CN105214614B - Linear thiazole ketone coadsorbent and preparation method thereof - Google Patents
Linear thiazole ketone coadsorbent and preparation method thereof Download PDFInfo
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- CN105214614B CN105214614B CN201510632948.3A CN201510632948A CN105214614B CN 105214614 B CN105214614 B CN 105214614B CN 201510632948 A CN201510632948 A CN 201510632948A CN 105214614 B CN105214614 B CN 105214614B
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- 0 CCNC(C(C(C)(C)N=C)=C(*)[C@]1C(C)=C*)=C(*C#C)C1C(C)(C)C Chemical compound CCNC(C(C(C)(C)N=C)=C(*)[C@]1C(C)=C*)=C(*C#C)C1C(C)(C)C 0.000 description 3
- NTAIXIGXKYZIKV-UHFFFAOYSA-N ONc1ccc(C(F)(F)F)cc1 Chemical compound ONc1ccc(C(F)(F)F)cc1 NTAIXIGXKYZIKV-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention discloses a linear thiazole ketone coadsorbent and a preparation method thereof. The structural formula of the coadsorbent is shown as follows, wherein R1 represents C1-C10 alkyl groups or C2-C10 allyl groups, and Ar is a bride chain formed by aromatic base, heterocyclic aryl and the like. The coadsorbent is easy to prepare, high in adsorption in an ultraviolet region and capable of being used for preparing a dye-sensitized solar cell, the adsorption of ruthenium-complex photosensitive dye in the ultraviolet region is enhanced, and the photoelectric property of the dye-sensitized solar cell can be improved.
Description
Technical field
The invention belongs to organic dyestuff technical field, and in particular to a kind of line for preparing DSSC
Type thiazole ketone coadsorbent and preparation method thereof.
Background technology
With the mankind to energy demand increase year by year and the environmental problem such as greenhouse effects appearance, develop it is new can be again
The raw energy receives the great attention of national governments.Low cost of manufacture, opto-electronic conversion effect due to DSSC
Rate is high, process is simple, therefore, this kind of battery is an emphasis of laboratory basic research and commercial Application exploitation.
In the component of DSSC, light-sensitive coloring agent is responsible for capture photoelectron and to TiO2Conduction band is noted
Enter the important function such as electronics, therefore light-sensitive coloring agent directly affects the photoelectric transformation efficiency of battery.In past two ten years
Various light-sensitive coloring agents are had been developed, such as ruthenium-complex compound, porphyrin compound and pure organic dye.One preferable photosensitive dye
Material molecule should be able to absorb photoelectron as much as possible so as to realize full spectral absorption, for example, ruthenium-complex compound N749 (black dyes
Material) photon of below 920nm can be captured, its photoelectric transformation efficiency is up to 11.1%.But design one is in whole spectrum model
The quick dyestuff of full spectrum light that enclosing has absorption is an extremely difficult job, additionally, widening light by reducing HOMO energy levels
Absorption spectrum of the quick dyestuff near infrared region can make electron injection become difficult, so as to reduce photoelectric transformation efficiency.On the other hand,
Quick altogether using the complementary light-sensitive coloring agent of two or more absorption spectrums is that another kind realizes the full spectrum of DSSC
Absorb practical approach.
Ruthenium-complex compound and organic dyestuff are the most frequently used light-sensitive coloring agents of two classes, the absorption band wide ranges of ruthenium-complex compound,
Whole visible region can be covered, near infrared region is even extended to, but their absorptances generally in ultra-violet (UV) band are weaker.And have
The absorption band of engine dyeing material is generally narrow, and positioned at below 600nm or more than 700nm (square type dye), but with ruthenium-complexing
The molar absorption coefficient of organic dyestuff is big unlike thing dyestuff.
The content of the invention
The technical problem to be solved is to overcome above-mentioned ruthenium-absorption of the complex compound light-sensitive coloring agent in ultra-violet (UV) band weak
Shortcoming, there is provided it is a kind of to have the line style thiazole ketone for absorbing, can be used to preparing DSSC to be by force total in ultra-violet (UV) band
Adsorbent, and provide a kind of preparation method simple to operate, high income for the coadsorbent.
