CN102924958A - Triphenylamine-based organic dye and synthesizing method and application of triphenylamine-based organic dye - Google Patents
Triphenylamine-based organic dye and synthesizing method and application of triphenylamine-based organic dye Download PDFInfo
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Abstract
The invention relates to an organic dye, in particular to a triphenylamine-based organic dye and a synthesizing method and application of the triphenylamine-based organic dye. An electron supplying part is a triphenylamine group, and an electron absorption part is a cyano crylic acid group. Compared with the prior art, the carboxyl (-COOH) in dye molecules is an optimally chosen absorption functional group which can ensure that the dye molecules are chemically absorbed to amphoteric TiO2 surfaces, so that electron cloud overlapping happens on an LUMO (lowest unoccupied molecular orbital) of the dye molecules and a 3d (three-dimensional) orbital of TiO2; and meanwhile, the triphenylamine group and derivatives of the triphenylamine group have strong electron supplying capability; three benzene rings have a non-coplanar structure and can prevent molecules from overlapping and reduce the aggregation of the dye; and the D-pi-A structure of the dye molecule has a larger conjugated system, so that the absorption spectrum of the dye is subjected to red shift and broadening, light capture capability of the dye molecules is effectively enhanced, and utilization rate of visible light is increased.
Description
Technical field
The present invention relates to organic dye, specifically a kind of triphenylamine base organic dye and synthetic method and application.
Background technology
Dye-sensitized solar cells is a kind of brand-new solar cell, it has the structure of similar sandwich, comprise working electrode and to electrode, in manufacturing process, with the nano titanium oxide sintering on conductive glass, again light-sensitive coloring agent is embedded in the porous nano titanium dioxide surface and forms working electrode, working electrode and to being to contain the right liquid electrolyte of redox materials between the electrode (being generally the conductive glass that has supported catalytic amount platinum or carbon), the hole that its immerses nano titanium oxide contacts with light-sensitive coloring agent.During work, under the irradiation of incident light, the light-sensitive coloring agent that is embedded in the nano titanium oxide surface absorbs photon, transit to excited state, then the conduction band to titanium dioxide injects electronics, dyestuff becomes the positive ion of oxidation state, electronics forms electric current by external circuit and arrives electrode, the dyestuff positive ion is accepted the electronics of reductive agent in the electrolyte solution, is reduced to initial dyestuff, and the oxygenant in the ionogen be diffused into to electrode obtain electronics and make reductive agent obtain regeneration, form a complete circulation, in whole process, apparent upper chemical substance does not change, and light energy conversion has become electric energy.
In present dye sensitization solar battery (DSSCs) technique, generally acknowledge that the best light-sensitive coloring agent of performance is the metal complex dye of ruthenium bipyridyliums, but, because the dyestuff of the type contains precious metal and preparation and the relatively difficulty of purifying all, be difficult to realize large-scale application.
Organic dye has the molar extinction coefficient height, synthetic and purify fairly simple, the advantage such as cost of manufacture is relatively cheap, and can independently change the structure of molecule various piece, this is conducive to probe into the dependence of dye structure and opto-electronic conversion performance.Therefore, the application of pure organic dye in DSSCs also caused increasing concern.Wherein triphenylamine and derivative thereof have good cavity transmission ability, and can be used as electron donor material, so have good opto-electronic conversion performance, be widely used in the organic photoelectrical material field, however nonmetal organic photosensitizing dyestuff Shortcomings aspect stability, efficient in the prior art.
Summary of the invention
The present invention is directed to the shortcoming and defect that exists in the prior art, propose low, the good stability of a kind of production cost, can effectively strengthen the light capture ability of dye molecule, improve triphenylamine base dyestuff and synthetic method and the application of visible light utilising efficiency.
