CN108276795A - Bridged ring Dithiophene-phenothiazine dyes and its application in dye-sensitized solar cells - Google Patents
Bridged ring Dithiophene-phenothiazine dyes and its application in dye-sensitized solar cells Download PDFInfo
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- CN108276795A CN108276795A CN201810164689.XA CN201810164689A CN108276795A CN 108276795 A CN108276795 A CN 108276795A CN 201810164689 A CN201810164689 A CN 201810164689A CN 108276795 A CN108276795 A CN 108276795A
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- dithiophene
- dye
- bridged ring
- sensitized solar
- phenothiazine dyes
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- 239000000975 dye Substances 0.000 title claims abstract description 74
- 229950000688 phenothiazine Drugs 0.000 title claims abstract description 21
- 206010070834 Sensitisation Diseases 0.000 claims abstract description 11
- 230000008313 sensitization Effects 0.000 claims abstract description 11
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical compound [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000004873 anchoring Methods 0.000 claims abstract description 7
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical group OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 claims abstract description 6
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000243 solution Substances 0.000 claims description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- 239000011521 glass Substances 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 230000005611 electricity Effects 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- 239000011259 mixed solution Substances 0.000 claims description 3
- 238000007654 immersion Methods 0.000 claims description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract description 17
- 150000001875 compounds Chemical class 0.000 abstract description 13
- 238000004220 aggregation Methods 0.000 abstract description 7
- 230000002776 aggregation Effects 0.000 abstract description 7
- 230000002401 inhibitory effect Effects 0.000 abstract description 6
- 239000004408 titanium dioxide Substances 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract description 4
- 230000001235 sensitizing effect Effects 0.000 abstract description 3
- 238000010276 construction Methods 0.000 abstract description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 abstract description 2
- 229930192474 thiophene Natural products 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 238000012512 characterization method Methods 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000010792 warming Methods 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
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- 238000001291 vacuum drying Methods 0.000 description 5
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
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- 239000008367 deionised water Substances 0.000 description 4
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- 239000003792 electrolyte Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
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- 229910052757 nitrogen Inorganic materials 0.000 description 3
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- 239000000377 silicon dioxide Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-OUBTZVSYSA-N Ammonia-15N Chemical compound [15NH3] QGZKDVFQNNGYKY-OUBTZVSYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
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- 239000007788 liquid Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000001172 regenerating effect Effects 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- ZZPNDIHOQDQVNU-UHFFFAOYSA-N 2-hydroxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OB(O)OC1(C)C ZZPNDIHOQDQVNU-UHFFFAOYSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- NFGOEORIETYSNP-UHFFFAOYSA-N N1C=NC=C1.I(=O)(=O)OCCCC Chemical class N1C=NC=C1.I(=O)(=O)OCCCC NFGOEORIETYSNP-UHFFFAOYSA-N 0.000 description 1
- WZHKCFDUDKJGBA-UHFFFAOYSA-N N1CCNCC1.S1C=CC=C1 Chemical compound N1CCNCC1.S1C=CC=C1 WZHKCFDUDKJGBA-UHFFFAOYSA-N 0.000 description 1
- 101150090068 PMII gene Proteins 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N SnO2 Inorganic materials O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 229910003074 TiCl4 Inorganic materials 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
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- 229940043376 ammonium acetate Drugs 0.000 description 1
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- 239000007864 aqueous solution Substances 0.000 description 1
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- 238000013375 chromatographic separation Methods 0.000 description 1
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- 239000003245 coal Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
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- 238000002484 cyclic voltammetry Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000005909 ethyl alcohol group Chemical group 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- ZJYYHGLJYGJLLN-UHFFFAOYSA-N guanidinium thiocyanate Chemical class SC#N.NC(N)=N ZJYYHGLJYGJLLN-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
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- 230000005693 optoelectronics Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
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- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- BFNYNEMRWHFIMR-UHFFFAOYSA-N tert-butyl 2-cyanoacetate Chemical compound CC(C)(C)OC(=O)CC#N BFNYNEMRWHFIMR-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B21/00—Thiazine dyes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/20—Light-sensitive devices
- H01G9/2059—Light-sensitive devices comprising an organic dye as the active light absorbing material, e.g. adsorbed on an electrode or dissolved in solution
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/542—Dye sensitized solar cells
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- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Power Engineering (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Hybrid Cells (AREA)
Abstract
Application the invention discloses bridged ring Dithiophene phenothiazine dyes and its in dye-sensitized solar cells.The bridged ring Dithiophene phenothiazine dyes are the pure organic dyes using phenthazine as electron donor, wherein, bridged ring Dithiophene is introduced as extra electron donor in phenthazine electron donor, bridged ring Dithiophene is the union II thiophene of cyclic alkyl chain package, with higher spatial steric hindrance, be conducive to improve the photoelectric properties of dyestuff, and play the effect for inhibiting dye molecule aggregation and inhibiting electronics compound, while introducing cyanoacetic acid group as electron acceptor and anchoring group.It is applied to the working electrode that sensitizing dyestuff is sensitized solar cell using the dyestuff as sensitizer, in the nano-titanium dioxide surface construction compacted zone of working electrode, it is covered in titanium dioxide surface, it is compound electronics can be effectively inhibited, open-circuit voltage is improved, to effectively improve the photoelectric properties of the dye sensitization sun.
