CN101982476B - Vinyl polymer with absorbancy-temperature response characteristic - Google Patents
Vinyl polymer with absorbancy-temperature response characteristic Download PDFInfo
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- CN101982476B CN101982476B CN2010105250221A CN201010525022A CN101982476B CN 101982476 B CN101982476 B CN 101982476B CN 2010105250221 A CN2010105250221 A CN 2010105250221A CN 201010525022 A CN201010525022 A CN 201010525022A CN 101982476 B CN101982476 B CN 101982476B
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Abstract
The invention discloses a polymer structure with absorbance-temperature response characteristic. The side group of a vinyl polymer contains a triaryl imidazole group shown in a general formula 1, wherein the optical wavelength of the vinyl polymer solution or a polymer film is between 220 and 450 nm and the temperature thereof is within a range of 20-90 DEG C, the absorbance of the vinyl polymer solution or the polymer film changes linearly with the temperature; the molecular weight of the polymer is within a range of 1000-10<6>g/mol; the polymer solution takes dimethylformamide (DMF) or dimethyl sulfoxide (DMSO) as solvent, the thickness of the polymer film is 8-300nm; R1, R2 and R3 in the general formula 1 can be hydrogen or electron donating group or electron withdraw group; and the R1, R2 and R3 can be the same or be different.
Description
(1) technical field
One type of structure with absorbancy-temperature response characteristics polymkeric substance.
(2) background technology
Also rarely found about report both at home and abroad at present with absorbancy-temperature linearity responsive polymer; Once reported that gathering (3-hexyl) thiophene solution absorbency reduced with the increase of temperature gradually in 2007 abroad, yet because the change of transition between electronic level, [J.Clark simultaneously also squints in its absorption peak position; Et al.Phys.Rev.Lett., 98,206406 (2007)].
(3) summary of the invention
The disclosed vinyl polymer that contains the triarylimidazoles side group of the present invention has absorbancy-temperature linearity responsiveness; Be absorbancy along with the variation of temperature (20-90 degree centigrade) presents linear change; And the absorption peak position does not change with temperature; Explain that the increase and decrease of temperature can not change the transition of electronic energy of polymer molecule, this characteristic makes it aspect TP, show huge potential using value.
The present invention discloses one type of structure and compound method with absorbancy-temperature response characteristics polymkeric substance.
For realizing above-mentioned purpose, polymer pendant groups provided by the invention contains triarylimidazoles group as follows (general formula 1):
R in the general formula 1
1, R
2, R
3Can be hydrogen or electron-donating group or electron-withdrawing group; R
2, R
3, R
1Group can be identical, also can have nothing in common with each other; Said solutions of vinyl polymers or polymeric film are at optical wavelength 220-450nm, and temperature is in 20-90 ℃ of scope, and the absorbancy of polymers soln and polymeric film presents linear change with temperature variation; Polymericular weight is at 1000-10
6In the g/mol scope, molecular weight distributing index is in the 1-50 scope; Polymers soln is to be solvent with N (DMF) or DMSO 99.8MIN. (DMSO).
Described electron-donating group is amino-NH
2, substituted-amino-NHR ,-NR
2, alkyl, alkoxyl group or aminoacyl; Described electron-withdrawing group is halogen atom, carboxyl, ester group, itrile group, sulfonic group; Substituent R
1The C number can between 1-4, change R
3And R
2Group C quantity can change between 1-5; Work as R
1C quantity when being 1-4, R
1In last four optional positions that replace the position of phenyl ring a; Work as R
2C quantity when being 1-5, R
2Can be in last five optional positions that replace the position of phenyl ring b; Work as R
3C quantity when being 1-5, R
3Can be in last five optional positions that replace the position of phenyl ring c;
The Vilaterm main chain can pass through ester group, and (COO-), (CO-), (O-), (Ph-), naphthyl, substituted-phenyl or heterocyclic group (like
) are connected with the phenyl ring a of triarylimidazoles group phenyl ether ketone group.
The monomeric raw material sources of described vinyl polymer can be for vinyl monomer or with the vinyl monomer of methyl.
The method that is used for synthetic above-mentioned polymkeric substance provided by the invention, its key step is:
(1) monomer of synthesis type 2 or formula 3;
(2) select corresponding polyreaction composite structure polymkeric substance as claimed in claim 1 according to monomer character, selected polyreaction includes but not limited to Raolical polymerizable, activity/controlled radical polymerization, ionic polymerization reaction and polycoordination reaction.
R
1, R
2, R
3Group definition is the same; X be ester group (COO-), ketone group (CO-), ether (O-), phenyl (Ph-), naphthyl, substituted-phenyl or heterocyclic group (as
Deng).
