CN103834190B - Benzothiadiazole-cyanocinnamic acid receptor-containing organic dye and its use in dye-sensitized solar cell - Google Patents
Benzothiadiazole-cyanocinnamic acid receptor-containing organic dye and its use in dye-sensitized solar cell Download PDFInfo
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Abstract
The invention provides benzothiadiazole-cyanocinnamic acid receptor-containing organic dye and its use in a dye-sensitized solar cell and belongs to the field of organic dye. The benzothiadiazole-cyanocinnamic acid receptor-containing organic dye utilizes triarylamine as an electron donor and utilizes benzothiadiazole-cyanocinnamic acid as a dye molecule receptor so that a molecular energy gap is reduced obviously, electron recombination in the cell is reduced and cell open-circuit voltage is effectively improved. The benzothiadiazole-cyanocinnamic acid receptor-containing organic dye has a simple synthesis route and can be purified easily. A dye-sensitized solar cell prepared from the benzothiadiazole-cyanocinnamic acid receptor-containing organic dye has open-circuit voltage of 839mV, a short-circuit photoelectric current of 17.95mA/m<2> and power conversion efficiency of 11%.
Description
Technical field
The invention belongs to organic dye technical field, be specifically related to a kind of containing the diazosulfide-organic dye of cyano group cinnamic acid acceptor and the application in dye-sensitized solar cells.
Background technology
Dye-sensitized solar cells (DSCs) is the novel solar cell of one imitating photosynthesis of plant principle and develop; its main advantage is abundant raw materials, with low cost, Technology is simple; in big area suitability for industrialized production, there is larger advantage; little to the pollution of environment; portion of material can fully reclaim, and has great importance to protection human environment.Since Lausanne, SUI senior engineer (EPFL) in 1991
the research group (Nature 1991,353,737) since this technically makes a breakthrough of professor leader, Europe, the United States, Deng developed country in succession drop into substantial contribution and research and develop this field.The dyestuff mainly bipyridyl ruthenium complex dye N749 and zinc protoporphyrin dyestuff YD2-o-C8 used in the high efficiency dye sensitization solar cell of the photoelectric transformation efficiency reported at present more than 12%, but ruthenium dye all limits further developing of this kind of metal complex dye to defects such as the dependency of precious metal and porphyrin dye stability.Metal-free organic dye has that raw material sources is abundant, cheap, molecular structure is easy to features such as cutting out, becomes the focus of dyestuff research and development gradually.Cut-off, to 2013, only has the efficiency of a few organic dye sensitized solar cell to reach 10%, and distance metal complex dye still also exists obvious distance, and existing organic dye spectral response range is narrower.
Summary of the invention
The object of the invention is to solve the narrower defect of existing organic dye spectral response range, and provide a kind of containing the diazosulfide-organic dye of cyano group cinnamic acid acceptor and the application in dye-sensitized solar cells.
The invention provides a kind of organic dye containing diazosulfide-cyano group cinnamic acid acceptor, structure is such as formula shown in (V):
In formula (V), R
1for
or
in any one; R
3, R
4, R
5respective is independently hydrogen atom, C
1~ C
12alkyl or C
1~ C
12any one in alkoxyl group;
R
2for
or
in any one; R
6, R
7, R
8and R
9respective is independently hydrogen atom, C
1~ C
12alkyl or C
1~ C
12any one in alkoxyl group.
Preferably, the described organic dye containing diazosulfide-cyano group cinnamic acid acceptor has the structure shown in formula I:
Preferably, the described organic dye containing diazosulfide-cyano group cinnamic acid acceptor has the structure shown in formula II:
The invention provides the application of organic dye in dye-sensitized solar cells containing diazosulfide-cyano group cinnamic acid acceptor described in a kind of technique scheme.
The present invention also provides a kind of organic dye sensitized solar cell, and dye coating is the organic dye containing diazosulfide-cyano group cinnamic acid acceptor described in technique scheme.
Beneficial effect of the present invention
The invention provides a kind of containing the diazosulfide-organic dye of cyano group cinnamic acid acceptor and the application in dye-sensitized solar cells.This organic dye has formula (V) structure, the present invention is using triaryl amine as electron donor(ED), select diazosulfide-cyano group cinnamic acid as the acceptor of dye molecule, two draw the introducing of electron acceptor(EA) to significantly reduce molecule lumo energy, reduce molecule energy gap, reduce the electron recombination in battery, effectively improve the open circuit voltage of battery.The synthetic route of the organic dye containing diazosulfide-cyano group cinnamic acid acceptor provided by the invention is easy, is easy to purifying; The dye-sensitized solar cells prepared by organic dye of the present invention, open circuit voltage reaches 839 millivolts, and short-circuit photocurrent reaches 17.95 milliamperes every square centimeter, and power-conversion efficiencies reaches 11%.
Embodiment
Below in conjunction with specific embodiment, further detailed description is done to technical solution of the present invention.
Reagent used in the embodiment of the present invention all obtains by being purchased mode.
Embodiment 1: containing the preparation of the organic dye (I) of diazosulfide-cyano group cinnamic acid acceptor
Synthetic route is as follows:
The synthesized reference document R.Li of raw material 1, J.Liu, N.Cai, M.Zhang, andP.Wang, J.Phys.Chem.B 2010,114,4461.
The synthesis of intermediate 2:
6 grams of raw materials 1 and 50 milliliters of tetrahydrofuran (THF)s are added in 100 milliliters of three mouthfuls of reaction flasks,-78 DEG C are cooled under argon shield, slow dropping 11 milliliters of n-Butyl Lithiums (1.6M), dropwise rear maintenance low-temp reaction 3 hours, disposablely add 3.5 grams of trimethyltin chlorides, reaction system is slowly risen to room temperature and stirs 12 hours, add 5 ml deionized water termination reactions, the mixing solutions extracted with diethyl ether obtained three times, merge organic phase, with anhydrous sodium sulfate drying, the crude product obtained after decompression is spin-dried for solvent can be directly used in reaction below, without the need to being further purified,
By 2.2 grams of above-mentioned crude products and 2.5 grams of N, N-4-hexyloxy benzene-N-4-Iodoaniline is placed in 50 milliliters of three mouthfuls of reaction flasks, add 30 milliliter 1, 4-dioxane, 0.6 milliliter of tri-butyl phosphine is added successively under argon shield, 60 milligram three (dibenzalacetone) two palladium and 1.44 grams of cesium fluorides, reaction system is heated to 60 DEG C and stirs 8 hours, room temperature is cooled to after reaction terminates, add 20 ml deionized water, the mixing solutions chloroform extraction obtained three times, merge organic phase, with anhydrous sodium sulfate drying, crude product toluene/the sherwood oil (1/5) obtained after decompression is spin-dried for solvent obtains intermediate 2 for yellow viscous liquid as eluent by silica gel column chromatography separation, productive rate is 76%.
The nucleus magnetic resonance characterization data of intermediate 2 is as follows:
Hydrogen is composed
1h NMR (600MHz, DMSO-d
6) δ: 7.46 (d, J=8.4Hz, 2H), 7.39 (d, J=4.8Hz, 1H), 7.34 (s, 1H), 7.08 (d, J=4.8Hz, 1H), 7.01 (d, J=8.4Hz, 4H), 6.90 (d, J=8.4Hz, 4H), 6.78 (d, J=8.4Hz, 2H), 3.93 (t, J=6.0Hz, 4H), 1.18 (m, 4H), 1.69 (m, 4H), 1.41 (m, 4H), 1.31 (m, 8H), 1.09 (m, 12H), 0.88 (m, 10H), 0.77 (t, J=7.2Hz, 6H);
Carbon is composed
13cNMR (150MHz, CDCl
3) δ: 158.96,157.36,155.48,147.88,144.44,140.60,136.85,134.61,127.51,126.44,125.79,124.23,121.56,120.92,116.36,115.28,68.28,60.37,53.62,37.87,31.61,29.73,29.34,25.76,24.50,22.61,14.03;
Mass spectrum (ESI): 790.5 ([M+H]
+);
Ultimate analysis: C, 77.21; H, 8.78; N, 1.89.
The synthesis of intermediate 3:
2.4 grams of intermediates 2 and 50 milliliters of tetrahydrofuran (THF)s are added in 100 milliliters of three mouthfuls of reaction flasks;-78 DEG C are cooled under argon shield; slow dropping 3.5 milliliters of tertiary butyl lithiums (1.3M); rise to stirring at room temperature after dropwising 2 hours, again reaction system is cooled to-78 DEG C, disposablely add 0; 91 grams of trimethyltin chlorides; rise to stirring at room temperature after dropwising 12 hours, add 20 ml deionized water termination reactions, the mixed solvent chloroform extraction obtained three times.Merge organic phase, with anhydrous sodium sulfate drying, the crude product obtained after decompression is spin-dried for solvent can be directly used in reaction below, without the need to being further purified;
By 1.16 grams of above-mentioned crude products and 0.39 gram of bromo-7-of 4-(4-phenyl aldehyde)-2, 1, 3-diazosulfide is placed in 50 milliliters of three mouthfuls of reaction flasks, add 30 milliliter 1, 4-dioxane, 0.2 milliliter of tri-butyl phosphine is added successively under argon shield, 17 milligram three (dibenzalacetone) two palladium and 0.4 gram of cesium fluoride, reaction system is heated to 60 DEG C and stirs 8 hours, room temperature is cooled to after reaction terminates, add 20 ml deionized water, the mixing solutions chloroform extraction obtained three times, merge organic phase, with anhydrous sodium sulfate drying, crude product toluene/the sherwood oil (1/1) obtained after decompression is spin-dried for solvent obtains intermediate 3 for orange thick liquid as eluent by silica gel column chromatography separation, productive rate is 70%.
The nucleus magnetic resonance characterization data of intermediate 3 is as follows:
Hydrogen is composed
1hNMR (400MHz, THF-d
8) δ: 10.05 (s, 1H), 8.27 (m, 3H), 8.01 (m, 3H), 7.92 (d, J=7.6Hz, 1H), 7.45 (d, J=8.4Hz, 2H), 7.27 (s, 1H), 7.02 (d, J=8.8Hz, 4H), 6.90 (d, J=8.8Hz, 2H), 6.84 (d, J=8.8Hz, 4H), 3.93 (m, 4H), 2.01 (m, 4H), 1.75 (m, 4H), 1.48 (m, 4H), 1.36 (m, 8H), 1.19 (m, 12H), 1.09 (m, 4H), 0.92 (m, 6H), 0.80 (m, 6H);
Carbon is composed
13cNMR (100MHz, THF-d
8) δ: 192.12,161.61,159.57,157.36,155.22,153.89,149.84,148.14,144.26,141.91,141.40,140.53,137.56,135.78,131.00,130.90,130.70,130.48,129.89,128.59,127.88,127.14,124.95,124.08,121.93,117.76,116.52,69.27,55.60,39.46,33.09,31.23,30.82,27.25,24.02,14.89;
Mass spectrum (ESI): 1028.6 ([M+H]
+);
Ultimate analysis: C, 74.26; H, 7.38; N, 4.10.
The synthesis of organic dye (I):
0.7 gram of intermediate, 3,47 milligrams of ammonium acetates and 1.16 grams of cyanoacetic acids are added in 100 milliliters of three mouthfuls of reaction flasks, add 60 milliliters of methylene dichloride and 30 milliliters of acetonitriles again, reaction system return stirring was cooled to room temperature after 24 hours, the reaction soln aqueous hydrochloric acid acidifying of 2 moles often liter, then three times are washed with deionized water, use anhydrous sodium sulfate drying subsequently, it is black solid that the crude product chloroform/methanol (10/1) obtained after decompression is spin-dried for solvent obtains target product dyestuff I as eluent by silica gel column chromatography separation, and productive rate is 90%.
The nucleus magnetic resonance characterization data of organic dye (I) is as follows:
Hydrogen is composed
1hNMR (400MHz, THF-d
8) δ: 8.39 (s, 1H), 8.29 (m, 3H), 8.21 (d, J=8.0Hz, 2H), 8.03 (d, J=7.2Hz, 1H), 7.95 (d, J=7.2Hz, 1H), 7.46 (d, J=7.2Hz, 2H), 7.27 (s, 1H), 7.02 (d, J=8.0Hz, 4H), 6.90 (d, J=7.2Hz, 2H), 6.84 (d, J=8.0Hz, 4H), 3.94 (m, 4H), 2.02 (m, 4H), 1.78 (m, 4H), 1.49 (m, 4H), 1.36 (m, 8H), 1.25 (m, 12H), 1.10 (m, 4H), 0.93 (m, 6H), 0.80 (m, 6H);
Carbon is composed
13cNMR (100MHz, THF-d
8) δ: 164.46,160.90,158.87,156.62,154.45,153.39,153.20,149.09,147.41,142.04,141.20,140.76,139.89,135.14,132.36,131.60,130.12,129.58,129.12,127.91,127.16,126.43,124.30,123.32,121.23,117.05,116.56,115.82,105.21,68.57,54.87,38.75,34.42,32.38,30.52,30.42,30.11,26.54,23.31,14.20;
High resolution mass spectrum (MALDI-TOF): 1094.48549;
Ultimate analysis: C, 73.36; H, 6.98; N, 5.10.
Embodiment 2: containing the preparation of the organic dye (II) of diazosulfide-cyano group cinnamic acid acceptor
Synthetic route is as follows:
The synthesized reference document M.Zhang of raw material 4, Y.Wang, M.Xu, W.Ma, R.LiandP.Wang, EnergyEnviron.Sci., 2013,6,2944.
The synthesis of intermediate 5:
0.24 gram of raw material 4 and 4 milliliters of tetrahydrofuran (THF)s are added in 50 milliliters of three mouthfuls of reaction flasks,-78 DEG C are cooled under argon shield, slow dropping 0.3 milliliter of tertiary butyl lithium (1.3M), dropwise rear maintenance low temperature and stir 3 hours, then 70 milligrams of trimethyltin chlorides are added, dropwise and slowly rise to stirring at room temperature 12 hours afterwards, add 20 ml deionized water termination reactions again, the mixed solvent chloroform extraction obtained three times, merge organic phase, with anhydrous sodium sulfate drying, the crude product obtained after decompression is spin-dried for solvent can be directly used in reaction below, without the need to being further purified,
By 0.27 gram of above-mentioned crude product and 55 milligrams of bromo-7-of 4-(4-phenyl aldehyde)-2, 1, 3-diazosulfide is placed in 50 milliliters of three mouthfuls of reaction flasks, add 10 milliliter 1, 4-dioxane, 0.03 milliliter of tri-butyl phosphine is added successively under argon shield, 3 milligram three (dibenzalacetone) two palladium and 61 milligrams of cesium fluorides, reaction system is heated to 60 DEG C and stirs 6 hours, room temperature is cooled to after reaction terminates, add 10 ml deionized water, the mixing solutions chloroform extraction obtained three times, merge organic phase, with anhydrous sodium sulfate drying, crude product toluene/the sherwood oil (1/1) obtained after decompression is spin-dried for solvent obtains intermediate 5 for orange thick liquid as eluent by silica gel column chromatography separation, productive rate is 85%.
The nucleus magnetic resonance characterization data of intermediate 5 is as follows:
Hydrogen is composed
1hNMR (400MHz, THF-d
8) δ: 10.06 (s, 1H), 8.29 (m, 3H), 8.07 (d, J=7.8Hz, 1H), 8.02 (d, J=8.4Hz, 2H), 7.95 (d, J=7.8Hz, 1H), 7.55 (m, 6H), 7.37 (s, 1H), 7.17 (s, 2H), 7.13 (d, J=8.4Hz, 2H), 7.08 (d, J=8.4Hz, 2H), 6.87 (m, 3H), 6.85 (s, 1H), 4.00 (t, J=6.4Hz, 4H), 2.03 (m, 4H), 1.93 (m, 8H), 1.80 (m, 4H), 1.52 (m, 4H), 1.37 (m, 8H), 1.19 (m, 12H), 1.10 (m, 4H), 0.93 (t, J=6.8Hz, 6H), 0.81 (t, J=6.8Hz, 6H), 0.36 (t, J=7.2Hz, 12H),
Carbon is composed
13cNMR (100MHz, THF-d
8) δ: 191.39,160.92,159.90,159.04,154.47,153.15,152.09,151.32,148.53,147.07,146.73,143.49,140.60,140.04,138.09,136.80,135.53,134.88,130.27,130.02,129.75,129.39,129.11,126.52,124.24,123.80,123.38,120.40,120.12,119.84,117.52,113.56,109.93,68.52,56.72,54.94,38.79,33.41,32.44,32.39,30.54,30.22,26.59,25.31,23.33,14.26,8.85;
Mass spectrum (ESI): 1316.5 ([M+H]
+);
Ultimate analysis C, 78.18; H, 7.91; N, 3.11.
The synthesis of organic dye (II):
0.2 gram of intermediate, 5,11 milligrams of ammonium acetates and 0.26 gram of cyanoacetic acid is added in 50 milliliters of three mouthfuls of reaction flasks, add 9 milliliters of methylene dichloride and 6 milliliters of acetonitriles again, reaction system return stirring was cooled to room temperature after 24 hours, the reaction soln aqueous hydrochloric acid acidifying of 2 moles often liter, then three times are washed with deionized water, use anhydrous sodium sulfate drying subsequently, it is black solid that the crude product chloroform/methanol (50/1) obtained after decompression is spin-dried for solvent obtains target product dyestuff II as eluent by silica gel column chromatography separation, and productive rate is 83%.
