CN103275060B - A kind of triaryl methane compounds and its preparation method and application - Google Patents
A kind of triaryl methane compounds and its preparation method and application Download PDFInfo
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/542—Dye sensitized solar cells
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- 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
- Y02E10/549—Organic PV cells
Abstract
The invention discloses a kind of triaryl methane compounds and its preparation method and application; Preparation method is first by R
2-CHO and and R
1-H is obtained by reacting chemical compounds I; Again the chemical compounds I obtained and Vilsmeier reagent react are generated compound ii; The compound ii obtained and cyanoacetic acid after back flow reaction, obtain triaryl methane compounds in acetum; Or, first the chemical compounds I obtained and N-bromo-succinimide generation bromo-reaction are generated compound III; By gained compound III and (OH)
2b-R
3-CHO obtains compounds Ⅳ after back flow reaction in toluene or chloroform; By the compounds Ⅳ of acquisition and cyanoacetic acid back flow reaction in acetum, obtain triaryl methane compounds; The triaryl methane compounds that the method obtains is applied to as light-sensitive coloring agent prepares dye sensitization solar battery material; These triaryl methane compounds raw material sources are wide, low price, and preparation method is simple, and cost is low, can suitability for industrialized production; Be expected to become a kind of novel dye sensitization solar battery material.
Description
Technical field
The present invention relates to a kind of triaryl methane compounds and its preparation method and application, belong to field of dye-sensitized solar cells.
Technical background
Solar cell is according to photogenic voltage principle, solar energy converting is become a kind of photoelectric device of electric energy.Dye sensitization solar battery (DSSC) is proposed in 1991 first by Lausanne senior engineer Gratzel research group of Swiss Confederation, and has started the upsurge of photovoltaic cell research.This kind of battery has that cost is low, structure is simple, excellent [the highest electricity conversion reaches 12.3%(A.Yella to electricity conversion, H.-W.Lee, M.Gratzel, Science, 334,2011,629) advantage such as], becomes the photoelectric conversion device that a class has application prospect.
Light-sensitive coloring agent is very part and parcel in dye sensitization solar battery, and its performance directly has influence on the electricity conversion of DSSC.At present, the dyestuff be applied in DSSC mainly contains metal complex dye and the large class of organic dye two.The electricity conversion of part metals complex dye more than 10%, but due to its cost high, limit its application.Therefore, synthesis is used for the study hotspot that efficient organic dye photosensitizers becomes this field.
Triarylmethane compounds is widely used as staining agent (R.Muthyala, A.R.Katritzky, X.Lan, DyesPigments, 25,1994,303) and thermo-sensitive material (M.Irie, J.Am.Chem.Soc.105,1983,2078), its color light is bright-coloured, and synthesis technique is simple.At present, triarylmethane is mainly used for dyeing (disclosed in China Patent Publication No. CN101326244A a class triarylmethane dye) to organic substances such as fiber, wool, leathers as dyestuff, but be applied to area of solar cell about triarylmethane compounds as dyestuff photosensitizers and do not see RELATED APPLICATIONS technology report, also never at home and abroad occur in public publication.
Summary of the invention
To the present invention is directed in prior art metal complex dye and organic dye for dye sensitization solar battery, there is the defects such as raw materials cost is high, preparation method is complicated, object is organic triaryl methane compounds of the novel texture providing a kind of cheapness, opto-electronic conversion performance good.
Another object of the present invention is to provide a kind of low cost to prepare the method for above-mentioned triaryl methane compounds, and extensively, preparation method is simple, can suitability for industrialized production for the method cheaper starting materials, source.
A further object of the invention is the application providing a kind of above-mentioned triaryl methane compounds, this triaryl methane compounds is applied to as light-sensitive coloring agent prepares dye sensitization solar battery material, this material is cheap, preparation method is simple, and opto-electronic conversion performance is good, the potentiality with widespread use in dye sensitization solar battery.
