao - Feng Pang, A F Jalbout. Conductivity properties of the proton transfer exposed in externally applied fields in hydrogen-bonded systems[J]. Physics Letters A, 2004,330: 245-253.
[22]胡滨,刘国军,张桂霞等.染料敏化太阳能电池中电解质的研究进展.化工新型材料,2009,37(9):14-17.
[23]秦国旭,袁希梅,李祥飞.染料敏化太阳能电池的染料敏化剂的研究进展.巢湖学院学报,2009,11(3):89-97.
[24] Palomares E, Clifford J N, Haque S A. , et al. Control of Charge Recombination Dynamics in Dye Sensitized Solar Cells by the Use of Conformally Deposited Metal Oxide Blocking Layers[J]. Journal of the American Chemical Society, 2003, 125: 475.
[25] Nazeeruddin M K, Angelis F D, Fantacci S, et al. Combined experimental and DFT- TDDFT computational study of photoelectrochemical cell ruthenium sensitizers[J]. Journal of the American Chemical Society,2005,127:16835-16847.
[26] K Sayama, S Tsukagoshi, et al. Photoelectrochemical properties of J aggregates of benzothiazole merocyanine dyes on a nanostructured TiO2 film[J]. Journal of Physical Chemistry B, 2002,106:1363.
[27] P Wang, S M Zakeeruddin, R Humphry-Baker, et al. Molecular-scale inferface engineering of TiO2 nanocrystals : Improving the efficiency and stability of dye-sensitized solar cells[J]. Advanced Materials,2003,15(24):2101-2104.
[28] P Wang, S M Zakeeruddin, J E Moser et al. Stable new sensitizer with improved light harvesting for nanocrystalline dye-sensitized solar cells[J]. Advanced Materials,2004,16(20):1806-1811.
[29] S M Zakeeruddin, M K Kalyanasundaram, P Pechy ea al. Molecular Engineering of Photosensitizers for Nanocrystalline Solar Cells: Synthesis and Characterization of Ru Dye Based on Phosphonated Terpyridies[J]. Inorganic Chemistry,1997,36(25):5937-5946.
[30] C R Rice, M D Ward, M K Zakeeruddin et al. Catechol as an efficient anchoring group for attachment of ruthenium-polypridine photosensitisers to solar cells based on nanocrystalline TiO2 films[J]. New Journal of Chemistry,2000,24(9):651-652.
[31] R Amadelli, R Argazzi, C A Bignozzi et al. Design of Antenna-Sensitizer Polynuclear Complexes Sensitization of Titanium Dioxide with [Ru(bpy)2(CN)2]2Ru(bpy(COO)2)22-[J]. Journal of the American Chemical Society,1990,112(20):7099-7103.
[32] K Hara, H Horiuchi, R Katoh et al. Effect of the ligand structure on the efficiency of electron injection from excited Ru-phenanthroline complexes to nanocrystalline TiO2 films[J]. Journal of Physical Chemistry B,2002,106(2):374-379.
[33] Gr(a|¨)tzel M. Mesoporous oxide junctions and nanostructured solar cells[J]. Current Opinion in Colloid & interface Science,1999,4:314.
[34] Y C Shen, L Wang, Z H Lu et al. Fabrication,characterization and photovoltaic study of a TiO2 microporous electrode[J]. Thin Solid Films,1995,572(1):144-146.
[35] K Hara, M Kurashige, Y Darroh et al. Design of new coumarin dyes having thiophene moieties for highly efficient organic-dye-sensitized solar cells. Chemical Communications,2003,27(5):783-785.
[36] S Ferrere, B A Gregg. New Perylenes for dye sensitization of TiO2. New Journal of Chemistry,2002,26(9):1155-1160.
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