The preparation process comprises solution polymerization, letex polymerization, suspension polymerization or solid state polymerization.
Resulting polymkeric substance can be formula 2 or formula 3 said monomeric homopolymer, or formula 3, formula 4 said monomeric multipolymers.
Described multipolymer comprises binary, ternary and tetrapolymer, and multipolymer is formed and can be regulated arbitrarily.
Preferred polymkeric substance of the present invention has following structure: n=2～2000
The present invention adopts the photophysical property of ultraviolet-visible spectrophotometer research polymkeric substance, mainly studies the absorbancy-temperature-responsive of polymkeric substance.
(4) description of drawings
1, Fig. 1 is the nucleus magnetic hydrogen spectrum figure of monomer 1; Fig. 2 is the nuclear-magnetism carbon spectrogram of monomer 1; Fig. 3 is the nucleus magnetic hydrogen spectrum figure of polymkeric substance 1; Fig. 4 is the nuclear-magnetism carbon spectrogram of polymkeric substance 1; Fig. 5 is the GPC figure (corresponding to embodiment 1 and 2) of polymkeric substance 1; Fig. 6 is the GPC figure (corresponding to embodiment 3) of polymkeric substance 1; Fig. 7 is the nucleus magnetic hydrogen spectrum figure of monomer 2; Fig. 8 is the GPC figure of polymkeric substance 2.2, the present invention adopts ultraviolet/visible/near infrared spectrometer that the DMF solution of polymkeric substance 1 and the absorbancy-temperature response performance of polymkeric substance 1 film are measured respectively, and total range of wavelength is 220nm～450nm.Respectively the solution of polymkeric substance 1 and membrane sample are recorded the absorption curve of sample under the differing temps for three times in Circularly liftable between the room temperature to 90 ℃.Fig. 9 and Figure 10 are respectively intensification, the absorption spectrogram when lowering the temperature of polymkeric substance 1DMF solution.Get different absorbing wavelength (solution: 297/307/317nm; Film: the absorbance 292/302/307/310nm) located is made the graph of a relation of itself and temperature.Figure 11 is the graph of a relation of polymkeric substance 1DMF solution absorbency-temperature; Figure 12 is the graph of a relation of the absorbancy-temperature at 300nm place for polymkeric substance 1DMSO solution wavelength, and (1H, 1C represent respectively and heat up and lower the temperature for the 1st time Figure 13 for the graph of a relation of the absorbancy-temperature of polymkeric substance 1 film; 2H, 2C represent the 2nd intensification and cooling; 3H, 3C are roughly the same), film thickness is 74nm.The result of Figure 13 shows that the absorbancy of polymkeric substance 1 changes with temperature linearity, and when temperature raise, the absorbancy linearity reduced, and when temperature reduced, absorbancy is linear to be increased; And after sample circulated through three coolings that heat up, its linear change still can repeat preferably, explains that the absorbancy-temperature response of this polymkeric substance has reversibility.
3, the present invention adopts ultraviolet/visible/near infrared spectrometer that the DMF solution absorbency-temperature response performance of polymkeric substance 2 is measured, and total range of wavelength is 280nm～400nm.Range of temperature is 35-65 ℃, and temperature cycle is gone up and down twice.Get absorbance that maximum absorption wavelength (300nm) locates and make the graph of a relation of itself and temperature.Figure 14 and Figure 15 are respectively intensification, the absorption spectrogram when lowering the temperature of polymkeric substance 1 solution.(1H, 1C represent respectively and heat up and cooling for the 1st time Figure 16 for the graph of a relation of polymkeric substance 2DMF solution absorbency-temperature; 2H, 2C represent the 2nd intensification and cooling).The result of Figure 16 shows that the absorbancy of polymkeric substance 2 changes with temperature linearity, and when temperature raise, the absorbancy linearity reduced, and when temperature reduced, absorbancy is linear to be increased; And after sample circulated through twice intensification cooling, its linear change still can repeat preferably, explains that the absorbancy-temperature response of this polymkeric substance has reversibility.
4, testing tool:
Nuclear magnetic spectrogram adopts INOVA 400 spectrometers to measure.
Molecular weight and MWD adopt Waters-1515 gel permeation chromatograph (GPC) to measure; Separator column is WatersStyragel Columns (
); The flow velocity of moving phase DMF is 1.0ml/min; Probe temperature is 45oC, mark in doing with monodispersed PS.
Ultraviolet-visible spectrum (UV-Vis) utilizes PE Lambda 750 type ultraviolets/visible/near infrared spectrometer to measure, and total range of wavelength is 350nm～750nm.
