A platinum-containing carbazole compound and its preparation method and co-sensitization application
By synthesizing carbazole compounds containing metal platinum and cosensitizing N719, the problem of unsatisfactory photoelectric conversion efficiency of existing metal complex dye sensitizers is solved, and a higher photoelectric conversion efficiency is achieved, and a dye-sensitized solar cells are achieved. New co-sensitizers are provided.
Patent Information
- Application Number
- CN202211704593.0
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2022-12-29
- Publication Date
- 2025-02-18
- Estimated Expiration
- 2042-12-29
AI Technical Summary
The photoelectric conversion efficiency of existing metal complex dye sensitizers in dye-sensitized solar cells is not ideal, and there is a lack of new applicable cosensitizers.
By designing and synthesizing carbazole compounds containing metal platinum, co-sensitizing with classic N719, assembled into dye-sensitized solar cells.
The photoelectric conversion efficiency of dye-sensitized solar cells is improved, and new applicable substances are provided for the cosensitizer screening of N719.
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Figure CN116239633B_ABST
Abstract
Description
Technical Field
[0001] The invention relates to a carbazole compound containing metal platinum and a preparation method and co-sensitization application thereof. Background Art
[0002] In recent years, dye-sensitized solar cells (DSSCs) have attracted extensive attention from researchers, among which dye sensitizers are an important component of DSSCs. Dye sensitizers can be divided into natural dyes, metal complex dyes and non-metallic organic dyes. Compared with natural dyes and non-metallic organic dyes, metal complex dyes have high photoelectric conversion efficiency, good stability and relatively long electron lifetime.
[0003] Most metal complex dyes are ruthenium complexes, using bipyridine or similar structures as ligands. The molecular structures of other metal sensitizers are mostly similar to ruthenium dyes. For example, when platinum complexes were first studied as sensitizers, bipyridine was used as a ligand, but the photoelectric conversion efficiency was not ideal. Subsequently, researchers began to look for ligands other than bipyridine to design and synthesize platinum complex sensitizers. The researchers designed the D-π-M-π-A type platinum metal dye sensitizer based on the D-π-A type structure of non-metallic organic sensitizers, and its photoelectric conversion efficiency was improved.
[0004] As an important linker part, platinum acetylene unit has been widely studied in the field of functional materials science due to its unique π-conjugated properties. In addition, platinum acetylene unit is also widely used in polymer solar cells, sensitized solar cells and other fields. However, there are no corresponding reports on carbazole compounds containing metal platinum and their applications. Summary of the invention
[0005] The purpose of the present invention is to provide a platinum-containing carbazole compound and a preparation method and application thereof. The platinum-containing carbazole compound can be used as a dye sensitizer. The assembled dye-sensitized solar cell has good photoelectric conversion efficiency, which adds new applicable substances to the screening of dye sensitizers.
[0006] The present invention discloses a carbazole compound containing metal platinum, the molecular structure of which is shown in formula (I);
[0007]
[0008] In formula (I), Ar is an aromatic heterocyclic ring, preferably a benzene ring, furan or thiophene, and A is
[0009] The present invention also discloses a method for preparing a carbazole compound containing metal platinum, which specifically comprises: dissolving a compound represented by formula (II) and cyanoacetic acid or rhodanine-3-acetic acid in a solvent, adding an alkaline substance, heating under reflux and stirring to react under the protection of a nitrogen atmosphere, concentrating the reaction liquid to remove the solvent after the reaction is completed, dissolving the obtained concentrate in an eluent, separating and purifying it through column chromatography silica gel, collecting the eluent and evaporating the eluent to obtain the target product;
[0010] The structural formula of the compound shown in formula (II) is as follows:
[0011]
[0012] In formula (II), Ar is an aromatic heterocyclic ring, preferably a benzene ring, furan or thiophene.
[0013] Furthermore, the present invention also discloses that the time of heating, reflux and stirring reaction is 10-16 hours.
[0014] Furthermore, the invention also discloses that the solvent is a mixed solvent consisting of chloroform and acetonitrile.
[0015] Furthermore, the present invention also discloses that the eluent is a mixed solvent consisting of dichloromethane, methanol and acetic acid, and the volume ratio of the dichloromethane, methanol and acetic acid is 200:5:1.
[0016] Furthermore, the present invention also discloses that the molar ratio of the compound represented by formula (II), cyanoacetic acid or rhodanine-3-acetic acid, and the alkaline substance is 1:3-5:8-12, preferably 1:4:10.
