CN102675349B - Pyrroledione phthalocyanine conjugate derivative and preparation method and application thereof - Google Patents
Pyrroledione phthalocyanine conjugate derivative and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a pyrroledione phthalocyanine conjugate derivative and a preparation method and application thereof. In the pyrroledione phthalocyanine conjugate derivative indicated in a formula I, R1 is C1-C3 alkyl; R2 is hydrogen or C1-C30 alkyl; X is an O, S or Se atom; M is Zn, Cu, Ni, Al-Cl, Mn, Ru, Fe or Co. The preparation method of the conjugate derivate comprises the following steps that: (1) 4-bromobenzene-1, 2-dicyano and bispinacolatodiboron are reacted under the catalysis of normal butyl lithium to obtain a compound indicated in a formula II; (2) the compound indicated in the formula II and the compound indicated in a formula III are reacted under the effect of an alkaline compound and a catalyst a; and (3) compound indicated in a formula IV and 1,8-diazabicyclo[5.4.0] 11-carbon-7-alkene are reacted under the effect of a catalyst b to obtain the pyrroledione phthalocyanine conjugate derivative. The pyrroledione phthalocyanine conjugate derivative indicated in the formula I can be used as a donor material in an active layer of a solar cell.
Description
Technical field
The present invention relates to a kind of and pyrroledione-phthalocyanine conjugate derivative and preparation method thereof and application.
Background technology
Phthalocyanine is the important organic molecule material of a class, and this compounds has good light stability, thermostability and unreactiveness, [Markus K.R.Fischer has a wide range of applications aspect solar cell, J.Am.Chem.Soc.2009,131,8669 – 8676; Alessandro Varotto, J. Am.Chem.Soc.2010,132,2552 – 2554; JeaUk Lee, J.Mater.Chem., 2011,21,17209 – 17218].Yet due to the solution poor processability of Phthalocyanine, conventionally adopt vacuum-deposited method evaporation active coating, this has limited the application of phthalein mountain valley with clumps of trees and bamboo derivative to a certain extent.
And pyrroledione (DPP) is common industrial dye, there is strong photoabsorption, wide light abstraction width, DPP conjugated pair is associated in and on phthalocyanine, forms large electron conjugated compound, the band gap of compound reduces, light abstraction width increases, be conducive to compound and absorb the formation exciton that is stimulated after sunlight, photoelectric current is enlarged markedly.Moreover, DPP group is connected by C-C singly-bound with phthalocyanine, the introducing of DPP makes compound have good processing characteristics, and will induction phthalocyanine group form reasonably and be separated with acceptor material in bulk-heterojunction battery, makes the exciton that forms can be effectively separated and be transferred to electrode.So far also not for and the relevant report of pyrroledione conjugation phthalocyanine compound and derivative thereof, therefore provide a kind of new and pyrroledione conjugation phthalocyanine derivates and preparation method thereof to have great importance.
Summary of the invention
The object of this invention is to provide a kind of and pyrroledione-phthalocyanine conjugate derivative and preparation method thereof and application.
Provided by the invention and pyrroledione-phthalocyanine conjugate derivative, its structure is suc as formula shown in I,
Formula I
In formula I, R
1for C
1~ C
30alkyl; R
2for hydrogen or C
1~ C
30alkyl; X is O, S or Se atom; M is Zn, Cu, Ni, Al-Cl, Mn, Ru, Fe or Co.
The present invention also provides shown in formula I and the preparation method of pyrroledione-phthalocyanine conjugate derivative, comprises the steps:
(1) under the condition of anhydrous and oxygen-free, 4-bromobenzene-1,2-dicyano and duplex tetramethyl ethylene ketone boric acid ester react and obtain compound shown in formula II under the catalysis of n-Butyl Lithium;
Formula II
(2), under inert atmosphere, shown in compound shown in formula II and formula III, compound reacts and obtains compound shown in formula IV under the effect of basic cpd and catalyzer a;
Formula III formula IV
In formula, R
1for C
1~ C
30alkyl; R
2for hydrogen or C
1~ C
30alkyl; X is O, S or Se atom;
(3) compound shown in formula IV and 1,8-diazabicylo [5.4.0], 11 carbon-7-alkene react and obtain shown in formula I and pyrroledione-phthalocyanine conjugate derivative under the effect of catalyzer b.
