CN1298752C - Poly(p-phenylene ethylene) and its prepn process and use - Google Patents
Poly(p-phenylene ethylene) and its prepn process and use Download PDFInfo
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- CN1298752C CN1298752C CNB2004100302794A CN200410030279A CN1298752C CN 1298752 C CN1298752 C CN 1298752C CN B2004100302794 A CNB2004100302794 A CN B2004100302794A CN 200410030279 A CN200410030279 A CN 200410030279A CN 1298752 C CN1298752 C CN 1298752C
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Abstract
The present invention relates to poly-phenylene vinylene, which is prepared by adopting 1, 4-bi-(3-bromine propoxy)-2, 5-diiodo benzene and 1, 4-bi-[(3-hydroxyl-2-methyl)-propoxy]-2, 5-divinylbenzene as raw material to react with palladium acetate and triphenylphosphine. The present invention can be used for preparing a nonlinear optical material thin film.
Description
Technical field
The present invention relates to a kind of nonlinear optical material and its production and use.
Background technology
The generation of nonlinear optical phenomena is because laser and nonlinear dielectric results of interaction.Under the light field effect, the charge distribution in the medium changes, and this variation causes the polarizability of medium not only with strength of electric field linear relationship (linear effect) to be arranged, and with strength of electric field nonlinear relationship (non-linear effect) is arranged.Non-linear optical effect is on the one hand as the effective tool of research material, is applied in the research field such as laser spectroscopy; On the other hand in laser technology, be applied to expanding aspects such as the laser of new wavelength and pulse width compression.The nonlinear optical material of early stage research mainly is an inorganic materials, expands to inorganic semiconductor material subsequently, and organic materials is a class novel non-linearity optical material of broad research both at home and abroad in recent years.The research of the non-linear nature of organic molecule starts from the sixties, and up to the eighties, people's anti-saturated absorption phenomenon that just begins one's study, and promptly when incident light is increased to a certain degree, the non-linear absorption phenomenon that the uptake factor of sample increases with incident intensity.1985, people such as W.Blau have reported anti-saturated absorption characteristic (Blau W, Burne H, the Dennis W M of metalloporphyrin, Kelly J M, Opt Commun., 1985,56,25.), its result of study finds, the excited state absorption cross section of having only molecule anti-saturated absorption just takes place during greater than the ground state cross section.The nonlinear material that searching has strong optical nonlinearity and fast response speed is an important topic of organic non-linear optical properties research all the time.
Summary of the invention
The object of the present invention is to provide a kind of chirality poly-phenylene vinylene (ppv) (PPV), its structure as shown in the formula:
Another object of the present invention is to provide the preparation method of above-mentioned poly-phenylene vinylene (ppv) (PPV).
Another purpose of the present invention is to provide above-mentioned poly-phenylene vinylene (ppv) (PPV) and the order thin film that corresponding negatively charged ion forms to have very big third-order nonlinear optical effect.
