CN115785693A - N-type organic dye of 1, 2-benzophenothiazine, preparation method and application - Google Patents
N-type organic dye of 1, 2-benzophenothiazine, preparation method and application Download PDFInfo
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Abstract
The invention relates to an n-type organic dye based on 1, 2-benzothiazol, a preparation method and application thereof. The molecule adopts triphenylamine, carbazole, indole units and the like as electron donating groups, 1, 2-benzophenothiazine as a pi conjugate bridge, a furan group as an auxiliary connecting group, and cyanoacrylate as an acceptor group and an anchoring group. The invention is mainly characterized in that 1, 2-benzophenothiazine is used as a donor or a pi conjugate bridge, furan and benzophenothiazine are connected to form an intramolecular hydrogen bond with the donor or the pi conjugate bridge, the intramolecular planarity is increased, the intramolecular charge transfer is effectively improved, the energy gap is adjusted, the spectral response range is improved, the light capture efficiency is enhanced, and the device performance is improved.
Description
Technical Field
The invention belongs to the technical field of organic photoelectric materials, and particularly relates to an n-type organic dye based on 1, 2-benzothiazol, and a preparation method and application thereof.
Background
New energy has received increasing attention, and solar energy is the fastest growing technology among renewable energy sources, with the potential to supply a large portion of the global energy demand in the future. Silicon (Si) solar cell technology currently dominates the photovoltaic market. Over the last decade, this technology has become very mature and represents a large market. While the future prospects of crystalline silicon solar cells are bright, problems such as their complex manufacturing processes, the use of hazardous chemicals, etc. may open up opportunities for future development of other photovoltaic technologies.
The third generation solar cell mainly comprises a dye-sensitized solar cell, an organic solar cell and a perovskite solar cell. Among them, dye-sensitized solar cells are easy and simple to fabricate, low in cost, high in stability, and have high industrial-scale manufacturing potential because they can be produced while using established scalable manufacturing methods (e.g., screen printing, inkjet printing, etc.). The working principle of the dye-sensitized solar cell is as follows: the dye molecule is used as the main material for absorbing light, when sunlight is absorbed, electrons are excited to the high-energy gap layer, but the excited state is an unstable state, so the electrons must be transmitted into the conductive layer of the adjacent dye molecule at the fastest speed, and the lost electrons of the dye molecule can be fed back from the electrolyte at the first time. The electrons in the conduction band of the dye molecule eventually pass through the electrodes to an external circuit to generate a photogenerated current.
The sensitizer is a crucial part of dye-sensitized solar cells. The light absorption efficiency and the electron injection rate are improved by designing different structures of the solar cell, so that the efficiency of the cell is improved. Therefore, in order to improve the cell efficiency and cost of the photosensitizers, the expansion of the photoresponse range and the development of novel dyes are the key points of research currently.
Disclosure of Invention
The invention aims to provide an n-type organic dye based on 1, 2-benzothiazol, which has the advantages of stable structure, common and easily-obtained raw materials, low production cost, proper energy gap and high absorption coefficient.
In order to achieve the purpose, the invention adopts the following technical scheme:
an n-type organic dye based on 1, 2-benzothiazol is shown in a structural general formula I or II:
wherein R is a linear or branched alkyl chain having 1 to 12 carbon atoms, or
Wherein R is 2 Is a straight chain or branched alkyl chain with 1 to 12 carbon atoms;
wherein R is 1 Is a hydrogen or C1-12 linear or branched alkyl chain or a C1-12 linear or branched alkyl chain containing an oxygen atom and a sulfur atom.
The synthesis method of the formula I comprises the following steps:
adding 2-aminobenzenethiol and 4-tetrahydrocyclic ketone into dimethyl sulfoxide, and stirring for 24 hours in air at the temperature of 110 ℃ to obtain a compound 1;
mixing the compound 1, R-Br, KOH, TBAB and dimethyl sulfoxide, and reacting for 10 hours at room temperature in a nitrogen atmosphere to obtain a compound 2;
mixing the compound 2 and chloroform, stirring and reacting for 6 hours in an ice-water bath under nitrogen atmosphere, and adding N-bromosuccinimide into a reaction bottle for three times in the first two hours to obtain a compound 3;
reacting a compound of 3, 5-formaldehyde furan-2-boric acid and K 2 CO 3 、Pd[P(C 6 H 5 ) 3 ] 4 TBAB and THF are put into a three-neck flask and heated and refluxed for 13 hours at 85 ℃ in the dark and nitrogen atmosphere to obtain a compound 4;
The synthetic route of the formula I is as follows:
preferably, the molar ratio of 2-aminobenzenethiol to 4-tetrahydrocyclic ketone is 1.5:1.