In above-mentioned preparation method, in step (1), 4-bromobenzene-1, the molfraction ratio of 2-dicyano, duplex tetramethyl ethylene ketone boric acid ester and n-Butyl Lithium can be 1:(1 ~ 1.3): (1 ~ 1.3), specifically can be 1:1.1:1.1.
In above-mentioned preparation method, in step (1), the solvent of described reaction can be tetrahydrofuran (THF); The consumption of described solvent can be: every 1mmol4-bromobenzene-1,2-dicyano needs (3mL ~ 6mL) described solvent, as 5mL.
In above-mentioned preparation method, in step (1), the temperature of described reaction can be-40 ℃ ~-78 ℃, specifically can be-78 ℃, and the time of described reaction can be 1.5 ~ 3h, specifically can be 2h.
In above-mentioned preparation method, in step (2), compound shown in formula II can be (1 ~ 2) with the molfraction ratio of compound shown in formula III: 1, specifically can be 2:1 or 1.9:1; Described catalyzer a can be tetrakis triphenylphosphine palladium, [1, two (diphenylphosphine) ferrocene of 1'-] palladium chloride or palladium, described catalyzer a can be (0.01 ~ 0.05) with the molfraction ratio of compound shown in formula II: 1, specifically can be 0.01:1 or 0.02:1.
In above-mentioned preparation method, in step (2), the solvent of described reaction can be toluene, N ' dinethylformamide or acetonitrile; The consumption of described solvent can be: compound shown in every 1mmol formula II needs (4mL ~ 6mL) described solvent, as 5mL; Described basic cpd can be salt of wormwood, specifically can adopt the form of unsaturated carbonate potassium solution, and unsaturated carbonate potassium solution used is (4 ~ 6) with the volume parts ratio of the described solvent reacting: 1, as 5:1; The temperature of described reaction can be 100 ℃ ~ 135 ℃, specifically can be 135 ℃, and the time can be 10h ~ 24h, specifically can be 24h; Described inert atmosphere can be nitrogen.
In above-mentioned preparation method, in step (3), described catalyzer b can be zinc chloride or cupric chloride; Compound, 1 shown in formula IV, 8-diazabicylo [5.4.0] 11 carbon-7-alkene can be 1:(1 ~ 1.2 with the molfraction ratio of catalyzer b): (1.3 ~ 1.6), specifically can be 1:1:1.4 or 1:1:1.5; The solvent of described reaction can be Pentyl alcohol, and the consumption of described solvent can be: compound shown in every 1mmol formula IV needs (20mL ~ 35mL) described solvent, as 25mL or 26mL; The temperature of described reaction can be 125 ℃ ~ 140 ℃, specifically can be 135 ℃, and the reaction times can be 4.5h ~ 6h, specifically can be 5h.
The present invention also further provides shown in formula I and the application of pyrroledione-phthalocyanine conjugate derivative in preparing organic solar batteries; Can prepare phase heterojunction photovoltaic device by solution spin-coating method, solve phthalocyanine material and be difficult to the problem of solution processing, and widened the absorption region of molecule, increase photoelectric current and device efficiency.
The present invention has following beneficial effect: provided by the invention and pyrroledione-phthalocyanine conjugate derivative can be prepared in a large number by simple synthesis step, be soluble in and common are machine solvent, in methylene dichloride, tetrahydrofuran (THF) or trichloromethane, compare with other phthalocyanine derivates, can prepare the uniform film of high quality by solution methods, light abstraction width broadening is to 700nm left and right, energy gap is narrower, the formation exciton that is easily stimulated after extinction, can be used as the donor material in solar cell active coating.