Differential scanning calorimetry spectrogram (DSC) adopts the automatic differential scanning calorimeter of DSC-7 type to measure, and in the nitrogen atmosphere, heat-up rate is 10 ℃ of min
-1
Thermal weight loss spectrogram (TGA) utilizes STA 449C type thermal gravimetric analyzer to measure, and in the nitrogen atmosphere, heat-up rate is 10 ℃ of min
-1
(5) embodiment
Further specify through concrete preparation instance below.
The structural formula of monomer 1 and polymkeric substance 1 is as follows respectively:
The synthetic route of monomer 1:
(1) 4-(4 '-vinyl benzyloxy base) phenyl aldehyde is synthetic
1.22g (10mmol) PARA HYDROXY BENZALDEHYDE, 1.54g (10mmol) p-chloromethyl styrene, 2.48g (18mmol) anhydrous K 2CO3 and 5mL DMF are joined in the 50mL round-bottomed flask; At 58-60 ℃ of lower magnetic force stirring reaction, follow the tracks of reaction through thin-layer chromatography TLC point plate.Reaction is poured reaction mixture in the zero(ppm) water of 120mL after accomplishing, and has brown white precipitate to separate out, and suction filtration and water washing and precipitating are repeatedly.After the crude product oven dry, use the absolute ethyl alcohol recrystallization, obtain light brown crystal 1.35g, productive rate is 56.7%.
(2) monomer 1 is synthetic
Take by weighing the 4-that above-mentioned steps (1) makes (4 '-vinyl benzyloxy base) phenyl aldehyde 2.38g, dibenzoyl 2.10g, ammonium acetate 7.71g (mol ratio is 1: 1: 10) successively in the 250mL there-necked flask; The Glacial acetic acid min. 99.5 that adds 50mL; Reflux is followed the tracks of reaction through TLC point plate.Reaction is poured reaction mixture in the 120mL water into after finishing, and shallow again white precipitate is separated out, and suction filtration and water are washed till neutrality.Crude product is 1: 1 N with volume ratio, and the mixed solvent recrystallization of dinethylformamide/methyl alcohol obtains white solid 2.48g, and productive rate is 58.4%.Referring to Fig. 1,2.
(3) compound method 1 of polymkeric substance 1
In the little flask of exsiccant 10mL round bottom, add 0.11g monomer 1,2mg Diisopropyl azodicarboxylate (4.7mol%) and 2mLDMF, reaction flask clogs with the turned welt plug, and good seal, drum nitrogen deoxygenation were placed in 70 ℃ of oil baths stirring reaction in 40 minutes 24 hours.Reaction is cooled off with ice bath after finishing.Polymkeric substance is used the methyl alcohol sedimentation, and vacuum-drying obtains polymkeric substance 41mg, monomer conversion 37.3%.This polymkeric substance has good solubility at N in dinethylformamide, THF, acetic acid, the DMSO 99.8MIN. equal solvent.Gel permeation chromatography (GPC) test result shows: number-average molecular weight Mn=20500, molecular weight distributing index PDI=1.28.Referring to Fig. 3,4,5
The compound method 2 of polymkeric substance 1
In the little flask of exsiccant 10mL round bottom, add 0.11g monomer 1,1.5mg Diisopropyl azodicarboxylate (3.5mol%) and 2mL DMF, reaction flask clogs with the turned welt plug, and good seal, drum nitrogen deoxygenation were placed in 70 ℃ of oil baths stirring reaction in 40 minutes 24 hours.Reaction is cooled off with ice bath after finishing.Polymkeric substance is used the methyl alcohol sedimentation, and vacuum-drying obtains polymkeric substance 16mg, monomer conversion 14.5%.The GPC test result shows: Mn=28000, PDI=1.35.Referring to Fig. 3,4,5
Embodiment 3
The compound method 3 of polymkeric substance 1
In the little flask of exsiccant 25mL round bottom, add 0.44g monomer 1,3.5mg Diisopropyl azodicarboxylate, 10mg chain-transfer agent (dithiobenzoic acid (2-cyanopropionic acid) ester) and 8mL DMF; Reaction flask clogs with the turned welt plug; Good seal, drum nitrogen deoxygenation were placed in the 50-80 ℃ of oil bath stirring reaction in 40 minutes 24 hours.Reaction is cooled off with ice bath after finishing.Polymkeric substance is used the methyl alcohol sedimentation, and vacuum-drying obtains polymkeric substance 160mg, monomer conversion 36.4%.The GPC test result shows: Mn=11059, PDI=1.12.Referring to Fig. 6
The second-order transition temperature that differential scanning calorimetric (DSC) analytical results shows polymkeric substance 1 is between 171-174 ℃, and the temperature that thermogravimetic analysis (TGA) (TGA) polymkeric substance 1 begins to decompose is at 295-305 ℃.
