CN113200957B - Acid/alkali dye co-sensitization system and preparation method and application thereof - Google Patents
Acid/alkali dye co-sensitization system and preparation method and application thereof Download PDFInfo
- Publication number
- CN113200957B CN113200957B CN202110382709.2A CN202110382709A CN113200957B CN 113200957 B CN113200957 B CN 113200957B CN 202110382709 A CN202110382709 A CN 202110382709A CN 113200957 B CN113200957 B CN 113200957B
- Authority
- CN
- China
- Prior art keywords
- dye
- acid
- small molecule
- compound
- basic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000002253 acid Substances 0.000 title claims abstract description 25
- 239000003513 alkali Substances 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 206010070834 Sensitisation Diseases 0.000 title claims abstract description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 47
- 150000003384 small molecules Chemical class 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000000243 solution Substances 0.000 claims description 19
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 239000012074 organic phase Substances 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000011259 mixed solution Substances 0.000 claims description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 230000002829 reductive effect Effects 0.000 claims description 4
- 238000002390 rotary evaporation Methods 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- IQTHEAQKKVAXGV-UHFFFAOYSA-N 4-ditert-butylphosphanyl-n,n-dimethylaniline Chemical compound CN(C)C1=CC=C(P(C(C)(C)C)C(C)(C)C)C=C1 IQTHEAQKKVAXGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 239000012153 distilled water Substances 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 abstract description 12
- 230000000295 complement effect Effects 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- 238000001179 sorption measurement Methods 0.000 abstract description 3
- 230000036963 noncompetitive effect Effects 0.000 abstract description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 44
- 230000002378 acidificating effect Effects 0.000 description 7
- 238000012360 testing method Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003775 Density Functional Theory Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical compound [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/10—The polymethine chain containing an even number of >CH- groups
- C09B23/105—The polymethine chain containing an even number of >CH- groups two >CH- groups
-
- 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
- H01G9/2022—Light-sensitive devices characterized by he counter electrode
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Materials Engineering (AREA)
- Hybrid Cells (AREA)
Abstract
The invention relates to an acid/alkali dye co-sensitive system, a preparation method and application thereof, wherein the system is a co-sensitive system of an acid micromolecule dye and a basic micromolecule dye, and the structural formula of the co-sensitive system is as follows:
wherein n-1 is
n-2 is
The acid/alkali dye co-sensitization system can be applied to co-sensitized TiO2A photo-anode; the acid/alkali dye co-sensitive system has the advantage of non-competitive adsorption, and when the acid/alkali organic dye is co-sensitive, the ultraviolet absorption on the photo-anode can have a good complementary absorption effect.
Description
Technical Field
The invention belongs to the technical field of organic sensitizers, and particularly relates to an acid/alkali dye co-sensitization system and a preparation method and application thereof.
Background
With the rapid development of high technology in recent years, the contradiction between the increasing energy demand and the increasingly depleted energy reserves on the earth has become more and more severe. Therefore, governments around the world are all focusing on the development and utilization of new energy. Solar energy is inexhaustible new energy, and the development and utilization of the solar energy become the most active field in the present generation. However, how to efficiently convert solar energy into electric energy becomes the core of this issue.
The dye-sensitized solar cell is prepared by using low-cost nano titanium dioxide and a sensitizer as main raw materials and converting solar energy into electric energy. Among them, the sensitizer is called as a photon motor of a solar cell, and is a key for capturing light energy, and the quality of the performance directly determines the photoelectric conversion efficiency of the cell. And the absorption of a single dye sensitizer on the photo-anode often causes low photoelectric conversion efficiency due to the defects of intermolecular aggregation, narrow light absorption range, desorption phenomenon and the like, and brings great obstruction to the development of organic dye-sensitized solar cells. Therefore, a co-sensitive adsorbent which can be used for co-sensitizing with organic dye and has no competitive adsorption is searched for the photoanode of the dye-sensitized solar cell so as to achieve the purpose of ultraviolet absorption complementation to improve the photoelectric conversion efficiency.
Disclosure of Invention
The invention aims to provide an acid/alkali dye co-sensitive system, a preparation method and application thereof, and solves the problem that the current dye sensitizer is low in photoelectric conversion efficiency.