The technical scheme that solution above-mentioned technical problem is adopted is that the structural formula of the coadsorbent is as follows：
In formula, R1Represent C1～C10Alkyl or C2～C10Thiazolinyl；Ar represents any one in following structure：
In formula, R2～R9Respective independent representative hydrogen atom, hydroxyl, C1～C10Alkyl, C1～C10Alkoxy or halogen, n is
1～3 integer.
Preferably R in the coadsorbent structural formula of the present invention1Represent C1～C10Alkyl, Ar is representedR2～R5Generation
Table hydrogen atom, n is 1.
The preparation method of above-mentioned line style thiazole ketone coadsorbent is：
1st, the compound of formula 1
Volume ratio with toluene and distilled water is as 1:1 mixed liquor is solvent, by benzothiazolone, C1～C10Bromoalkane
Hydrocarbon or C2～C10Bromo alkene, NaOH, TBAB 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 the compound of formula 1, and its chemical equation is as follows：
R in formula1Represent C1～C10Alkyl or C2～C10Thiazolinyl.
2nd, the compound of formula 2
It is in molar ratio 1 by the compound of formula 1 and bromine with chloroform as solvent:0.5～0.6,60～80 DEG C of reactions 3～5 are little
When, product is isolated and purified, the compound of formula 2 is obtained, its chemical equation is as follows：
3rd, the compound of formula 4
Volume ratio with tetrahydrofuran and water is as 4:1 mixed liquor be solvent, under nitrogen protection, by the compound of formula 2 with
Aryl boric acid aldehyde, sodium acid carbonate, four (triphenyl phosphorus) palladiums shown in formula 3 is in molar ratio 1:1～1.3:1～1.3:0.04～
0.06,50～70 DEG C are reacted 3～5 hours, isolate and purify product, obtain the compound of formula 4, and its chemical equation is as follows：
4th, line style thiazolone class coadsorbent is prepared
It is in molar ratio 1 by the compound of formula 4, cyanoacetic acid, ammonium acetate with glacial acetic acid as solvent:1～1.3:1.5～
2.5,100～120 DEG C are reacted 3～5 hours, isolate and purify product, obtain line style thiazole ketone coadsorbent, its chemical reaction side
Formula is as follows：
Line style thiazole ketone coadsorbent preparation method of the present invention is simple, absorbs strong in ultra-violet (UV) band, can strengthen ruthenium-complex compound
Light-sensitive coloring agent and can improve the photoelectric properties of DSSC in the absorption of ultra-violet (UV) band.
Description of the drawings
Fig. 1 is the UV absorption of the line style thiazole ketone coadsorbent and N719 of the preparation of embodiment 1～3 in dichloromethane
Spectrogram.
Fig. 2 is that line style thiazole ketone coadsorbent prepared by embodiment 1～3 is total to quick and N719 photoelectricity with N719 respectively
Conversion efficiency figure.
Specific embodiment
With reference to the accompanying drawings and examples the present invention is described in more detail, but protection scope of the present invention is not limited only to
These embodiments.