[0017] Furthermore, the present invention also discloses that the alkaline substance is piperidine.
[0018] Furthermore, the present invention also discloses that the ratio of the amount of substance of the compound represented by formula (II) to the volume of the solvent is 1:15-45, the unit of the amount of substance is mmol, and the unit of volume is mL.
[0019] Furthermore, the present invention also discloses a method for synthesizing the compound represented by formula (II), which is as follows:
[0020] 9-Butyl-3-alkynylcarbazole, cuprous iodide and the compound represented by formula (III) are added into a Shrek tube, and tetrahydrofuran and triethylamine are added under nitrogen protection, and the reaction is carried out at room temperature. After the reaction is completed, the solvent is dried by spin-drying, extracted with ethyl acetate, washed with saturated brine, the organic phase is dried over anhydrous sodium sulfate, and the solvent is dried by spin-drying; the residue is purified by column chromatography to obtain the compound represented by formula (II).
[0021] The structure of the compound shown in formula (III) is as follows:
[0022]
[0023] In formula (III), Ar is an aromatic heterocyclic ring, preferably a benzene ring, furan or thiophene.
[0024] Furthermore, the present invention also discloses the synthesis of the compound represented by formula (II), wherein the eluent is petroleum ether and ethyl acetate in a volume ratio of 10-20:1, wherein the column chromatography separation process is as follows: the concentrate is dissolved in the eluent and then separated and purified by column chromatography silica gel, the eluent is collected and the eluent is evaporated to remove the eluent, and the solid powder product is obtained by drying, namely the compound represented by formula (II), and the reaction process is as follows:
[0025]
[0026] Furthermore, the present invention also discloses the application of a carbazole compound containing metal platinum in a dye sensitizer.
[0027] By adopting the above technology, compared with the prior art, the beneficial effects of the present invention are as follows: the present invention synthesizes a carbazole compound containing metal platinum by using N-n-butyl carbazole as a donor, aromatic heterocycles such as thiophene, furan and benzene ring containing platinum acetylene as a bridge bond, and cyanoacetic acid or rhodanine-3-acetic acid as an acceptor. The carbazole compound containing metal platinum can be used for co-sensitization with the classic metal dye sensitizer N719. The dye-sensitized solar cell assembled with the compound and N719 as dye sensitizers has good photoelectric conversion efficiency, which adds new applicable substances to the screening of co-sensitizers for N719. DETAILED DESCRIPTION
[0028] The present invention will be further described below in conjunction with specific embodiments, but the protection scope of the present invention is not limited thereto.
[0029] Example 1 Synthesis of the compound represented by formula (I-1):
[0030]
[0031] 1) Synthesis of the compound represented by formula (III-1)
[0032] Weigh cis-di(tri-n-butylphosphine)platinum dichloride (273.2 mg, 0.4 mmol), 5-ethynylthiophene-2-aldehyde (20.6 mg, 0.2 mmol) and cuprous iodide (7.7 mg, 0.04 mmol) into a Shrek bottle, evacuate and backfill with nitrogen, repeat the operation three times. Add dichloromethane (5 mL) and triethylamine (5 mL), stir at 15 ° C for 4 h. After the reaction is completed, extract with dichloromethane, wash the organic layer with saturated brine, dry with anhydrous sodium sulfate, remove the solvent by rotary evaporation, and purify by column chromatography to obtain 180.6 mg of yellow-brown liquid III-1, with a yield of 58.6%.
[0033] The eluent is petroleum ether and dichloromethane in a volume ratio of 9:1, and the column chromatography separation process is as follows: the concentrate is dissolved in the eluent and then separated and purified by column chromatography silica gel, the eluent is collected and the eluent is evaporated to remove the eluent, and a solid powder product is obtained by drying. The steps of the following Examples 2, 3, 4, and 5 are equivalent, except that 5-ethynylthiophene-2-aldehyde is replaced by the corresponding raw material.
[0034] Compound represented by formula (III-1) 1 H NMR(500MHz, CDCl3)δ9.76(s,1H),7.57(d,J=3.9Hz,1H),6.86(d,J=3.9Hz,1H),2.03-1 .97(m,12H),1.58-1.53(m,12H),1.46(dd,J=14.6,7.3Hz,12H),0.93(d,J=7.3Hz,18H).