preferably, the molar ratio of compound 1, R-Br, KOH, tetrabutylammonium bromide (TBAB) is 1:1.3:3:0.3.
preferably, the compounds 3, 5-carboxaldehyde furan-2-boronic acid, K 2 CO 3 、Pd[P(C 6 H 5 ) 3 ] 4 TBAB in a 1:1.2:2.5:0.05:0.3.
preferably, the molar ratio of the compound 4, the cyanoacetic acid and the ammonium acetate is 1:2:1.
the synthesis method of the formula II comprises the following steps:
mixing the compound 4 and chloroform, stirring and reacting for 6 hours in an ice-water bath under nitrogen atmosphere, and adding N-bromosuccinimide into a reaction bottle for three times in the first two hours to obtain a compound 5;
compound 6, cyanoacetic acid, ammonium acetate and acetic acid were combined and heated to reflux at 90 ℃ for 24 hours under nitrogen atmosphere and purified to give the product of formula II.
The synthetic route of the formula II is as follows:
preferably, compound 5, compound
K 2 CO 3 、Pd[P(C 6 H 5 ) 3 ] 4 The molar ratio of TBAB is 1.2.
The invention also provides application of the n-type organic dye of the 1, 2-benzophenothiazine as a sensitizer in a dye-sensitized solar cell.
Compared with the prior art, the invention has the following beneficial technical effects:
the invention relates to an n-type organic dye based on 1, 2-benzothiazol, wherein the molecule adopts 1, 2-benzothiazol as a pi conjugate bridge, triphenylamine, carbazole, indole and the like as donor groups, furan as a connecting unit and cyanoacrylate as an anchoring group. The furan serving as a connecting unit has an electron-rich characteristic, and the furan and the phenothiazine are connected to form an intramolecular field effect, so that the molecular planarity is increased, the intramolecular charge transfer is effectively improved, and the harmful charge recombination in a device is reduced, thereby improving the device performance. And triphenylamine, carbazole, indole and other groups introduced are used as donor structures, so that the spectral response range can be further widened, the spectral response range can be moved to a near infrared region, the intramolecular charge transfer is enhanced, the light capture efficiency is enhanced, and the device performance is improved.
The n-type organic dye based on 1, 2-benzophenothiazine has the advantages of stable structure, proper energy gap, high absorption coefficient, common and easily-obtained raw materials of the preparation method, low production cost and capability of being used for preparing dye-sensitized solar cells.
Drawings
FIG. 1 is a graph of the UV-vis absorption spectrum of the dye PP-OX;
FIG. 2 is a graph of the UV-vis absorption spectrum of the dye CZ-PP-OX;
FIG. 3 is a graph of the UV-vis absorption spectrum of the dye TAP-PP-OX;
FIG. 4 is a J-V map of a DSSC device made with the dye PP-OX;
FIG. 5 is a J-V map of a DSSC device fabricated with the dye CZ-PP-OX;
FIG. 6 is a J-V map of a DSSC device fabricated with the dye TAP-PP-OX.
Detailed Description
The invention is further described with reference to specific examples. The following examples are only for illustrating the technical solutions of the present invention more clearly, and the protection scope of the present invention is not limited thereby.
Example 1:
the synthetic route is as follows:
preparation of Compound 1 2-aminobenzenethiol (0.375 mmoL) and 4-tetrahydrocyclic ketone (0.250 mmoL) (1.5. After completion, the reaction mixture was diluted with ethyl acetate and filtered through a layer of silica gel covered with wollastonite. The volatiles were removed in vacuo to obtain the crude product. Further silica gel column chromatography (dichloromethane/petroleum ether) was required to give pure compound 1 in 70% yield. 1 H NMR(400MHz,DMSO-d 6 )δ8.66(s,1H),8.35(dd,J＝8.5,1.3Hz,1H),7.80(dd,J＝8.1,1.4Hz,1H),7.52(ddd,J＝8.4,6.8,1.4Hz,1H),7.48–7.37(m,2H),7.13(dd,J＝8.0,1.4Hz,1H),7.10–7.02(m,2H),6.97(dd,J＝7.6,1.5Hz,1H),6.84(td,J＝7.4,1.4Hz,1H).