Embodiment 1
With the following line style thiazole ketone coadsorbent of preparation structure formula, its preparation method is：
1st, the compound of formula 1
150mL toluene and 150mL distilled water are added in three neck round bottom flask, 22.65g (0.15mol) benzo is added
Thiazolone, 27.0g (0.165mol) bromohexane, 6.6g (0.165mol) NaOH, 4.8g (0.015mol) tetrabutyl phosphonium bromide
Ammonium, 60 DEG C are reacted 8 hours, are down to room temperature, and point liquid, organic phase distillation is washed to neutrality, are dried with anhydrous magnesium sulfate, are filtered,
It is evaporated off solvent, residue uses column chromatography that (eluant, eluent is petroleum ether:Ethyl acetate=2:1 mixed liquor), obtain the chemical combination of formula 1
Thing 32.4g, yield 92%.Its chemical equation is as follows：
2nd, the compound of formula 2
200mL chloroforms are added in three neck round bottom flask, the compound of 23.5g (0.1mol) formula 1,8.7g is added
(0.055mol) bromine, 70 DEG C are reacted 4 hours, are down to room temperature, add 200mL saturated sodium bicarbonate aqueous solutions, and point liquid is organic
Neutrality is washed to distillation, is dried with anhydrous magnesium sulfate, solvent is evaporated off, (eluant, eluent is oil to residue column chromatography purifying
Ether:Ethyl acetate=4:1 mixed liquor), obtain the compound 23.2g of formula 2, yield 74%.Its chemical equation is as follows：
3rd, the compound of formula 4
Under nitrogen protection, 32mL tetrahydrofurans and 8mL water are added in three neck round bottom flask, 3.0g is added
(0.01mol) shown in the compound of formula 2,1.6g (0.011mol) formula 3 to aldehyde radical phenyl boric 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, and 40mL dichloromethanes are added in flask
Alkane and 40mL distilled water, point liquid, water is extracted twice with dichloromethane, merges organic phase, is dried with anhydrous magnesium sulfate, is evaporated off molten
Agent, (eluant, eluent is petroleum ether to residue column chromatography purifying:Ethyl acetate=3:1 mixed liquor), eluant, eluent is evaporated off, obtain formula
4 compound 2.6g, yield 88%.Its chemical equation is as follows：
4th, line style thiazolone class coadsorbent is prepared
20mL glacial acetic acids are added in three neck round bottom flask, the compound of 1.4g (0.004mol) formula 4,0.4g is added
(0.0044mol) cyanoacetic acid, 0.4g (0.008mol) ammonium acetate, 110 DEG C are reacted 4 hours, are down to room temperature, are added in flask
20mL dichloromethane and 20mL distilled water, point liquid, water is extracted twice with dichloromethane, merges organic phase, uses anhydrous magnesium sulfate
It is dried, solvent is evaporated off, (eluant, eluent is petroleum ether to residue column chromatography purifying:Ethyl acetate=3:1 mixed liquor, it is another plus mixed
Close the acetic acid of liquid product 1%), eluant, eluent is evaporated off, obtain line style thiazole ketone coadsorbent 1.2g, yield 84%.Its chemistry is anti-
Answer equation as follows：
The spectral data of prepared line style thiazole ketone coadsorbent is：1H NMR (300MHz, CDCl3, TMS) and δ：
8.20 (s, 1H), 7.68-7.47 (m, 7H), 3.94 (t, J=6.8Hz, 2H), 1.82-1.78 (m, 2H), 1.72-1.69 (m,
2H), 1.43-1.26 (m, 4H), 0.92 (t, J=6.8Hz, 3H).
Embodiment 2
With the following line style thiazole ketone coadsorbent of preparation structure formula, its preparation method is：
In 1 the step of embodiment 1, bromohexane used is replaced with equimolar iodomethane, other steps of the step
Same as Example 1, other steps are same as Example 1, are prepared into line style thiazole ketone coadsorbent.
Embodiment 3
With the following line style thiazole ketone coadsorbent of preparation structure formula, its preparation method is：
In 1 the step of embodiment 1, bromohexane used is replaced with equimolar bromo-decane, other steps of the step
Same as Example 1, other steps are same as Example 1, are prepared into line style thiazole ketone coadsorbent.
Embodiment 4
With the following line style thiazole ketone coadsorbent of preparation structure formula, its preparation method is：
In 1 the step of embodiment 1, bromohexane used is replaced with equimolar bromine ethene, other steps of the step
Same as Example 1, other steps are same as Example 1, are prepared into line style thiazole ketone coadsorbent.
Embodiment 5
With the following line style thiazole ketone coadsorbent of preparation structure formula, its preparation method is：
In 1 the step of embodiment 1, bromohexane used is replaced with the bromo- alkene of 1- ten of equimolar 10-, the step its
Its step is same as Example 1, and other steps are same as Example 1, is prepared into line style thiazole ketone coadsorbent.
