CN105219119B - A kind of thiazolone anthracene amine light-sensitive coloring agent and preparation method thereof - Google Patents
A kind of thiazolone anthracene amine light-sensitive coloring agent and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a kind of thiazolone anthracene amine light-sensitive coloring agent and preparation method thereof, the structural formula of this light-sensitive coloring agent is as follows：R in formula1Represent C1～C10Alkyl or C2～C10Thiazolinyl；The bridge chain that Ar is aromatic radical, heterocyclic aryl etc. is constituted.Heteroatomic for the electron riches such as nitrogenous, oxygen and sulfur thiazolone is introduced in triphenylamine electron donor the present invention, the electron supplying capacity of donor can be improved, the spectral absorption scope of light-sensitive coloring agent can more effectively be widened, can be used for preparing solaode, it does not contain noble ruthenium, preparation cost is low, and purification process is simple, has broad application prospects.
Description
Technical field
The invention belongs to organic dyestuff technical field and in particular to thiazolone anthracene amine be electron donor, aromatic hydrocarbon or
Heterocyclic arene and its derivant structure unit are bridge chain the organic dyestuff connecting electron withdraw group.
Background technology
With the appearance of the environmental problem of increase and greenhouse effect etc. year by year to energy demand for the mankind, what exploitation was new can be again
The raw energy receives the great attention of national governments.Because the low cost of manufacture of DSSC, opto-electronic conversion are imitated
Rate is high, process is simple, and therefore, this kind of battery is laboratory basic research and an emphasis of commercial Application exploitation.
Generally, DSSC is thin by conductive substrates material (transparency conductive electrode), nano porous semiconductor
Film, light-sensitive coloring agent, electrolyte and a few part compositions to electrode etc..Wherein, light-sensitive coloring agent directly affects battery to efficiency of light absorption,
The good and bad light utilization ratio determining battery of its performance and photoelectric transformation efficiency.
Light-sensitive coloring agent can be divided into two big class：Metal complex and pure organic photosensitive dyestuff.Metal complex with N3, N719 and
Some many pyridines ruthenium compounds such as CYC-B11 are representative, and its photoelectric transformation efficiency has reached 11%, and shows well
Stability.But ruthenium is noble metal, scarcity of resources, the development and application of this kind of light-sensitive coloring agent receives certain restriction.Thus by
Gradually develop the pure organic photosensitive dyestuff without noble metal, and pure organic photosensitive dyestuff photoelectric transformation efficiency has also breached
10%.
The key structural feature of organic photosensitive dyestuff is D- π-A structure, that is, so-called electron donor-conjugated bridge chain-
Electron acceptor structure, the feature in this structure is easy to design and is synthesized new light-sensitive coloring agent, can adjust the absorbing light of light-sensitive coloring agent
Spectral limit, can also adjust HOMO and the lumo energy of light-sensitive coloring agent molecule.
Triphenylamine units easily aoxidize, and have excellent charge-conduction ability and stability.In recent years, research shows
Fluorine-triphenylamine structure has very excellent photoelectric functional, can be used as the electron donor moiety of organic photosensitive dyestuff.In order to further
Improve the electron supplying capacity of donor and the absorption region widening light-sensitive coloring agent, some nitrogenous, oxygen and sulfur can be introduced to donor
Deng the heteroatomic heterocycle of electron rich, such as：Two sulfur fulvalenes, tetrathiafulvalene, phenothiazine etc..Recently, ring-type urea and ring-type sulfur
Urea is also introduced in electron donor, has reached the electron supplying capacity further enhancing triaryl amine and has widened light-sensitive coloring agent absorption
The effect (CN201210154785.9) of scope.But the steric hindrance of adjacent alkyl causes the planar distortion of donor in donor,
This is unfavorable for that electronics transmits to receptor from donor, in addition, this distortion destroys molecule to a certain extent to a certain extent
Coplanarity, thus the spectral absorption scope of light-sensitive coloring agent molecule narrows.
Content of the invention
The technical problem to be solved is to overcome the shortcoming of above-mentioned organic photosensitive dyestuff, provides a kind of electric charge to pass
Ability of leading is excellent, the thiazolone anthracene amine light-sensitive coloring agent of good stability, and provides a kind of simple to operate, yield for this dyestuff
High preparation method.