[0035] 2) Synthesis of the compound represented by formula (II-1)
[0036] Compound III-1 (543.2 mg, 0.7 mmol), 9-butyl-3-ethynylcarbazole (342.3 mg, 1.4 mmol) and cuprous iodide (26.7 mg, 0.1 mmol) were weighed into a Shrek tube, evacuated and backfilled with nitrogen, and the operation was repeated three times; tetrahydrofuran (15 mL) and triethylamine (15 mL) were then added, stirred at room temperature for 6 h, and after the reaction was complete, extracted three times with ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation. The mixture was purified by column chromatography (V PE :V EtOAc =10:1) to obtain yellow liquid II-1538.5 mg with a yield of 79.7%.
[0037] Compound represented by formula (II-1): 1 H NMR(500MHz, CDCl3)δ9.76(s,1H),8.02(dd,J=4.4,3.2Hz,2H),7.58(d,J=3.9Hz,1H),7.47-7.37(m,4H),7.21(dd,J=10.9,3.9Hz,1H),6 .88(d,J=3.9Hz,1H),4.28(t,J=7.2Hz,2H),2.22-2.13(m,14H),1.68-1.62(m,12H),1.50(dd,J=14.6,7.3Hz,14H),0.98-0.94(m,21H).
[0038] 2) Synthesis of the compound represented by formula (I-1):
[0039] Weigh compound II-1 (200.0 mg, 0.2 mmol) and cyanoacetic acid (84.2 mg, 1.0 mmol) into a Shrek tube, evacuate and backfill with nitrogen, repeat the operation three times. Add acetonitrile (6 mL) and chloroform (3 mL), stir at room temperature for 5 min, slowly add 0.24 mL of piperidine, and heat to reflux for 16 h. After the reaction is completed, the reaction solution is cooled to room temperature, the solvent is dried in vacuo, and the residue is purified by column chromatography (V DCM :V MeOH: V AcOH =200:5:1), to obtain yellow liquid I-1121.5mg, yield 58%.
[0040] Compound represented by formula (I-1): 1 H NMR(500MHz,DMSO)δ8.36(s,1H),8.02(d,J=6.1Hz,2H),7.53(t,J=11.8Hz,1H),7 .41(ddd,J=15.6,9.9,4.5Hz,3H),7.27(d,J=9.6Hz,1H),7.22(d,J=7.4Hz,1H),6 .81(d,J=3.6Hz,1H),4.28(t,J=7.2Hz,2H),2.23-2.12(m,12H),1.65(dd,J=7.2, 3.6Hz,14H),1.50(dd,J=14.6,7.3Hz,14H),0.97(t,J=7.3Hz,21H).HRMS(ESI)m / z calcd for C 52 H 75 N2O2P2PtS + (M+H) + 1048.46667, found 1048.46692.
[0041] Example 2 Synthesis of the compound represented by formula (I-2):
[0042]
[0043] 1) Synthesis of the compound represented by formula (II-2)
[0044] Weigh compound III-2 (290.4 mg, 0.4 mmol), 9-butyl-3-ethynylcarbazole (187.2 mg, 0.8 mmol) and cuprous iodide (28.8 mg, 0.2 mmol) into a Shrek tube, evacuate and backfill with nitrogen, repeat the operation three times. Then add tetrahydrofuran (10 mL) and triethylamine (10 mL), stir at room temperature under nitrogen protection for 8 h. After the reaction is completed, extract with ethyl acetate, wash the organic layer with saturated brine, dry with anhydrous sodium sulfate, spin dry the solvent, and column chromatography (VPE :V EA =20:1) to obtain 163.9 mg of yellow liquid II-2 with a yield of 42.5%.
[0045] Compound represented by formula (II-2): 1 H NMR (500MHz, CDCl3) δ9.48 (s, 1H), 7.48-7.34 (m, 4H), 7.27 (t, J = 4.2Hz, 2H), 7.22-7.17 (m, 2H), 6.28 (d, J = 3.6Hz, 1H), 4.28(t,J=7.2Hz,2H),2.21-2.16(m,12H),1.68-1.61(m,14H),1.50(dd,J=14.6,7.3Hz,14H),0.97(t,J=6.1Hz,21H).
[0046] 2) Synthesis of the compound represented by formula (I-2)
[0047] Weigh compound II-2 (192.8 mg, 0.2 mmol) and cyanoacetic acid (50.5 mg, 0.6 mmol) into a Shrek tube, evacuate and backfill with nitrogen, repeat the operation three times. Add acetonitrile (2 mL) and chloroform (1 mL), stir at room temperature for 5 min, slowly add 0.16 mL of piperidine, and heat under reflux for 10 h. After the reaction is complete, vacuum dry the solvent, and purify the residue by column chromatography (V DCM :V MeOH: V AcOH =200:5:1) to obtain 104.0 mg of yellow liquid I-2 with a yield of 50.4%.
