CN113264916A - Fluorine-containing dye sensitizer and application thereof - Google Patents
Fluorine-containing dye sensitizer and application thereof Download PDFInfo
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- CN113264916A CN113264916A CN202110497816.XA CN202110497816A CN113264916A CN 113264916 A CN113264916 A CN 113264916A CN 202110497816 A CN202110497816 A CN 202110497816A CN 113264916 A CN113264916 A CN 113264916A
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- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 33
- 239000011737 fluorine Substances 0.000 title claims abstract description 31
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 229960000583 acetic acid Drugs 0.000 claims description 4
- 239000012153 distilled water Substances 0.000 claims description 4
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 3
- 239000005695 Ammonium acetate Substances 0.000 claims description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 3
- 229940043376 ammonium acetate Drugs 0.000 claims description 3
- 235000019257 ammonium acetate Nutrition 0.000 claims description 3
- DWOZNANUEDYIOF-UHFFFAOYSA-L bis(di-tert-butyl(4-dimethylaminophenyl)-phosphine)dichloropalladium(II) Substances Cl[Pd]Cl.CN(C)C1=CC=C(P(C(C)(C)C)C(C)(C)C)C=C1.CN(C)C1=CC=C(P(C(C)(C)C)C(C)(C)C)C=C1 DWOZNANUEDYIOF-UHFFFAOYSA-L 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 239000012362 glacial acetic acid Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 239000012295 chemical reaction liquid Substances 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000012074 organic phase Substances 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract description 13
- 230000005540 biological transmission Effects 0.000 abstract description 8
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 230000004298 light response Effects 0.000 abstract description 2
- 230000007774 longterm Effects 0.000 abstract description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 2
- 230000008569 process Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- BFMYDTVEBKDAKJ-UHFFFAOYSA-L disodium;(2',7'-dibromo-3',6'-dioxido-3-oxospiro[2-benzofuran-1,9'-xanthene]-4'-yl)mercury;hydrate Chemical compound O.[Na+].[Na+].O1C(=O)C2=CC=CC=C2C21C1=CC(Br)=C([O-])C([Hg])=C1OC1=C2C=C(Br)C([O-])=C1 BFMYDTVEBKDAKJ-UHFFFAOYSA-L 0.000 description 3
- 241000282414 Homo sapiens Species 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 230000001235 sensitizing effect Effects 0.000 description 2
- 235000013024 sodium fluoride Nutrition 0.000 description 2
- 239000011775 sodium fluoride Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 241001464837 Viridiplantae Species 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229930002875 chlorophyll Natural products 0.000 description 1
- 235000019804 chlorophyll Nutrition 0.000 description 1
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000029553 photosynthesis Effects 0.000 description 1
- 238000010672 photosynthesis Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Materials Engineering (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Hybrid Cells (AREA)
Abstract
The invention relates to a fluorine-containing dye sensitizer and application thereof, wherein fluorine atom substituent groups are introduced at 3-position, 2-position and 2, 6-position of a pi-bridged benzene ring of triphenylamine dye, and the strong electron-withdrawing effect of fluorine atoms is utilized to increase the efficiency of electron transmission from a donor to an acceptor, thereby improving the photoelectric conversion efficiency of a device. The fluorine-containing dye sensitizer has the advantages of simple synthesis process, wide visible light response range and good long-term stability of the prepared dye-sensitized solar cell.
Description
Technical Field
The invention belongs to the technical field of dye sensitizers, and particularly relates to a fluorine-containing dye sensitizer and application thereof.
Background
With the development of economy, the energy crisis caused by the excessive consumption of human beings and the non-regeneration of fossil energy becomes an important problem to be solved urgently in the human society of the twenty-first century, and the development of novel clean energy is an effective path for solving the energy crisis.
The dye-sensitized solar cell mainly simulates absorption and utilization of chlorophyll in green plants in the nature on visible light through photosynthesis, and a sensitizer is the core of the dye-sensitized solar cell and is the most important part in the cell, and the performance of the sensitizer is decisive for the final device. The structure of the pure organic sensitizing dye is generally D-pi-A type, and the pure organic sensitizing dye is composed of an electron donor (donor), an electron transmission pi-bridge chain and an electron acceptor (anchor). The electron donor is generally an electron-rich group capable of generating electrons under the excitation of sunlight; the pi-bridge chain is a group with a conjugated planar structure, is a transmission channel of electrons, and can also play a role in widening the absorption range of the dye and increasing the molar extinction coefficient; the electron acceptor is generally an electron-deficient group having an anchor group, and accepts the transported electron and injects it into the semiconductor thin film. However, due to the fact that a plurality of conjugated groups are connected, the sizes of a dye molecule donor and a pi-bridge chain are increased, the conjugation degree is increased, photoelectrons can be directly compounded with redox couples in electrolyte in the transmission process due to transverse transmission of electrons, and in addition, TiO is injected2Electrons of the conduction band can overflow and be compounded with redox couples in the electrolyte, so that the dark current of the DSSCs is increased, the transmission of effective electrons is reduced, and the photoelectric conversion efficiency is reduced.
Disclosure of Invention
The invention provides a fluorine-containing dye sensitizer and application thereof, which solve the problems in the prior art.
In order to achieve the purpose, the technical scheme of the invention is as follows:
a fluorine-containing dye sensitizer, said sensitizer having the formula:
wherein R is1、R2、R3And R4Each represents a hydrogen atom or a fluorine atom.
Further, the structural formula of the sensitizer is as follows:
further, the structural formula of the sensitizer is as follows:
further, the structural formula of the sensitizer is as follows:
a preparation method of a fluorine-containing dye sensitizer comprises the following synthetic route:
further, the preparation method comprises the following steps:
preparation of Compound c
Mixing compound a, compound b, tetrabutylammonium bromide and Pd (amphos) Cl2Adding a catalyst and NaF into a mixed solution of N, N-dimethylformamide and distilled water according to a molar ratio of 1:1.3:0.5:0.02:3, reacting for 5 hours at 75 ℃, stopping the reaction, cooling the reaction solution to room temperature, pouring the reaction solution into dichloromethane, washing the dichloromethane to be neutral, drying an organic phase by anhydrous magnesium sulfate, filtering, concentrating under reduced pressure, and purifying to prepare a compound c;
preparation of fluorine-containing dye sensitizer d
Under the protection of nitrogen, adding the compound c, cyanoacetic acid and ammonium acetate into glacial acetic acid according to the molar ratio of 1:3:3, stirring, carrying out reflux reaction for 5 hours, stopping the reaction, pouring the reaction liquid into distilled water to separate out a solid, filtering, and purifying to prepare the fluorine-containing dye sensitizer d.
The fluorine-containing dye sensitizer is applied to the preparation of dye-sensitized solar cells.
Compared with the prior art, the invention has the following beneficial effects:
fluorine atom substituent groups are introduced at 3-position, 2-position and 2, 6-position of a pi-bridged chain benzene ring of the triphenylamine dye, and the efficiency of electron transmission from a donor to an acceptor is increased by utilizing the strong electron-withdrawing action of fluorine atoms, so that the photoelectric conversion efficiency of a device is improved.
The fluorine-containing dye sensitizer has the advantages of simple synthesis process, wide visible light response range and good long-term stability of the prepared dye-sensitized solar cell.
Drawings
FIG. 1 is a UV-visible absorption spectrum of three fluorochrome sensitizers in methylene chloride solution;
figure 2 is a current-voltage curve for a dye-sensitized solar cell device based on three fluorine-containing dye sensitizers.
Detailed Description
To facilitate an understanding of the invention, the invention will now be described more fully with reference to the accompanying drawings. Preferred embodiments of the present invention are shown in the drawings. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
The fluorine-containing dye sensitizer introduces fluorine atoms into a pi-bridge chain part of triphenylamine dye, accelerates the transmission of electrons through the strong electron-withdrawing action of the fluorine atoms, improves the photoelectric conversion efficiency, and has the following structural general formula:
wherein R is1、R2、R3And R4Each represents a hydrogen atom (H) or a fluorine atom (F).
Example 1:
the 3-position fluorine substituted dye sensitizer I is synthesized by the following specific synthetic route and method:
1. preparation of Compound f
Into a 150mL three-necked flask were charged 0.50g (1.10mmol) of Compound a, 30mL of N, N-dimethylformamide, 0.40g (1.40mmol) of Compound e, and 20.0mg (22.0. mu. mol) of Pd (Amphos) Cl2Catalyst, 0.17g (0.54mmol) tetrabutylammonium bromide, dissolving 0.14g (3.30mmol) sodium fluoride in 5mL water, finally stirring uniformly, slowly dropping, reacting at 75 ℃ for 5h, stopping the reaction, adding 200mL dichloromethane, washing to neutrality, drying over anhydrous magnesium sulfate, rotary steaming to obtain a crude product, and finally purifying by column chromatography (developer EA: PE ═ 1:6(v/v)) to obtain 0.58g of orange viscous solid with the yield of 86.0%.
The nuclear magnetic data of the prepared compound f are:1H NMR(600MHz,CDCl3)δ9.94(s,1H),7.78(t,J＝7.6Hz,1H),7.68–7.61(m,3H),7.59(d,J＝3.5Hz,1H),7.44(d,J＝6.5Hz,2H),7.20–6.92(m,6H),6.85(d,J＝8.5Hz,4H),3.98(t,J＝6.6Hz,4H),1.85(dp,J＝13.4,6.7Hz,2H),1.69(q,J＝6.7Hz,4H),0.98(d,J＝6.7Hz,12H).
2. preparation of 3-position fluorine substituted dye sensitizer I
30mL of glacial acetic acid, 0.30g (0.48mmol) of compound f, 0.12g (1.50mmol) of cyanoacetic acid and 0.11g (1.50mmol) of ammonium acetate are sequentially added into a 150mL three-neck flask, the reaction is stopped after refluxing for 5 hours, the reaction solution is slowly dropped into water and continuously stirred, a solid is observed to be precipitated in the water, a crude product is obtained by filtration, and finally, the crude product is purified by column chromatography (a developing agent EA: PE: 1:2(v/v), 5% acetic acid) to obtain 0.24g of dark brown solid powder, wherein the yield is 73.0%.
The nuclear magnetic data of the prepared 3-position fluorine substituted dye sensitizer I is as follows:1H NMR(600MHz,DMSO-d6)δ8.31(s,1H),8.02–7.94(m,3H),7.75(d,J＝3.9Hz,1H),7.50(d,J＝8.7Hz,2H),7.42(d,J＝2.7Hz,1H),7.02(d,J＝8.9Hz,4H),6.91(d,J＝9.0Hz,4H),6.76(d,J＝8.8Hz,2H),3.95(t,J＝6.6Hz,4H),1.78(dp,J＝13.4,6.7Hz,2H),1.60(q,J＝6.7Hz,4H),0.93(d,J＝6.7Hz,12H).
example 2:
the specific synthetic route and the method for synthesizing the 2-position fluorine substituted dye sensitizer II are as follows:
in step 1 of example 1, compound e was substituted with an equimolar amount of compound g to synthesize compound h, and the other steps were the same as in example 1 to prepare a 2-position fluorine-substituted dye sensitizer II.
The nuclear magnetic data of the prepared 2-position fluorine substituted dye sensitizer II are as follows:1H NMR(600MHz,DMSO-d6)δ8.29(s,1H),7.76(d,J＝3.9Hz,1H),7.69(dd,J＝12.0,1.5Hz,1H),7.66(d,J＝9.5Hz,1H),7.47(d,J＝8.8Hz,2H),7.39(d,J＝3.9Hz,1H),7.02(d,J＝8.9Hz,4H),6.90(d,J＝9.0Hz,4H),6.75(d,J＝8.8Hz,2H),3.95(t,J＝6.6Hz,4H),1.78(dp,J＝13.4,6.7Hz,2H),1.60(q,J＝6.7Hz,4H),0.93(d,J＝6.7Hz,12H).
example 3:
the specific synthetic route and the method for synthesizing the 2, 6-fluorine substituted dye sensitizer III are as follows:
in step 1 of example 1, compound j was synthesized by replacing compound e with equimolar compound i, and the other steps were the same as in example 1 to prepare a 2, 6-fluoro-substituted Y-type alkyl chain sensitizer iii.