Accompanying drawing explanation
Fig. 1 is the ultraviolet-visible absorption spectroscopy figure of compound shown in the formula 5 of embodiment 1 preparation.
Fig. 2 is the hydrogen spectrogram of compound shown in the formula 5 of embodiment 1 preparation.
Fig. 3 is the structural representation of the photovoltaic device of preparation in embodiment 4.
Fig. 4 is the current-voltage relation curve figure of the photovoltaic device of preparation in embodiment 4.
Embodiment
The experimental technique using in following embodiment if no special instructions, is ordinary method.
In following embodiment, material used, reagent etc., if no special instructions, all can obtain from commercial channels.
Embodiment 1, preparation pyrroledione-ZnPc conjugate derivative
The synthetic route of the present embodiment is shown below:
(1) under anhydrous and oxygen-free condition, by 4-bromobenzene-1,2-dicyano (412mg, 2mmol) be dissolved in 10ml tetrahydrofuran (THF) (THF), low temperature-78 ℃ stirring, then adding concentration is the n-Butyl Lithium (1.0ml of 2.2M, 2.2mmol), low-temp reaction adds duplex tetramethyl ethylene ketone boric acid ester (280mg, 2.2mmol) after 0.5 hour, react 2 hours at-78 ℃; Reaction finishes after washing, and extraction obtains compound shown in formula II (340mg, 1.34mmol, productive rate 67%) by the separation of chromatographic silica gel post.
The nuclear-magnetism structural characterization data of this product are as follows:
1h-NMR (400MHz, CHCl
3, δ (ppm)): 8.21 (d, 2H), 7.87 (s, 2H), 7.82 (d, 2H), 1.24 (s, 12H); The structure of confirming product is correct.
(2) under nitrogen protection; by 2-cyano thiophene (3.27g; 30mmol) and succinate (1.46g; 10mmol) successively join sodium tert-butoxide (3.36g; in 2-methyl amyl alcohol (25ml) solution 30mmol), return stirring is 2 hours at 110 ℃, adds after acetic acid cancellation filtered water and methyl alcohol to wash and obtains compound (2.29g shown in product formula 1; productive rate 63%), without purifying, directly carry out next step reaction.
(3) under nitrogen protection, by compound (1.3g, 4.3mmol) shown in formula 1, anhydrous K
2cO
3(2.4g, 17mmol) is dissolved in 25ml DMF, is heated to 145 ℃, adds 2-ethylhexyl bromine (3.86g, 20mmol), reacts 12 hours; After reaction finishes, reaction soln is poured in a large amount of cold water, filtered, residue water and methyl alcohol repeatedly clean, and the dry rear silicagel column of crossing, obtains compound shown in formula 2 (1.6g, 2.4mmol, productive rate 59%).
The nuclear-magnetism structural characterization data of this product are as follows:
1h-NMR (400MHz, CHCl
3, δ (ppm)): 8.11 (d, 2H), 8.05 (d, 2H), 7.52 (m, 2H), 4.01 (d, 4H) 2.10 (m, 2H), 1.2-1.5 (m, 16H) 0.88 (m, 12H); MALDI-TOF MS:m/z=524.3 (M
+), confirm that the structure of product is correct.
(4) under room temperature condition, compound (1.6g, 2.4mmol) shown in formula 2 is joined in chloroformic solution, lucifuge reaction, then adds NBS(384mg, 2.1mmol) reaction obtains compound shown in formula 3 (472mg, 0.9mmol, productive rate 38%) after 2 hours.
The nuclear-magnetism structural characterization data of this product are as follows:
1h-NMR (400MHz, CHCl
3, δ (ppm)): 8.11 (d, 1H), 8.05 (d, 1H), 7.78 (m, 1H); 7.52 (m, 1H), 7.26 (d, 1H), 4.01 (d, 4H); 2.10 (m, 2H), 1.2-1.5 (m, 16H), 0.88 (m, 12H); MALDI-TOFMS:m/z=604.2 (M
+), confirm that the structure of product is correct.