[0048] Compound represented by formula (I-2): 1 H NMR (500MHz, DMSO) δ8.01(d,J=7.7Hz,1H),7.90(s,1H),7.67(s,1H),7.57(d,J=8.2Hz,1H),7.45(dt,J=20.6,10.5Hz,2H),7.29-7.13(m,3H),6.37 (d,J=3.5Hz,1H),4.35(t,J=6.9Hz,2H),2.56-2.45(m,12H),1.64-1.51( m,14H),1.45(dt,J=14.5,7.2Hz,14H),0.92-0.83(m,21H).HRMS(ESI)m / z calcd forC 52 H 75 N2O3P2Pt + (M+H) +1032.4895, found 1032.48987.
[0049] Example 3 Synthesis of the compound represented by formula (I-3):
[0050]
[0051] 1) Synthesis of the compound represented by formula (II-3)
[0052] Weigh compound III-3 (480.3 mg, 0.5 mmol), 9-butyl-3-ethynylcarbazole (201.9 mg, 0.8 mmol) and cuprous iodide (20.4 mg, 0.1 mmol) into a Shrek tube, evacuate and backfill with nitrogen, repeat the operation three times. Then add tetrahydrofuran (15 mL) and triethylamine (15 mL), stir at room temperature under nitrogen protection for 12 h. After the reaction is completed, extract with ethyl acetate, wash the organic layer with saturated brine, dry with anhydrous sodium sulfate, spin dry the solvent to obtain a brown liquid II-3279.3 mg, with a yield of 53.0%, and proceed directly to the next step without purification.
[0053] 2) Synthesis of the compound represented by formula (I-3)
[0054] Weigh compound II-3 (193.6 mg, 0.2 mmol) and cyanoacetic acid (67.6 mg, 0.8 mmol) into a Shrek tube, evacuate and backfill with nitrogen, repeat the operation three times. Add acetonitrile (4 mL) and chloroform (2 mL), stir at room temperature for 5 min, slowly add 0.2 mL of piperidine, and heat under reflux for 14 h. After the reaction is complete, the reaction solution is cooled to room temperature, the solvent is dried under vacuum, and the residue is purified by column chromatography (V DCM :V MeOH: V AcOH =200:5:1), to obtain yellow liquid I-3164.6 mg, yield 79.0%.
[0055] Compound represented by formula (I-3): 1H NMR (500MHz, DMSO) δ8.22 (s, 1H), 8.01 (d, J = 7.6Hz, 1H), 7.97-7.88 (m, 3H), 7.57 (d,J=8.2Hz,1H),7.49(d,J=8.5Hz,1H),7.43(t,J=7.7Hz,1H),7.31-7.24(m,3H) ,7.18(t,J=7.4Hz,1H),4.35(t,J=6.9Hz,2H),2.13(d,J=3.4Hz,12H),1.66-1.52 (m,14H),1.44(dq,J=14.4,7.2Hz,14H),0.92-0.83(m,21H).HRMS(ESI)m / zcalcd for C 54 H 77 N2O2P2Pt + (M+H) + 1042.51025, found 1042.51086.
[0056] Example 4 Synthesis of the compound represented by formula (I-4)
[0057]
[0058] 1) Synthesis of the compound represented by formula (II-4)
[0059] Compound III-4 (170 mg, 0.2 mmol), 9-butyl-3-ethynylcarbazole (100.1 mg, 0.4 mmol) and cuprous iodide (3.8 mg, 0.02 mmol) were added to a Shrek tube, and the mixture was evacuated and backfilled with nitrogen. The operation was repeated three times, and tetrahydrofuran (5 mL) and triethylamine (5 mL) were added, and stirred at room temperature for 10 h. After the reaction was completed, the mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was dried and separated by column chromatography (V PE :V EA =20:1), to obtain yellow liquid II-4135.7mg, yield 63.7%.
[0060] Compound represented by formula (II-4): 1H NMR (500MHz, CDCl3) δ9.84 (s, 1H), 8.02 (d, J = 5.3Hz, 2H), 7.65 (d, J = 4.0Hz, 1H),7.47-7.36(m,4H),7.21(d,J=7.0Hz,1H),7.18(d,J=3.8Hz,1H),7.16(d ,J=4.0Hz,1H),6.79(d,J=3.8Hz,1H),4.28(t,J=7.2Hz,2H),2.24-2.13(m,1 2H),1.70-1.62(m,14H),1.56-1.46(m,14H),0.97(dd,J=12.0,4.7Hz,21H).