In order to achieve the purpose, the technical scheme of the invention is as follows:
an acid/alkali dye co-sensitive system is a co-sensitive system of an acid micromolecule dye and a basic micromolecule dye, and the structural formula of the co-sensitive system is as follows:
wherein n-1 is
n-2 is
Further, the synthetic route of the basic small molecule dye is as follows:
further, the preparation process of the basic small molecule dye is as follows:
adding a compound a, a compound b, tetrabutylammonium bromide, a catalyst, namely bis (di-tert-butyl-4-dimethylaminophenylphosphine) palladium chloride and NaF into a mixed solution of N, N-dimethylformamide and distilled water according to a molar ratio of 1:1.2:2.5:0.02:3, reacting for 8 hours at 75 ℃, stopping the reaction, cooling the reaction solution to room temperature, pouring the reaction solution into dichloromethane, washing the dichloromethane to neutrality, separating an organic phase, concentrating under reduced pressure, and purifying to prepare a compound c;
under vacuum conditions, compound c, compound d, in a molar ratio of 1: 2 adding the mixture into an acetic anhydride solution, reacting for 24 hours at 140 ℃, stopping the reaction, pouring the reaction solution into a saturated potassium hydroxide aqueous solution, adding dichloromethane, stirring, separating an organic phase, performing rotary evaporation, and purifying to obtain the basic micromolecule dye.
The acid/alkali dye co-sensitive system is applied to the preparation of a novel photo-anode of a solar cell; that is, it is a TiO co-sensitized with an acidic small molecule dye and a basic small molecule dye2And a photo-anode.
Compared with the prior art, the invention has the following beneficial effects:
1. the acid/alkali dye co-sensitive system has the advantage of non-competitive adsorption.
2. When the acid/alkali organic dye is co-sensitive, the ultraviolet absorption on the photo-anode can have good complementary absorption effect.
Drawings
FIG. 1 shows the UV absorption spectrum of the basic small molecule dye I, the acidic small molecule dye NP-1 and the mixture of the basic small molecule dye I and the acidic small molecule dye NP-1 in the dichloromethane solution, which are prepared in example 1.
FIG. 2 is the ultraviolet absorption spectrum of the basic small molecule dye II, the acidic small molecule dye NP-1 and the mixture of the basic small molecule dye II and the acidic small molecule dye NP-1 in the dichloromethane solution prepared in example 2.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention clearer, the present invention will be described in further detail with reference to embodiments, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
An acid/alkali dye co-sensitive system is a co-sensitive system of an acid micromolecule dye and a basic micromolecule dye, and the structural formula of the co-sensitive system is as follows:
wherein n-1 is
n-2 is
The basic small molecule dye is preferably shown as formula I or formula II, and respectively:
example 1:
in this embodiment, the specific synthetic route of the synthetic basic small molecule dye i is as follows:
the preparation method comprises the following specific steps:
s1 preparation of Compound c
1.50g of the compound a (5.19mmol), 1.19g of the compound b (6.23mmol) and 0.836g of tetrabutylammonium bromide (2.59mmol) are sequentially added into a 150mL three-neck flask with a thermometer, 20mL of solvent N, N-dimethylformamide is then added, a catalyst of 93.69mg of bis (di-tert-butyl-4-dimethylaminophenylphosphine) palladium chloride (0.104mmol) is added, after the reaction solution is stirred uniformly, 5mL of aqueous solution of NaF (0.15mmol) is slowly dropped, the reaction system reacts for 5.5 hours at 75 ℃, dichloromethane is then washed with water, an organic phase is separated and rotary evaporated to obtain a crude product, and the crude product is purified by column chromatography (a developing agent is a mixed solution of ethyl acetate and petroleum ether with the volume ratio of 1: 10, and a filler is 200-300 mesh silica gel) to obtain 0.8g of the compound c, and the yield is 53.5%.