The present invention can reach by following measures:
A kind of triphenylamine base organic dye is characterized in that having the structure of being shown below:
A kind of synthetic method of as mentioned above triphenylamine base dyestuff is characterized in that comprising the steps:
Step 1: synthetic N, N-hexichol amido-4-vinylbenzene is specially in potassium tert.-butoxide and the methyl triphenyl iodate phosphorus adding reactor; dry under vacuum condition, then under nitrogen protection, add the tetrahydrofuran (THF) that is dissolved with 4-pentanoic benzaldehyde; after the stirring; react 4h under the room temperature, react complete rear water-dichloromethane extraction reaction product, get organic phase; carry out column chromatography after revolving steaming; eluent is normal hexane, and the gained solid gets white crystal with the methylene chloride-methanol recrystallization
Step 2: synthetic 4-(4-diphenyl benzene ethene)-Benzaldehyde,2-methoxy; be specially the product with gained in the step 1; with 4-bromo-Benzaldehyde,2-methoxy; yellow soda ash; 2; 6-di-tert-butyl-4-methy phenol and Pd catalyzer add in the reactor; dry under vacuum condition, then under nitrogen protection, add DMAC, back flow reaction 6h; react complete rear water-dichloromethane extraction reaction product; organic phase, carry out column chromatography after revolving steaming, normal hexane-methylene dichloride is eluent; adopt recrystallization method to be further purified and obtain orange crystal
Step 3: synthetic 2-cyano group-3-(4-(4-diphenyl benzene ethene)-2-p-methoxy-phenyl)-vinylformic acid; be specially product and cyanoacetic acid with gained in the step 2; ammonium acetate joins in the reactor, and is dry under vacuum condition, then under the nitrogen protection condition; add toluene; cool off behind the backflow 8h, separate out red material in the solution, filter; use successively normal hexane, normal hexane-ether mixed solvent (5:1) washing precipitation, obtain red solid.
N described in the step 1 of the present invention, the cinnamic synthetic middle chemical equation of N-hexichol amido-4-is as follows:
The building-up reactions equation of 4-described in the step 2 of the present invention (4-diphenyl benzene ethene)-Benzaldehyde,2-methoxy is as follows:
Wherein the Pd catalyzer can adopt CAS:14221-01-3, CAS:95464-05-4.
(4-(4-diphenyl benzene ethene)-2-p-methoxy-phenyl)-acrylic acid synthetic reaction equation is as follows for the cyano group-3-of 2-described in the step 3 among the present invention:
A kind of method that adopts aforesaid triphenylamine organic dye to be used as liquid sensitization solar battery sensitizing agent is characterized in that may further comprise the steps:
Step (1): make optoelectronic pole, be specially the rectangle that first conductive glass is cut into 1.8cm * 1.5cm, use successively deionized water, ethanol, Virahol, acetone, deionized water ultrasonic cleaning, for subsequent use after the oven dry, then adopt the method for silk screen printing that titania slurry is coated on the conductive glass, repeating print obtains the titanium dioxide film that thickness is about 12 μ m 6 times, and the titanium dioxide film for preparing is placed 500 ℃ of sintering 60min of tube furnace, then it is dipped in 40mM TiCl
4In the aqueous solution, be warming up to 70
oC processes 30min, takes out TiO after processing finishes
2Film is rinsed well with deionized water, again places 500 ℃ of sintering 60min of tube furnace, and when cooling temperature was down to 70 ℃, it was 2 * 10 that titanium dioxide film is immersed in concentration
-4In the triphenyl amine dyes ethanolic soln of mol/L, take out behind the 24h, and with the dehydrated alcohol flushing, dry,
Step (2): preparation is specially and adopts silk screen print method that platinum acid chloride solution is coated in conductive glass surface electrode, puts into 500 ℃ of sintering 30min of tube furnace, cools off for subsequent use.
Step (3): the assembling of battery, a titanium dioxide film 2-3 who is specially at optoelectronic pole drips electrolytic solution, and platinum electrode is assembled with optoelectronic pole down, and the sheet glass of two plate electrodes staggers slightly, so that test, firmly compression is rear clamps two plate electrodes with clip.