Preparation of compound 2 compound 1, bromohexane, KOH, TBAB (1.3. When the reaction time reached, water was added to the reaction solution to terminate the reaction. The reaction solution was then washed by extraction with Dichloromethane (DCM) and brine three times and dried over anhydrous sodium sulfate (Na) 2 SO 4 ) And (5) drying. The crude product was finally purified by column chromatography using Petroleum Ether (PE)/DCM (15). 1 H NMR(400MHz,DMSO-d6)δ8.07(d,J＝8.5Hz,1H),7.85(dd,J＝8.2,1.3Hz,1H),7.60(d,J＝8.5Hz,1H),7.53(ddd,J＝8.4,6.8,1.4Hz,1H),7.44(ddd,J＝8.0,6.8,1.2Hz,1H),7.30(dd,J＝8.0,1.4Hz,1H),7.26–7.14(m,3H),7.00(td,J＝7.5,1.3Hz,1H),4.11–3.54(m,2H),1.57–1.34(m,2H),1.32–0.90(m,6H),0.66(t,J＝7.0Hz,3H).
Preparation of compound 3: compound 2 (333mg, 1mmol) and chloroform (CHCl) 3 10 mL) was added to a three-necked flask, the reaction was stirred in an ice-water bath under a nitrogen atmosphere for 6 hours, and N-bromosuccinimide (NBS, 534mg, 3mmol) was added to the reaction flask three times over the first two hours. When the reaction was complete, water was added to stop the reaction. The reaction was then extracted 3 times with DCM and brine and dried over anhydrous Na 2 SO 4 And (5) drying. The crude product was then purified by column chromatography using PE/DCM (1). 1 H NMR(400MHz,DMSO-d 6 )δ8.16–8.08(m,1H),8.08–8.00(m,1H),7.68–7.57(m,3H),7.32(dd,J＝8.0,1.4Hz,1H),7.24(td,J＝7.7,1.5Hz,1H),7.18(dd,J＝7.7,1.5Hz,1H),7.03(td,J＝7.5,1.3Hz,1H),4.18–3.48(m,2H),1.58–1.34(m,2H),1.33–0.82(m,6H),0.65(t,J＝7.0Hz,3H).
Preparation of compound 4: mixing compound 3 (412mg, 1mmol), 5-formaldehyde furan-2-boronic acid (168mg, 1.2mmol), and K 2 CO 3 (345mg,2.5mmol)、Pd[P(C 6 H 5 ) 3 ] 4 (57mg, 0.05mmol), TBAB (96.5mg, 0.3mmol) and THF (15 mL) were placed in a three-necked flask and heated under reflux in the dark under nitrogen at 85 ℃ for 13h. When the post reaction should be completed, water is added to quench the reaction. After the reaction was cooled to room temperature, it was extracted 3 times with DCM and brine, and with NaSO 4 And (5) drying. The crude product was subsequently purified by column chromatography using PE/DCM (2). 1 H NMR(400MHz,DMSO-d 6 )δ9.67(s,1H),8.41–8.32(m,1H),8.21–8.12(m,1H),7.73(d,J＝3.7Hz,1H),7.69–7.55(m,3H),7.38(dd,J＝8.1,1.3Hz,1H),7.31–7.23(m,2H),7.20(dd,J＝7.8,1.5Hz,1H),7.05(td,J＝7.5,1.3Hz,1H),4.20(s,1H),3.72(s,1H),1.51(dq,J＝14.6,7.2Hz,2H),1.35–0.92(m,6H),0.68(t,J＝7.0Hz,3H).
Preparation of Compound PP-OX: compound 4, cyanoacetic acid, ammonium acetate and acetic acid were placed in a three-necked flask and heated under reflux at 110 ℃ for 12 hours under a nitrogen atmosphere, and the PP-OX was purified by column chromatography in a yield of 70%. 1 H NMR(400MHz,DMSO-d 6 )δ8.56(d,J＝8.4Hz,1H),8.18(d,J＝8.4Hz,1H),8.12(s,1H),7.80(s,1H),7.64(d,J＝3.8Hz,2H),7.61(dd,J＝6.2,1.5Hz,1H),7.61–7.54(m,1H),7.42(d,J＝3.9Hz,2H),7.38(s,1H),7.27(td,J＝7.6,1.5Hz,1H),7.22(dd,J＝7.8,1.5Hz,1H),7.05(t,J＝7.5Hz,1H),4.24(s,1H),3.74(s,1H),1.52(t,J＝7.4Hz,2H),1.34–0.96(m,6H),0.69(t,J＝7.0Hz,3H).