The invention provides a kind of triaryl methane compounds, there is formula 1 or formula 2 structure:
Wherein,
R
1be selected from
in one;
R
2be selected from
in one;
R
3be selected from
in one;
R
4, R
5, R
6, R
7and R
8be selected from C independently of one another
3 ~ 9alkyl in a kind of, or C
1 ~ 6alkoxyl group in a kind of, or hydrogen atom
Preferred triaryl methane compounds, R
2be selected from
in one; R
3be selected from
in one; R
1be selected from
in one; Wherein, R
4, R
5, R
6, R
7and R
8be selected from C independently of one another
3 ~ 9straight chained alkyl in a kind of, or C
1 ~ 6unbranched alkoxy in a kind of, or hydrogen atom.
More preferably triaryl methane compounds, R
2be selected from
in one; R
3be selected from
in one; R
1be selected from
in one; Wherein, R
4, R
5, R
6, R
7and R
8be selected from C independently of one another
3 ~ 9straight chained alkyl in a kind of, or methoxyl group, oxyethyl group, one in propoxy-, or hydrogen atom.
Present invention also offers a kind of preparation method of triaryl methane compounds as above, the method is under protection of inert gas, first by R
2-CHO and and R
1-H is obtained by reacting chemical compounds I under 80 ~ 100 ° of C; Again by the chemical compounds I that obtains and Vilsmeier reagent reacting generating compound II under 25 ~ 120 ° of C; The compound ii obtained and cyanoacetic acid after back flow reaction, obtain the triaryl methane compounds of formula 2 structure in acetum;
Or, first the chemical compounds I obtained and N-bromo-succinimide be there is under-5 ~ 5 ° of C bromo-reaction and generate compound III; By gained compound III and (OH)
2b-R
3-CHO obtains compounds Ⅳ after back flow reaction in toluene or chloroform; By the compounds Ⅳ of acquisition and cyanoacetic acid back flow reaction in acetum, obtain the triaryl methane compounds of formula 1 structure.
R in above-mentioned preparation method
2-CHO and R
1the mol ratio of-H is 1:8 ~ 12.
Chemical compounds I and POCl in above-mentioned preparation method
3mol ratio be 1:1 ~ 8.
In above-mentioned preparation method, the mol ratio of compound ii and cyanoacetic acid is 1:6 ~ 10.
In above-mentioned preparation method, the mol ratio of compounds Ⅳ and cyanoacetic acid is 1:6 ~ 10.
In above-mentioned preparation method, the mol ratio of chemical compounds I and N-bromo-succinimide is 1:1.
Compound III and (OH) in above-mentioned preparation method
2b-R
3the mol ratio of-CHO is 1:1.
Compound III and (OH) in above-mentioned preparation method
2b-R
3the K of compound III molar weight 8 ~ 10 times is added during-CHO reaction
2cO
3.
Described Vilsmeier reagent is POCl
3dMF solution, wherein, DMF and POCl
3mol ratio be 5 ~ 1:1; Described Vilsmeier reagent is under ice-water bath, by POCl
3dropwise join in DMF (DMF), stir 1 ~ 2h and obtain.
R in above-mentioned preparation method
2-CHO and and R
1the reaction times of-H is 4 ~ 8h.
In above-mentioned preparation method, the reaction times of chemical compounds I and Vilsmeier reagent is 8 ~ 24h.
In above-mentioned preparation method, the reaction times of compound ii and cyanoacetic acid is 8 ~ 12h.
In above-mentioned preparation method, the time of chemical compounds I and N-bromo-succinimide generation bromo-reaction is 2 ~ 4h.
Compound III and (OH) in above-mentioned preparation method
2b-R
3the reaction times of-CHO is 8 ~ 16h.
In above-mentioned preparation method, the reaction times of compounds Ⅳ and cyanoacetic acid is 8 ~ 12h.