Description
Technical field
The present invention relates to organic dyestuff technical fields, and in particular to the sensitizing dyestuff of dye-sensitized solar cells and its answers
With.
Background technology
With the rapid development of economic society, the raising of industrialization degree, the energy is in human society produces and lives
It is more and more important to act on role.Meanwhile constantly accelerating with process of industrialization as global economy level is continuously improved, people
The demand of the energy is constantly increased, the consumption of traditional fossil energy such as coal, oil increasingly increases traditional fossil energy face
Face exhausted predicament.At the same time, a large amount of uses of traditional fossil energy also result in the whole world such as greenhouse effects, atmosphere pollution
Property environmental problem, bring and seriously affect to human being's production life.Therefore, it finds and disclosure satisfy that human future production and life
The regenerative resource of demand substitutes traditional fossil energy, and a kind of free of contamination clean energy resource of searching becomes the current entire mankind's
Common objective, therefore also become the emphasis of current scientist research, also future science is badly in need of the major issue solved.
Currently, the new energy such as solar energy, wind energy, tide energy, geothermal energy, nuclear energy have obtained Part Development and utilization.Its
In, solar energy is used as with it not to the utmost, and inexhaustible regenerative resource takes that approach is more, and use scope is wide, will be become not
Carry out one of a big main energy sources for human social development.Meanwhile either in world wide or in national range, to solar energy
Exploitation active demand and fund, the investment of manpower and materials all reached unprecedented height, especially China
Solar energy industry scale occupied No. 1 in the world, and also riseing rapidly to the utilization of solar energy.Therefore, Devoting Major Efforts To Developing
Solar energy has important strategic meaning and global meaning.
Dye-sensitized solar cells are rapidly developed what is reported for the first time by gratzel since 1991 over nearly 25 years,
Its efficiency is also rapidly promoted in recent years.Sensitizer is the important component of dye-sensitized solar cells, is to determine dyestuff
It is sensitized the key factor of solar cell superior performance, with can research and with feasibility.By improving dye molecule
Structure fundamentally can effectively change the performance of dye-sensitized solar cells.Phenthazine is a superior donor residues
Group, because its nitrogen and sulphur atom containing electron rich on center ring, and its nonplanar buttferfly-type conformation also contributes to press down
Molecule aggregation processed；In addition, charge recombination can usually be postponed to prevent by introducing long alkyl chain on No. 10 position N atoms of phenthazine
Current loss.These advantages make phenothiazine derivative have prodigious development potentiality in the efficient fields DSSCs, and are increasingly becoming
Research hotspot.Introducing accessory receptor in recent years also becomes a kind of effective ground plan for improving dye-sensitized solar cells efficiency
Slightly.However, two main resistances that dye molecule aggregation and the compound always limitation dye-sensitized solar cells efficiency of electronics improve
Hinder, inhibits a weight of aggregation and the compound performance for being raising dye-sensitized solar cells of electronics by designing suitable group
Want approach.
Invention content
It is an object of the invention to the deficiencies for present technology, provide a kind of bridged ring Dithiophene-phenothiazine dyes.It should
Bridged ring Dithiophene-phenothiazine dyes are the pure organic dyes using phenthazine as electron donor, wherein in phenthazine electron donor
No. 7 positions introduce bridged ring Dithiophene (the union II thiophene of cyclic alkyl chain package) and are used as extra electron donor, to improve the light of dyestuff
Electrical property, and the effect for inhibiting dye molecule aggregation and inhibiting electronics compound is played, while introducing cyanoacetic acid group conduct
Electron acceptor and anchoring group.