Step of the present invention is made optoelectronic pole described in (1), when the method for employing silk screen printing is coated in titania slurry on the conductive glass, after the titanium dioxide film of each printing need at room temperature leave standstill 5min, be placed on again in the baking oven in 120 ℃ of baking 6min, in order to carry out printing next time.
A kind of liquid dye sensitization solar battery comprises optoelectronic pole, electrolytic solution and to electrode, it is characterized in that adopting as above, method makes.
The sensitization of liquid dye described in the present invention too can battery, wherein said electrolytic solution can adopt at present common on the market electrolytic solution product, prescription such as the Dalian seven-colour-light is the related products of DHS-E23, and its main component is DMPII/LiI/I2/TBP/GuSCN and acetonitrile solvent.
The present invention compared with prior art, (COOH) be the preferential adsorption functional group of selecting, it may guarantee that the dye molecule chemisorption is to both sexes TiO to the carboxyl in the described dye molecule
2The surface makes lowest unoccupied molecular orbital (LUMO) and the TiO of dye molecule
23d track generation electronic cloud overlapping.Simultaneously trianilino group and derivative thereof have very strong electron donation, and three phenyl ring wherein have non-coplanar structure, can prevent from piling up between the molecule, reduce the gathering of dyestuff.The D-π of dye molecule-A structure has larger conjugated system, makes absorption spectrum Einstein shift and the broadening of dyestuff, has effectively strengthened the light capture ability of dye molecule, has improved the utilising efficiency of visible light.
Description of drawings:
Accompanying drawing 1 is chemical structural formula of the present invention.
Embodiment:
The present invention is further illustrated below in conjunction with the drawings and specific embodiments.
The present invention is directed to the deficiencies in the prior art and propose a kind of triphenylamine base organic dye, it has the structure of being shown below:
Step 1: synthetic N; N-hexichol amido-4-vinylbenzene; be specially 3.08g; 27.46mmol potassium tert.-butoxide and 11.11g; 24.47mmol methyl triphenyl iodate phosphorus add in the reactor, dry under vacuum condition, then under nitrogen protection; add and be dissolved with 5.03g; 18.31mmol the tetrahydrofuran (THF) 50ml of 4-pentanoic benzaldehyde, stir, react 4h under the room temperature; react complete rear water-dichloromethane extraction reaction product; organic phase, carry out column chromatography after revolving steaming, eluent is normal hexane; the gained solid gets white crystal with the methylene chloride-methanol recrystallization
Step 2: synthetic 4-(4-diphenyl benzene ethene)-Benzaldehyde,2-methoxy; be specially the product 0.43g with gained in the step 1; 1.57mmol; with 0.41g; 1.89mmol 4-bromo-Benzaldehyde,2-methoxy, 0.42g, the yellow soda ash of 3.94mmol; 0.07g; 0.31mmol 2,6 di tert butyl 4 methyl phenol, 0.015g; 0.015mmol the Pd catalyzer add in the reactor; dry under vacuum condition, then adding DMAC is an amount of under nitrogen protection, back flow reaction 6h; react complete rear water-dichloromethane extraction reaction product; organic phase, carry out column chromatography after revolving steaming, normal hexane-methylene dichloride is eluent; adopt recrystallization method to be further purified and obtain orange crystal
Step 3: synthetic 2-cyano group-3-(4-(4-diphenyl benzene ethene)-2-p-methoxy-phenyl)-vinylformic acid; be specially the product 40.5mg with gained in the step 2; 0.1mol; cyanoacetic acid 9.45mg; 0.11mmol; ammonium acetate 12.8mg; 17.0mmol join in the reactor, dry under vacuum condition, then under the nitrogen protection condition; add an amount of toluene; cool off behind the backflow 8h, separate out red material in the solution, filter; use successively normal hexane, normal hexane-ether mixed solvent (5:1) washing precipitation, obtain red solid.