Embodiment 6
In the structural formula of the line style thiazole ketone coadsorbent of embodiment 1～5, R1It is identical with corresponding embodiment；Ar
Structural formula be
R in formula6And R7For hydrogen atom, n is 1.R6And R7Also can select 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 phenyl boric acid
Replaced with equimolar corresponding aryl boric acid aldehyde.
Embodiment 7
In the structural formula of the line style thiazole ketone coadsorbent of embodiment 1～5, R1It is identical with corresponding embodiment；Ar
Structural formula be
R in formula8And R9For hydrogen atom, n is 1.R6And R7Also can select 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 phenyl boric acid
Replaced with equimolar corresponding aryl boric acid aldehyde.
In order to prove beneficial effects of the present invention, the line style thiazole ketone coadsorbent that inventor prepares embodiment 1～3
It is dissolved in respectively in dichloromethane, is made into 10-5The dichloromethane solution of mol/L line style thiazole ketone coadsorbent, using UV-Vis
Spectrometer (Hitachi U-3900/3900H) measures the ultra-violet absorption spectrum of line style thiazole ketone coadsorbent, as a result sees Fig. 1,
Its maximum absorption wavelength is followed successively by 352nm (curve 1, correspondence embodiment 1), 350nm (curve 2, correspondence embodiment 2) and 354nm
(curve 3, correspondence embodiment 3), molar extinction coefficient is followed successively by 65120M-1cm-1、65780M-1cm-1And 66270M-1cm-1.Together
When, inventor is by 10-5The dichloromethane solution and 10 of mol/L line style thiazole ketone coadsorbent-5Mol/L rutheniums-complex compound is photosensitive
The dichloromethane solution of dyestuff N719 is by volume 2:3 mixing, survey its ultra-violet absorption spectrum, as a result see Fig. 1.By the survey of Fig. 1
Test result is visible, and the line style thiazole ketone coadsorbent of the present invention can strengthen absorption intensity (curve N719+s of the N719 in ultra-violet (UV) band
1、N719+2、N719+3)。
In addition, the line style thiazole ketone coadsorbent that inventor prepares embodiment 1～3 is used to prepare the dye sensitization sun
Energy battery, concrete preparation method is as follows：
By FTO electro-conductive glass pieces (14 Ω/sq, it is seen that the light transmittance in light area>90%) it is cleaned by ultrasonic in the following order：Cleaning
15min in 15min, deionized water in 30min, acetone, then applies thereon one layer of TiO with method for printing screen in agent2Slurry,
Nanoporous TiO is prepared by following procedure sintering2Working electrode：300 DEG C are burnt 5min, 400 DEG C of burning 5min, 450 DEG C of burning 30min.
After room temperature is down to, by gained nanoporous TiO2Working electrode immerses respectively：The ethanol solution of (a) 0.3mmol/L N719；
24h is sensitized in the ethanol solution of (b) 0.3mmol/L N719 and 0.2mmol/L line style thiazole ketone coadsorbent under room temperature.
Platinum slurry is brushed with screen printing on FTO electro-conductive glass pieces, and 15min is sintered at 400 DEG C, be obtained to electrode.Sealant (25 μ
M, Surlyn1702) it is placed in the TiO of dye sensitization in the middle of two electrodes2Working electrode with to electrode assembling into encapsulation
DSSCs batteries, using vacuum-suck-back method by electrolyte solution by being filled in battery to the aperture on electrode, electrolyte is molten
Liquid is consisted of：0.6mol/L iodate 1- butyl -3- methylimidazoles (BMII), 0.1mol/L LiI, 0.03mol/L I2、
0.5mol/L 4- tert .-butylpyridines and the acetonitrile solution of 0.1mol/L sulphur nitriles guanidine acid.Finally, fill orifice cover glass and sealant
Sealing, is prepared into DSSC.