(5) under nitrogen protection, compound (310mg, 1.8mmol) shown in formula II is mixed and added in toluene (10ml) with compound (472mg, 0.9mmol) shown in formula 3, add the saturated K of 2ml
2cO
3solution, adds catalyzer four (triphenyl phosphorus) palladium (20mg, 0.018mmol) back flow reaction 24 hours at 135 ℃, by the silicagel column compound shown in the formula that obtains 4 (468mg, 0.72mmol, productive rate 80%) of purifying.
The nuclear-magnetism structural characterization data of this product are as follows:
1h-NMR (400MHz, CHCl
3, δ (ppm)): 8.24 (d, 1H), 8.11 (d; 1H), 8.05 (m, 3H), 7.91 (d; 1H), 7.78 (d, 1H), 7.52 (m; 1H), 4.01 (d, 4H); 2.10 (m, 2H), 1.2-1.5 (m; 16H), 0.88 (m, 12H); MALDI-TOF MS:m/z=650.3 (M
+), confirm that the structure of product is correct.
(6) under nitrogen protection, by compound (468mg, 0.72mmol) shown in formula 4,1,8-diazabicylo [5.4.0], 11 carbon-7-alkene DBU(110mg, 0.72mmol) and ZnCl
2(136mg, 1mmol) return stirring in Pentyl alcohol (18ml) obtains the also pyrroledione-ZnPc conjugate derivative (270mg, 0.1mmol, productive rate 54%) shown in formula 5 for 5 hours.
The nuclear-magnetism structural characterization data of this product are as follows:
1H-NMR(400MHz，CHCl
3，δ(ppm)):9.17(m,4H),8.90(d,4H),8.24(m,4H),7.65(d,4H),7.50(s,4H),7.42(d,4H),7.26(d,4H),7.22(d,4H),4.01(m,16H),1.84(m,8H),1.25-1.55(m,64H),0.88(m,48H);MALDI-TOF?MS:m/z=2729.1(M+)；
As shown in Figure 2, its ultraviolet-visible absorption spectroscopy figure as shown in Figure 1 for the hydrogen spectrogram of product.
Embodiment 2, preparation pyrroledione-copper phthalocyanine conjugate derivative
Concrete synthesis step is in the same manner as in Example 1, and difference is: in step (6) by ZnCl
2be replaced by CuCl
2, obtain the also pyrroledione-copper phthalocyanine conjugate derivative shown in formula 6.
MALDI-TOF?MS：m/z=2728.3(M
+)。
Embodiment 3, preparation pyrroledione-ZnPc conjugate derivative
The synthetic route of the present embodiment is shown below:
(1) by compound (800mg, 1.2mmol) shown in the formula obtaining in embodiment 12, join anhydrous CH
2cl
2(15ml) in, add hexyl acyl chlorides (160mg, 1.2mmol) stirring at room after 30 minutes, to be cooled to 0 ℃, add afterwards AlCl
3(215mg, 1.6mmol), stirring at room was reacted with frozen water cancellation after 2 hours; Filter extraction, utilize silicagel column purification acquisition formula 7 to show compound (680mg, 1.1mmol, productive rate 90%);
The nuclear-magnetism structural characterization data of this product are as follows:
1H-NMR(400MHz，CHCl
3,δ(ppm)):8.27(d,1H),8.11(d,1H),8.05(d,2H),7.52(d,1H),4.01(d,4H),3.30(d,2H),2.10(m,2H),1.2-1.5(m,22H),0.88(m,15H);MALDI-TOFMS:m/z=622.3(M
+)。
(2) under nitrogen protection, by LiAlH
4(300mg, 8mmol) and AlCl
3(400mg, 3mmol) join in anhydrous diethyl ether, at 0 ℃, then formula 7 is shown to compound (680mg, 1.1mmol) join in reaction soln, room temperature reaction is 3 hours afterwards, after reaction finishes, reaction soln is poured in cold water, extraction, cross silicagel column purification and obtain compound shown in formula 8 (600mg, 1mmol, productive rate 88%);
The nuclear-magnetism structural characterization data of this product are as follows:
1H-NMR(400MHz，CHCl
