CN105214614A - A kind of line style thiazole ketone coadsorbent and preparation method thereof - Google Patents
A kind of line style thiazole ketone coadsorbent and preparation method thereof Download PDFInfo
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- CN105214614A CN105214614A CN201510632948.3A CN201510632948A CN105214614A CN 105214614 A CN105214614 A CN 105214614A CN 201510632948 A CN201510632948 A CN 201510632948A CN 105214614 A CN105214614 A CN 105214614A
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Abstract
The invention discloses a kind of line style thiazole ketone coadsorbent and preparation method thereof, the structural formula of this coadsorbent is as follows:
r in formula
1represent C
1~ C
10alkyl or C
2~ C
10thiazolinyl; The bridge chain that Ar is formed for aromatic radical, heterocyclic aryl etc.This coadsorbent preparation method is simple, absorbs strong, can be used for preparing DSSC, strengthen the ruthenium-absorption of complex compound light-sensitive coloring agent in ultra-violet (UV) band, and can improve the photoelectric properties of DSSC in ultra-violet (UV) band.
Description
Technical field
The invention belongs to organic dyestuff technical field, be specifically related to a kind of line style thiazole ketone coadsorbent for the preparation of DSSC and preparation method thereof.
Background technology
Along with the mankind are to the appearance of the environmental problem of increase and greenhouse effects etc. year by year of energy demand, develop the great attention that new regenerative resource receives national governments.Due to DSSC low cost of manufacture, photoelectric transformation efficiency is high, technique is simple, therefore, this kind of battery be laboratory basic research and commercial Application exploitation an emphasis.
In the assembly of DSSC, light-sensitive coloring agent is responsible for catches photoelectron and to TiO
2conduction band injects the important function such as electronics, and therefore light-sensitive coloring agent directly affects the photoelectric transformation efficiency of battery.Two ten years in the past have developed multiple light-sensitive coloring agent, such as ruthenium-complex compound, porphyrin compound and pure organic dye.A desirable light-sensitive coloring agent molecule should be able to absorb photoelectron as much as possible thus realize full spectral absorption, and such as, ruthenium-complex compound N749 (black dyestuff) can catch the photon of below 920nm, and its photoelectric transformation efficiency is up to 11.1%.But designing one has the quick dyestuff of the full spectrum light of absorption to be a very difficult job in whole spectral region, in addition, widening the absorption spectrum of light-sensitive coloring agent near infrared region by reduction HOMO energy level can make electron injection become difficulty, thus reduces photoelectric transformation efficiency.On the other hand, using the light-sensitive coloring agent of two or more absorption spectrum complementations quick is altogether that another kind realizes the full spectral absorption practical approach of DSSC.
Ruthenium-complex compound and organic dyestuff are the most frequently used light-sensitive coloring agents of two classes, and the absorption band wide ranges of ruthenium-complex compound, can cover whole visible region, even extend near infrared region, but they are usually more weak in the absorptance of ultra-violet (UV) band.And the absorption band of organic dyestuff is usually narrow, and be positioned at below 600nm or more than 700nm (square type dye), but large unlike the molar absorption coefficient of organic dyestuff with ruthenium-Complex dyes.
Summary of the invention
Technical problem to be solved by this invention is to overcome above-mentioned ruthenium-complex compound light-sensitive coloring agent in the weak shortcoming of the absorption of ultra-violet (UV) band, there is provided a kind of and have strong absorption in ultra-violet (UV) band, can be used for preparing the line style thiazole ketone coadsorbent of DSSC, and provide a kind of simple to operate, preparation method that yield is high for this coadsorbent.
Solving the problems of the technologies described above adopted technical scheme is that the structural formula of this coadsorbent is as follows:
In formula, R
1represent C
1~ C
10alkyl or C
2~ C
10thiazolinyl; Ar represents any one in following structure:
In formula, R
2~ R
9independently represent hydrogen atom, hydroxyl, C separately
1~ C
10alkyl, C
1~ C
10alkoxy or halogen, n is the integer of 1 ~ 3.
Preferred R in coadsorbent structural formula of the present invention
1represent C
1~ C
10alkyl, Ar represents
r
2~ R
5represent hydrogen atom, n is 1.
The preparation method of above-mentioned line style thiazole ketone coadsorbent is:
1, preparation formula 1 compound
The mixed liquor being 1:1 with the volume ratio of toluene and distilled water for solvent, by benzothiazolone, C
1~ C
10brominated alkanes or C
2~ C
10bromo alkene, NaOH, TBAB be 1:1 ~ 1.3:1 ~ 1.3:0.05 ~ 0.15 in molar ratio, 50 ~ 70 DEG C of reactions 6 ~ 12 hours, separation and purification product, obtain formula 1 compound, its chemical equation is as follows:
R in formula
1represent C
1~ C
10alkyl or C
2~ C
10thiazolinyl.
2, preparation formula 2 compound
Taking chloroform as solvent, is 1:0.5 ~ 0.6 by formula 1 compound and bromine in molar ratio, and 60 ~ 80 DEG C are reacted 3 ~ 5 hours, separation and purification product, and obtain formula 2 compound, its chemical equation is as follows:
3, preparation formula 4 compound
The mixed liquor being 4:1 with the volume ratio of oxolane and water is for solvent; under nitrogen protection; be 1:1 ~ 1.3:1 ~ 1.3:0.04 ~ 0.06 in molar ratio by the aryl boric acid aldehyde shown in formula 2 compound and formula 3, sodium acid carbonate, four (triphenyl phosphorus) palladium; 50 ~ 70 DEG C are reacted 3 ~ 5 hours; separation and purification product; obtain formula 4 compound, its chemical equation is as follows:
4, line style thiazole ketone coadsorbent is prepared
Taking glacial acetic acid as solvent, is 1:1 ~ 1.3:1.5 ~ 2.5 by formula 4 compound, cyanoacetic acid, ammonium acetate in molar ratio, and 100 ~ 120 DEG C are reacted 3 ~ 5 hours, separation and purification product, and obtain line style thiazole ketone coadsorbent, its chemical equation is as follows:
Line style thiazole ketone coadsorbent preparation method of the present invention is simple, absorbs strong, can strengthen the ruthenium-absorption of complex compound light-sensitive coloring agent in ultra-violet (UV) band, and can improve the photoelectric properties of DSSC in ultra-violet (UV) band.
Accompanying drawing explanation
Fig. 1 is line style thiazole ketone coadsorbent and the uv absorption spectra of N719 in carrene of embodiment 1 ~ 3 preparation.
Fig. 2 is that line style thiazole ketone coadsorbent prepared by embodiment 1 ~ 3 is total to photoelectric transformation efficiency figure that is quick and N719 respectively with N719.
Detailed description of the invention
Below in conjunction with 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
To prepare the following line style thiazole ketone coadsorbent of structural formula, its preparation method is:
1, preparation formula 1 compound
150mL toluene and 150mL distilled water is added in three mouthfuls of round-bottomed flasks, add 22.65g (0.15mol) benzothiazolone, 27.0g (0.165mol) bromohexane, 6.6g (0.165mol) NaOH, 4.8g (0.015mol) TBAB again, 60 DEG C are reacted 8 hours, be down to room temperature, separatory, organic phase distilled water is washed till neutrality, with anhydrous magnesium sulfate drying, filter, steaming desolventizes, residue uses column chromatography (eluant, eluent is benzinum: the mixed liquor of ethyl acetate=2:1), obtains formula 1 compound 32.4g, yield 92%.Its chemical equation is as follows:
2, preparation formula 2 compound
200mL chloroform is added in three mouthfuls of round-bottomed flasks, add 23.5g (0.1mol) formula 1 compound, 8.7g (0.055mol) bromine again, 70 DEG C are reacted 4 hours, are down to room temperature, add 200mL saturated sodium bicarbonate aqueous solution again, separatory, organic phase distilled water is washed till neutrality, with anhydrous magnesium sulfate drying, steaming desolventizes, residue column chromatography purification (eluant, eluent is benzinum: the mixed liquor of ethyl acetate=4:1), obtains formula 2 compound 23.2g, yield 74%.Its chemical equation is as follows:
3, preparation formula 4 compound
Under nitrogen protection, 32mL oxolane and 8mL water is added in three mouthfuls of round-bottomed flasks, add 3.0g (0.01mol) formula 2 compound again, shown in 1.6g (0.011mol) formula 3 to aldehyde radical phenyl boric acid, 0.8g (0.011mol) sodium acid carbonate, 0.4g (0.50mmol) four (triphenyl phosphorus) palladium, 60 DEG C are reacted 4 hours, be down to room temperature, 40mL carrene and 40mL distilled water is added in flask, separatory, aqueous phase dichloromethane extraction twice, merge organic phase, with anhydrous magnesium sulfate drying, steaming desolventizes, residue column chromatography purification (eluant, eluent is benzinum: the mixed liquor of ethyl acetate=3:1), steam except eluant, eluent, obtain formula 4 compound 2.6g, yield 88%.Its chemical equation is as follows:
4, line style thiazole ketone coadsorbent is prepared
20mL glacial acetic acid is added in three mouthfuls of round-bottomed flasks, add 1.4g (0.004mol) formula 4 compound again, 0.4g (0.0044mol) cyanoacetic acid, 0.4g (0.008mol) ammonium acetate, 110 DEG C are reacted 4 hours, be down to room temperature, 20mL carrene and 20mL distilled water is added in flask, separatory, aqueous phase dichloromethane extraction twice, merge organic phase, with anhydrous magnesium sulfate drying, steaming desolventizes, (eluant, eluent is benzinum to residue column chromatography purification: the mixed liquor of ethyl acetate=3:1, separately add the acetic acid of mixeding liquid volume 1%), steam except eluant, eluent, obtain line style thiazole ketone coadsorbent 1.2g, yield 84%.Its chemical equation is as follows:
The spectral data of prepared line style thiazole ketone coadsorbent is:
1hNMR (300MHz, CDCl
3, 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
To prepare the following line style thiazole ketone coadsorbent of structural formula, its preparation method is:
In the step 1 of embodiment 1, the equimolar iodomethane of bromohexane used is replaced, and other step of this step is identical with embodiment 1, and other step is identical with embodiment 1, is prepared into line style thiazole ketone coadsorbent.
Embodiment 3
To prepare the following line style thiazole ketone coadsorbent of structural formula, its preparation method is:
In the step 1 of embodiment 1, the equimolar bromo-decane of bromohexane used is replaced, and other step of this step is identical with embodiment 1, and other step is identical with embodiment 1, is prepared into line style thiazole ketone coadsorbent.
Embodiment 4
To prepare the following line style thiazole ketone coadsorbent of structural formula, its preparation method is:
In the step 1 of embodiment 1, the equimolar bromine ethene of bromohexane used is replaced, and other step of this step is identical with embodiment 1, and other step is identical with embodiment 1, is prepared into line style thiazole ketone coadsorbent.
Embodiment 5
To prepare the following line style thiazole ketone coadsorbent of structural formula, its preparation method is:
In the step 1 of embodiment 1, bromohexane used equimolar 10-bromo-1-ten alkene is replaced, and other step of this step is identical with embodiment 1, and other step is identical with embodiment 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, R
1identical with corresponding embodiment; The structural formula of Ar is
R in formula
6and R
7for hydrogen atom, n is 1.R
6and R
7also can select hydroxyl, C
1~ C
10alkyl, C
1~ C
10any one in alkoxyl, halogen, the value of n can be 2 or 3; Its preparation method is identical with corresponding embodiment, only needs to replace the equimolar corresponding aryl boric acid aldehyde of aldehyde radical phenyl boric acid.
Embodiment 7
In the structural formula of the line style thiazole ketone coadsorbent of embodiment 1 ~ 5, R
1identical with corresponding embodiment; The structural formula of Ar is
R in formula
8and R
9for hydrogen atom, n is 1.R
6and R
7also can select hydroxyl, C
1~ C
10alkyl, C
1~ C
10any one in alkoxyl, halogen, the value of n can be 2 or 3; Its preparation method is identical with corresponding embodiment, only needs to replace the equimolar corresponding aryl boric acid aldehyde of aldehyde radical phenyl boric acid.
In order to prove beneficial effect of the present invention, the line style thiazole ketone coadsorbent that embodiment 1 ~ 3 is prepared by inventor is dissolved in carrene respectively, is made into 10
-5the dichloromethane solution of mol/L line style thiazole ketone coadsorbent, UV-Vis spectrometer (HitachiU-3900/3900H) is adopted to record the ultra-violet absorption spectrum of line style thiazole ketone coadsorbent, the results are shown in Figure 1, its maximum absorption wavelength is followed successively by 352nm (curve 1, corresponding embodiment 1), 350nm (curve 2, corresponding embodiment 2) and 354nm (curve 3, corresponding embodiment 3), molar extinction coefficient is followed successively by 65120M
-1cm
-1, 65780M
-1cm
-1and 66270M
-1cm
-1.Meanwhile, inventor is by 10
-5the dichloromethane solution and 10 of mol/L line style thiazole ketone coadsorbent
-5the dichloromethane solution of mol/L ruthenium-complex compound light-sensitive coloring agent N719 is 2:3 mixing by volume, surveys its ultra-violet absorption spectrum, the results are shown in Figure 1.From the test result of Fig. 1, line style thiazole ketone coadsorbent of the present invention can strengthen the absorption intensity (curve N 719+1, N719+2, N719+3) of N719 in ultra-violet (UV) band.
In addition, the line style thiazole ketone coadsorbent that embodiment 1 ~ 3 is prepared by inventor is for the preparation of DSSC, and concrete preparation method is as follows:
By FTO electro-conductive glass sheet (14 Ω/sq, the light transmittance >90% of visible region) ultrasonic cleaning in the following order: 15min in 15min, deionized water in 30min, acetone in cleaning agent, is then coated with one deck TiO thereon with method for printing screen
2slurry, prepares nanoporous TiO by following program sintering
2working 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 TiO
2working electrode immerses respectively: the ethanolic solution of (a) 0.3mmol/LN719; Sensitization 24h under room temperature in the ethanolic solution of (b) 0.3mmol/LN719 and 0.2mmol/L line style thiazole ketone coadsorbent.FTO electro-conductive glass sheet brushes platinum slurry with screen printing, and sinter 15min at 400 DEG C, obtained to electrode.Sealant (25 μm, Surlyn1702) is placed in the TiO of dye sensitization in the middle of two electrodes
2working electrode becomes the DSSCs battery of encapsulation with to electrode assembling, adopt vacuum-suck-back method by electrolyte solution by being filled in battery to the aperture on electrode, consisting of of electrolyte solution: 0.6mol/L iodate 1-butyl-3-methylimidazole (BMII), 0.1mol/LLiI, 0.03mol/LI
2, 0.5mol/L4-tert .-butylpyridine and the acid of 0.1mol/L sulphur nitrile guanidine acetonitrile solution.Finally, fill orifice cover glass and sealant sealing, be prepared into DSSC.
Receive respectively on battery performance test device by the working electrode of the DSSC of preparation with to electrode extraction wire, density of photocurrent-voltage (J-V) characteristic curve of battery records under AM1.5G simulated solar light intensity, simulator is 300W xenon lamp (94022A, NewportCo., the U.S.), incident intensity standard silicon solar cell is calibrated to 100mW/cm
2, the data source table (Keithley2400) of Current density-voltage characteristic curve data conputer controlled gathers, and the work area of battery is 0.16cm
2.As seen from Figure 2, the electricity conversion of the DSSC adopting N719 (N719 sensitizing dyestuff is bought and taught Instrument Ltd. in Wuhan Ge Aoke) to prepare is 7.08%, short circuit current is 12.6mA/cm
2, open-circuit voltage is 756mV, fill factor, curve factor is 0.71, adopt the line style thiazole ketone coadsorbent of embodiment 1 and N719 quick altogether prepared by the electricity conversion of DSSC brings up to 7.39%, short circuit current brings up to 13.6mA/cm
2, open-circuit voltage brings up to 765mV, fill factor, curve factor is 0.72 (in figure curve 1+N719); Adopt line style thiazole ketone coadsorbent and the N719 of embodiment 2 quick altogether prepared by the electricity conversion of battery brings up to 7.27%, short circuit current brings up to 13.3mA/cm
2, open-circuit voltage brings up to 758mV, fill factor, curve factor is 0.72 (in figure curve 2+N719); Adopt line style thiazole ketone coadsorbent and the N719 of embodiment 3 quick altogether prepared by the electricity conversion of battery brings up to 7.33%, short circuit current brings up to 13.4mA/cm
2, open-circuit voltage brings up to 772mV, fill factor, curve factor is 0.71 (in figure curve 3+N719).Contrast test result shows, adopts line style thiazole ketone coadsorbent of the present invention can improve the photoelectric properties of DSSC.
Claims (3)
1. a line style thiazole ketone coadsorbent, is characterized in that the structural formula of this coadsorbent is as follows:
In formula, R
1represent C
1~ C
10alkyl or C
2~ C
10thiazolinyl; Ar represents any one in following structure:
In formula, R
2~ R
9independently represent hydrogen atom, hydroxyl, C separately
1~ C
10alkyl, C
1~ C
10alkoxy or halogen, n is the integer of 1 ~ 3.
2. line style thiazole ketone coadsorbent according to claim 1, is characterized in that: described R
1represent C
1~ C
10alkyl, Ar represents
r
2~ R
5represent hydrogen atom, n is 1.
3. a preparation method for line style thiazole ketone coadsorbent according to claim 1, is characterized in that it is made up of following step:
(1) preparation formula 1 compound
The mixed liquor being 1:1 with the volume ratio of toluene and distilled water for solvent, by benzothiazolone, C
1~ C
10brominated alkanes or C
2~ C
10bromo alkene, NaOH, TBAB be 1:1 ~ 1.3:1 ~ 1.3:0.05 ~ 0.15 in molar ratio, 50 ~ 70 DEG C of reactions 6 ~ 12 hours, separation and purification product, obtains formula 1 compound;
R in formula
1represent C
1~ C
10alkyl or C
2~ C
10thiazolinyl;
(2) preparation formula 2 compound
Taking chloroform as solvent, is 1:0.5 ~ 0.6 by formula 1 compound and bromine in molar ratio, and 60 ~ 80 DEG C are reacted 3 ~ 5 hours, and separation and purification product, obtains formula 2 compound;
(3) preparation formula 4 compound
The mixed liquor being 4:1 with the volume ratio of oxolane and water is for solvent, under nitrogen protection, be 1:1 ~ 1.3:1 ~ 1.3:0.04 ~ 0.06 in molar ratio by the aryl boric acid aldehyde shown in formula 2 compound and formula 3, sodium acid carbonate, four (triphenyl phosphorus) palladium, 50 ~ 70 DEG C are reacted 3 ~ 5 hours, separation and purification product, obtains formula 4 compound;
(4) line style thiazole ketone coadsorbent is prepared
Taking glacial acetic acid as solvent, is 1:1 ~ 1.3:1.5 ~ 2.5 by formula 4 compound, cyanoacetic acid, ammonium acetate in molar ratio, and 100 ~ 120 DEG C are reacted 3 ~ 5 hours, and separation and purification product, obtains 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 |
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| 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 |
| CN102847511A (en) * | 2012-09-27 | 2013-01-02 | 赵思沉 | Preparation method and application of purification, sterilization and self-cleaning integrated photosensitive adsorption column material |
-
2015
- 2015-09-29 CN CN201510632948.3A patent/CN105214614B/en not_active Expired - Fee Related
Patent Citations (4)
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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 |
| CN102847511A (en) * | 2012-09-27 | 2013-01-02 | 赵思沉 | Preparation method and application of purification, sterilization and self-cleaning integrated photosensitive adsorption column material |
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