Example 2:
the synthetic route is as follows:
preparation of compound 6: compound 4 (427mg, 1mmol) and chloroform (CHCl) 3 10 mL) was added to a three-necked flask, the reaction was stirred in an ice-water bath under a nitrogen atmosphere for 6 hours, and N-bromobutane was added three times in the first two hoursDiimide (NBS, 534mg, 3mmol) was added to the reaction flask. When the reaction was complete, water was added to stop the reaction. The reaction was then extracted 3 times with DCM and brine, and dried over anhydrous Na 2 SO 4 And (5) drying. The crude product was then purified by column chromatography using PE/DCM (1) as eluent to give compound 6 in 70% yield. 1 H NMR(400MHz,DMSO-d 6 )δ9.69(s,1H),8.10(dd,J＝8.1,1.6Hz,1H),7.97–7.92(m,1H),7.60(td,J＝8.0,1.3Hz,1H),7.53(td,J＝7.5,1.3Hz,1H),7.53(s,1H),7.48–7.41(m,2H),7.38(d,J＝1.9Hz,1H),7.09–7.02(m,2H),4.20(s,1H),3.72(s,1H),1.51(dq,J＝14.6,7.2Hz,2H),1.35–0.92(m,6H),0.68(t,J＝7.0Hz,3H).
Preparation of compound 8: compounds No. 6 (505mg, 1mmol), 4- (9H-carbazol-9-yl) phenylboronic acid (344mg, 1.2mmol) and K 2 CO 3 (345mg,2.5mmol)、Pd[P(C 6 H 5 ) 3 ] 4 (57mg, 0.05mmol), TBAB (96.6 mg,0.3 mmol) and THF (15 mL) were placed in a three-necked flask and heated at reflux under nitrogen in the dark at 85 ℃ for 13h. When the post reaction should be completed, water is added to quench the reaction. After the reaction was cooled to room temperature, it was extracted 3 times with DCM and brine, and with NaSO 4 And (5) drying. The crude product was then purified by column chromatography using PE/DCM (2). 1 H NMR(400MHz,DMSO-d 6 )δ9.69(s,1H),8.17–8.11(m,2H),8.10(dd,J＝8.1,1.6Hz,1H),7.97–7.92(m,1H),7.69–7.50(m,10H),7.46(d,J＝5.3Hz,1H),7.39–7.24(m,5H),7.16(d,J＝7.3Hz,1H),7.07(d,J＝5.3Hz,1H),4.21(s,1H),3.76(s,1H),1.58(q,J＝6.2Hz,2H),1.40–1.25(m,6H),0.94–0.84(m,3H).
Preparation of compound CZ-PP-OX: compound 8, cyanoacetic acid, ammonium acetate and acetic acid were placed in a three-necked flask and heated under reflux at 90 ℃ for 24 hours under a nitrogen atmosphere, followed by purification by column chromatography to give the compound CZ-PP-OX in 70% yield. 1 H NMR(400MHz,DMSO-d 6 )δ8.17–8.11(m,2H),8.10(dd,J＝8.2,1.4Hz,1H),8.05(s,1H),7.97–7.92(m,1H),7.69–7.62(m,4H),7.62–7.55(m,4H),7.57–7.50(m,2H),7.41(d,J＝5.5Hz,1H),7.39–7.24(m,5H),7.16(d,J＝7.3Hz,1H),7.08(d,J＝5.3Hz,1H),4.38(s,1H),3.82(s,1H),1.88(q,J＝6.2Hz,2H),1.43–1.05(m,6H),0.84–0.70(m,3H).
Example 3:
the synthetic route is as follows:
preparation of compound 7: the compound 6 (505mg, 1mmol), 4- (diphenylamino) phenylboronic acid (346mg, 1.2mmol), and K were added 2 CO 3 (345mg,2.5mmol)、Pd[P(C 6 H 5 ) 3 ] 4 (57mg, 0.05mmol), TBAB (96.6 mg,0.3 mmol) and THF (15 mL) were placed in a three-necked flask and heated at reflux under nitrogen in the dark at 85 ℃ for 13h. When the post reaction should be completed, water is added to quench the reaction. After the reaction solution was cooled to room temperature, it was extracted 3 times with DCM and brine, and with NaSO 4 And (5) drying. The crude product was then purified by column chromatography using PE/DCM (2). 1 H NMR(400MHz,DMSO-d 6 )δ9.69(s,1H),8.09(dd,J＝8.4,1.4Hz,1H),8.00–7.95(m,1H),7.77(dd,J＝7.1,1.8Hz,1H),7.64–7.57(m,1H),7.57–7.50(m,2H),7.50(s,1H),7.45(d,J＝5.2Hz,1H),7.40(s,1H),7.34(d,J＝1.9Hz,1H),7.32–7.25(m,4H),7.23–7.15(m,3H),7.14–7.08(m,4H),7.08–6.98(m,3H),4.31(s,1H),3.80(s,1H),1.65-1.55(q,J＝6.2Hz,2H),1.34–1.05(m,6H),0.84–0.70(m,3H).