Triaryl methane compounds synthetic route of the present invention:
The concrete synthesis step of triaryl methane compounds of the present invention is as follows:
Triaryl methane compounds building-up process is carried out all under an inert atmosphere;
(1) by R
2-CHO and and R
1-H is that 1:8 ~ 12 mix in molar ratio, adds a small amount of NaHSO
4siO
2as catalyzer, at 80 ~ 100 ° of C stirring and refluxing 4 ~ 8h, be cooled to room temperature; Suction filtration, filtrate organic solvent washing, is spin-dried for solvent; Carry out column chromatography for separation after the solid drying obtained and obtain chemical compounds I;
(2) under ice-water bath, by POCl
3dropwise join in DMF (DMF), DMF and POCl
3mol ratio be 5 ~ 1:1, stir 1 ~ 2h obtain Vilsmeier reagent; Then gained Vilsmeier reagent dropwise is dissolved in the chemical compounds I of solvent, chemical compounds I and POCl
3mol ratio be 1:1 ~ 8, stirring reaction 8 ~ 24h under 25 ~ 120 ° of C, product is poured in frozen water, regulates PH to neutral with the NaOH aqueous solution; Crude by column chromatography is separated obtained compound ii;
(3) chemical compounds I is dissolved in DMF, is placed in the ice-water bath of-5 ~ 5 ° of C, in chemical compounds I, slowly add N-bromo-succinimide, mol ratio is 1:1, stirs 10 ~ 30min, then at stirring at room temperature reaction 2 ~ 4h; Reaction product is poured in trash ice, extraction into ethyl acetate, merges organic phase, after removal of solvent under reduced pressure, obtains compound III through column chromatography for separation;
(4) by compound III, (OH)
2b-R
3-CHO, K
2cO
3join in reactor by the mol ratio of 1:1:8 ~ 12, with four triphenyl phosphorus palladiums for catalyzer, stir with toluene or chloroform give solvent refluxing; Product is poured into water, and with dichloromethane extraction, separatory, merge organic phase, drying removes desolventizing and obtains compounds Ⅳ through column chromatography for separation;
(5) compound ii or IV, cyanoacetic acid adds in flask by the mol ratio of 1:6 ~ 10, adds a small amount of ammonium acetate, take acetic acid as solvent, after heated and stirred backflow 8 ~ 12h; Pour in frozen water, with chloroform extraction, separatory, dry organic phase; Revolve steaming solvent and obtain triaryl methane compounds through column chromatography.
Present invention also offers a kind of application of triaryl methane compounds as above, this application is the preparation triaryl methane compounds of formula 1 or formula 2 structure being used for dye sensitization solar battery material as light-sensitive coloring agent.
Described application be had by Tu the FTO conductive glass of titanium dioxide nanocrystalline to soak in the tetrahydrofuran solution of described triaryl methane compounds after, make the light anode of dye sensitization solar battery.
The preparation process of solar cell of the present invention and battery performance test:
(1) preparation of light anode: rinse FTO conductive glass (3.5cm*10cm), dry for standby with deionized water and dehydrated alcohol successively; Silk screen printing titanium dioxide transparent layer slurry in cleaned FTO substrate, then places it in 130 ° of dry 6min of C on temperature programmed control titanium hot-plate, obtains TiO
2film; Then the above-mentioned titanium deoxid film printed is carried out calcination processing under fluidizing air condition, slow near room temperature after 500 ° of C high temperature sintering 30min; Be placed on the TiCl of 40mM again
4in the aqueous solution, 70 ° of C constant temperature process 40min, dry up with deionized water and alcohol flushing successively, cure 25min at 500 ° of C;
(2) sensitization of light anode: by the above-mentioned mesoporous titanium dioxide film prepared at 500 ° of C thermal treatment 30min, put into dye solution (5*10 after naturally cooling to 80 ° of C
-4mol.L
-1tHF solution) in, sensitization 12 ~ 24h; Clean with acetonitrile after sensitization and dry up stand-by;
(3) to the preparation of electrode: on pretreated FTO conducting glass substrate, plate Pt and do catalyst layer, and then the large aperture of nonconductive surface drill point head is for subsequent use;
(4) assembling of battery: light anode good for sensitization is upwards positioned on thermocompressor, at TiO
2the Surlyn ring that around film, 30 μm, cover is thick, covers electrode, then seals 2min at 100 ° of C;
(5) ionogen injects: dripping 1 ionogen on the aperture of electrode, after using surge pump to vacuumize not have bubble between two electrodes that make, seal, obtains dye sensitization solar battery;
(6) battery performance test: by the working electrode from battery with draw wire respectively to electrode, receives on battery performance test device; Effective illuminating area of this battery is: 0.16cm
2: testing light source is: solar simulator (LS1000-4S-AM1.5G-1000W type) provides 100mWcm
-2radiant light; Data gathering: Keithley2602 digital sourcemeter.