Solve above-mentioned technical problem and be employed technical scheme comprise that the structural formula of this light-sensitive coloring agent is as follows：
In formula, R1Represent C1～C10Alkyl or C2～C10Thiazolinyl；Ar represents any one in following structure：
In formula, R2～R9Each independent representative hydrogen atom, hydroxyl, C1～C10Alkyl, C1～C10Alkoxy or halogen, n is
1～3 integer.
The preferred R of the present invention1Represent C1～C10Alkyl, Ar representsR2～R5Represent hydrogen atom, n is 1.
The preparation method of above-mentioned thiazolone anthracene amine light-sensitive coloring agent is：
1st, formula 1 compound
With the volume ratio of toluene and distilled water for 1:1 mixed liquor is solvent, by benzothiazolone, C1～C10Bromoalkane
Hydrocarbon or C2～C10Bromo alkene, sodium hydroxide, tetrabutyl ammonium bromide in molar ratio be 1:1～1.3:1～1.3:0.05～
0.15,50～70 DEG C are reacted 6～12 hours, isolate and purify product, obtain formula 1 compound, its chemical equation is as follows：
R in formula1Represent C1～C10Alkyl or C2～C10Thiazolinyl.
2nd, formula 2 compound
With chloroform as solvent, formula 1 compound and bromine are 1 in molar ratio:0.5～0.6,60～80 DEG C of reactions 3～5 are little
When, isolate and purify product, obtain formula 2 compound, its chemical equation is as follows：
3rd, formula 3 compound
With toluene as solvent, under nitrogen protection, formula 2 compound, aniline, potassium tert-butoxide are in molar ratio 1:0.5～
0.6:2～2.5,120～140 DEG C are reacted 20～30 hours, isolate and purify product, obtain formula 3 compound, its chemical reaction equation
Formula is as follows：
4th, formula 4 compound
With DMF as solvent, formula 3 compound with N- bromo-succinimide (NBS) is in molar ratio
1:React 4～8 hours at 1～1.3,70～90 DEG C, isolate and purify product, obtain formula 4 compound, its chemical equation is such as
Under：
5th, formula 6 compound
With the volume ratio of oxolane and water for 4:1 mixed liquor be solvent, under nitrogen protection, by formula 4 compound with
Aryl boric acid aldehyde shown in formula 5, sodium bicarbonate, four (triphenyl phosphorus) palladium are 1 in molar ratio:1～1.3:1～1.3:0.04～
0.06,50～70 DEG C are reacted 3～5 hours, isolate and purify product, obtain formula 6 compound, its chemical equation is as follows：
In formula, Ar represents any one in following structure：
Wherein R2～R9Each independent representative hydrogen atom, hydroxyl, C1～C10Alkyl, C1～C10Alkoxy or halogen, n is 1
～3 integer.
6th, prepare thiazolone anthracene amine light-sensitive coloring agent
With glacial acetic acid as solvent, formula 6 compound, cyanoacetic acid, ammonium acetate are in molar ratio 1:1～1.3:1.5～
2.5,100～120 DEG C are reacted 3～5 hours, isolate and purify product, obtain thiazolone anthracene amine light-sensitive coloring agent, and its chemistry is anti-
Answer equation as follows：
Heteroatomic for the electron riches such as nitrogenous, oxygen and sulfur thiazolone is introduced in triphenylamine electron donor the present invention, Ke Yiti
The electron supplying capacity of high donor, and only one of which N-position alkylation or alkenyl, will not cause the torsion of donor plane
Song, can more effectively widen the spectral absorption scope of light-sensitive coloring agent.
The thiazolone anthracene amine light-sensitive coloring agent of the present invention does not contain noble ruthenium, and preparation cost is low, and purification process letter
Single, the electricity conversion that gained thiazolone anthracene amine light-sensitive coloring agent is used for preparing solaode can reach the same terms
The 80%～90% of lower N719 DSSC electricity conversion, has broad application prospects.