The method for preparing above-mentioned materials provided by the invention, its synthetic route is as follows:
The synthetic sequential steps of above-mentioned poly-phenylene vinylene (ppv) is:
1. (1) with 1,4-diiodo-Resorcinol is dissolved in the acetone fully, under 2-5 salt of wormwood effect doubly, with 1, the reaction of 3-dibromopropane, its add-on are 1-2 times of raw material, and reflux temperature reacted 30-50 hour down, steam solvent, solids constituent fits in water and the chloroform, and organic phase with 10% potassium hydroxide aqueous solution, distilled water, saturated common salt water washing, anhydrous sodium sulfate drying, filtration, concentrated, recrystallization, obtains product 1 respectively, 4-two-(3-bromine propoxy-)-2, the 5-diiodo-benzene;
(2) product that obtains of step (1) and 3-5 trimethylamine aqueous solution reaction backflow doubly is 14-28 hour, adds ethanol and acetone, and the 10-20 that its add-on is respectively reactant doubly is spin-dried for solvent, and recrystallization obtains the product quaternary ammonium salt;
2. (1) nitrogen atmosphere, under the dimethyl formamide, with 1,4-diiodo-Resorcinol and S-(+)-3-bromo-2-methyl isophthalic acid-propyl alcohol is in 1: the ratio of 2-3 obtains (3-hydroxy-2-methyl)-propoxy--2, the 5-diiodo-benzene in 60-80 ℃ of reaction 10-20 hour;
(2) under the dimethyl formamide, product that step (1) obtains and 2 times organotin reagent were 80-100 ℃ of reaction 3-10 hour, and product is with dichloromethane extraction, and the organic phase dried over mgso is spin-dried for solvent, the column chromatography purifying.Obtain product 1,4-two [(3-hydroxy-2-methyl)-propoxy-]-2,5-Vinylstyrene;
3. nitrogen atmosphere, under the dimethyl formamide, the product that step 1 and step 2 are obtained is separately seen in 80-100 ℃ with palladium, the trimethylphenyl of 1: 1 ratio and catalytic amount, generated product in 10-20 hour, place 10-20 acetone doubly to separate out precipitation, this resolution of precipitate is removed small-molecule substance with dialyzer in deionized water, be spin-dried for moisture content, get final poly-phenylene vinylene (ppv) product.
Above-mentioned poly-phenylene vinylene (ppv) provided by the invention and corresponding negatively charged ion (4 '; 4 "-diamyl-5,2 ': 5 '; 2 ": 5 "; 2 -four thiophene-2; 5 -carboxylic acid sodium salt) order thin film that is assembled into has big third-order non-linear response, is a kind of polymkeric substance nonlinear optical material that potential application foreground is arranged.4 ', 4 "-diamyl-5,2 ': 5 ', 2 ": 5 ", 2 -four thiophene-2,5 -carboxylic acid sodium salt structural formula as follows:
Adopt layer by layer self-assembling method that above-mentioned water-soluble PPV and connection four thiophene carboxylic acids are assembled on the quartz plate, adopt the Z-scanning technique that the third-order non-linear of the self-assembled film of preparation is measured.
Light source is the q-multiplier Nd:YAG pulse laser system of Continuum company in the experimental installation, and incident wavelength is 532nm, pulsewidth 8ns, and repetition rate is 1Hz.Incident laser to obtain Gaussian beam, passes through the dim light rod by pin hole filtering then, regulates the input light intensity in the sample.Beam splitter BS is divided into two bundles with light, a branch ofly is used to monitor incident intensity, another bundle by a focal length be after the lens focus of 10cm by sample, then behind an aperture by Rjp-735 integral energy meter probe detection.Monitoring light is by another Rjp-735 integral energy meter probe detection.
Specimen is fixed on the movable stand that scale arranged, and sample position is read by scale.Incoming beam will be all the time and samples vertical, and incide same point, so will accurately regulate light beam to meet the demands before sweep measurement.Light source output pulse energy has certain fluctuation, therefore two energy that probe detection arrives of record in the experiment, ratio between two as transmitance, to reduce the error that the incident intensity fluctuation is introduced.
Experimental result sees Table 1:
| The self-assembly number of plies | Linear transmittance T 0 | Nonlinear refractive index n 2 |
| 30 70 | 88％ 76％ | 8.3×10 -13m 2/W 14.2×10 -13m 2/W |
Table 1
Experimental result shows that self-assembled film has big third-order non-linear response, is a kind of polymkeric substance nonlinear optical material that potential application foreground is arranged.
Embodiment
In following examples, will the specifically synthetic of compound of each reactions steps of the present invention be described.