3，δ(ppm)):8.11(d,1H),8.05(d,1H),7.81(d,1H),7.52(m,1H),7.18(d,1H),4.01(d,4H),2.77(t,2H),2.10(m,2H),1.2-1.5(m,22H),0.88(m,15H);MALDI-TOF?MS:m/z=608.4(M
+)。
(3) under room temperature condition, compound (600mg, 1mmol) shown in formula 8 is joined in chloroformic solution to lucifuge reaction, then add NBS(84mg, 2.1mmol), react after washing extraction in 2 hours, cross silicagel column and obtain compound shown in formula 9 (460mg, 0.67mmol, productive rate 67%);
The nuclear-magnetism structural characterization data of this product are as follows:
1H-NMR(400MHz，CHCl
3，δ(ppm)):7.81(d,1H),7.78(d,1H),7.32(d,1H),7.18(d,1H),4.01(d,4H),2.77(t,2H),2.10(m,2H),1.2-1.5(m,16H),0.88(m,12H);MALDI-TOFMS:m/z=688.3(M
+)。
(4) under nitrogen protection, compound (460mg, 0.67mmol) shown in formula 9 and compound (230mg, 1.3mmol) shown in formula II are mixed to join in toluene solution, add afterwards the saturated K of 2ml
2cO
3solution, catalyzer four (triphenyl phosphorus) palladium (23mg, 0.02mmol) is at 25mg, and at 135 ℃, back flow reaction is 24 hours, and reaction finishes after washing extraction, by chromatographic silica gel post, is purified and is obtained compound shown in formula 10 (367mg, 0.5mmol, productive rate 73%);
The nuclear-magnetism structural characterization data of this product are as follows:
1H-NMR(400MHz，CHCl
3，δ(ppm)):7.24(d,1H),8.05(m,2H),7.91(s,1H),7.88(d,1H),7.81(d,1H),7.18(d,1H),4.01(d,4H),2.77(t,2H),2.10(m,2H),1.2-1.5(m,16H),0.88(m,12H);MALDI-TOF?MS:m/z=734.4(M
+)。
(5) under nitrogen protection, by compound (367mg, 0.5mmol) shown in formula 10, DBU(76mg, 0.5mmol) and ZnCl
2(100mg, 0.75mmol) return stirring in Pentyl alcohol (13ml) obtains shown in formula 11 for 5 hours and pyrroledione-ZnPc derivative (130mg, 0.04mmol, productive rate 34%);
The nuclear-magnetism structural characterization data of this product are as follows:
1H-NMR(400MHz，CHCl
3，δ(ppm)):9.17(m,4H),8.90(d,4H),8.24(m,4H),7.65(d,4H),7.50(s,4H),7.42(d,4H),7.26(d,4H),7.22(d,4H),4.01(m,18H),1.20-1.55(m,120H),0.88(m,60H);MALDI-TOF?MS:m/z=3065.2(M+)。
Embodiment 4, preparation take shown in formula 5 and pyrroledione-ZnPc conjugate derivative organic solar batteries that is electron donor material
The ultraviolet-visible absorption spectroscopy of the phthalocyanine derivates of embodiment 1 preparation as shown in Figure 1, from this absorption spectrum, can find out, this compound has wide absorption peak in visible region, this improves its photoabsorption for solar cell, and then improve photoelectric current and have very great help, can be for the preparation of the organic photovoltaic battery of solution processing.
Shown in the formula 5 of 1mg and [6,6]-phenyl-C61 methyl-butyrate (PC of pyrroledione-ZnPc conjugate derivative and 1mg
61bM) mix, add the super dry chloroform solvent of 100 microlitre to dissolve, mixed at room temperature stirs 4 hours, by spin coating mode, at warp, gather (3,4-ethene dioxythiophene) on the conductive glass that-polystyrolsulfon acid (PEDOT:PSS) is modified, prepare the film of about 100nm, then by vacuum-deposited mode evaporation thickness, be respectively the calcium of 20nm and the aluminium electrode of 80nm, prepare the photovoltaic cell that area is 2mm*2mm.