Brief description
Fig. 1 is the thiazolone anthracene amine light-sensitive coloring agent and N719 using the preparation of embodiment 1, embodiment 2 and embodiment 3
It is prepared into the photoelectric transformation efficiency figure of dyestuff quick China solaode respectively.
Specific embodiment
The present invention is described in more detail with reference to the accompanying drawings and examples, but protection scope of the present invention is not limited only to
These embodiments.
Embodiment 1
, its preparation method is taking the following thiazolone anthracene amine light-sensitive coloring agent of preparation structure formula as a example：
1st, formula 1 compound
Add 300mL toluene and 300mL distilled water in three neck round bottom flask, add 45.3g (0.3mol) benzo thiophene
Oxazolone, 54.0g (0.33mol) bromohexane, 13.2g (0.33mol) sodium hydroxide, 9.6g (0.03mol) tetrabutyl ammonium bromide, 60
DEG C reaction 8 hours, is down to room temperature, point liquid, and organic faciess distillation is washed to neutrality, is dried with anhydrous magnesium sulfate, filters, is evaporated off molten
Agent, residue use column chromatography (eluant be petroleum ether:Ethyl acetate=2:1 mixed liquor), obtain formula 1 compound
64.8g, yield 92%.Its chemical equation is as follows：
2nd, formula 2 compound
Add 400mL chloroform in three neck round bottom flask, add 47.0g (0.2mol) formula 1 compound, 17.4g
(0.11mol) bromine, 70 DEG C are reacted 4 hours, are down to room temperature, add 400mL saturated sodium bicarbonate aqueous solution, and point liquid is organic
It is washed to neutrality with distillation, is dried with anhydrous magnesium sulfate, solvent is evaporated off, (eluant is oil to residue column chromatography purification
Ether:Ethyl acetate=4:1 mixed liquor), obtain formula 2 compound 46.4g, yield 74%.Its chemical equation is as follows：
3rd, formula 3 compound
Under nitrogen protection, add 200mL toluene in three neck round bottom flask, add 31.3g (0.1mol) formula 2 chemical combination
Thing, 5.1g (0.055mol) aniline, 24.8g (0.22mol) potassium tert-butoxide, 130 DEG C are reacted 24 hours, and stopped reaction drops naturally
To room temperature, and add 200mL distilled water, point liquid, organic faciess distillation is washed to neutrality, is dried with anhydrous magnesium sulfate, is evaporated off molten
Agent, (eluant is petroleum ether to residue column chromatography purification:Ethyl acetate=3:1 mixed liquor), eluant is evaporated off, obtains formula
3 compound 26.9g, yield 48%.Its chemical equation is as follows：
4th, formula 4 compound
Add 160mL DMF in three neck round bottom flask, add 22.4g (0.04mol) formula 3 and change
Compound, 7.84g (0.044mol) N- bromo-succinimide (NBS), react 6 hours at 80 DEG C, are down to room temperature, proceed to beaker
In, add 160mL dichloromethane and 160mL saturated sodium bicarbonate aqueous solution in reactant liquor, point liquid, aqueous phase dichloromethane extracts
Take twice, merge organic faciess, be dried with anhydrous magnesium sulfate, solvent is evaporated off, (eluant is oil to residue column chromatography purification
Ether:Ethyl acetate=6:1 mixed liquor), eluant is evaporated off, obtains formula 4 compound 20.0g, yield 78%.Its chemical reaction side
Formula is as follows
5th, formula 6 compound
Under nitrogen protection, add 32mL oxolane and 8mL water in three neck round bottom flask, add 6.4g
(0.01mol) shown in formula 4 compound, 1.6g (0.011mol) formula 5 to aldehyde radical phenylboric acid, 0.8g (0.011mol) bicarbonate