Beneficial effect of the present invention is: the present invention by repetition test, synthesizes a kind of triaryl methane compounds of novel texture, and this raw materials of compound source is wide, low price, and preparation method is simple, and cost is low, can suitability for industrialized production; And Late Cambrian triaryl methane compounds has good opto-electronic conversion performance, it can be applied to as light-sensitive coloring agent and prepare dye sensitization solar battery material, for dye sensitization solar battery has widened material selection range, reduce the cost of dye sensitization solar battery, be expected to become a kind of novel dye sensitization solar battery material.
Accompanying drawing explanation
[Fig. 1] is the dye sensitization solar battery basic structure schematic diagram of triaryl methane compounds of the present invention as sensitizing dye: 1 is ionogen; 2 is triaryl methane compounds of the present invention; 3 is to electrode; 4 is titanium dioxide; 5 is light anode.
[Fig. 2] is triaryl methane compounds (2*10 in tetrahydrofuran (THF) synthesized in embodiment 1 ~ 4
-5m) ultraviolet-visible absorption spectra figure: 1 is the triaryl methane compounds 3 that enforcement 1 is synthesized; 2 for implementing the triaryl methane compounds 6 of 2-in-1 one-tenth; Implement the triaryl methane compounds 10 of 3 synthesis; 4 triaryl methane compounds 13 synthesized for enforcement 1.
Embodiment
Do detailed stating clearly by by embodiment to the present invention below, its object is only to understand content of the present invention better but not limit
Protection scope of the present invention processed.
Embodiment 1
The synthesis of triaryl methane compounds 3
The synthesis of (1) three thiophene methane 1:
By the 2 thiophene carboxaldehyde of 1.12g, 20mL thiophene, 2gNaHSO
4siO
2be placed in there-necked flask, 85 ° of C stirring and refluxing; After 6h, be cooled to room temperature.Reactant suction filtration, by washed with dichloromethane, is spin-dried for solvent; With sherwood oil as leacheate, 200 ~ 300 object silica gel column chromatography purification & isolation obtain pure products, are white solid, productive rate 41%.Fusing point: 51 ~ 53 ° of C.
The synthesis of (2) three thiophene methane formaldehyde 2:
Argon shield, under ice-water bath, by 2.45gPOCl
3dropwise join in 1, the 2-dichloroethane solution of 1.17gDMF, stir, continue reaction 1h; Add the compound 1(1.04g being dissolved in 1,2-ethylene dichloride), stirring at room temperature 2h, temperature rising reflux 12h; Be cooled to room temperature, pour in trash ice, add sodium acetate solution (1mol/L), with dichloromethane extraction twice, dry, after screwing out solvent, column chromatography obtains product 2, productive rate 45%;
1hNMR (CDCl
3) δ (ppm): 6.14 (s, 1H), 6.96-6.98 (m, 4H), 7.04 (d, 1H), 7.26-7.27 (m, 2H), 7.63 (d, 1H), 9.85 (s, 1H).
(3) synthesis of triaryl methane compounds 3:
0.435g intermediate 2,0.88g cyanoacetic acid is added, the acetic acid of 0.03g ammonium acetate and 20mL, stirring and refluxing 8h under 120 ° of C in the there-necked flask of 100mL; Be cooled to room temperature, poured into by crude product in frozen water, with chloroform extraction, merge organic phase, obtain triaryl methane compounds 3 through column chromatography after drying, productive rate is 58.7%.；
1HNMR([D6]DMSO)δ(ppm):6.52(s,1H)，6.99-7.00(m,4H)，7.33(d,1H)，7.47-7.49(m,2H)，7.55(d,1H)，8.03(s,1H)。
Embodiment 2
The synthesis of triaryl methane compounds 6
(1) synthesis of bromo three thiophene methane 4:
The DMF solution of 0.5g compound 1 is placed in-5 ° of C ice-water baths, dropwise drips the DMF solution of 0.338gNBS, stir 20min, stirring at room temperature 2h; Then pour in frozen water by crude product, be extracted with ethyl acetate, merge organic phase, dry, vacuum rotary steam solvent obtains pink oil through column chromatography (sherwood oil), and productive rate is 45%;
1hNMR (CDCl
3) δ (ppm): 6.03 (s, 1H), 6.68 (d, 1H), 6.9 (d, 1H), 6.96-6.97 (m, 4H), 7.25 (d, 2H).