The structural representation of device prepared by this embodiment is as Fig. 3.
The photovoltaic performance of this device shows as: at simulated solar irradiation, (AM 1.5,100mw/cm
2) under irradiation, produce photoelectric conversion, the current-voltage curve of testing as shown in Figure 4, short-circuit current=5.69mA/cm
2, open circuit voltage=0.76V, packing factor=0.38, efficiency of conversion=1.63%.
Claims (1)
1. shown in formula I and the preparation method of pyrroledione-phthalocyanine conjugate derivative, comprise the steps:
In formula I, R
1for C
1～C
30alkyl; R
2for hydrogen or C
1～C
30alkyl; X is O, S or Se atom; M is Zn, Cu, Ni, Al-Cl, Mn, Ru, Fe or Co;
(1) under the condition of anhydrous and oxygen-free, 4-bromobenzene-1,2-dicyano and duplex tetramethyl ethylene ketone boric acid ester react and obtain compound shown in formula II under the catalysis of n-Butyl Lithium;
(2), under inert atmosphere, shown in compound shown in formula II and formula III, compound reacts and obtains compound shown in formula IV under the effect of basic cpd and catalyzer a;
In formula III and formula IV, R
1for C
1～C
30alkyl; R
2for hydrogen or C
1～C
30alkyl; X is O, S or Se atom;
Described catalyzer a is tetrakis triphenylphosphine palladium, [two (diphenylphosphine) ferrocene of 1,1'-] palladium chloride or palladium;
(3) compound shown in formula IV and 1,8-diazabicylo [5.4.0], 11 carbon-7-alkene react and obtain shown in formula I and pyrroledione-phthalocyanine conjugate derivative under the effect of catalyzer b; Described catalyzer b is zinc chloride or cupric chloride;
In step (1), 4-bromobenzene-1, the molfraction of 2-dicyano, duplex tetramethyl ethylene ketone boric acid ester and n-Butyl Lithium is than being 1:1～1.3:1～1.3;
In step (1), the solvent of described reaction is tetrahydrofuran (THF); The consumption of described solvent is: every 1mmol4-bromobenzene-1, and 2-dicyano needs solvent described in 3mL～6mL;
In step (1), the temperature of described reaction is-40 ℃～-78 ℃, and the time is 1.5h～3h;
In step (2), compound shown in formula II is 1～1.5:1 with the molfraction ratio of compound shown in formula III; Described catalyzer a is 0.01～0.05:1 with the molfraction ratio of compound shown in formula II;
In step (2), the solvent of described reaction is toluene, N ' dinethylformamide or acetonitrile; The consumption of described solvent is: compound shown in every 1mmol formula II needs solvent described in 4mL～6mL; Described basic cpd is salt of wormwood; The temperature of described reaction is 100 ℃～135 ℃, and the time is 10h～24h;
In step (3), compound, 1 shown in formula IV, 8-diazabicylo [5.4.0] 11 carbon-7-alkene is 1:1～1.2:1.3～1.6 with the molfraction ratio of catalyzer b; The solvent of described reaction is Pentyl alcohol, and the consumption of described solvent is: compound shown in every 1mmol formula IV needs solvent described in 20mL～35mL; The temperature of described reaction is 125 ℃～140 ℃, and the time is 4.5～6h.
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| US6051702A (en) * | 1997-05-08 | 2000-04-18 | Rutgers, The University Of New Jersey | Organic dyes for photovoltaic cells and for photoconductive electrophotography systems |
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| CN102007615A (en) * | 2007-10-12 | 2011-04-06 | 南加利福尼亚大学 | Organic photosensitive optoelectronic devices containing tetra-azaporphyrins |
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