Sodium, 0.4g (0.50mmol) four (triphenyl phosphorus) palladium, 60 DEG C are reacted 4 hours, are down to room temperature, add 40mL dichloromethane in flask
Alkane and 40mL distilled water, point liquid, aqueous phase dichloromethane is extracted twice, and merges organic faciess, is dried with anhydrous magnesium sulfate, is evaporated off molten
Agent, (eluant is petroleum ether to residue column chromatography purification:Ethyl acetate=3:1 mixed liquor), eluant is evaporated off, obtains formula
6 compound 5.6g, yield 86%.Its chemical equation is as follows：
6th, prepare thiazolone anthracene amine light-sensitive coloring agent
Add 20mL glacial acetic acid in three neck round bottom flask, add 1.3g (0.002mol) formula 6 compound, 0.2g
(0.0022mol) cyanoacetic acid, 0.2g (0.004mol) ammonium acetate, 110 DEG C are reacted 4 hours, are down to room temperature, add in flask
20mL dichloromethane and 20mL distilled water, point liquid, aqueous phase dichloromethane is extracted twice, and merges organic faciess, uses anhydrous magnesium sulfate
It is dried, solvent is evaporated off, (eluant is petroleum ether to residue column chromatography purification:Ethyl acetate=3:1 mixed liquor, another plus mixed
Close the acetic acid that liquid amasss 1%), eluant is evaporated off, obtains thiazolone anthracene amine light-sensitive coloring agent 1.2g, yield 82%.It is changed
Learn reaction equation as follows：
The spectral data of prepared thiazolone anthracene amine light-sensitive coloring agent is：1H NMR (300MHz, CDCl3, TMS) and δ
(ppm)：8.17 (s, 1H), 7.59-7.54 (m, 4H), 7.44-7.40 (m, 4H), 7.29-7.23 (m, 6H), 3.91 (t, J=
6.8Hz, 4H), 1.79-1.76 (m, 4H), 1.70-1.67 (m, 4H), 1.40-1.24 (m, 8H), 0.91 (t, J=6.8Hz,
6H)；13C NMR (75MHz, CDCl3, TMS) and δ (ppm)：171.4,169.0,142.5,142.4,140.7,139.2,136.0,
134.3,133.5,129.4,129.2,127.1,125.6,124.2,123.7,117.3,114.6,112.5,96.3,41.5,
31.5,28.5,26.5,22.4,13.9.
Prepared thiazolone anthracene amine light-sensitive coloring agent is used for preparing DSSC, concrete preparation side
Method is as follows：
By FTO electro-conductive glass piece, (14 Ω/sq is it is seen that the light transmittance in light area>90%) it is cleaned by ultrasonic in the following order：Cleaning
15min in 15min in 30min in agent, acetone, deionized water, then applies one layer of TiO thereon with method for printing screen2Slurry,
Prepare nanoporous TiO by following procedure sintering2Working electrode：300 DEG C are burnt 5min, 400 DEG C of burning 5min, 450 DEG C of burning 30min.
After being down to room temperature, by gained nanoporous TiO2Working electrode immerses 0.5mmol/L thiazolone anthracene amine light-sensitive coloring agent
Ethanol solution in, under room temperature be sensitized 24h.Brush platinum slurry with screen printing on FTO electro-conductive glass piece, and burn at 400 DEG C
Knot 15min, is obtained to electrode.Sealant (25 μm, Surlyn 1702) is placed in the TiO of dye sensitization in the middle of two electrodes2Work
The DSSCs battery made electrode and electrode group is dressed up with encapsulation, using vacuum-suck-back method by electrolyte solution by electrode
Aperture is filled in battery, the consisting of of electrolyte solution：0.6mol/L iodate 1- butyl -3- Methylimidazole. (BMII),
0.1mol/L LiI、0.03mol/L I2, 0.5mol/L 4- tert .-butylpyridine and 0.1mol/L sulfur nitrile guanidine acid acetonitrile solution.
Finally, fill orifice coverslip and sealant sealing, are prepared into DSSC.