[0061] 2) Synthesis of the compound represented by formula (I-4)
[0062] Weigh compound II-4 (114.9 mg, 0.1 mmol) and cyanoacetic acid (33.6 mg, 0.4 mmol) into a Shrek tube, evacuate and backfill with nitrogen, repeat the operation three times, add chloroform (1 mL) and acetonitrile (2 mL), stir at room temperature to dissolve, and slowly add 0.1 mL of piperidine. Heat to reflux for 12 h. After the reaction is complete, vacuum dry the solvent, and separate the residue by column chromatography (V DCM :V MeOH :V AcOH =200:5:1), to obtain yellow liquid I-40.30g, yield 43.0%.
[0063] The compound represented by formula (I-4): 1 H NMR(500MHz,DMSO)δ8.44(s,1H),8.00(d,J=7.7Hz,1H),7.93(d,J=4.2Hz,1H),7.90(s, 1H),7.56(d,J=8.3Hz,1H),7.48-7.40(m,4H),7.28-7.24(m,1H),7.18(t,J=7.5Hz,1H) ,6.78(d,J=3.8Hz,1H),4.34(t,J=7.0Hz,2H),2.09(dd,J=19.2,15.5Hz,12H),1.64-1. 53(m,14H),1.44(dt,J=14.3,7.2Hz,14H),0.89(dt,J=6.2,4.5Hz,21H).HRMS(ESI)m / z calcd for C 56 H 77 N2O2P2PtS2 + (M+H) + 1130.45439, found1130.45483.
[0064] Example 5 Synthesis of the compound represented by formula (I-5)
[0065]
[0066] Weigh compound II-1 (88.8 mg, 0.1 mmol) and rhodanine-3-acetic acid (52.2 mg, 0.3 mmol) into a Shrek tube, evacuate and backfill with nitrogen, repeat the operation three times. Add acetonitrile (3 mL) and chloroform (1.5 mL), stir at room temperature for 5 min, slowly add 0.1 mL of piperidine, and heat to reflux for 12 h. After the reaction is completed, the solvent is dried under vacuum, and the residue is purified by column chromatography (V DCM :V MeOH: V AcOH =200:5:1), to obtain red liquid I-578.1mg, yield 65.2%.
[0067] Compound represented by formula (I-5): 1 H NMR (500MHz, DMSO) δ8.02(d,J=5.3Hz,2H),7.91(s,1H),7.66(d,J=4.2Hz,1H),7.57(d,J=8.3 Hz,1H),7.50(d,J=8.5Hz,1H),7.43(dd,J=17.5,9.4Hz,1H),7.27(d,J=8.5Hz,1H),7.19(t,J =7.4Hz,1H),6.92(d,J=3.9Hz,1H),4.69-4.51(m,2H),4.36(t,J=6.9Hz,2H),2.23-2.07(m,1 2H),1.61(d,J=3.2Hz,14H),1.47(dd,J=14.4,7.2Hz,14H),0.97-0.84(m,21H).HRMS(ESI)m / z calcd for C 54 H 77 N2O3P2PtS3 + (M+H) + 1154.4213, found 1154.42188.
[0068] Example 6 Application of carbazole compounds containing metal platinum as dye sensitizers:
[0069] When used as a dye sensitizer, the application includes the following steps:
[0070] The platinum-containing carbazole compound and the dye N719 were dissolved in a CH3Cl-CH3OH mixed solvent to obtain a mixed solution of the platinum-containing carbazole compound and N719 (the concentrations of the platinum-containing carbazole compound and N719 were both 3×10 - 4 mol·L -1 ); the volume ratio of CH3Cl and CH3OH in the CH3Cl-CH3OH mixed solvent is 10:1;
[0071] The double-layer TiO2 nanoparticle film prepared by screen printing was used as the photoelectrode: First, a layer of 20nm TiO2 particles with a thickness of 12μm was printed on the conductive glass FTO, and calcined in a muffle furnace at 450℃ for 30min. After cooling to room temperature, the calcined film was immersed in 0.04mol·L -1 The film was pretreated with TiCl4 aqueous solution at 70℃ for 30min, then taken out from the TiCl4 aqueous solution and rinsed with water and ethanol respectively, and dried with a hair dryer. After calcination again at 450℃ in a muffle furnace for 30min, a double-layer TiO2 nanoparticle film photoelectrode was obtained.