Wherein the catalyzer of Pd described in the step 2 can adopt CAS:14221-01-3, CAS:95464-05-4, wherein CAS:95464-05-4 is [two (diphenylphosphine) ferrocene of 1,1'-] palladium chloride methylene dichloride complex compound (1,1'-Bis (diphenylphosphino) ferrocene
-palladium (II) dichloride dichloromethane complex), CAS:14221-01-3 four (triphenyl phosphines) by name are changed palladium (tetrakis (triphenylphosphine) palladium).
Can be as the sensitizing agent of liquid sensitization solar battery by the triphenylamine organic dye that above step obtains, this application may further comprise the steps: step (1): make optoelectronic pole, be specially the rectangle that first conductive glass is cut into 1.8cm * 1.5cm, use successively deionized water, ethanol, Virahol, acetone, the deionized water ultrasonic cleaning, for subsequent use after the oven dry, then adopt the method for silk screen printing that titania slurry is coated on the conductive glass, the main component of described titania slurry is titanium dioxide, Terpineol 350 and ethyl cellulose, can adopt present ordinary titanium dioxide slurry on the market to implement, for example be purchased from the related products of Dalian seven-colour-light, repeat print and obtain the titanium dioxide film that thickness is about 12 μ m 6 times, the titanium dioxide film for preparing is placed 500 ℃ of sintering 60min of tube furnace, then it is dipped in 40mM TiCl
4In the aqueous solution, be warming up to 70
oC processes 30min, and this processing can be at TiO
2Surface growth one deck small-particle TiO
2, can further strengthen TiO
2Intergranular contact has changed TiO simultaneously
2Conduction level, more be conducive to the excited state electronics and inject the Nano semiconductor conduction band from dyestuff, take out TiO after processing finishes
2Film is rinsed well with deionized water, again places 500 ℃ of sintering 60min of tube furnace, and when cooling temperature was down to 70 ℃, it was 2 * 10 that titanium dioxide film is immersed in concentration
-4In the triphenyl amine dyes ethanolic soln of mol/L, take out behind the 24h, and with the dehydrated alcohol flushing, dry,
Step (2): preparation is to electrode, be specially and adopt silk screen print method that platinum acid chloride solution is coated in conductive glass surface, put into 500 ℃ of sintering 30min of tube furnace, cool off for subsequent use, described platinum acid chloride solution can adopt at present common on the market related products, as the main component that is purchased from the Dalian seven-colour-light is the platinum acid chloride solution of Platinic chloride
Step (3): the assembling of battery, a titanium dioxide film 2-3 who is specially at optoelectronic pole drips electrolytic solution, and platinum electrode is assembled with optoelectronic pole down, and the sheet glass of two plate electrodes staggers slightly, so that test, firmly compression is rear clamps two plate electrodes with clip.
Step of the present invention is made optoelectronic pole described in (1), when the method for employing silk screen printing is coated in titania slurry on the conductive glass, after the titanium dioxide film of each printing need at room temperature leave standstill 5min, be placed on again in the baking oven in 120 ℃ of baking 6min, in order to carry out printing next time.
By the triphenylamine base organic dye being carried out the photoelectric properties test, can find out: novel triphenylamine base organic dye of the present invention has good light capturing ability, be applied to the photosensitizers of DSCCs, can obtain the electricity conversion more than 5.15%, this comes from the strong electron donation of triphenylamine, effective transfer of electronics in the molecule that D-π-the A structure causes that non-coplanar space structure and dyestuff have, novel triphenylamine base organic dye novel structure provided by the invention, be easy to synthesizing and purifying, with low cost, demonstrate the application prospect of potential replacement precious metal dyestuff.