It is coupled with battery performance by the working electrode of the DSSC of preparation with to electrode extraction wire
In test device, density of photocurrent-voltage (J-V) characteristic curve of battery records under AM 1.5G simulated solar light intensity, simulation
Device is 300W xenon lamp (94022A, Newport Co., the U.S.), and incident intensity standard silicon solar cell is calibrated to 100mW/
cm2, Data source table (Keithley 2400) collection that Current density-voltage characteristic curve data is controlled with computer, the work of battery
Making area is 0.16cm2.From curve in Fig. 11, using dyestuff prepared by thiazolone anthracene amine light-sensitive coloring agent of the present invention
The electricity conversion of sensitization solar battery is 6.16%, short circuit current is 12.6mA/cm2, open-circuit voltage be 720mV, fill out
Filling the factor is 0.68.(N719 sensitizing dyestuff is bought difficult to understand in Wuhan lattice to record N719 DSSC in the method
Science ＆ Teaching Instrument company limited) electricity conversion be 7.08%, short circuit current be 13.2mA/cm2, open-circuit voltage be 756mV,
Fill factor, curve factor is 0.71 (see curve N719 in Fig. 1).Contrast test result shows, using thiazolone anthracene amine light of the present invention
The electricity conversion of the DSSC of quick dyestuff preparation can reach the N719 dye sensitization sun under the same terms
The 87% of energy cell photoelectric transformation efficiency.
Embodiment 2
, its preparation method is taking the following thiazolone anthracene amine light-sensitive coloring agent of preparation structure formula as a example：
In formula 1 chemical procedure 1 of embodiment 1, bromohexane used is replaced with equimolar iodomethane, this step
Rapid other steps are same as Example 1, and other steps are identical with corresponding embodiment, are prepared into thiazolone anthracene amine photosensitive
Dyestuff.
The thiazolone anthracene amine light-sensitive coloring agent of the present embodiment is prepared into dye sensitization too by the method according to embodiment 1
Sun can battery, after tested its electricity conversion be 5.96%, short circuit current be 12.9mA/cm2, open-circuit voltage be 690mV, fill out
Filling the factor is 0.67 (see curve in Fig. 1 2), and its electricity conversion reaches N719 DSSC under the same terms
The 84% of electricity conversion.
Embodiment 3
, its preparation method is taking the following thiazolone anthracene amine light-sensitive coloring agent of preparation structure formula as a example：
In formula 1 chemical procedure 1 of embodiment 1, bromohexane used is replaced with equimolar bromo-decane, this step
Rapid other steps are same as Example 1, and other steps are identical with corresponding embodiment, are prepared into thiazolone anthracene amine photosensitive
Dyestuff.
The thiazolone anthracene amine light-sensitive coloring agent of the present embodiment is prepared into dye sensitization too by the method according to embodiment 1
Sun can battery, after tested its electricity conversion be 5.85%, short circuit current be 12.0mA/cm2, open-circuit voltage be 739mV, fill out
Filling the factor is 0.66 (see curve in Fig. 1 3), and its electricity conversion reaches N719 DSSC under the same terms
The 82% of electricity conversion.
Embodiment 4
, its preparation method is taking the following thiazolone anthracene amine light-sensitive coloring agent of preparation structure formula as a example：
In formula 1 chemical procedure 1 of embodiment 1, bromohexane used is replaced with equimolar bromine ethylene, this step
Rapid other steps are same as Example 1, and other steps are identical with corresponding embodiment, are prepared into thiazolone anthracene amine photosensitive
Dyestuff.
Embodiment 5
, its preparation method is taking the following thiazolone anthracene amine light-sensitive coloring agent of preparation structure formula as a example：
In formula 1 chemical procedure 1 of embodiment 1, bromohexane used is replaced with the bromo- 1- of equimolar 10- ten alkene
Change, other steps of this step are same as Example 1, other steps are identical with corresponding embodiment, be prepared into thiazolone three
Aniline light-sensitive coloring agent.
Embodiment 6
In the structural formula of the thiazolone anthracene amine light-sensitive coloring agent of embodiment 1～5, R1Identical with corresponding embodiment；
The structural formula of Ar is
R in formula6And R7For hydrogen atom, n is 1.R6And R7Also can be selected for hydroxyl, C1～C10Alkyl, C1～C10Alkoxyl, halogen
Any one in element, the value of n can be 2 or 3；Its preparation method is identical with corresponding embodiment, and only needing will be to aldehyde radical benzene boron
Acid is replaced with equimolar corresponding aryl boric acid aldehyde.