Embodiment 1:
1) compound 1 is synthetic
In the 250mL there-necked flask, add 1, the 3-dibromopropane (3.36g, 16.7mmol), salt of wormwood (5.85g, 42mmol) and 80mL acetone, 70 ℃ of heated and stirred.With 1, (3.01g 8.32mmol) is dissolved in the 30mL acetone 4-diiodo-Resorcinol, is added drop-wise in the reaction flask in 48 hours.Reaction finishes, and is chilled to room temperature, steams solvent, and solids constituent fits in water and the chloroform, and organic layer is used 10% potassium hydroxide aqueous solution respectively, distilled water, saturated common salt water washing, anhydrous sodium sulfate drying.Filter, concentrate, recrystallization obtains colorless solid 2g, yield 40%.
1HNMR(CDCl
3，TMS)：2.33(dt，4H)，3.69(t，4H)，4.08(t，4H)，7.24(s，2H)。
2) compound 2 is synthetic
In the 250mL there-necked flask, and adding compound 1 (0.93g, 1.54mmol), 20mL 40% triethylamine aqueous solution, 30mL ethanol and 30mL acetone, 130 ℃ of reflux 18h.Be spin-dried for solvent, recrystallization obtains white solid 1.10g, yield 99%.
1HNMR(CD
3OD，TMS)：2.33(M，4H)，3.24(s，18H)，3.66(m，4H)，4.11(m，4H)，7.37(s，2H)。
3) compound 3 is synthetic
In the 100mL three-necked bottle; add salt of wormwood (2.212g, 16mmol) and 15mL anhydrous dimethyl formamide (DMF) solution, under nitrogen protection and stirring; drip 1; (0.724g, 15mL anhydrous DMF solution 2mmol) dropwise the back and continue to stir 30min 4-diiodo-Resorcinol; drip S-(+)-3-bromo-2-methyl isophthalic acid-propyl alcohol (1.224g again; 10mL anhydrous DMF solution 8mmol), temperature rise to 75 ℃, stir 16h.After being chilled to room temperature, mixture filters, and solid washs with 4mLDMF, merges, be spin-dried for, add 30mL ethylene dichloride and 12mL water, and add a little NaCl ionogen, transfer to the pH value with 2N HCl and be about 2, water extracts with methylene dichloride (10mL * 2), merge organic layer, and use the 20mL water washing, anhydrous MgSO
4Drying is spin-dried for solvent, and recrystallization obtains white solid 0.69g, yield 68%.Fusing point: 107-109 ℃.
1HNMR (CDCl
3, ppm): δ=1.07 (s, 3H), 1.08 (s, 3H), 2.24 (m, 2H), 3.75 (d, 4H), 3.88 (dd, J
1=4.9Hz, J
2=8.8Hz, 2H), 3.98 (dd, J
1=6.8Hz, J
2=8.8Hz, 2H), 7.19 (s, 2H). mass spectrum: m/z=506 (M
+). results of elemental analyses: C
14H
20I
2O
4, theoretical value: C 33.22; H 3.98, measured value: C 33.06, H 3.88.
4) compound 4 is synthetic
Adding compound 3 in the 25mL round-bottomed flask (0.506g, 1mmol), (Bu)
3SnCH=CH
2(0.634g, 2mmol), Pd (PPh
3)
4(0.046g, 0.04mmol) and 8mL DMF, 100 ℃ of heated and stirred 5h.After being chilled to room temperature, mixture filters, and filtrate is poured in the water, with dichloromethane extraction, and collected organic layer, anhydrous magnesium sulfate drying.Be spin-dried for solvent, residuum obtains yellow solid 0.181g with the column chromatography purifying, yield 59%,
1HNMR (CDCl
3, ppm): δ=1.04 (s, 3H), 1.06 (s, 3H), 2.23 (m, 2H), 3.74 (m, 4H), 3.94 (m, 4H), 5.27 (dd, J
1=1.2Hz, J
2=11.1Hz, 2H), 5.71 (dd, J
1=1.2Hz, J
2=17.8Hz, 2H), 7.00 (dd, J
1=11.3Hz, J
2=17.5Hz, 2H), 7.01 (s, 2H). mass spectrum: m/z=306 (M
+). results of elemental analyses: C
18H
26O
4, theoretical value: C 70.56, H 8.55. measured value: C 70.28, H8.32.