[0072] The double-layer TiO2 nanoparticle film photoelectrode obtained by the calcination was cooled to 80°C and then immersed in the solution of the platinum-containing carbazole compound and N719 compound obtained above, and sensitized at room temperature for 24 hours to obtain a TiO2 electrode loaded with platinum-containing carbazole compounds and N719 compounds.
[0073] Preparation of platinum counter electrode: The H2PtCl6 aqueous solution is printed on the FTO conductive glass by screen printing. The H2PtCl6 aqueous solution wets the surface of the FTO conductive glass, dries it, and then sinters it at 400°C in a muffle furnace for 20 minutes to obtain the platinum counter electrode.
[0074] The double-layer TiO2 nanoparticle film photoelectrode and the platinum counter electrode prepared above were assembled into a sandwich structure, and electrolyte was dripped into the edge of the sandwich structure and introduced into the battery by the capillary permeation principle to form a dye-sensitized solar cell. 2 Under light intensity irradiation, the current-voltage curve of the DSSC assembled by the carbazole compound containing metal platinum and N719 was measured, and the performance parameter results are shown in Table 1:
[0075] Table 1 Performance parameters of DSSCs assembled from carbazole compounds containing metal platinum
[0076]
[0077] It can be seen from Table 1 that the dye-sensitized solar cell assembled with the platinum-containing carbazole compound of the present invention and N719 as a dye sensitizer has a good photoelectric conversion efficiency of 5.04-6.54%, which is higher than that of the solar cell sensitized by N719 alone, adding new applicable substances to the screening of co-sensitizers of N719.
[0078] The contents described in this specification are merely an enumeration of the implementation forms of the inventive concept. The protection scope of the present invention should not be regarded as limited to the specific forms described in the embodiments. The protection scope of the present invention is also limited to the equivalent technical means that can be thought of by those skilled in the art based on the inventive concept.
Claims
1. A carbazole compound containing metal platinum, characterized in that Its molecular structure is shown in formula (I); , In formula (I), Ar is a benzene ring, furan or thiophene, and A is or .
2. The method for preparing a platinum-containing carbazole compound according to claim 1, characterized in that The compound represented by formula (II) and cyanoacetic acid or rhodanine-3-acetic acid are dissolved in a solvent, an alkaline substance is added, and the mixture is heated under reflux with stirring under the protection of a nitrogen atmosphere. After the reaction is completed, the reaction solution is concentrated to remove the solvent, the obtained concentrate is dissolved in an eluent, and then separated and purified by column chromatography on silica gel, the eluent is collected, and the eluent is evaporated to remove the eluent, so as to obtain the target product, wherein the alkaline substance is piperidine; The structural formula of the compound represented by formula (II) is as follows: , In formula (II), Ar is a benzene ring, furan or thiophene.
3. The method for preparing a platinum-containing carbazole compound according to claim 2, characterized in that The heating reflux reaction time is 10-16 h.
4. The method for preparing a platinum-containing carbazole compound according to claim 2, characterized in that The solvent is a mixed solvent consisting of chloroform and acetonitrile.
5. The method for preparing a platinum-containing carbazole compound according to claim 2, characterized in that The molar ratio of the compound represented by formula (II), cyanoacetic acid or rhodanine-3-acetic acid, and the alkaline substance is 1:3-5:8-12.
6. The method for preparing a platinum-containing carbazole compound according to claim 2, characterized in that The molar ratio of the compound represented by formula (II), cyanoacetic acid or rhodanine-3-acetic acid, and the alkaline substance is 1:4:
10.
7. The method for preparing a carbazole compound containing metal platinum according to claim 2, characterized in that The ratio of the amount of the compound represented by formula (II) to the volume of the solvent is 1:15-45, the unit of the amount of the substance is mmol, and the unit of the volume is mL.
8. The method for preparing a carbazole compound containing metal platinum according to claim 2, characterized in that The eluent is a mixed solvent consisting of dichloromethane, methanol and acetic acid, and the volume ratio of the dichloromethane, methanol and acetic acid is 200:5:
1.
9. Use of the platinum-containing carbazole compound according to claim 1 in a dye sensitizer.
Citation Information
Patent Citations
Photoelectrode for a dye-sensitized solar cell, method for manufacturing the photoelectrode, and dye-sensitized solar cell using the photoelectrode
CN103918051A
Benzocarbarzole dye sensitizer synthesis and application
CN107253946A