The nuclear magnetic data of the prepared 2, 6-fluoro-substituted Y-type alkyl chain sensitizer III are as follows:1H NMR(600MHz,DMSO-d6)δ8.15(s,1H),7.82(d,J＝3.9Hz,1H),7.61(d,J＝10.0Hz,2H),7.49(d,J＝8.7Hz,2H),7.42(d,J＝3.9Hz,1H),7.03(d,J＝8.9Hz,4H),6.92(d,J＝8.9Hz,4H),6.76(d,J＝8.7Hz,2H),3.96(t,J＝6.6Hz,4H),1.78(dp,J＝13.4,6.7Hz,2H),1.60(q,J＝6.7Hz,4H),0.93(d,J＝6.7Hz,12H).
ultraviolet-visible absorption performance tests were performed on methylene chloride solutions of three fluorochrome sensitizers using an ultraviolet-visible spectrophotometer (shimadzu UV-2250), and the results are shown in fig. 1, where it can be seen that there are two distinct absorption bands in the ultraviolet-visible absorption spectra of the three sensitizers.
Example 4:
three fluorine-containing dye sensitizers obtained in example 1, example 2, and example 3 were prepared into dye-sensitized Solar cells, and the prepared Solar cells were tested using a J-V characteristic testing System (QTest definition 5 Solar Cell IPCE test System), and the results are shown in table 1.
Table 1 solar cell performance test results
FIG. 1 is a graph of the UV-visible absorption spectra of three fluorochrome sensitizers of example 1, example 2, and example 3 in methylene chloride solution; fig. 2 is a current-voltage curve of a dye-sensitized solar cell device based on three fluorine-containing dye sensitizers of example 1, example 2, and example 3.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (7)
1. A fluorine-containing dye sensitizer, characterized in that the structural formula of the sensitizer is as follows:
wherein R is1、R2、R3And R4Each represents a hydrogen atom or fluorineAn atom.
2. The fluorine-containing dye sensitizer of claim 1, wherein said sensitizer has the following structural formula:
3. the fluorine-containing dye sensitizer of claim 1, wherein said sensitizer has the following structural formula:
4. the fluorine-containing dye sensitizer of claim 1, wherein said sensitizer has the following structural formula:
5. the preparation method of the fluorine-containing dye sensitizer is characterized in that the synthetic route is as follows:
6. the method of preparing a fluorine-containing dye sensitizer according to claim 6, wherein the method comprises the steps of:
preparation of Compound c
Mixing compound a, compound b, tetrabutylammonium bromide and Pd (amphos) Cl2Adding a catalyst and NaF into a mixed solution of N, N-dimethylformamide and distilled water according to the molar ratio of 1:1.3:0.5:0.02:3Reacting at 75 ℃ for 5 hours, stopping the reaction, cooling the reaction solution to room temperature, pouring the reaction solution into dichloromethane, washing the reaction solution to be neutral, drying an organic phase by anhydrous magnesium sulfate, filtering, concentrating under reduced pressure, and purifying to prepare a compound c;
preparation of fluorine-containing dye sensitizer d
Under the protection of nitrogen, adding the compound c, cyanoacetic acid and ammonium acetate into glacial acetic acid according to the molar ratio of 1:3:3, stirring, carrying out reflux reaction for 5 hours, stopping the reaction, pouring the reaction liquid into distilled water to separate out a solid, filtering, and purifying to prepare the fluorine-containing dye sensitizer d.
7. Use of the fluorine-containing dye sensitizer according to claim 1 for the preparation of dye-sensitized solar cells.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100076205A1 (en) * | 2008-09-25 | 2010-03-25 | Academia Sinica | Dye compound and dye-sensitized solar cell |
| CN108440988A (en) * | 2018-03-06 | 2018-08-24 | 西安工业大学 | A kind of polynitrogen heterocycle supermolecule sensitizer and its application |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100076205A1 (en) * | 2008-09-25 | 2010-03-25 | Academia Sinica | Dye compound and dye-sensitized solar cell |
| CN108440988A (en) * | 2018-03-06 | 2018-08-24 | 西安工业大学 | A kind of polynitrogen heterocycle supermolecule sensitizer and its application |
Non-Patent Citations (3)
| Title |
|---|
| MILAN KLIKAR 等: "Dipolar NLO Chromophores Bearing Diazine Rings as π‑Conjugated Linkers", 《JOURNAL OF ORGANIC CHEMISTRY》 * |
| SHI-BIN WANG 等: "Efficient triphenylamine photosensitizers with alkoxy- or fluorinesubstituted phenylene spacer for dye-sensitized solar cells", 《JOURNAL OF MATERIALS SCIENCE》 * |
| 卢冰洋: "胆固醇共敏太阳能电池研究及Y型烷基链染料的合成", 《工程科技II辑》 * |
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