太阳能电池偶氮型敏化染料的合成
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摘要
本文首先在微波辐射条件下,利用邻氨基苯酚和对氨基苯甲酸在多聚磷酸催化下进行缩合反应,合成了2-(4-氨基苯基)苯并噁唑,考察了辐射时间、辐射功率和催化剂等因素对反应收率的影响,得到了较佳的反应条件:多聚磷酸(PPA)为催化剂,辐射功率260W,辐射时间为4min,产物收率为61%。
此中间体与亚硝酸钠在盐酸水溶液进行重氮化,所得的重氮盐与3-羟基-2-萘甲酸、对羟基苯甲酸和对氨基苯甲酸进行偶合反应合成了一系列单偶氮染料。研究了原料配比、反应时间和反应温度等反应条件对重氮化反应和偶合反应的影响,确定了较佳的反应条件。对粗产品进行了提纯处理,最终产物通过MS、红外吸收光谱和紫外光谱进行了表征,确定了结构。并对它们的电化学性能进行了测试。
通过对氨基苯甲酸进行重氮化,然后与3-羟基-2-萘甲酸、对羟基苯甲酸、咪唑和苯酚进行偶合反应,合成了另一系列单偶氮染料,考察了反应时间和反应温度等因素对反应及收率的影响。最终产物通过1HNMR、红外吸收光谱和紫外光谱进行了表征。
通过循环伏安法测得了偶氮染料的氧化还原电位,从热动力学上说明了其作为敏化染料的可能性。
尝试了对所合成的单偶氮化合物进行与金属化合物CuCl2、醋酸铜和RuCl3的络合反应。通过红外光谱、紫外可见吸收光谱初步证明了络合反应。
Under microwave irradiation, the compound 2-(4-aminophenyl) benzoxazole was synthesized by condensation of o-aminophenol and p-aminophenol acid catalyzed by polyphosphoric acid. The influences of reaction time, microwave power output and catalyst were studied. The optimum reaction condition was as follows: PPA as catalyst, microwave power 260W and microwave irradiation time 4 min. The yield was 61%.
The 2-(4-aminophenyl) benzoxazole compound was first diazotized with sodium nitrite in hydrochloric acid to generate aniline diazonium salt and then reacted with compounds such as 3-hydroxy-2-naphthoic acid, p-hydroxybenzoic acid and p-amino- benzoic acid. The influences of molar ratio of raw materials, reaction time and reaction temperature were studied and the optimum reaction condition was getted separately. The crude products were purified and the final compounds were characterized with MS, IR spectroscope and UV-visible absorption spectra. The electrochemical performances of these azo compounds were tested.
Another kind of azo dye was synthesized firstly by the diazotizing of p-amino- phenol acid and secondly by the coupling of diazonium salt with 3-hydroxy-2-naph- thoic acid, p-hydroxy benzoic acid, imidazole and phenol separately. The influences of reaction time and reaction temperature to the reaction and yield were studied. The final compounds were characterized with 1HNMR, MS, IR spectroscope and UV-visible absorption spectra.
At last the complexation of azo dyes with CuCl2、Cu(Ac)2 and RuCl3 was attempted. The final complexes were proved not the result we expected by the characterization of IR and UV-visible absorption spectra.
此中间体与亚硝酸钠在盐酸水溶液进行重氮化,所得的重氮盐与3-羟基-2-萘甲酸、对羟基苯甲酸和对氨基苯甲酸进行偶合反应合成了一系列单偶氮染料。研究了原料配比、反应时间和反应温度等反应条件对重氮化反应和偶合反应的影响,确定了较佳的反应条件。对粗产品进行了提纯处理,最终产物通过MS、红外吸收光谱和紫外光谱进行了表征,确定了结构。并对它们的电化学性能进行了测试。
通过对氨基苯甲酸进行重氮化,然后与3-羟基-2-萘甲酸、对羟基苯甲酸、咪唑和苯酚进行偶合反应,合成了另一系列单偶氮染料,考察了反应时间和反应温度等因素对反应及收率的影响。最终产物通过1HNMR、红外吸收光谱和紫外光谱进行了表征。
通过循环伏安法测得了偶氮染料的氧化还原电位,从热动力学上说明了其作为敏化染料的可能性。
尝试了对所合成的单偶氮化合物进行与金属化合物CuCl2、醋酸铜和RuCl3的络合反应。通过红外光谱、紫外可见吸收光谱初步证明了络合反应。
Under microwave irradiation, the compound 2-(4-aminophenyl) benzoxazole was synthesized by condensation of o-aminophenol and p-aminophenol acid catalyzed by polyphosphoric acid. The influences of reaction time, microwave power output and catalyst were studied. The optimum reaction condition was as follows: PPA as catalyst, microwave power 260W and microwave irradiation time 4 min. The yield was 61%.
The 2-(4-aminophenyl) benzoxazole compound was first diazotized with sodium nitrite in hydrochloric acid to generate aniline diazonium salt and then reacted with compounds such as 3-hydroxy-2-naphthoic acid, p-hydroxybenzoic acid and p-amino- benzoic acid. The influences of molar ratio of raw materials, reaction time and reaction temperature were studied and the optimum reaction condition was getted separately. The crude products were purified and the final compounds were characterized with MS, IR spectroscope and UV-visible absorption spectra. The electrochemical performances of these azo compounds were tested.
Another kind of azo dye was synthesized firstly by the diazotizing of p-amino- phenol acid and secondly by the coupling of diazonium salt with 3-hydroxy-2-naph- thoic acid, p-hydroxy benzoic acid, imidazole and phenol separately. The influences of reaction time and reaction temperature to the reaction and yield were studied. The final compounds were characterized with 1HNMR, MS, IR spectroscope and UV-visible absorption spectra.
At last the complexation of azo dyes with CuCl2、Cu(Ac)2 and RuCl3 was attempted. The final complexes were proved not the result we expected by the characterization of IR and UV-visible absorption spectra.
引文
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[2] J. He, G. Benko, F. Korodi, T. Polivka, R. Lomoth. Modified phthalocyanines for efficient near-IR sensitization of nanostructured TiO2 electrode, J. Am. Chem. Soc.124 (2002)4922
[3] Anita solbrand, Henrik Lindstron, et al. Electron Transport in the Nanostructured TiO2-Electrolyte System Studied with Time-Resolved Photocurrents, J. Phys Chem B.1997,101:2514～2518.
[4] A.F. Nogueira, C. Longo, M.-A. De Paoli; Polymers in dye sensitized solar cells: overview and perspectives, J. Coordination Chemistry Reviews 248 (2004) 1455～1468.
[5] G. Kron, T. Egerter, J.H. Werner, U. Rau, Electronic Transport in Dye-Sensitized Nanoporous TiO2 Solar Cells-Comparison of Electrolyte and Solid-State Devices, J. Phys. Chem. B 107(2003) 3556-3564.
[6]陈学刚,程延祥,耿延侯等,双核三联吡啶钌(Ⅱ)配合物的合成及其光谱和电化学性质,应用化学,2006,23:465～470
[7] J Delilvestro, M Gr?tzel, L Kavan et al, Highly efficient sensitization of titanium dioxide, J . Am. Chem. Soc., 1985 , 107 :2988～2990
[8]郭淑英,潘利华,曲晓春等,固相时间分辨荧光免疫分析螯合剂(Ⅰ)中间体-4,4’-二溴-6,6’-二甲基2,2’-联吡啶的合成,中国卫生检验杂志,2006,16:264～266。
[9] S. M. Zakeeruddin, M. K. Nazeeruddin, P. Pechy et al . Molecular Engineering of Photosensitizers for Nanocrystalline Solar Cells: Synthesis and Characterization of Ru Dyes Based on Phosphonated Terpyridines, Inorg. Chem., 36 (25), 5937～5946.