Embodiment 7
In the structural formula of the thiazolone anthracene amine light-sensitive coloring agent of embodiment 1～5, R1Identical with corresponding embodiment；
The structural formula of Ar is
R in formula8And R9For hydrogen atom, n is 1.R6And R7Also can be selected for hydroxyl, C1～C10Alkyl, C1～C10Alkoxyl, halogen
Any one in element, the value of n can be 2 or 3；Its preparation method is identical with corresponding embodiment, and only needing will be to aldehyde radical benzene boron
Acid is replaced with equimolar corresponding aryl boric acid aldehyde.
Claims (3)
1. a kind of thiazolone anthracene amine light-sensitive coloring agent is it is characterised in that the structural formula of this light-sensitive coloring agent is as follows：
In formula, R1Represent C1～C10Alkyl or C2～C10Thiazolinyl；Ar represents any one in following structure：
In formula, R2～R9Each independent representative hydrogen atom, hydroxyl, C1～C10Alkyl, C1～C10Alkoxy or halogen, n is 1～3
Integer.
2. thiazolone anthracene amine light-sensitive coloring agent according to claim 1 it is characterised in that：Described R1Represent C1~
C10Alkyl, Ar representsR2～R5Represent hydrogen atom, n is 1.
3. the thiazolone anthracene amine light-sensitive coloring agent described in a kind of claim 1 preparation method it is characterised in that it by under
State step composition：
(1) formula 1 compound
With the volume ratio of toluene and distilled water for 1:1 mixed liquor is solvent, by benzothiazolone, C1～C10Brominated alkanes or
C2～C10Bromo alkene, sodium hydroxide, tetrabutyl ammonium bromide in molar ratio be 1:1～1.3:1～1.3:0.05～0.15,50
～70 DEG C are reacted 6～12 hours, isolate and purify product, obtain formula 1 compound；
(2) formula 2 compound
With chloroform as solvent, formula 1 compound and bromine are 1 in molar ratio:0.5～0.6,60～80 DEG C are reacted 3～5 hours,
Isolate and purify product, obtain formula 2 compound；
(3) formula 3 compound
With toluene as solvent, under nitrogen protection, formula 2 compound, aniline, potassium tert-butoxide are in molar ratio 1:0.5～0.6:2
～2.5,120～140 DEG C are reacted 20～30 hours, isolate and purify product, obtain formula 3 compound；
(4) formula 4 compound
With DMF as solvent, formula 3 compound and N- bromo-succinimide are 1 in molar ratio:1～1.3,
React 4～8 hours at 70～90 DEG C, isolate and purify product, obtain formula 4 compound；
(5) formula 6 compound
With the volume ratio of oxolane and water for 4:1 mixed liquor is solvent, under nitrogen protection, by formula 4 compound and formula 5 institute
The aryl boric acid aldehyde that shows, sodium bicarbonate, four (triphenyl phosphorus) palladium are 1 in molar ratio:1～1.3:1～1.3:0.04～0.06,50
～70 DEG C are reacted 3～5 hours, isolate and purify product, obtain formula 6 compound；
(6) prepare thiazolone anthracene amine light-sensitive coloring agent
With glacial acetic acid as solvent, formula 6 compound, cyanoacetic acid, ammonium acetate are in molar ratio 1:1～1.3:1.5～2.5,100
～120 DEG C are reacted 3～5 hours, isolate and purify product, obtain thiazolone anthracene amine light-sensitive coloring agent.
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| CN109705612B (en) * | 2018-11-27 | 2020-05-05 | 西安近代化学研究所 | 4,4' -di (alkoxybenzene) bithiophene bridged thiourea triphenylamine photosensitive dye and preparation method thereof |
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| US2656271A (en) * | 1949-10-24 | 1953-10-20 | Keuffel & Esser Co | Method of developing aged photosensitive material containing silver halide and a chromate |
| JPS58159548A (en) * | 1982-03-18 | 1983-09-21 | Ricoh Co Ltd | Carrier for electrophotographic developer |
| CA2005933A1 (en) * | 1989-01-09 | 1990-07-09 | Jesse Hipps, Sr. | Photohardenable composition containing five member aromatic group with imine moiety |
| JPH03198043A (en) * | 1989-12-27 | 1991-08-29 | Konica Corp | Silver halide color photographic sensitive material |
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