S2 preparation of basic small molecular dye I
And sequentially adding 0.65g of the compound c (1.83mmol) and 0.596g of the compound d (6.4mmol) into a 25mL sealed tube filled with magnetons, adding 5mL of acetic anhydride, vacuumizing, heating and refluxing for 24 hours, pouring a reaction solution into 100mL of ice water, adding 100mL of saturated potassium hydroxide aqueous solution, adding 50mL of dichloromethane, stirring for 30 minutes, analyzing an organic phase, carrying out reduced pressure rotary evaporation, and purifying by column chromatography (a developing agent is a mixed solution of ethanol and dichloromethane in a volume ratio of 1: 5, and a filler is 200-300-mesh silica gel) to obtain 0.13g of the basic micromolecular dye I, wherein the yield is 29.23%.
The nuclear magnetic data of the prepared basic micromolecular dye I are as follows:1H NMR(600MHz,CDCl3)δ8.46(d,J＝3.6Hz,2H),7.38(d,J＝8.6Hz,2H),7.28(d,J＝16.0Hz,1H),7.21–7.16(m,6H),7.05–7.03(m,5H),6.99–6.95(m,5H),6.68(d,J＝16.0Hz,1H)。
example 2:
in this embodiment, taking the synthesis of basic small molecule dye ii as an example, the specific synthetic route is as follows:
the preparation method comprises the following specific steps:
in this example, a basic small molecule dye ii was prepared in the same manner as in example 1 except that the compound b used in this example was replaced with an equimolar amount of the compound e.
And sequentially putting 0.3g of the compound b (0.686mmol) and 0.096g of 4-methylpyridine (1.03mmol) into a 25mL sealed tube filled with magnetons, adding 5mL of acetic anhydride, vacuumizing, heating and refluxing for 24 hours, pouring a reaction solution into 100mL of ice water, adding 100mL of saturated potassium hydroxide aqueous solution, adding 50mL of dichloromethane, stirring for 30min, analyzing an organic phase, carrying out reduced pressure rotary evaporation, and purifying by column chromatography (a developing agent is a mixed solution of ethanol and dichloromethane in a volume ratio of 1: 5, and a filler is 200-300-mesh silica gel) to obtain 0.1g of the compound c, wherein the yield is 28.6%.
The nuclear magnetic data of the prepared basic micromolecular dye II are as follows:1H NMR(600MHz,CDCl3)δ8.47(d,J＝3.6Hz,2H),7.37(d,J＝8.7Hz,2H),7.28(d,J＝16.0Hz,1H),7.21–7.17(m,6H),7.06–7.03(m,6H),6.99–6.97(m,6H),6.67(d,J＝16.0Hz,1H).
to prove the beneficial effects of the invention, the inventors dissolved the basic small molecular dyes I and II prepared in examples 1 and 2 in dichloromethane to prepare 1 × 10-5A co-sensitive adsorbent solution of mol/L. The solution was subjected to an ultraviolet absorption test using an ultraviolet visible near infrared tester (model number UV-2250, manufactured by Shimadzu corporation, Japan). The detection result shows that the maximum absorption wavelength is 410nm and 438nm respectively, and the molar absorption coefficient is 38600M-1cm-1And 39000M-1cm-1。
Will be 1 × 10-5methylene chloride solution of mol/L basic small molecular dye I, II and 1X 10-5mixing mol/L of NP-1 dichloromethane solution according to a volume ratio of 4:6, and carrying out an ultraviolet absorption test on the solution by adopting an ultraviolet visible near-infrared tester. Test results show that the basic micromolecular dyes I and II and the acidic micromolecular dye NP-1 achieve good complementary absorption effect in ultraviolet absorption spectrum.
The acid small molecule dye comprises the following components:
the three-dimensional configurations and the molecular sizes of the basic micromolecule dyes I and II and the acidic micromolecule dye NP-1 are respectively obtained by adopting density functional theory calculation through Gaussian 03 software (RB3LYP/6-311G (d, p) level)
And
the acid/alkali co-sensitizer has a better molecular matching structure.
A comparison test was carried out with the basic small-molecule dyes I, II of example 1 and example 2. The prepared Solar Cell was tested using a J-V characteristic test System (QTest height 5Solar Cell IPCE test System) and the results are shown in Table 1, and the ultraviolet absorption results are shown in FIGS. 1 and 2.