A kind of bridged ring Dithiophene-phenothiazine dyes of the present invention, preparation method is simple for process, and yield is high, can be effective
Large-scale production is carried out, there is universality.
Another object of the present invention also reside in provide a kind of bridged ring Dithiophene-phenothiazine dyes dye sensitization too
Application in positive electricity pond, it is specific to be applied to the working electrode that sensitizing dyestuff is sensitized solar cell as sensitizer, in working electrode
Nano-titanium dioxide surface construction compacted zone, be covered in titanium dioxide surface, can effectively inhibit that electronics is compound, and raising is opened
Road voltage, to effectively improve the photoelectric properties of the dye sensitization sun.
The purpose of the present invention is achieved through the following technical solutions.
A kind of bridged ring Dithiophene-phenothiazine dyes, chemical structural formula are as follows：
In formula, R C4~C8Straight chained alkyl or branched alkyl, or be C4~C8Alkoxy benzene；The numerical value of n be 0,
2,4,6 or 8；
Wherein, cyanoacetic acid group is as electron acceptor and anchoring group.
A kind of bridged ring Dithiophene-application of the phenothiazine dyes in dye-sensitized solar cells described above, will be described
Bridged ring Dithiophene-phenothiazine dyes are applied to as sensitizer in dye-sensitized solar cells, specially：Nano-silica will be loaded
The electro-conductive glass substrate for changing titanium is immersed in the dye bath solution that bridged ring Dithiophene-phenothiazine dyes are prepared, bridged ring Dithiophene-pheno thiophene
Piperazine dyestuff is adsorbed on nano-titanium dioxide surface by anchoring group, is prepared into the working electrode of dye-sensitized solar cells.
Further, the solvent of the dye bath solution is the mixed solution of acetonitrile and tert-butyl alcohol volume ratio 1: 4~4: 1.
Further, a concentration of 0.1~0.5mM of the dye bath solution.
Further, the immersion is to be protected from light lower impregnate 6~48 hours in room temperature.
Compared with prior art, the invention has the advantages that and advantageous effect：
The bridged ring Dithiophene of the present invention-phenothiazine dyes introduce bridged ring Dithiophene as extra electron donor, to improve dye
The photoelectric properties of material, while the effect for inhibiting dye molecule aggregation and inhibiting electronics compound is played, it is applied to dye sensitization too
In positive electricity pond, make dye-sensitized solar cells that there is higher open-circuit voltage.
Description of the drawings
Fig. 1 is ultraviolet/visible suction of the bridged ring Dithiophene-phenothiazine dyes of the preparation of embodiment 1 in dichloromethane solution
Receive spectrogram；
Fig. 2 is the dye sensitization sun electricity that bridged ring Dithiophene-phenothiazine dyes prepared by embodiment 1 make as sensitizer
The J-V curve graphs in pond.
Specific implementation mode
Technical solution of the present invention is described in further detail below in conjunction with specific embodiment and attached drawing, but the present invention
Protection domain and embodiment are without being limited thereto.
Embodiment 1
Bridged ring Dithiophene-phenothiazine dyes PTZ1 (n=2,) synthesis, synthetic route
It is as follows：
(1) synthesis of compound 2 and characterization, synthetic route are as follows：
It is as follows：
In 50mL single necked round bottom flask, compound 1 (200mg, 0.50mmol) and 15mL tetrahydrofurans (THF) is added,
It is placed under ice bath and stirs；NBS (N-bromosuccinimide, 96.9mg, 0.55mmol) is dissolved in 10mL THF, is transferred to constant pressure
Dropping funel (band glass stopper), and be slowly added dropwise into reaction system；After stirring 2 hours under ice bath, continue at room temperature
React 8 hours；It waits for after reaction, reaction solution is fully transferred in the separatory funnel equipped with enough water, uses dichloromethane
Three times, anhydrous magnesium sulfate drying is added in extraction, and the filtrate obtained after filtering removes solvent by vacuum rotary steam, and residue passes through silicon
Rubber column gel column chromatographic separation and purification, vacuum rotary steam remove solvent, faint yellow solid (i.e. compound 2) 206mg are obtained after vacuum drying, produce
Rate is 85.7%.