Preparation of the Compound TAP-PP-OX: compound 7, cyanoacetic acid, ammonium acetate and acetic acid were placed in a three-necked flask, and heated under reflux at 90 ℃ for 24 hours under a nitrogen atmosphere, followed by purification by column chromatography to give the compound TAP-PP-OX in a yield of 70%. 1 H NMR(400MHz,DMSO-d 6 )δ8.09(dd,J＝8.4,1.4Hz,1H),8.05(s,1H),8.00–7.95(m,1H),7.78(dd,J＝7.1,1.8Hz,1H),7.64–7.57(m,1H),7.57–7.50(m,2H),7.50(s,1H),7.42–7.34(m,4H),7.32–7.25(m,4H),7.23–7.15(m,3H),7.14–7.08(m,2H),7.04(tt,J＝7.7,1.4Hz,2H),4.36(s,1H),3.78(s,1H),1.63-1.54(q,J＝7.5Hz,2H),1.38–1.07(m,6H),0.75–0.71(m,3H).
Example 4
Absorption spectral properties of the 3 dyes PP-OX, CZ-PP-OX, TAP-PP-OX:
the absorption spectra of the PP-OX, CZ-PP-OX, TAP-PP-OX dyes are shown in FIGS. 1 to 3: the three dyes all show strong absorption at 220-650nm in ultraviolet and visible light regions, and the most red absorption peaks are respectively located at 480nm, 487nm and 486nm.
Example 5
Device properties of 3 dyes PP-OX, CZ-PP-OX, TAP-PP-OX:
FIGS. 4, 5, 6 are J-V maps of devices fabricated with the dyes PP-OX, CZ-PP-OX, TAP-PP-OX in standard AM 1.5G simulated sunlight.
The preparation method of the n-type organic dye-sensitized solar cell based on the benzothiazol comprises the following steps: ultrasonically cleaning an FTO glass sheet in acetone and ethanol for 15 minutes, and drying under the protection of nitrogen; then preparing TiO by electrostatic spraying process 2 Nanocrystalline thin film, about 16 microns thick. The nanocrystalline thin film is immersed into methylene dichloride solution containing dye after being subjected to thermal sintering treatment (the common immersion time is not less than 24 h); tiO having adsorbed dye 2 The nanocrystalline film serves as a photo-anode. Cleaning and drying the other FTO glass sheet in the manner, drilling a small hole in the middle of the non-FTO surface, adhering an adhesive tape on the non-FTO surface, coating chloroplatinic acid on a table type refiner twice, and performing thermal sintering treatment to manufacture the platinum counter electrode. Then, assembling the photo-anode and the platinum counter electrode together into an electrode assembly of the solar cell, packaging the two electrodes by using AB glue, and finally injecting electrolyte solution on the platinum counter electrode with the small holes, wherein the electrolyte solution enters the electrode assembly through the small holes on the platinum counter electrode by virtue of capillary action; and finally, sealing the small hole by using a heat-sealing film to obtain the dye-sensitized solar cell.
Under the standard AM 1.5G simulated sunlight, the light intensity is 100mW/cm 2 Under simulated sunlight, test temperatureThe short-circuit current density J of the PP-OX organic dye-sensitized solar cell of the example was measured at 25 DEG C sc ＝14.88mA/cm 2 Open circuit voltage V oc =0.84V, fill factor FF =0.51, photovoltaic cell efficiency PCE =6.41%. Short-circuit current density J based on CZ-PP-OX organic dye sensitized solar cell sc ＝18.05mA/cm 2 Open circuit voltage V oc =0.76V, fill factor FF =0.56, photovoltaic cell efficiency PCE =7.68%. Short-circuit current density J of organic dye-sensitized solar cell based on TAP-PP-OX sc ＝19.25mA/cm 2 Open circuit voltage V oc =0.84V, fill factor FF =0.55, photovoltaic cell efficiency PCE =8.85%.
The present invention has been disclosed in terms of the preferred embodiment, but is not intended to be limited to the embodiment, and all technical solutions obtained by substituting or converting equivalents thereof fall within the scope of the present invention.