Table 1 solar cell performance test results
As can be seen from table 1, the use of an acid/base in combination with a photoanode in a volume ratio of 4: the photoelectric conversion efficiency of the solar cell prepared after 6 sensitization is respectively improved by 95.5 percent and 70.9 percent.
The present invention has been described in terms of specific examples, which are provided to aid understanding of the invention and are not intended to be limiting. Any partial modification or replacement within the technical scope of the present disclosure by a person skilled in the art should be included in the scope of the present disclosure.
Claims (4)
1. The acid and alkali dye co-sensitization system is characterized by comprising an acid small molecule dye and a basic small molecule dye, wherein the acid small molecule dye has the following structural formula:
the structural formula of the basic micromolecular dye is as follows:
wherein n is 1 or 2.
2. The acid and alkali dye co-sensitization system according to claim 1, wherein the basic small molecule dye is synthesized by the following route:
3. the acid and alkali dye co-sensitization system according to claim 2, wherein the basic small molecule dye is prepared by the following process:
adding a compound a, a compound b, tetrabutylammonium bromide, a catalyst, namely bis (di-tert-butyl-4-dimethylaminophenylphosphine) palladium chloride and NaF into a mixed solution of N, N-dimethylformamide and distilled water according to a molar ratio of 1:1.2:2.5:0.02:3, reacting for 8 hours at 75 ℃, stopping the reaction, cooling the reaction solution to room temperature, pouring the reaction solution into dichloromethane, washing the dichloromethane to neutrality, separating an organic phase, concentrating under reduced pressure, and purifying to prepare a compound c;
under vacuum conditions, compound c, compound d, in a molar ratio of 1: 2 adding the mixture into an acetic anhydride solution, reacting for 24 hours at 140 ℃, stopping the reaction, pouring the reaction solution into a saturated potassium hydroxide aqueous solution, adding dichloromethane, stirring, separating an organic phase, performing rotary evaporation, and purifying to obtain the basic micromolecule dye.
4. Use of the acid and base dye co-sensitization system according to claim 1 for the preparation of a solar cell photo-anode.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110382709.2A CN113200957B (en) | 2021-04-09 | 2021-04-09 | Acid/alkali dye co-sensitization system and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110382709.2A CN113200957B (en) | 2021-04-09 | 2021-04-09 | Acid/alkali dye co-sensitization system and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN113200957A CN113200957A (en) | 2021-08-03 |
| CN113200957B true CN113200957B (en) | 2022-02-22 |
Family
ID=77026528
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110382709.2A Active CN113200957B (en) | 2021-04-09 | 2021-04-09 | Acid/alkali dye co-sensitization system and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113200957B (en) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20080104616A (en) * | 2007-05-28 | 2008-12-03 | 주식회사 동진쎄미켐 | Novel organic dye and preparation thereof |
| CN101821250A (en) * | 2007-10-15 | 2010-09-01 | 株式会社东进世美肯 | Novel thiophene dye and preparation method thereof |
| CN102212274A (en) * | 2011-04-11 | 2011-10-12 | 天津理工大学 | Triphenylamine-phenyl organic dye and application thereof |
| CN103003903A (en) * | 2010-06-29 | 2013-03-27 | 迪纳莫公司 | High efficiency dye-sensitized solar cells |
| KR20190107866A (en) * | 2018-03-13 | 2019-09-23 | 울산과학기술원 | Organic dyes, compositions and dye-sensitized solar cell |
| CN110423486A (en) * | 2019-07-25 | 2019-11-08 | 南京理工大学 | Triphen amine organic dyestuff and its synthetic method |
-
2021
- 2021-04-09 CN CN202110382709.2A patent/CN113200957B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20080104616A (en) * | 2007-05-28 | 2008-12-03 | 주식회사 동진쎄미켐 | Novel organic dye and preparation thereof |
| CN101821250A (en) * | 2007-10-15 | 2010-09-01 | 株式会社东进世美肯 | Novel thiophene dye and preparation method thereof |