(COOH) be the preferential adsorption functional group of selecting, it may guarantee that the dye molecule chemisorption is to both sexes TiO to carboxyl described in the present invention in the dye molecule
2The surface makes lowest unoccupied molecular orbital (LUMO) and the TiO of dye molecule
23d track generation electronic cloud overlapping, trianilino group and derivative thereof have very strong electron donation simultaneously, and three phenyl ring wherein have non-coplanar structure, can prevent from piling up between the molecule, reduce the gathering of dyestuff.The D-π of dye molecule-A structure has larger conjugated system, makes absorption spectrum Einstein shift and the broadening of dyestuff, has effectively strengthened the light capture ability of dye molecule, has improved the utilising efficiency of visible light.
Claims (9)
1. triphenylamine base organic dye is characterized in that having the structure of being shown below:
, wherein supplied for electronic partly is trianilino group, electrophilic partly is the alpha-cyanoacrylate group.
2. the synthetic method of a triphenylamine base dyestuff as claimed in claim 1 is characterized in that comprising the steps:
Step 1: synthetic N, N-hexichol amido-4-vinylbenzene is specially in potassium tert.-butoxide and the methyl triphenyl iodate phosphorus adding reactor; dry under vacuum condition, then under nitrogen protection, add the tetrahydrofuran (THF) that is dissolved with 4-pentanoic benzaldehyde; after the stirring; react 4h under the room temperature, react complete rear water-dichloromethane extraction reaction product, get organic phase; carry out column chromatography after revolving steaming; eluent is normal hexane, and the gained solid gets white crystal with the methylene chloride-methanol recrystallization
Step 2: synthetic 4-(4-diphenyl benzene ethene)-Benzaldehyde,2-methoxy; be specially the product with gained in the step 1; with 4-bromo-Benzaldehyde,2-methoxy; yellow soda ash; 2; 6-di-tert-butyl-4-methy phenol and Pd catalyzer add in the reactor; dry under vacuum condition, then under nitrogen protection, add DMAC, back flow reaction 6h; react complete rear water-dichloromethane extraction reaction product; organic phase, carry out column chromatography after revolving steaming, normal hexane-methylene dichloride is eluent; adopt recrystallization method to be further purified and obtain orange crystal
Step 3: synthetic 2-cyano group-3-(4-(4-diphenyl benzene ethene)-2-p-methoxy-phenyl)-vinylformic acid; be specially product and cyanoacetic acid with gained in the step 2; ammonium acetate joins in the reactor, and is dry under vacuum condition, then under the nitrogen protection condition; add toluene; cool off behind the backflow 8h, separate out red material in the solution, filter; use successively normal hexane, normal hexane-ether mixed solvent (5:1) washing precipitation, obtain red solid.
3. the synthetic method of a kind of triphenylamine base dyestuff according to claim 2 is characterized in that N described in the step 1, and the cinnamic synthetic middle chemical equation of N-hexichol amido-4-is as follows:
4. the synthetic method of a kind of triphenylamine base dyestuff according to claim 2 is characterized in that the building-up reactions equation of 4-described in the step 2 (4-diphenyl benzene ethene)-Benzaldehyde,2-methoxy is as follows:
Wherein the Pd catalyzer is for adopting CAS:14221-01-3, CAS:95464-05-4.
5. the synthetic method of a kind of triphenylamine base dyestuff according to claim 2, (4-(4-diphenyl benzene ethene)-2-p-methoxy-phenyl)-acrylic acid synthetic reaction equation is as follows to it is characterized in that the cyano group-3-of 2-described in the step 3:
6. the application of a triphenylamine base organic dye as claimed in claim 1 is characterized in that the sensitizing agent as the liquid dye sensitization solar battery.