5) PPV's is synthetic
Adding compound 2 in the 25mL round-bottomed flask (144mg, 0.2mmol), compound 4 (62.4mg, 0.204mmol), Pd (OAc)
2(1.8mg, 0.008mmol), P (Ph-Me)
3(12mg, 0.04mmol), 70 μ L triethylamines and 5mL DMF, the following 80 ℃ of stirrings of nitrogen protection are spent the night.Solution is poured into while hot in the 50mL acetone and is separated out precipitation, and the resolution of precipitate collected in deionized water, is removed small-molecule substance with dialyzer, is spin-dried for moisture content, obtains dark red solid 41.7mg, yield 26%.
1HNMR (D
2O, ppm): δ=1.07 (br, 6H), 1.81-2.29 (m, 12H), 2.83-3.10 (m, 22H), 3.48-4.02 (br, 12H), 6.24-7.45 (br, 12H), 6.24-7.45 (br, 8H) .FT-IR (KBr compressing tablet, cm
-1): 3011,2953,2872,1600,1202,966. results of elemental analyses: C
38H
62Br
2N
2O
6, theoretical value: C 56.86, H 8.55. measured value: C 54.96, H 7.66.
Embodiment 2:
1) compound 1 is synthetic
In the 250mL there-necked flask, add 1, the 3-dibromopropane (3.36g, 16.7mmol), salt of wormwood (5.85g, 42mmol) and 80mL acetone, 70 ℃ of heated and stirred.With 1, (3.01g 8.32mmol) is dissolved in the 30mL acetone 4-diiodo-Resorcinol, is added drop-wise in the reaction flask in 48 hours.Reaction finishes, and is chilled to room temperature, steams solvent, and solids constituent fits in water and the chloroform, and organic layer is used 10% potassium hydroxide aqueous solution respectively, distilled water, saturated common salt water washing, anhydrous sodium sulfate drying.Filter, concentrate, recrystallization obtains colorless solid 2g, yield 40%.
2) compound 2 is synthetic
In the 250mL there-necked flask, and adding compound 1 (0.93g, 1.54mmol), 20mL 40% triethylamine aqueous solution, 30mL ethanol and 30mL acetone, 130 ℃ of reflux 18h.Be spin-dried for solvent, recrystallization obtains white solid 1.10g, yield 99%.
3) compound 3 is synthetic
In the 100mL three-necked bottle; add salt of wormwood (1.106g, 8mmol) and 15mL anhydrous dimethyl formamide (DMF) solution, under nitrogen protection and stirring; drip 1; (0.362g, 15mL anhydrous DMF solution 1mmol) dropwise the back and continue to stir 30min 4-diiodo-Resorcinol; drip S-(+)-3-bromo-2-methyl isophthalic acid-propyl alcohol (0.612g again; 10mL anhydrous DMF solution 4mmol), temperature rise to 75 ℃, stir 16h.After being chilled to room temperature, mixture filters, and solid merges with 4mL DMF washing, be spin-dried for, add 30mL ethylene dichloride and 12mL water, and add a little NaCl ionogen, transfer to the pH value with 2N HCl and be about 2, water extracts with methylene dichloride (10mL * 2), merge organic layer, and use the 20mL water washing, anhydrous MgSO
4Drying is spin-dried for solvent, and recrystallization obtains white solid 0.34g, yield 67%.Fusing point: 107-109 ℃.