Battery performance is coupled with by the working electrode of the DSSC of preparation and to electrode extraction wire
In test device, density of photocurrent-voltage (J-V) characteristic curve of battery is measured under AM 1.5G simulated solar light intensity, simulation
Device is 300W xenon lamps (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 are controlled with computer, the work of battery
Make area for 0.16cm2.From Figure 2 it can be seen that using N719, (N719 sensitizing dyestufves buy public affairs limited in Wuhan lattice Austria Science ＆ Teaching Instrument
Department) prepare DSSC electricity conversion be 7.08%, short circuit current be 12.6mA/cm2, open circuit electricity
It is 0.71 to press as 756mV, fill factor, curve factor, and line style thiazole ketone coadsorbent and the N719 using embodiment 1 is quick prepared altogether
The electricity conversion of DSSC brings up to 7.39%, short circuit current and brings up to 13.6mA/cm2, open circuit electricity
Pressure brings up to 765mV, fill factor, curve factor for 0.72 (curve 1+N719 in figure)；Using the line style thiazole ketone eutectoid content of embodiment 2
The electricity conversion of agent quick prepared battery common with N719 brings up to 7.27%, short circuit current and brings up to 13.3mA/cm2, open
Road voltage brings up to 758mV, fill factor, curve factor for 0.72 (curve 2+N719 in figure)；It is total to using the line style thiazole ketone of embodiment 3
The electricity conversion of adsorbent quick prepared battery common with N719 brings up to 7.33%, short circuit current and brings up to 13.4mA/
cm2, open-circuit voltage bring up to 772mV, fill factor, curve factor for 0.71 (curve 3+N719 in figure).Contrast test result shows, adopts
The line style thiazole ketone coadsorbent of the present invention can improve the photoelectric properties of DSSC.
Claims (3)
1. a kind of line style thiazole ketone coadsorbent, it is characterised in that the structural formula of the coadsorbent is as follows：
In formula, R1Represent C1～C10Alkyl or C2～C10Thiazolinyl；Ar represents any one in following structure：
In formula, R2～R9Respective independent representative hydrogen atom, hydroxyl, C1～C10Alkyl, C1～C10Alkoxy or halogen, n is 1～3
Integer.
2. line style thiazole ketone coadsorbent according to claim 1, it is characterised in that：Described R1Represent C1～C10Alkane
Base, Ar is representedR2～R5Hydrogen atom is represented, n is 1.
3. the preparation method of the line style thiazole ketone coadsorbent described in a kind of claim 1, it is characterised in that it is by following steps
Rapid composition：
(1) compound of formula 1
Volume ratio with toluene and distilled water is as 1:1 mixed liquor is solvent, by benzothiazolone, C1～C10Brominated alkanes or
C2～C10Bromo alkene, NaOH, TBAB 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 the compound of formula 1；
(2) compound of formula 2
It is in molar ratio 1 by the compound of formula 1 and bromine with chloroform as solvent:0.5～0.6,60～80 DEG C are reacted 3～5 hours,
Product is isolated and purified, the compound of formula 2 is obtained；
(3) compound of formula 4
Volume ratio with tetrahydrofuran and water is as 4:1 mixed liquor is solvent, under nitrogen protection, by the compound of formula 2 and the institute of formula 3
Aryl boric acid aldehyde, sodium acid carbonate, four (triphenyl phosphorus) palladiums for showing are in molar ratio 1:1～1.3:1～1.3:0.04～0.06,50
～70 DEG C are reacted 3～5 hours, isolate and purify product, obtain the compound of formula 4；
(4) line style thiazolone class coadsorbent is prepared
It is in molar ratio 1 by the compound of formula 4, cyanoacetic acid, ammonium acetate with glacial acetic acid as solvent:1～1.3:1.5～2.5,100
～120 DEG C are reacted 3～5 hours, isolate and purify product, obtain line style thiazole ketone coadsorbent.
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| US7446207B2 (en) * | 2005-09-27 | 2008-11-04 | Ctci Foundation | Organic dye used in dye-sensitized solar cell |
| CN102241822A (en) * | 2011-06-17 | 2011-11-16 | 绍兴文理学院 | Fatty group polyamidoimide, its preparation method and its application |
| CN102516239A (en) * | 2011-12-13 | 2012-06-27 | 华东师范大学 | Aromatic thiazole compounds, analogues thereof, uses thereof and preparation methods thereof |
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