7. the application of a kind of triphenylamine base organic dye according to claim 6 is characterized in that may further comprise the steps:
Step (1): make optoelectronic pole, be specially the rectangle that first conductive glass is cut into 1.8cm * 1.5cm, use successively deionized water, ethanol, Virahol, acetone, deionized water ultrasonic cleaning, for subsequent use after the oven dry, then adopt the method for silk screen printing that titania slurry is coated on the conductive glass, repeating print obtains the titanium dioxide film that thickness is about 12 μ m 6 times, and the titanium dioxide film for preparing is placed 500 ℃ of sintering 60min of tube furnace, then it is dipped in 40mM TiCl
4In the aqueous solution, be warming up to 70
oC processes 30min, takes out TiO after processing finishes
2Film is rinsed well with deionized water, again places 500 ℃ of sintering 60min of tube furnace, and when cooling temperature was down to 70 ℃, it was 2 * 10 that titanium dioxide film is immersed in concentration
-4In the triphenyl amine dyes ethanolic soln of mol/L, take out behind the 24h, and with the dehydrated alcohol flushing, dry,
Step (2): preparation is specially and adopts silk screen print method that platinum acid chloride solution is coated in conductive glass surface electrode, puts into 500 ℃ of sintering 30min of tube furnace, cool off for subsequent use,
Step (3): the assembling of battery, a titanium dioxide film 2-3 who is specially at optoelectronic pole drips electrolytic solution, and platinum electrode is assembled with optoelectronic pole down, and the sheet glass of two plate electrodes staggers slightly, so that test, firmly compression is rear clamps two plate electrodes with clip.
8. triphenylamine organic dye according to claim 7 is as the method for liquid sensitization solar battery sensitizing agent, it is characterized in that making optoelectronic pole described in the step (1), when the method for employing silk screen printing is coated in titania slurry on the conductive glass, after the titanium dioxide film of each printing need at room temperature leave standstill 5min, be placed on again in the baking oven in 120 ℃ of baking 6min, in order to carry out printing next time.
9. liquid dye sensitization solar battery comprises optoelectronic pole, electrolytic solution and to electrode, it is characterized in that adopting method as claimed in claim 8 to make.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105175583A (en) * | 2015-08-09 | 2015-12-23 | 同济大学 | Acetophenone photoinitiator with biphenyl as conjugate structure, preparation method and application thereof |
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| CN101007904A (en) * | 2007-01-19 | 2007-08-01 | 南开大学 | Organic dye containing triphenylamine and its preparation method and uses |
| CN101928469A (en) * | 2009-06-18 | 2010-12-29 | 精磁科技股份有限公司 | Organic dye and dye-sensitized solar cell (DSSC) using same |
| CN102212274A (en) * | 2011-04-11 | 2011-10-12 | 天津理工大学 | Triphenylamine-phenyl organic dye and application thereof |
| KR20120105961A (en) * | 2011-03-17 | 2012-09-26 | 서울대학교산학협력단 | Photosensitizer containing benzothiazole for photovoltaic cell, and photovoltaic cell including the same |
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| CN101007904A (en) * | 2007-01-19 | 2007-08-01 | 南开大学 | Organic dye containing triphenylamine and its preparation method and uses |
| CN101928469A (en) * | 2009-06-18 | 2010-12-29 | 精磁科技股份有限公司 | Organic dye and dye-sensitized solar cell (DSSC) using same |
| KR20120105961A (en) * | 2011-03-17 | 2012-09-26 | 서울대학교산학협력단 | Photosensitizer containing benzothiazole for photovoltaic cell, and photovoltaic cell including the same |
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| CN105175583A (en) * | 2015-08-09 | 2015-12-23 | 同济大学 | Acetophenone photoinitiator with biphenyl as conjugate structure, preparation method and application thereof |
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Effective date of registration: 20221118 Address after: 264209 No.2 Wenhua West Road, torch hi tech Industrial Development Zone, Weihai City, Shandong Province Patentee after: Liu Ronggang Patentee after: Du Yufu Address before: 150000 No. 7, C building, Xin Heng City, Nangang District, Harbin, Heilongjiang. Patentee before: Heilongjiang Dingxin Building Co.,Ltd. |
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