Characterization result is as follows：1H NMR (400MHz, CDCl3)：δ=9.69 (s, 1H), 7.42 (d, J=1.6Hz, 1H),
7.28 (dd, 3J=8.6Hz, 4J=1.6Hz, 1H), 7.23 (d, J=8.8Hz, 2H), 7.12 (d, J=8.8Hz, 2H), 7.06
(d, J=2.2Hz, 1H), 6.90 (dd, 3J=8.8Hz, 4J=2.2Hz, 1H), 6.20 (d, J=8.6Hz, 1H), 6.00 (d, J
=8.8Hz, 1H), 4.04 (t, J=6.5Hz, 2H), 1.89-1.80 (m, 2H), 1.56-1.46 (m, 2H), 1.42-1.33 (m,
4H), 0.93 (t, J=6.9Hz, 3H)
(2) synthesis of compound 3 and characterization, synthetic route are as follows：
It is as follows：
In 50mL twoport round-bottomed flasks, compound 2 (860mg, 1.79mmol), t-butylcyanoacetate is added
(635mg, 4.5mmol), ammonium acetate (348mg, 4.5mmol), 2mL glacial acetic acid and 25mL toluene under magnetic agitation, are passed through nitrogen
The air in reaction system is discharged, it is warming up to 130 DEG C within 5 minutes, reacts 4 hours；To the end of reaction, reaction solution is cooled to often
Reaction solution is fully transferred in the separatory funnel equipped with enough water by Wen Hou, three times with dichloromethane extraction, anhydrous slufuric acid is added
Magnesium is dried, and the filtrate obtained after filtering removes solvent by vacuum rotary steam, and residue passes through silica gel column chromatogram separating purification, decompression
Revolving removes solvent, and red solid (i.e. compound 3) 853mg, yield 78.9% are obtained after vacuum drying.
Characterization result is as follows：1H NMR (400MHz, CDCl3)：δ=7.84 (s, 1H), 7.52-7.44 (m, 2H), 7.20
(d, J=8.8Hz, 2H), 7.10 (d, J=8.8Hz, 2H), 7.02 (s, 1H), 6.88 (dd, 3J=8.8Hz, 4J=1.6Hz,
1H), 6.15 (d, J=8.8Hz, 1H), 5.99 (d, J=8.8Hz, 1H), 4.03 (t, J=6.5Hz, 2H), 1.89-1.79 (m,
2H), 1.55 (s, 9H), 1.56-1.46 (m, 2H), 1.44-1.31 (m, 4H), 0.93 (t, J=6.9Hz, 3H)
(3) synthesis of compound 4 and characterization, synthetic route are as follows：
It is as follows：
Into 50mL two mouth flasks, be added compound 3 (1.29g, 2.13mmol), connection boric acid pinacol ester (1.08g,
4.26mmol), potassium acetate (627mg, 6.39mmol) and 25mL steam processed Isosorbide-5-Nitrae-dioxane again, under magnetic agitation, lead to
Enter nitrogen 15 minutes so that the air in reaction system is discharged, then the Pd (dppf) of 80mg is added into reaction system rapidly2Cl2, after
It is continuous to be passed through nitrogen 15 minutes, 95 DEG C are warming up to, 18 hours are reacted, the process of TCL monitoring reactions is utilized in reaction process；It waits for anti-
After should being fully completed, above-mentioned mixed liquor is cooled to room temperature, water quenching is added and goes out reaction, dichloromethane is used in combination to extract 3 times, addition nothing
Water magnesium sulfate is dried, and the filtrate obtained after filtering removes solvent by vacuum rotary steam, is detached using column chromatography chromatogram technology
Purifying, vacuum rotary steam remove solvent, red solid (i.e. compound 4) 4890mg, yield 64.3% are obtained after vacuum drying.
Characterization result is as follows：1H NMR (400MHz, CDCl3)：δ=7.87 (s, 2H), 7.53 (dd,3J=8.8Hz,4J=
2Hz, 1H), 7.47 (d, J=2Hz, 1H), 7.38 (d, J=1.2Hz, 1H), 7.28-7.23 (m, 3H), 7.13 (d, J=
8.8Hz, 2H), 6.14 (t, J=8.8Hz, 2H), 4.06 (t, J=6.4Hz, 2H), 1.90-1.83 (m, 2H), 1.57 (s, 9H),
1.41-1.39 (m, 4H), 1.32 (s, 12H), 0.96ppm (t, J=6.8Hz, 3H).