The synthesis of (2) three thiophene methane thiophenecarboxaldehydes 5:
In there-necked flask, by 1g compound 4,0.45g5-aldehyde radical-2-thienyl boric acid, be dissolved in 30mL toluene, add solution of potassium carbonate and Pd (PPh3) 4(0.15g of 5mL), displacement argon gas; 90 DEG C of backflows, stir 10h; Cooling, is spin-dried for toluene; Washing extraction, merges organic phase, dry, and revolve silica gel column chromatography after desolventizing, obtain light red solid 5, productive rate is 34.3%;
1hNMR (CDCl
3) δ (ppm): 6.09 (s, 1H), 6.88-6.89 (m, 2H), 6.97-6.98 (m, 4H),, 7.17 (d, 1H), 7.21 (d, 1H), 7.27 (d, 1H), 7.640 (d, 1H), 9.84 (s, 1H).
(3) synthesis of triaryl methane compounds 6:
Synthetic method is identical with (3) in embodiment 1, and just raw material changes;
1hNMR ([D6] DMSO) δ (ppm): 6.47 (s, 1H), 6.96-6.97 (m, 2H), 7.01-7.03 (m, 3H), 7.34 (d, 1H), 7.38 (d, 1H), 7.49 (d, 1H), 7.65 (d, 1H), 8.07 (s, 1H).
Embodiment 3
The synthesis of triaryl methane compounds 10
(1) synthesis of hexyl three thiophene methane thiophenecarboxaldehyde 9:
Synthetic method is identical with (2) in embodiment 2, and just raw material is replaced;
1hNMR (CDCl
3) δ (ppm): 5.91 (s, 1H), 6.61 (d, 2H), 6.75 (d, 2H), 6.89 (d, 1H), 7.17 (d, 1H), 7.20 (d, 1H), 7.63 (d, 1H), 9.83 (s, 1H).
(2) synthesis of triaryl methane compounds 10:
Synthetic method is identical with (3) in embodiment 1, and just raw material is replaced;
1hNMR ([D6] DMSO) δ (ppm): 6.24 (s, 1H), 6.68 (d, 2H), 6.79 (d, 2H), 6.94 (d, 1H), 7.31 (d, 1H), 7.36 (d, 1H), 7.63 (d, 1H), 8.05 (s, 1H).
Embodiment 4
The synthesis of triaryl methane compounds 13
(1) synthesis of triarylmethane thiophenecarboxaldehyde 12:
Synthetic method is identical with (2) in embodiment 2, and just raw material is replaced;
1hNMR (CDCl
3) δ (ppm): 5.90 (s, 1H), 6.86 (d, 2H), 6.96-6.97 (m, 2H), 7.24-7.25 (m, 2H), 7.37-7.40 (m, 3H), 7.65 (d, 2H), 7.74 (s, 1H), 9.89 (s, 1H).
(2) synthesis of triaryl methane compounds 13:
Synthetic method is identical with (3) in embodiment 1, and just raw material is replaced;
1hNMR ([D6] DMSO) δ (ppm): 6.16 (s, 1H), 6.90-6.91 (m, 2H), 6.99-7.01 (m, 2H), 7.43-7.47 (m, 4H), 7.75 (d, 1H), 7.79 (d, 2H), 8.01 (d, 1H), 8.47 (s, 1H), 13.78 (s, 1H).