Claims (9)
1. An n-type organic dye based on 1, 2-benzophenothiazine is characterized in that the structural general formula is shown as formula I or formula II:
wherein R is a linear or branched alkyl chain having 1 to 12 carbon atoms, or
Wherein R is 2 Is a straight chain or branched alkyl chain with 1 to 12 carbon atoms;
wherein R is 1 Is hydrogen or a linear or branched alkyl chain having 1 to 12 carbon atoms containing an oxygen atom and a sulfur atom.
2. The method for preparing 1, 2-benzothiazol-based n-type organic dye according to claim 1, wherein the synthesis method of formula I is:
adding 2-aminobenzenethiol and 4-tetrahydrocyclic ketone into dimethyl sulfoxide, and stirring for 24 hours in air at the temperature of 110 ℃ to obtain a compound 1;
mixing the compound 1, R-Br, KOH, TBAB and dimethyl sulfoxide, and reacting for 10 hours at room temperature in a nitrogen atmosphere to obtain a compound 2;
mixing the compound 2 and chloroform, stirring and reacting for 6 hours in an ice-water bath under nitrogen atmosphere, and adding N-bromosuccinimide into a reaction bottle for three times in the first two hours to obtain a compound 3;
reacting a compound of 3, 5-formaldehyde furan-2-boric acid and K 2 CO 3 、Pd[P(C 6 H 5 ) 3 ] 4 TBAB and THF are put into a three-neck flask and heated and refluxed for 13 hours at 85 ℃ in the dark and nitrogen atmosphere to obtain a compound 4;
compound 4, cyanoacetic acid, ammonium acetate and acetic acid were combined, heated to reflux at 110 ℃ for 12 hours under nitrogen atmosphere and purified to give the product of formula I.
3. The method according to claim 2, wherein the synthetic route of formula I is:
4. the process according to claim 2 or 3, wherein the compound 3, 5-formylfuran-2-boronic acid, K 2 CO 3 、Pd[P(C 6 H 5 ) 3 ] 4 TBAB in a 1:1.2:2.5:0.05:0.3.
5. the process according to claim 2 or 3, wherein the molar ratio of compound 4, cyanoacetic acid and ammonium acetate is 1:2:1.
6. the preparation method according to claim 2, wherein the synthesis method of formula II is as follows:
mixing the compound 4 and chloroform, stirring and reacting for 6 hours in an ice-water bath under nitrogen atmosphere, and adding N-bromosuccinimide into a reaction bottle for three times in the first two hours to obtain a compound 5;
compound 5, compound
K 2 CO 3 、Pd[P(C 6 H 5 ) 3 ] 4 TBAB and THF, heating and refluxing for 13h at 85 deg.C in the dark and nitrogen atmosphere, and purifying to obtain compound 6;
compound 6, cyanoacetic acid, ammonium acetate and acetic acid were combined and heated to reflux at 90 ℃ for 24 hours under nitrogen atmosphere and purified to give the product of formula II.
7. The method according to claim 3, wherein the synthetic route of formula II is:
8. the process according to claim 6 or 7, wherein Compound 5 is Compound
K 2 CO 3 、Pd[P(C 6 H 5 ) 3 ] 4 The molar ratio of TBAB is 1.2.
9. Use of the n-type organic dye of 1, 2-benzophenothiazine according to claim 1 as sensitizer in dye-sensitized solar cells.
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|---|---|---|---|---|
| US20100275986A1 (en) * | 2009-04-29 | 2010-11-04 | Academia Sinica | Organic dye and dye-sensitized solar cell using the same |
| CN108795084A (en) * | 2018-08-03 | 2018-11-13 | 桂林理工大学 | A kind of preparation method of phenothiazinyl D-A- π-A type organic dyestuff |
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2022
- 2022-12-06 CN CN202211578481.5A patent/CN115785693B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100275986A1 (en) * | 2009-04-29 | 2010-11-04 | Academia Sinica | Organic dye and dye-sensitized solar cell using the same |
| CN108795084A (en) * | 2018-08-03 | 2018-11-13 | 桂林理工大学 | A kind of preparation method of phenothiazinyl D-A- π-A type organic dyestuff |
Non-Patent Citations (1)
| Title |
|---|
| 潘彬等: "含苯并噻二唑的吩噻嗪染料分子的设计合成及其在染料敏化太阳能电池中的应用", 化学学报, vol. 76, no. 3, pages 215 - 223 * |
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