(4) synthesis of compound 6 and characterization, synthetic route are as follows：
It is as follows：
Sequentially added into 50mL two mouth flasks compound 4 (120mg, 0.176mmol), compound 5 (115mg,
0.176mmol), sodium carbonate (56mg, 0.528mmol), 2mL ethyl alcohol, 2mL water and 20mL toluene, under magnetic agitation, to reaction
It is passed through 15 minutes nitrogen in system so that the air in reaction system is discharged, then is rapidly added 20mg Pd (PPh3)4, continue to be passed through nitrogen
Gas 15 minutes is warming up to 90 DEG C, the process reacted 24 hours and reacted with TCL monitorings；After complete reaction, by above-mentioned mixing
Liquid is cooled to room temperature, and three times using dichloromethane extraction, anhydrous sulphur is added in combined gained organic phase saturated common salt water washing
Sour magnesium drying, the filtrate obtained after filtering remove solvent by vacuum rotary steam and are subtracted by column chromatography silica gel column chromatography separating purification
Pressure revolving removes solvent, and dark red solid 98mg, i.e. compound 6, yield 46% are obtained after vacuum drying.
Characterization result is as follows：1H NMR (400MHz, CDCl3)：δ=7.85 (s, 1H), 7.51 (s, 1H), 7.47 (d, J=
8.8Hz, 1H), 7.33 (t, J=8.4Hz, 2H), 7.21 (d, J=8.4Hz, 2H), 7.10 (d, J=8.4Hz, 2H), 6.96 (t,
J=5.4Hz, 2H), 6.80 (d, J=8.4Hz, 2H), 6.69 (d, J=5.2Hz, 1H), 6.60 (d, J=8.0Hz, 4H), 6.13
(d, J=8.8Hz, 1H), 6.03 (d, J=8.4Hz, 1H), 4.03 (t, J=6Hz, 2H), 3.92 (s, 8H), 1.88-1.81 (m,
2H), 1.51-1.50 (m, 19H), 1.39-1.32 (m, 4H), 1.25-1.02 (m, 16H), 0.99-0.88ppm (m, 3H)
(5) synthesis of organic dyestuff PTZ1 and characterization, synthetic route are as follows：
It is as follows：
The compound 6 for weighing 90mg is placed in 50ml single-necked flasks, the analytically pure trifluoroacetic acids of 20ml is then added, in room
Temperature is lower to be stirred, the carry out situation reacted using TCL monitoring, after 3h, after reactant reaction is complete, stops reaction；By the reaction
Liquid is poured into the distilled water of 100ml, is stirred continuously, and until the precipitation of a large amount of solids, is then filtered, is obtained filter residue, and use always
Distilled water cleans, and after filtrate is in neutrality, stops cleaning；By filter residue be placed in vacuum drying chamber with 60 DEG C under the conditions of it is dry
For 24 hours, reddish black solid, i.e. target product PTZ1, yield 93% are obtained.
Characterization result is as follows：1H NMR (400MHz, CDCl3) δ 7.91 (s, 1H), 7.57 (s, 1H), 7.42 (d, J=
7.6Hz, 1H), 7.34 (t, J=8Hz, 2H), 7.20 (d, J=8Hz, 2H), 7.11 (d, J=8Hz, 2H), 6.96 (d, J=
4Hz, 1H), 6.92 (s, 1H), 6.80 (s, 1H), 6.76 (d, J=8.4Hz, 1H), 6.69 (d, J=4.4Hz, 1H), 6.61 (d,
J=7.6Hz, 4H), 6.10 (d, J=8.4Hz, 1H), 6.00 (d, J=8.4Hz, 1H), 4.04 (t, J=6Hz, 2H), 3.93
(m, 8H), 1.85 (t, J=6Hz, 2H), 1.56-1.50 (m, 10H), 1.39-1.34 (m, 4H), 1.23-1.01 (m, 16H),
0.94 (t, J=10Hz, 3H)
Embodiment 2
Uv-visible absorption spectra test carried out to the organic dyestuff PTZ1 prepared by embodiment 1, specific test condition and
Instrument is as follows：
Solvent：Dichloromethane
Concentration：1×10-5M
Temperature：Room temperature
Instrument：Shimadzu UV-2450 ultraviolet-uisible spectrophotometers.
Obtained UV-visible absorption spectrum is tested as shown in Figure 1, it is seen in fig. 1, that PTZ1 dye molecules are in 300-
It is main in the regions 650nm that there are two apparent absorption peaks.Wherein, it is mainly π-π * electron transitions in the absorption peak of 300-450nm
In addition peak is mainly to be generated due to cyclic voltammetry method in the absorption peak in the regions 450-650nm, this and common dye molecule
Absorption do not distinguish significantly, the main distinction is that the introducing of bridged ring Dithiophene keeps absorption spectrum Einstein shift, absorption region wider.
Embodiment 3
The preparation of dye-sensitized solar cells
Organic dyestuff PTZ1 prepared by embodiment 1 is as sensitizer in dye-sensitized solar cells, preparation to be based on
The dye-sensitized solar cells of dyestuff PTZ1 sensitizers, specifically using dyestuff PTZ1 as the sensitizer portion of dye-sensitized solar cells
Point, by load nano-titanium dioxide (TiO2) electro-conductive glass substrate be immersed in the dye bath solution that dyestuff PTZ1 is prepared, dyestuff
PTZ1 is adsorbed on nano-titanium dioxide surface by anchoring group (cyanoacetic acid group), to be prepared into working electrode, dyestuff
PTZ1 is to determine the superior key factor of battery performance as the sensitizer moiety of dye-sensitized solar cells.
Dye-sensitized solar cells further include following device：Electro-conductive glass substrate (doping SnO2Electro-conductive glass, i.e.,
FTO), electrolyte (iodine electrolyte), platinum are to electrode (electro-conductive glass of platinum plating) and external circuit.
The specific process for preparing dye-sensitized solar cells includes the following steps：
The pretreatment of a.FTO electro-conductive glass：The FTO electro-conductive glass (2 × 5cm) of well cutting is put into ultrasonic cleaner
In be cleaned by ultrasonic, the spot of conductive glass surface is cleaned up using clean hairbrush after the completion of cleaning, then successively
Respectively it is cleaned by ultrasonic 10min with acetone, ethyl alcohol, deionized water, is preserved after dry, for use；
B. nano-titanium dioxide (TiO2) electrode preparation：First by 15ml (TiOBu)4And 20ml absolute ethyl alcohols are in room
Then under agitation the deionized water of 18ml glacial acetic acid and 50ml is added to above-mentioned mixing by the lower uniform stirring 10min of temperature
In liquid, and 1h still is stirred at room temperature, after baking 12h under the conditions of being subsequently placed in 230 DEG C, naturally cools to room temperature, filters,
Again filter residue is washed with deionized water and absolute ethyl alcohol successively；
The solid of gained is again placed in baking oven, is warming up to 50 DEG C of baking 6h, is then obtained the nano titania of 20nm
Particle is sealed, spare；
The titanium dioxide nanoparticle for weighing 1g preparations is put into crucible, and ethyl alcohol, the 0.2ml of 8ml are then sequentially added
Glacial acetic acid, 0.5g ethyl cellulose and 3g terpinols, 40min is until obtain slimy, uniform suspension for grinding, surpasses
Sound 15 minutes forms the titanium dioxide cementitious slurry shape substance of white；
The titanium dioxide cementitious slurry shape substance of the white prepared is printed onto by screen printing technique and is pre-processed
FTO electro-conductive glass above, form porous silica titanium layer, pass through the prepared poriferous titanium dioxide of film thickness determination instrument test
The thickness of layer, is printed successively, until the thickness of porous silica titanium layer reaches 16mm, then by way of temperature programming
Gradually sintering solidification in Muffle furnace, until forming stable light anode；Wherein, temperature programming is as follows：First from
Room temperature is to 375 DEG C and maintains 5min, then is warming up to 450 DEG C from 375 DEG C and maintains 15min at such a temperature, then from 450
It DEG C is warming up to 500 DEG C and maintains 15min at such a temperature, be then cooled to room temperature；
The light anode sintered is being impregnated into 40mM TiCl4Aqueous solution in, and stand 30 under the conditions of being placed in 70 DEG C together
Minute, optoelectronic pole is then taken out, and cleaned up successively in deionized water, ethyl alcohol, is subsequently placed at 520 DEG C and handles 30min,
Then 70 DEG C are cooled to, nano-TiO is obtained2Electrode, it is spare；
C. the preparation of dye bath solution：The dyestuff PTZ1 of preparation is dissolved in the mixed solution of acetonitrile and the tert-butyl alcohol (v/v=1: 1)
In, it is ultrasonically treated 20 minutes, dyestuff PTZ1 is made to be completely dissolved, be configured to the dye bath solution of the 0.3mM of stable homogeneous, sealing is protected
It deposits, it is spare；
D. the preparation of working electrode：By the nano-TiO of preparation2Electrode is immersed in the dye bath solution of preparation, black in room temperature
It is impregnated under dark condition 24 hours, is then rinsed and was impregnated with the mixed liquor of analytically pure ethyl alcohol and acetonitrile (v/v=1: 1)
Nano-TiO2Electrode surface all washes away nano-titanium dioxide electrode surface by physical absorption, adherency dye molecule,
Working electrode is obtained, post package preservation is dried, it is spare；
E. the preparation of electrolyte：0.6M 1- methyl -3- propyl iodate imidazoles (PMII), 0.05M guanidine thiocyanates, 0.05M
LiI、0.03MI2With the acetonitrile solution of 0.25M tert .-butylpyridines (TBP)；
F. the assembling of dye-sensitized solar cells：Suitable endoporus is made in polyvinyl chloride insulation adhesive tape with card punch to mould
This insulation film is placed in the work electricity for completing sensitization by material, i.e. insulation film (film that i.e. above-mentioned insulating tape is prepared)
Pole makes working electrode just in insulation film endoporus；To working electrode surface (the insulation film endoporus position of dye bath
Set) it is added dropwise in 1~2 drop electrolyte, and the platinum prepared is covered on the working electrode (s to electrode, i.e. shape is fixed in both sides with clip
At dye-sensitized solar cells to be measured.
Battery performance test：According to the test request of sensitization solar cell, the sensitization solar cell device prepared is led to
It crosses external circuit to be respectively connected on corresponding instrument, be connected on battery performance test device, the work area of battery is
0.16cm2, with solar simulator simulated solar irradiation, luminous intensity is adjusted to 100mW/cm2Test the electricity based on the dye sensitization
The J-V curves in pond.
The J-V curves of measured dye-sensitized solar cells as shown in Fig. 2, data summarization in table 1.
1 dyestuff PTZ1 of table is used for the performance data of dye-sensitized solar cells
From the J-V curves of Fig. 2 and the data of table 1 it can be found that the dye sensitization that dyestuff PTZ1 prepared by embodiment 1 is sensitized
Solar cell shows higher photoelectric conversion efficiency, possesses good short circuit current and open-circuit voltage, shows dyestuff PTZ1 tools
There are wider absorption spectrum, the introducing of bridged ring Dithiophene to help to inhibit the aggregation of dye molecule, there is preferable inhibition electronics
Compound effect.
The above embodiment is a preferred embodiment of the present invention, but embodiments of the present invention are not by the embodiment
Limitation, it is other it is any without departing from the spirit and principles of the present invention made by changes, modifications, substitutions, combinations, simplifications,
Equivalent substitute mode is should be, is included within the scope of the present invention.
Claims (4)
1. a kind of bridged ring Dithiophene-phenothiazine dyes, which is characterized in that chemical structural formula is as follows：
In formula, R C4~C8Straight chained alkyl or branched alkyl, or be C4~C8Alkoxy benzene；The numerical value of n is 0,2,4,6
Or 8；
Wherein, cyanoacetic acid group is as electron acceptor and anchoring group.
2. a kind of bridged ring Dithiophene-application of the phenothiazine dyes in dye-sensitized solar cells described in claim 1, special
Sign is, is applied to the bridged ring Dithiophene-phenothiazine dyes as sensitizer in dye-sensitized solar cells, specially：
The electro-conductive glass substrate of load nano-titanium dioxide is immersed in the dye bath solution that bridged ring Dithiophene-phenothiazine dyes are prepared,
Bridged ring Dithiophene-phenothiazine dyes are adsorbed on nano-titanium dioxide surface by anchoring group, are prepared into dye sensitization sun electricity
The working electrode in pond.
3. application according to claim 2, which is characterized in that the solvent of the dye bath solution is acetonitrile and tert-butyl alcohol volume
Mixed solution than 1: 4~4: 1；A concentration of 0.1~0.5mM of the dye bath solution.
4. application according to claim 2, which is characterized in that the immersion is to be protected from light lower impregnate 6~48 hours in room temperature.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110183437A (en) * | 2019-05-21 | 2019-08-30 | 华南理工大学 | A kind of double D- π-A type column [5] aromatic hydrocarbons dyestuff and its synthetic method and its application |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101125960A (en) * | 2007-06-11 | 2008-02-20 | 大连理工大学 | Phenothiazines dye used for dye sensitization solar battery |
| US20100132796A1 (en) * | 2008-11-28 | 2010-06-03 | Samsung Electro-Mechanics Co., Ltd. | Dye compound for dye-sensitized solar cells, dye-sensitized photoelectric converter and dye-sensitized solar cells |
| JP2011026376A (en) * | 2009-07-21 | 2011-02-10 | Fujifilm Corp | Dye, photoelectric conversion element, and photo-electrochemical battery using the same |
| JP2011032198A (en) * | 2009-07-31 | 2011-02-17 | National Institute For Materials Science | Electroconductive monomer, polymer or oligomer thereof, and organic phosphor |
| JP2014205729A (en) * | 2013-04-10 | 2014-10-30 | 独立行政法人物質・材料研究機構 | Rotaxane type bithiophene derivative, dye-sensitized oxide semiconductor electrode and dye-sensitized solar cell |
| CN105669591A (en) * | 2016-03-22 | 2016-06-15 | 北京化工大学 | Double-donor aromatic amine photosensitizer and application thereof in LED visible light curing |
| CN105949814A (en) * | 2016-05-06 | 2016-09-21 | 南京邮电大学 | Phenothiazine derivative, preparation method and application thereof in dye-sensitized solar cells |
| CN107417680A (en) * | 2017-09-13 | 2017-12-01 | 浙江工业大学上虞研究院有限公司 | A kind of dye sensitizing agent and preparation method and application |
-
2018
- 2018-02-27 CN CN201810164689.XA patent/CN108276795A/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101125960A (en) * | 2007-06-11 | 2008-02-20 | 大连理工大学 | Phenothiazines dye used for dye sensitization solar battery |
| US20100132796A1 (en) * | 2008-11-28 | 2010-06-03 | Samsung Electro-Mechanics Co., Ltd. | Dye compound for dye-sensitized solar cells, dye-sensitized photoelectric converter and dye-sensitized solar cells |
| JP2011026376A (en) * | 2009-07-21 | 2011-02-10 | Fujifilm Corp | Dye, photoelectric conversion element, and photo-electrochemical battery using the same |
| JP2011032198A (en) * | 2009-07-31 | 2011-02-17 | National Institute For Materials Science | Electroconductive monomer, polymer or oligomer thereof, and organic phosphor |
| JP2014205729A (en) * | 2013-04-10 | 2014-10-30 | 独立行政法人物質・材料研究機構 | Rotaxane type bithiophene derivative, dye-sensitized oxide semiconductor electrode and dye-sensitized solar cell |
| CN105669591A (en) * | 2016-03-22 | 2016-06-15 | 北京化工大学 | Double-donor aromatic amine photosensitizer and application thereof in LED visible light curing |
| CN105949814A (en) * | 2016-05-06 | 2016-09-21 | 南京邮电大学 | Phenothiazine derivative, preparation method and application thereof in dye-sensitized solar cells |
| CN107417680A (en) * | 2017-09-13 | 2017-12-01 | 浙江工业大学上虞研究院有限公司 | A kind of dye sensitizing agent and preparation method and application |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110183437A (en) * | 2019-05-21 | 2019-08-30 | 华南理工大学 | A kind of double D- π-A type column [5] aromatic hydrocarbons dyestuff and its synthetic method and its application |
| WO2020232973A1 (en) * | 2019-05-21 | 2020-11-26 | 华南理工大学 | DOUBLE D-π-A TYPE PILLAR[5]ARENE DYE, SYNTHESIS METHOD AND APPLICATION THEREOF |
| CN110183437B (en) * | 2019-05-21 | 2021-10-26 | 华南理工大学 | Double D-pi-A type column [5] arene dye and synthetic method and application thereof |
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