Embodiment 5
Carry out ultraviolet-visible absorption spectroscopy and fluorescence spectrum test to four triaryl methane compounds in embodiment 1-4, the data obtained is summarized in following table:
In table 1 embodiment 1 ~ 4, the maximal ultraviolet visible absorbance wavelength of dyestuff and maximum emission wavelength (nm) data compare
| Dyestuff | Maximal ultraviolet visible absorbance wavelength (nm) | Maximum emission wavelength (nm) |
| 3(embodiment 1) | 343 | 430 |
| 6(embodiment 2) | 404 | 497 |
| 10(embodiment 3) | 405 | 504 |
| 13(embodiment 4) | 392 | 449 |
Example 6
By the preparation process of dye sensitization solar battery in specifications, the triaryl methane compounds synthesized with embodiment 1 ~ 4 is respectively assembled into battery, draws wire respectively, receive on battery performance test device from light anode and photocathode; Effective illuminating area of battery is 0.16cm2, provides 100mWcm by solar simulator (LS1000-4S-AM1.5G-1000W type)
-2radiant light; Table 2 for be assembled into battery standard sunlight AM1.5G irradiate under photovoltaic parameter gather.
The photovoltaic parameter of the battery that in table 2 embodiment 1 ~ 4, triaryl methane compounds is assembled under standard sunlight AM1.5G irradiates
Claims (7)
1. a triaryl methane compounds, is characterized in that, has formula 1 or formula 2 structure:
Wherein,
R
1be selected from
in one;
R
2be selected from
in one;
R
3be selected from
in one;
R
4, R
5, R
6and R
8be selected from C independently of one another
3 ~ 9straight chained alkyl in a kind of, or methoxyl group, oxyethyl group, one in propoxy-, or hydrogen atom.
2. a preparation method for triaryl methane compounds as claimed in claim 1, is characterized in that, under protection of inert gas, first by R
2-CHO and and R
1-H is obtained by reacting chemical compounds I at 80 ~ 100 DEG C; Again by the chemical compounds I that obtains and Vilsmeier reagent reacting generating compound II at 25 ~ 120 DEG C; The compound ii obtained and cyanoacetic acid after back flow reaction, obtain the triaryl methane compounds of formula 2 structure in acetum;
Or, first the chemical compounds I obtained and N-bromo-succinimide be there is at-5 ~ 5 DEG C bromo-reaction and generate compound III; By gained compound III and (OH)
2b-R
3-CHO obtains compounds Ⅳ after back flow reaction in toluene or chloroform; By the compounds Ⅳ of acquisition and cyanoacetic acid back flow reaction in acetum, obtain the triaryl methane compounds of formula 1 structure;
Chemical compounds I
Compound ii
Compound III
Compounds Ⅳ.
3. preparation method as claimed in claim 2, is characterized in that, R
2-CHO and R
1the mol ratio of-H is 1:8 ~ 12; Chemical compounds I and POCl
3mol ratio be 1:1 ~ 8; The mol ratio of compound ii and cyanoacetic acid is 1:6 ~ 10; The mol ratio of compounds Ⅳ and cyanoacetic acid is 1:6 ~ 10; Described Vilsmeier reagent is POCl
3dMF solution.
4. preparation method as claimed in claim 2, it is characterized in that, described Vilsmeier reagent is POCl
3dMF solution, wherein, DMF and POCl
3mol ratio be 5 ~ 1:1.
5. preparation method as claimed in claim 2, is characterized in that, R
2-CHO and and R
1the reaction times of-H is 4 ~ 8h; The reaction times of chemical compounds I and Vilsmeier reagent is 8 ~ 24h; The reaction times of compound ii and cyanoacetic acid is 8 ~ 12h; The time of chemical compounds I and N-bromo-succinimide generation bromo-reaction is 2 ~ 4h; Compound III and (OH)
2b-R
3the reaction times of-CHO is 8 ~ 16h; The reaction times of compounds Ⅳ and cyanoacetic acid is 8 ~ 12h.
6. an application for triaryl methane compounds as claimed in claim 1, is characterized in that, the triaryl methane compounds of formula 1 or formula 2 structure is used for the preparation of dye sensitization solar battery material as light-sensitive coloring agent.
7. apply as claimed in claim 6, it is characterized in that, after being had by Tu the FTO conductive glass of titanium dioxide nanocrystalline to soak in the tetrahydrofuran solution of described triaryl methane compounds, make the light anode of dye sensitization solar battery.
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|---|---|
| CN103275060A (en) | 2013-09-04 |
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