[10] M K Nazeeruddin , A Ray , I.Rodicio et al. Conversion of light to electricity by cis-X2bis(2,2'-bipyridyl-4,4'-dicarboxylate)ruthenium(II) charge-transfer sensiti- zeers (X = Cl-, Br-, I-, CN-, and SCN-) on nanocrystalline titanium dioxide electrodes. J . Am. Chem. Soc. , 1993 ,115 (14) : 6382～6390
[11] M Gr?tzel. Yanagida, Improved dyesensitized solar cells using ionic nanocomposite gel electrolytes, J. Photochem. Photobiol. A: Chem., 2004 , 164(1～3) : 3～14
[12] C Klein, M K Nazeeruddin, P Liska et al, Engineering of a Novel RutheniumSensitizer and Its Application in Dye-Sensitized Solar Cells for Conversion of Sunlight into Electricity, Inorg. Chem. , 2005 , 44(2) : 178～180
[13] M K Nazeeruddin, P Péchy, T Renouard et al, Engineering of efficient panchromatic sensitizers for nanocrystalline TiO2-based solar cells, J. Am. Chem. Soc. , 2001 , 123 (8) : 1613～1624
[14] P Wang, S M Zakeeruddin, R Humphry -Baker et al, Molecular-Scale Interface Engineering of TiO2 Nanocrystals: Improving the Efficiency and Stability of Dye-Sensitized Solar Cells, Adv. Mater., 2003 , 15 (24) : 2101～2104
[15] P Wang, S M Zakeeruddin, J E Moser et al, A Solvent-Free, SeCN-/(SeCN)3- Based Ionic Liquid Electrolyte for High-Efficiency Dye-Sensitized Nanocrystalline Solar Cells, Adv. Mater., 2004 , 16(20) : 1806～1811
[16] P Wang, C Klein, R Humphry -Baker et al, Stable 8% efficient nanocrystalline dye-sensitized solar cell based on an electrolyte of low volatility, J. Am. Chem. Soc., 2005, 127(3): 808～809
[17] 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(CN)2)22-. J. Am. Chem. Soc., 1990, 112(20) : 7099～7103
[18]于凌宇,冯玉萍,国际纳米太阳能电源研制技术新动向,今日电子,2002,(9):21-23
[19] O Kohle, S Ruile, M Gratzel, Ruthenium(II) Charge-Transfer Sensitizers Containing 4,4'-Dicarboxy-2,2'-bipyridine. Synthesis, Properties, and Bonding Mode of Coordinated Thio- and Selenocyanates, Inorg. Chem. , 1996 , 35 (16) : 4779～4787
[20] C A Bignozzi, R Argazzi, C J Kleverlaan, Molecular and supramolecular sensitization of nanocrystalline wide band-gap semiconductors with mononuclear and polynuclear metal complexes, Chem. Soc. Rev. , 2000 , 29 (2) : 87～96
[21] S M Zakeeruddin, M K Kalyanasundaram, P Pechy et al, Molecular Engineering of Photosensitizers for Nanocrystalline Solar Cells: Synthesis and Characterization of Ru Dyes Based on Phosphonated Terpyridines, Inorg. Chem. , 1997 , 36 (25) : 5937～5946
[22] C R Rice, M D Ward, M K Nazeeruddin et al, Catechol as an efficient anchoring group for attachment of ruthenium–polypyridine photosensitisers, New J . Chem. , 2000 , 24 (9) : 651～652
[23] Lammi, R. K., Wagner, R. W. et al, Mechanisms of excited-state energy-transfer gating in linear versus branched multiporphyrin arrays, J. Phys. Chem. B 2001, 105, 5341
[24]纪云,蔡显荣,霍二福等,卟啉衍生物敏化纳米TiO2多孔膜电极的光电性质研究,化学研究与应用,2006,18: 685～687
[25] S.Cherian,C.C. Wamser, Adsorption and Photoactivity of Tetra (4-carboxyphenyl) porphyrin (TCPP) on Nanoparticulate TiO2, J. Phys. Chem. B 104 (2000) 3624
[26] Y.Tachibana, S.A.Haque, I.P. Mercer et al. Electron Injection and Recombination in Dye Sensitized Nanocrystalline Titanium Dioxide Films: A Comparison of Ruthenium Bipyridyl and Porphyrin Sensitizer Dyes, J.Phys. Chem. B 104 (2000) 1198～1205
[27] F. Odobel, E. Blart, M. Lagree et al. Porphyrin dyes for TiO2 sensitization, J. Mater. Chem. 13 (2003)502～510
[28] R.B.M. Koehorst, G.K. Boschloo, T.J. Savenije et al. Spectral Sensitization of TiO2 Substrates by Monolayers of Porphyrin Heterodimers, J. Phys. Chem. B 104 (2000) 2371
[29] K. Kalyanasundaram, J.A. Shelnutt, M. Gr?tzel. Sensitization and photoredox reactions of zinc (II) and antimony (V) uroporphyrins in aqueous media, Inorg. Chem. 27(1988) 2820
[30] A. Kay, M. Gr?tzel, Photosensitization of titania solar cells with chlorophyll derivatives and related natural porphyrins, J. Phys. Chem. 97 (1993) 6272
[31] A. Kay, R. Humphry-Baker, M. Gr?tzel, Investigations on the Mechanism of Photosensitization of Nanocrystalline Ti02 Solar Cells by Chlorophyll Derivatives, J. Phys. Chem. 98 (1994)952～959
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