| CN103003903A (en) * | 2010-06-29 | 2013-03-27 | 迪纳莫公司 | High efficiency dye-sensitized solar cells |
| CN102212274A (en) * | 2011-04-11 | 2011-10-12 | 天津理工大学 | Triphenylamine-phenyl organic dye and application thereof |
| KR20190107866A (en) * | 2018-03-13 | 2019-09-23 | 울산과학기술원 | Organic dyes, compositions and dye-sensitized solar cell |
| CN110423486A (en) * | 2019-07-25 | 2019-11-08 | 南京理工大学 | Triphen amine organic dyestuff and its synthetic method |
Non-Patent Citations (3)
| Title |
|---|
| Aggregation-Induced Emission Luminogens Married to 2D Black Phosphorus Nanosheets for Highly Efficient Multimodal Theranostics;Jiachang Huang 等;《Advanced Materials》;20200806;第32卷(第37期);全文 * |
| Large Enhancement of Dye Sensitized Solar Cell Efficiency by Cosensitizing Pyridyl- and Carboxylic Acid-Based Dyes;Hamsa M. Hilal 等;《ACS Applied Energy Materials》;20180314;第1卷(第6期);全文 * |
| Theoretical study on the correlations between dye–iodine interactions and open-circuit voltages in dyes containing furan and thiophene;Mannix P. Balanay 等;《Computational and Theoretical Chemistry》;20140201;第1029卷;全文 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN113200957A (en) | 2021-08-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110183437B (en) | Double D-pi-A type column [5] arene dye and synthetic method and application thereof | |
| CN106433187B (en) | A kind of organic dyestuff based on four Thienopyrroles and its preparation method and application | |
| CN103554957A (en) | Triphenylamine-thiophene organic dyestuff as well as preparation method and application thereof | |
| US7538217B1 (en) | Ruthenium complex | |
| CN109694464A (en) | A kind of N-shaped organic semiconducting materials and its preparation method and application | |
| CN102093367A (en) | Preparation method of spiro quaternary ammonium salt for organic electrolyte of super capacitor | |
| CN103554958A (en) | Dithiophene pyrrole bridge-indoline organic dyes as well as preparation method and application thereof | |
| CN112409190A (en) | Method for efficiently synthesizing cyclic carbonate by using amine salt ionic liquid as catalyst | |
| CN113200957B (en) | Acid/alkali dye co-sensitization system and preparation method and application thereof | |
| CN104163785A (en) | A series of asymmetric squarine micromolecules containing indoline derivative structure, and application thereof | |
| CN108976249B (en) | Preparation method of cycloindene corrole-fullerene star-shaped compound | |
| CN110922392B (en) | Carbazole co-sensitizer with phenyl as terminal bridge chain and preparation method thereof | |
| CN115304529B (en) | Ligand, metal organic framework material and application thereof, and perovskite solar cell | |
| CN103992658B (en) | A kind of triphen amine organic dye of thiocarbamide functionalization and application thereof | |
| CN104672237B (en) | Based on phenanthroline for electron acceptor organic photosensitive dyestuff and preparation method and application | |
| CN113999217B (en) | New compound, preparation method and application thereof as co-sensitizer | |
| CN108219512B (en) | Indoline-quinoxaline-dithieno quinoxaline dyestuff and its application in dye-sensitized solar cells | |
| CN106810898B (en) | Organic dye sensitized dose of the triphen amine of pyrroles's dithione modification and its application | |
| CN111100099B (en) | Triphenylamine co-sensitizer with phenyl as tail-end bridge chain and preparation method thereof | |
| CN110343100B (en) | Phenothiazine co-sensitizer and preparation method and application thereof | |
| CN105153182B (en) | A kind of Dihydrobenzofuranes C of 5 alkyl 2,360Fullerene double adduct and its production and use | |
| CN110627667B (en) | Dumbbell-type hole transport material, synthesis method and perovskite solar cell | |
| CN109942572B (en) | V-type organic dye sensitizer and preparation method and application thereof | |
| CN108623595B (en) | A kind of monocrystal, preparation method and its application of loop coil aromatic condensed ring imide analog compounds | |
| CN113429431A (en) | Star-shaped compound of BODIPY (BODIPY) bridged triperylene diimide derivative and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |