CN102702145B - Triphenylamine derivative, preparation method and application thereof in dye sensitization solar cell - Google Patents

Triphenylamine derivative, preparation method and application thereof in dye sensitization solar cell Download PDF

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CN102702145B
CN102702145B CN201210178977.3A CN201210178977A CN102702145B CN 102702145 B CN102702145 B CN 102702145B CN 201210178977 A CN201210178977 A CN 201210178977A CN 102702145 B CN102702145 B CN 102702145B
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styryl
phenyl
diphenylamino
furans
formaldehyde
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贾俊辉
薛鹏冲
卢然
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Jilin University
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Abstract

The invention belongs to the technical field of dye sensitization solar cells and particularly relates to a triphenylamine derivative taking (E)-3-((E)-4-(di (4-((E)-4-(dianiline) styryl) phenyl)amino) as an electron donating group and cyanoacetic acid as an electron withdrawing group of furan, thiophene or styryl of benzene ring bridging. The invention also relates to a preparation method and the application of the triphenylamine derivative in a dye sensitization solar cell. The dye sensitization agent provided by the invention is simple in synthesis method, and tests show that the photoelectricity conversion efficiency of the final dye sensitization solar cell is up to 4.97 to 6.10 percent, therefore, the triphenylamine derivative and the preparation method is expected to be applied in the actual production to a certain degree.

Description

Triphenylamine derivative, preparation method and the application in dye sensitization solar battery thereof
Technical field
The invention belongs to dye sensitization solar battery technical field, what be specifically related to a kind of furans, thiophene or phenyl ring bridging take (E)-3-(5-((E)-4-(two (4-((E)-4-(diphenylamino) styryl) phenyl) amino) styryl be electron-withdrawing group as electron donating group, cyanoacetic acid triphenylamine derivative, its preparation method and the application in dye sensitization solar battery thereof.
Background technology
Along with social development, environmental pollution and energy dilemma have become the Achilles' heel of survival and development of mankind, find as early as possible alternative clean energy extremely urgent.We know that sun power is a kind of inexhaustible environmental friendliness energy, therefore develop and utilize sun power to become people's research emphasis.One of main path that utilizes sun power is exactly solar cell.Mainly contain in the market three kinds of solar cells: inorganic semiconductor battery, silicon solar cell, organic solar batteries.With respect to first two solar cell, organic solar batteries development is relatively slow, but it possesses lot of advantages, thereby receives much concern.
What in organic dye sensitized solar cell, play a crucial role is exactly sensitizing agent.Generally there is larger molar absorptivity, be convenient to control the advantages such as absorption region, synthesis technique is simple and convenient, production cost is relatively low, environmental pollution is little it is had wide practical use in fields such as city resident's electricity consumptions due to nonmetal organic dye sensitized dose.In recent years, research worker synthesizes and has studied many organic dye sensitized dose, comprise coumarin derivatives, triphenylamine derivative, phenothiazine derivative, carbazole derivative, tetrahydroquinoline derivative, N, N-diaryl amino benzenes derivates, polythiofuran derivative, half cyanines derivative etc.Because triphenylamine has good electron donation and good hole transport performance is extensively subject to investigator's favor, Yanagida study group is incorporated in organic dye triphenylamine units as electron donor(ED) for the first time, obtains the electricity conversion of 3.3%-5.3% through device detection.
Up to now, the triphenylamine electron-donating group in most of organic dye molecule structure is to be connected with conjugation abutment group with singly-bound.
Summary of the invention
What the object of this invention is to provide three kinds of furans, thiophene or phenyl ring bridging take (E)-3-(5-((E)-4-(two (4-((E)-4-(diphenylamino) styryl) phenyl) amino) styryl be electron-withdrawing group as electron donating group, cyanoacetic acid triphenylamine derivative, preparation method and the application in solar cell thereof.
The molecular formula of the compounds of this invention is as follows, and wherein carbon-carbon double bond is trans existence.
Figure BDA00001715575500021
Its reaction formula is as follows:
Figure BDA00001715575500022
a.Pd(OAc) 2,K 2CO 3,TBAB,dry?DMF,N 2;b.AcOH,NH 4OAc
Concrete steps are as follows:
In preparation method provided by the invention, compound 1(4-((E)-4-(diphenylamino) styryl)-N-(4-((E)-4-hexichol amido styryl)-N-(4-ethenylphenyl) aniline) presses the synthetic (Li of literature method, KP, Qu, JL, Xu, B, et al., New J.Chem.2009,33,2120).
1.(1) compound 1 and 5-bromine furans-2-formaldehyde are dissolved in dry DMF, add salt of wormwood, Tetrabutyl amonium bromide and palladium, under nitrogen protection, at 100-140 ℃, react 20-48 hour.Wherein the mol ratio of 5-bromine furans-2-formaldehyde, compound 1, salt of wormwood, Tetrabutyl amonium bromide and palladium is 1:1.0-1.3:4.0-5.0:4.0-5.0:0.01-0.02, and in DMF solvent, the concentration of compound 1 is 0.02-0.1g/ml;
(2) reaction soln of step (1) is cooled to room temperature, be poured into water, solid is separated out in stirring, through silica gel column chromatography separation, obtains compound 2(5-((E)-4-(two (4-((E)-4-(diphenylamino) styryl) phenyl) amino) styryl) furans-2-formaldehyde);
2. preparation method compound 4(5-((E)-4-(two (4-((E)-4-(diphenylamino) styryl) phenyl) amino) styryl) thiophene-2-formaldehyde) and compound 2 similar, just becomes 5-bromothiophene-2-formaldehyde by 5-bromine furans-2-formaldehyde;
3. preparation method compound 6(4-((E)-4-(two (4-((E)-4-(diphenylamino) styryl) phenyl) amino) styryl) phenyl aldehyde) and compound 2 similar, just becomes 4-bromobenzaldehyde by 5-bromine furans-2-formaldehyde;
4.(1) compound 2 is mixed in organic solvent with cyanoacetic acid, add the salt of catalytic amount, under 100-120 ℃ of condition, react 8-12 hour, wherein the mol ratio of compound 2, cyanoacetic acid and catalyzer is 1:2.0-2.5:0.01-0.04; The salt of the catalytic amount using is ammonium acetate, sodium-acetate or Potassium ethanoate.
(2) after reaction finishes, the reaction soln of step (1) is cooled to room temperature, be poured into water, solid is separated out in stirring, suction filtration obtains thick product, then obtains compound 3((E through silica gel column chromatography separation)-3-(5-((E)-4-(two (4-((E)-4-(diphenylamino) styryl) phenyl) amino) styryl) furans-2-base-2-cyanoacetic acid).
In step (1), organic solvent is commercially available acetic acid, ethanol or tetrahydrofuran (THF).
The eluent using at step (2) silica gel column chromatography is methylene chloride/methanol (V/V=10/1).
5. preparation method compound 5((E)-3-(5-((E)-4-(two (4-((E)-4-(diphenylamino) styryl) phenyl) amino) styryl) thiophene-2-base-2-cyanoacetic acid) and compound 3 similar, just becomes compound 4 by compound 2.
6. preparation method compound 7((E)-3-(4-((E)-4-(two (4-((E)-4-(diphenylamino) styryl) phenyl) amino) styryl) phenyl-2-cyanoacetic acid) and compound 3 similar, just becomes compound 6 by compound 2.
The separating and purifying method of compound 5 and compound 7 is identical with the separating and purifying method of compound 3.
Above-claimed cpd can be used as photosensitizers in dye sensitization solar battery.
Compound 3 is prepared into dye sensitization solar battery as organic dye sensitized dose, and tests its electricity conversion, and under our test condition, the electricity conversion of battery reaches 6.10%.
Compound 5 is prepared into dye sensitization solar battery as organic dye sensitized dose, and tests its electricity conversion, and under our test condition, the electricity conversion of battery reaches 5.92%.
Compound 7 is prepared into dye sensitization solar battery as organic dye sensitized dose, and tests its electricity conversion, and under our test condition, the electricity conversion of battery reaches 4.97%.
The preparation of battery and test reference literature method (Jia JH, Cao KY, Xue PC, et al., Tetrahedron, 2012,68:3626-3632).Conductive glass is that 2.2mm is thick, square resistance is 15 Ω cm -2fTO conductive glass, TiO 2film thickness is 10 μ m, buys from Dalian HeptaChroma SolarTech Co., Ltd..Electrolyte solution consist of 0.6M PMII (1-propyl group-3-Methylimidazole quinoline iodine), 0.1M LiI, 0.05M I 2, 0.5M TBP (4-tert .-butylpyridine), 0.05mM GUSCN (guanidine thiocyanate) acetonitrile solution.Photoelectric current test records at CHI 604B chem workstation.Light source is AM1.5 simulated solar irradiation, and light intensity is 100mW/cm 2.IPCE records by the method that standard element is reference.
Beneficial effect of the present invention
The derivative of three triphenylamines in the present invention has good absorption in visible region, maximum absorption wavelength even reaches 600nm place (Fig. 7).Such as compound 3 at the maximum absorption wavelength of long wave strong point at 496nm, compound 5 is at 492nm, compound 7 is at 451nm.The absorption spectrum of three dyestuffs of presentation of results of absorption spectrum is all wider, and furans and thiphene ring are the pi bridge bond groups more more outstanding than phenyl ring.Fig. 8 has provided the IPCE figure of embodiment 10,11 and 12 batteries that obtain.Therefrom can find out, the IPCE value that the compound 3 of take is basic battery is greater than 70% at 424-500nm place, the IPCE value that the compound 3 of take is basic battery and compound 3 similar.The IPCE value of the battery of compound 7 is lower.After tested, the electricity conversion of dye sensitization solar battery is between 4.97-6.10%.
Accompanying drawing explanation
Fig. 1: the mass spectrum of the compound 3 that the embodiment of the present invention 2 obtains;
Fig. 2: nucleus magnetic hydrogen spectrum (500MHz, the DMSO-d of the compound 3 that the embodiment of the present invention 2 obtains 6, TMS);
Fig. 3: the mass spectrum of the compound 5 that the embodiment of the present invention 4 obtains;
Fig. 4: nucleus magnetic hydrogen spectrum (500MHz, the DMSO-d of the compound 5 that the embodiment of the present invention 4 obtains 6, TMS);
Fig. 5: the mass spectrum of the compound of the compound 7 that the embodiment of the present invention 6 obtains;
Fig. 6: nucleus magnetic hydrogen spectrum (500MHz, the DMSO-d of the compound 7 that the embodiment of the present invention 6 obtains 6, TMS);
Fig. 7: the embodiment of the present invention 7,8 and the 9 normalized uv-visible absorption spectroscopies that obtain;
Fig. 8: the IPCE figure of the embodiment of the present invention 10,11 and 12 batteries that obtain.
Embodiment
Below in conjunction with embodiment, the present invention is described further, but be not limited to this.
Embodiment 1:
Synthesizing of compound 2: 1.0g compound 1,1.45g salt of wormwood, 0.196g 5-bromine furans-2-formaldehyde and 0.62g Tetrabutyl amonium bromide are mixed in the DMF that 10ml is dry, then add 5mg palladium, under nitrogen protection, be heated to 110 ℃ of reactions 24 hours.After being cooled to room temperature, pour in the beaker that fills 200ml cold water, dichloromethane extraction three times (3 * 50ml), collects organic phase anhydrous sodium sulfate drying, organic solvent is removed in decompression, through the silica gel column chromatography orange red solid 2(0.80g that purifies to obtain), productive rate is 78%, fusing point is 66-68 ℃, mass spectrum C 65h 49n 3o 2calculated value: 903.38, experimental value: 904.1. 1H-NMR(500MHz，CDCl 3，TMS):δ=9.57(s，1H)，7.38(m，12H)，7.33(s，1H)，7.27(s，2H)，7.27(s，2H)，7.10(m，15H)，7.08(s，1H)，7.03(m，8H)，7.01(s，1H)，6.97(d，J=3.0Hz，4H)，6.49(d，J=3.5Hz，1H)。
Embodiment 2:
Synthesizing of compound 3: 0.10g compound 1,23.50mg cyanoacetic acid and 20mg ammonium acetate are mixed in 10ml acetic acid, slowly be warming up to 120 ℃, stirring reaction 12 hours, after reaction finishes, be cooled to room temperature, pour in the beaker that fills 150ml cold water, stir and separate out solid, suction filtration obtains thick product, through silica gel column chromatography (methylene chloride/methanol=10/1) separating-purifying, obtain garnet solid 3, productive rate 77%, fusing point is 200-202 ℃; Mass spectrum C 68h 50n 4o 3, calculated value: 970.39, experimental value: 971.2(Fig. 1), 1h-NMR(500MHz, DMSO-d 6, TMS) δ=7.79 (s, 1H), 7.53 (d, J=8.5Hz, 2H), 7.50 (d, J=8.5Hz, 6H), 7.32 (t, J=8.0Hz, 8H), 7.24 (d, J=7.0Hz, 2H), 7.20 (s, 1H), 7.11 (s, 4H), 7.04 (m, 18H), 6.95 (d, J=8.5Hz, 4H), 6.76 (d, J=3.5Hz, 1H) (Fig. 2).
Embodiment 3:
Synthesizing of compound 4: method is similar to Example 1, just 5-bromine furans-2-formaldehyde is become to 5-thiophene-2-formaldehyde, productive rate 75%, fusing point is 32-34 ℃; Mass spectrum C 65h 49n 3oS calculated value: 919.36, experimental value: 920.4. 1H-NMR(500MHz，CDCl 3，TMS):δ=9.84(s，1H)，7.92(d，J=4.0Hz，1H)，7.54(m，3H)，7.48(m，6H)，7.39(t，J=8.5Hz，1H)，7.32(m，10H)，7.21(m，2H)，7.11(d，J=7.0Hz，1H)，7.07(m，6H)，7.02(m，12H)，6.97(s，1H)，6.94(t，J=5.5Hz，4H)，5.74(s，1H)。
Embodiment 4:
Synthesizing of compound 5: method is similar to Example 2, just compound 2 is become to compound 4, productive rate 74%, fusing point is 230-232 ℃; Mass spectrum C 68h 50n 4o 2s calculated value: 986.37, experimental value: 987.7(Fig. 3) 1h-NMR (500MHz, DMSO-d 6): δ=7.98 (s, 1H), 7.56 (m, 4H), 7.50 (m, 6H), 7.37 (d, J=8.5Hz, 1H), 7.32 (m, 9H), 7.24 (d, J=3.5Hz, 1H), 7.10 (m, 8H), 7.04 (m, 12H), 7.00 (s, 1H), 6.96 (t, J=7.5Hz, 6H) (Fig. 4).
Embodiment 5:
Synthesizing of compound 6: method is similar to Example 1, just the bromo-furans-2-of 5-formaldehyde is become to 4-bromobenzaldehyde, productive rate 75%, fusing point is 80-82 ℃; Mass spectrum C 67h 51n 3O, calculated value: 913.4, experimental value: 914.2. 1H-NMR(500MHz，CDCl 3，TMS):δ=9.83(s，1H)，7.70(d，J=8.5Hz，2H)，7.45(d，J=8.5Hz，4H)，7.37(d，J=8.5Hz，4H)，7.04(m，8H)，7.02(s，1H)，7.00(s，2H)，6.98(s，2H)，6.95(s，1H)。
Embodiment 6:
Synthesizing of compound 7: method is similar to Example 2, productive rate 64%, fusing point is 168-170 ℃; Mass spectrum C 70h 52n 4o 2, calculated value: 980.41, experimental value: 981.7(Fig. 5). 1h-NMR (500MHz, DMSO-d 6): δ=8.01 (s, 1H), 7.87 (d, J=8.5Hz, 2H), 7.57 (d, J=8.5Hz, 2H), 7.49 (d, J=8.5Hz, 4H), 7.31 (t, J=8.0Hz, 10H), 7.12 (t, J=9.0Hz, 8H), 7.07 (d, J=7.5Hz, 4H), 7.02 (m, 14H), 6.95 (d, J=8.5Hz, 4H) (Fig. 6).
Embodiment 7:
Accurately take 9.7mg compound 3, be placed in 100ml capacity flask, with dry THF constant volume, obtain 10 -4the THF solution of M.Preparation measures this solution 1ml, is diluted to 100ml obtains 10 of compound 3 by dry THF -6the THF solution of M.Test its absorption spectrum.
Embodiment 8:
Method is similar to Example 10, just compound 3 is become to compound 5.The quality that takes compound 5 is 9.8mg.Test its absorption spectrum.
Embodiment 9:
Method is similar to Example 10, just compound 3 is become to compound 7.The quality that takes compound 7 is 9.8mg.Test its absorption spectrum.
Embodiment 10:
The preparation of the dye sensitization solar battery of compound 3: by TiO 2membrane electrode is heated to 100 ℃, is immersed the dichloromethane solution (0.05M) of compound 3 after half an hour, takes out after placing 12 hours in dark place, uses dichloromethane rinse electrode, naturally dries to obtain the TiO of dye sensitization 2membrane electrode.By TiO 2membrane electrode, platinum black are prepared into sandwich type cell apparatus to electrode and She Lin polymkeric substance packing ring, then utilize vacuum suck-back principle by the aperture of electrode is injected to electrolyte solution.Prepare three small batteries for test simultaneously.
Embodiment 11:
The preparation of the dye sensitization solar battery of compound 5: method is similar to Example 7, just changes compound 3 into compound 5.
Embodiment 12:
The preparation of the dye sensitization solar battery of compound 5: method is similar to Example 7, just changes compound 3 into compound 7.
Embodiment 13:
The test of dye sensitization solar battery electricity conversion: every battery is according to literature method (Jia JH, Cao KY, Xue PC, et al., Tetrahedron, 2012,68:3626-3632) carry out three tests, the mean value of electricity conversion η that obtains the dye sensitization solar battery of example 7,8 and 9 is respectively 6.10%, 5.92%, 4.97%.

Claims (6)

1. a triphenylamine derivative for furans, thiophene or phenyl ring bridging, its structural formula is as follows:
Figure FDA0000467549770000011
2. the preparation method of the triphenylamine derivative of a kind of furans claimed in claim 1, thiophene or phenyl ring bridging, its step is as follows:
(1) by 4-((E)-4-(diphenylamino) styryl)-N-(4-((E)-4-hexichol amido styryl) phenyl)-N-(4-ethenylphenyl) aniline and 5-bromine furans-2-formaldehyde, 5-bromothiophene-2-formaldehyde or 4-bromobenzaldehyde be dissolved in dry DMF, add salt of wormwood, Tetrabutyl amonium bromide and palladium, under nitrogen protection, at 100-140 ℃, react 20-48 hour; Wherein 5-bromine furans-2-formaldehyde, 5-bromothiophene-2-formaldehyde or 4-bromobenzaldehyde, 4-((E)-4-(diphenylamino) styryl)-N-(4-((E)-4-hexichol amido styryl) phenyl)-N-(4-ethenylphenyl) aniline, salt of wormwood, the mol ratio of Tetrabutyl amonium bromide and palladium is 1:1.0-1.3:4.0-5.0:4.0-5.0:0.01-0.02, in DMF solvent, 4-((E)-4-(diphenylamino) styryl) concentration of-N-(4-((E)-4-hexichol amido styryl) phenyl)-N-(4-ethenylphenyl) aniline is 0.02-0.1g/ml;
(2) reaction soln of step (1) is cooled to room temperature, be poured into water, solid is separated out in stirring, through silica gel column chromatography separation, obtains 5-((E)-4-(two (4-((E)-4-(diphenylamino) styryl) phenyl) amino) styryl) furans-2-formaldehyde, 5-((E)-4-(two (4-((E)-4-(diphenylamino) styryl) phenyl) amino) styryl) thiophene-2-formaldehyde or 4-((E)-4-(two (4-((E)-4-(diphenylamino) styryl) phenyl) amino) styryl) phenyl aldehyde;
(3) by 5-((E)-4-(two (4-((E)-4-(diphenylamino) styryl) phenyl) amino) styryl) furans-2-formaldehyde, 5-((E)-4-(two (4-((E)-4-(diphenylamino) styryl) phenyl) amino) styryl) thiophene-2-formaldehyde or 4-((E)-4-(two (4-((E)-4-(diphenylamino) styryl) phenyl) amino) styryl) phenyl aldehyde mixes in organic solvent with cyanoacetic acid, the salt that adds catalytic amount, under 100-120 ℃ of condition, react 8-12 hour, 5-((E wherein)-4-(two (4-((E)-4-(diphenylamino) styryl) phenyl) amino) styryl) furans-2-formaldehyde, 5-((E)-4-(two (4-((E)-4-(diphenylamino) styryl) phenyl) amino) styryl) thiophene-2-formaldehyde or 4-((E)-4-(two (4-((E)-4-(diphenylamino) styryl) phenyl) amino) styryl) phenyl aldehyde, the mol ratio of cyanoacetic acid and catalyzer is 1:2.0-2.5:0.01-0.04,
(4) after reaction finishes, reaction soln is cooled to room temperature, is poured into water, stir and separate out solid, suction filtration obtains thick product, then through silica gel column chromatography separation, obtains the triphenylamine derivative 1,2 or 3 of furans, thiophene or phenyl ring bridging.
3. the preparation method of the triphenylamine derivative of a kind of furans as claimed in claim 2, thiophene or phenyl ring bridging, is characterized in that: in step (3), organic solvent is acetic acid, ethanol or tetrahydrofuran (THF).
4. the preparation method of the triphenylamine derivative of a kind of furans as claimed in claim 2, thiophene or phenyl ring bridging, is characterized in that: in step (3), the salt of catalytic amount is ammonium acetate, sodium-acetate or Potassium ethanoate.
5. the preparation method of the triphenylamine derivative of a kind of furans as claimed in claim 2, thiophene or phenyl ring bridging, is characterized in that: the eluent that in step (4), silica gel column chromatography is used is methylene dichloride and the methyl alcohol that volume ratio is 10:1.
6. the triphenylamine derivative of a kind of furans claimed in claim 1, thiophene or phenyl ring bridging is used as photosensitizers in dye sensitization solar battery.
CN201210178977.3A 2012-06-01 2012-06-01 Triphenylamine derivative, preparation method and application thereof in dye sensitization solar cell Expired - Fee Related CN102702145B (en)

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