The nucleus magnetic resonance characterization data of organic dye (II) is as follows:
Hydrogen is composed
1hNMR (400MHz, THF-d
8) δ: 8.34 (m, 3H), 8.29 (s, 1H), 8.22 (d, J=8.0Hz, 2H), 8.08 (d, J=7.2Hz, 1H), 7.99 (d, J=7.2Hz, 1H), 7.55 (m, 6H), 7.36 (s, 1H), 7.16 (s, 2H), 7.12 (d, J=8.0Hz, 2H), 7.08 (d, J=8.0Hz, 2H), 6.87 (m, 3H), 6.85 (s, 1H), 4.00 (t, J=6.4Hz, 4H), 2.03 (m, 4H), 1.93 (m, 8H), 1.80 (m, 4H), 1.52 (m, 4H), 1.38 (m, 8H), 1.19 (m, 12H), 1.09 (m, 4H), 0.93 (t, J=6.8Hz, 6H), 0.81 (t, J=6.8Hz, 6H), 0.36 (t, J=7.2Hz, 12H),
Carbon is composed
13cNMR (100MHz, THF-d
8) δ: 163.89,160.92,159.93,159.03,154.48,153.58,153.23,152.09,151.33,148.55,147.05,146.76,142.23,140.73,140.13,138.13,135.59,134.91,132.28,131.64,130.20,129.63,129.45,129.16,126.51,124.39,124.22,123.82,123.30,120.38,120.12,119.84,117.53,116.32,113.60,109.91,104.67,68.54,56.74,54.95,38.82,33.40,32.45,32.39,30.53,30.22,26.59,25.32,23.32,14.19,8.79;
High resolution mass spectrum (MALDI-TOF): 1382.67697.;
Ultimate analysis: C, 77.03; H, 7.47; N, 4.01.
Embodiment 3
By nano-TiO
2structure duplicature electrode is immersed in and often rises in the chloroformic solution of dyestuff (I) 12 hours containing 150 micromoles, and then by spin coating, the glass electrode of Platinum Nanoparticles melts ring and TiO by the heat of 35 micron thickness
2structure duplicature heated by electrodes seals, and is finally injected into by ionogen in the gap of two electrodes, namely constitutes dye-sensitized solar cells.Test the dye-sensitized solar cells performance structure obtained as shown in table 1.
Embodiment 4
By nano-TiO
2structure duplicature electrode is immersed in and often rises in the chloroformic solution of dyestuff (II) 12 hours containing 150 micromoles, and then by spin coating, the glass electrode of Platinum Nanoparticles melts ring and TiO by the heat of 35 micron thickness
2structure duplicature heated by electrodes seals, and is finally injected into by ionogen in the gap of two electrodes, namely constitutes dye-sensitized solar cells.Test the dye-sensitized solar cells performance structure obtained as shown in table 1.
Table 1
Claims (5)
1., containing an organic dye for diazosulfide-cyano group cinnamic acid acceptor, it is characterized in that, structure is such as formula shown in (V):
In formula (V), R
1for
in any one; R
3, R
4, R
5respective is independently hydrogen atom, C
1~ C
12alkyl or C
1~ C
12any one in alkoxyl group;
R
2for
in any one; R
6, R
7and R
8respective is independently hydrogen atom, C
1~ C
12alkyl or C
1~ C
12any one in alkoxyl group, R
9for C
1~ C
12alkyl or C
1~ C
12any one in alkoxyl group.
2. a kind of organic dye containing diazosulfide-cyano group cinnamic acid acceptor according to claim 1, it is characterized in that, described organic dye has the structure shown in formula I:
3. a kind of organic dye containing diazosulfide-cyano group cinnamic acid acceptor according to claim 1, it is characterized in that, described organic dye has the structure shown in formula II:
4. the organic dye application in dye-sensitized solar cells containing diazosulfide-cyano group cinnamic acid acceptor of claim 1-3 described in any one.
5. an organic dye sensitized solar cell, is characterized in that, dye coating is the organic dye containing diazosulfide-cyano group cinnamic acid acceptor of claim 1-3 described in any one.
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| CN105440729B (en) * | 2015-12-17 | 2017-11-17 | 中国科学院长春应用化学研究所 | A kind of organic dyestuff and preparation method thereof and the sensitization solar cell comprising the organic dyestuff |
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Effective date of registration: 20191230 Address after: Changzhou City, Jiangsu province Hehai road 213000 No. 9 Patentee after: Changzhou Institute of Energy Storage Materials & Devices Address before: 130022 No. 5625 Renmin Street, Changchun, Jilin, Chaoyang District Patentee before: Changchun Institue of Applied Chemistry, Chinese Academy of Sciences |