4) compound 4 is synthetic
Adding compound 3 in the 25mL round-bottomed flask (0.253g, 0.5mmol), (Bu)
3SnCH=CH
2(0.317g, 1mmol), Pd (PPh
3)
4(0.023g, 0.02mmol) and 8mL DMF, 100 ℃ of heated and stirred 5h.After being chilled to room temperature, mixture filters, and filtrate is poured in the water, with dichloromethane extraction, and collected organic layer, anhydrous magnesium sulfate drying.Be spin-dried for solvent, residuum obtains yellow solid 0.09g with the column chromatography purifying, yield 58%,
5) PPV's is synthetic
Adding compound 2 in the 25mL round-bottomed flask (144mg, 0.2mmol), compound 4 (62.4mg, 0.204mmol), Pd (OAc)
2(1.8mg, 0.008mmol), P (Ph-Me)
3(12mg, 0.04mmol), 70 μ L triethylamines and 5mL DMF, the following 80 ℃ of stirrings of nitrogen protection are spent the night.Solution is poured into while hot in the 50mL acetone and is separated out precipitation, and the resolution of precipitate collected in deionized water, is removed small-molecule substance with dialyzer, is spin-dried for moisture content, obtains dark red solid 41.7mg, yield 26%.
Embodiment 3:
1) compound 1 is synthetic
In the 250mL there-necked flask, add 1, the 3-dibromopropane (3.36g, 16.7mmol), salt of wormwood (5.85g, 42mmol) and 80mL acetone, 70 ℃ of heated and stirred.With 1, (3.01g 8.32mmol) is dissolved in the 30mL acetone 4-diiodo-Resorcinol, is added drop-wise in the reaction flask in 48 hours.Reaction finishes, and is chilled to room temperature, steams solvent, and solids constituent fits in water and the chloroform, and organic layer is used 10% potassium hydroxide aqueous solution respectively, distilled water, saturated common salt water washing, anhydrous sodium sulfate drying.Filter, concentrate, recrystallization obtains colorless solid 2g, yield 40%.
2) compound 2 is synthetic
In the 250mL there-necked flask, and adding compound 1 (0.93g, 1.54mmol), 20mL 40% triethylamine aqueous solution, 30mL ethanol and 30mL acetone, 130 ℃ of reflux 18h.Be spin-dried for solvent, recrystallization obtains white solid 1.10g, yield 99%.
3) compound 3 is synthetic
In the 100mL three-necked bottle; add salt of wormwood (2.212g, 16mmol) and 15mL anhydrous dimethyl formamide (DMF) solution, under nitrogen protection and stirring; drip 1; (0.724g, 15mL anhydrous DMF solution 2mmol) dropwise the back and continue to stir 30min 4-diiodo-Resorcinol; drip S-(+)-3-bromo-2-methyl isophthalic acid-propyl alcohol (1.224g again; 10mL anhydrous DMF solution 8mmol), temperature rise to 75 ℃, stir 16h.After being chilled to room temperature, mixture filters, and solid washs with 4mLDMF, merges, be spin-dried for, add 30mL ethylene dichloride and 12mL water, and add a little NaCl ionogen, transfer to the pH value with 2N HCl and be about 2, water extracts with methylene dichloride (10mL * 2), merge organic layer, and use the 20mL water washing, anhydrous MgSO
4Drying is spin-dried for solvent, and recrystallization obtains white solid 0.69g, yield 68%.Fusing point: 107-109 ℃.
4) compound 4 is synthetic
Adding compound 3 in the 25mL round-bottomed flask (0.506g, 1mmol), (Bu)
3SnCH=CH
2(0.634g, 2mmol), Pd (PPh
3)
4(0.046g, 0.04mmol) and 8mL DMF, 100 ℃ of heated and stirred 5h.After being chilled to room temperature, mixture filters, and filtrate is poured in the water, with dichloromethane extraction, and collected organic layer, anhydrous magnesium sulfate drying.Be spin-dried for solvent, residuum obtains yellow solid 0.181g with the column chromatography purifying, yield 59%.
5) PPV's is synthetic
Adding compound 2 in the 25mL round-bottomed flask (72mg, 0.1mmol), compound 4 (31.2mg, 0.102mmol), Pd (OAc)
2(0.9mg, 0.004mmol), P (Ph-Me)
3(6.0mg, 0.02mmol), 35 μ L triethylamines and 5mL DMF, the following 80 ℃ of stirrings of nitrogen protection are spent the night.Solution is poured into while hot in the 50mL acetone and is separated out precipitation, and the resolution of precipitate collected in deionized water, is removed small-molecule substance with dialyzer, is spin-dried for moisture content, obtains dark red solid 22.1mg, yield 28%.
Claims (3)
1. poly-phenylene vinylene (ppv) is characterized in that the structure of described poly-phenylene vinylene (ppv) is as follows:
N=8-10 in the formula
2. the preparation method of the described poly-phenylene vinylene (ppv) of claim 1 is characterized in that step is carried out in the following order:
(1) preparation of quaternary ammonium salt:
1. with 1,4-diiodo-Resorcinol is dissolved in the acetone fully, under 2-5 salt of wormwood effect doubly, with 1, the reaction of 3-dibromopropane, its add-on are 1-2 times of raw material, and reflux temperature reacted 30-50 hour down, steam solvent, solids constituent fits in water and the chloroform, and organic phase with 10% potassium hydroxide aqueous solution, distilled water, saturated common salt water washing, drying, filtration, concentrated, recrystallization, obtains product 1 respectively, 4-two-(3-bromine propoxy-)-2, the 5-diiodo-benzene;
2. above-mentioned product that obtains and 3-5 trimethylamine aqueous solution are doubly reacted backflow 14-28 hour, add ethanol and acetone, its add-on is respectively 10-20 times of reactant, is spin-dried for solvent, and recrystallization obtains the product quaternary ammonium salt;
(2)
1. nitrogen atmosphere, under the dimethyl formamide, with 1,4-diiodo-Resorcinol and S-(+)-3-bromo-2-methyl isophthalic acid-propyl alcohol is in 1: the ratio of 2-3 obtains (3-hydroxy-2-methyl)-propoxy--2, the 5-diiodo-benzene in 60-80 ℃ of reaction 10-20 hour;
2. under the dimethyl formamide, 80-100 ℃ of reaction 3-10 hour, product was with dichloromethane extraction with the organotin reagent of the above-mentioned product that obtains and 2 times, drying is spin-dried for solvent, obtains product 1,4-two [(3-hydroxy-2-methyl)-propoxy-]-2, the 5-Vinylstyrene;
(3) nitrogen atmosphere, under the dimethyl formamide, the product that step (1) and step (2) are obtained separately in 80-100 ℃, generated product with the palladium of 1: 1 ratio and catalytic amount, trimethylphenyl phosphine in 10-20 hour, place 10-20 acetone doubly to separate out precipitation, get final product.
3. the purposes of the described poly-phenylene vinylene (ppv) of claim 1 is characterized in that having in order to preparation the film of third-order nonlinear optical effect.
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| CN107573287A (en) * | 2017-09-18 | 2018-01-12 | 北京工商大学 | A kind of cation poly-phenylene vinylene (ppv) derivative and its preparation method and application |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1066163C (en) * | 1994-09-30 | 2001-05-23 | 赫彻斯特股份公司 | Nitrogenous polymers used as electroluminescent materials |
| US6403238B1 (en) * | 1998-07-10 | 2002-06-11 | Hoerhold Hans-Heinrich | Organic light-emitting diodes (OLED) including poly[2-methoxy-5-(2′-ethyl-hexyloxy)-1,4-phenylene-1,2-ethenylene-2,5-dimethoxy-1,4-phenylene-1,2-ethenylene] as electroluminescent material |
-
2004
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1066163C (en) * | 1994-09-30 | 2001-05-23 | 赫彻斯特股份公司 | Nitrogenous polymers used as electroluminescent materials |
| US6403238B1 (en) * | 1998-07-10 | 2002-06-11 | Hoerhold Hans-Heinrich | Organic light-emitting diodes (OLED) including poly[2-methoxy-5-(2′-ethyl-hexyloxy)-1,4-phenylene-1,2-ethenylene-2,5-dimethoxy-1,4-phenylene-1,2-ethenylene] as electroluminescent material |
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