Embodiment 4
The structural formula of monomer 2 and polymkeric substance 2 is distinguished as follows:
(1) 4-alkynes propoxy-phenyl aldehyde is synthetic
With 1.19g (0.01mol) 3-propargyl bromide, 1.22g (0.01mol) PARA HYDROXY BENZALDEHYDE, 4.14g (0.03mol) anhydrous K
2CO
3Join in the there-necked flask of 100mL with 30mL N (DMF),, follow the tracks of reaction through TLC point plate at 80 ℃ of following stirring reactions.Behind the stopped reaction, filter away inorganic salt, the part that reduces pressure away DMF pours remaining reactants in the 200mL water into, has deposition to separate out, and suction filtration and water washing and precipitating are repeatedly.After the crude product oven dry, use the absolute ethyl alcohol recrystallization again, obtain brown crystal 1.02g, productive rate is 63.7%.
(2) 2-(4 '-alkynes propoxy-phenyl)-4,5-diphenyl-imidazole synthetic
Take by weighing the 4-alkynes propoxy-phenyl aldehyde 0.81g (0.005mol) that makes in the above-mentioned steps (1), dibenzoyl 1.05g (0.005mol), ammonium acetate 3.85g (0.005mol) successively in the 50mL round-bottomed flask; Add the 15mL Glacial acetic acid min. 99.5 again; At 120 ℃ of following stirring reactions, follow the tracks of reaction through TLC point plate.Reaction is poured reactant in the 120mL water into after finishing, and has deposition to separate out, and suction filtration and water washing and precipitating repeatedly after the crude product oven dry, are used the absolute ethyl alcohol recrystallization, obtain brown crystal 1.45g, and productive rate is 82.4%.
(3) methylacrylic acid-2-azido-ethyl ester is synthetic
26.2g (0.180mol) ethylene bromohyrin, 20.5g (0.320mol) sodiumazide and 100mL zero(ppm) water are added in the there-necked flask of 250mL, nitrogen protection was stirred 10 minutes for following 0 ℃, under room temperature, stirred 4 hours again.At last in 80 ℃ of reactions 12 hours.With extracted with diethyl ether three times, organic phase is used dried over sodium sulfate behind the stopped reaction, filters, rotary evaporation removes ether, and it is 64 ℃ cut that temperature is collected in underpressure distillation.Obtain colourless liquid nitrine ethanol 10.2g, productive rate is 65.0%.
3.44g (0.0400mol) methylacrylic acid, 3.91g (0.0450mol) nitrine ethanol, 1.65g (13.5mmol) tetramethylammonium yl pyridines and 80mL methylene dichloride are joined in the 250mL round-bottomed flask; Ice bath is cooled to 0 ℃; To be dissolved with 9.28g (45mmol) N again; The 30mL dichloromethane solution of the inferior diamide of N-dicyclohexyl carbon (DCC) slowly adds in the reaction flask, drips back stirring at room reaction 48 hours.Reaction removes by filter insolubles after finishing, and the crude product after concentrating is that the mixed solvent of 1: 9 ethyl acetate/petroleum ether is that eluent is crossed the post separation with volume ratio, obtains colourless liquid methylacrylic acid-2-azido-ethyl ester 3.84g, and productive rate is 62.0%.
(4) monomer 2 is synthetic
Take by weighing the 2-that above-mentioned steps (2) makes (4 '-alkynes propoxy-phenyl)-4 successively; The methylacrylic acid that 5-diphenyl-imidazole 1.76g (0.005mol), above-mentioned steps (3) make-2-azido-ethyl ester 0.78g (0.005mol), CuBr 0.71g (0.005mol), five methyl diethylentriamine 0.86g (0.005mol) are in the round-bottomed bottle of 25mL; Add 10mL DMF again, the stirring at room reaction is 24 hours under the nitrogen protection.Behind the stopped reaction reactant is poured in the water, used ethyl acetate extraction again three times, organic phase is used dried over sodium sulfate, filters, and rotary evaporation is removed part ETHYLE ACETATE, obtains white solid 1.39g with the sherwood oil sedimentation, and productive rate is 55.0%.Referring to Fig. 7
(5) polymkeric substance 2 is synthetic
In the little flask of exsiccant 10mL round bottom, add 0.13g monomer 2,2mg Diisopropyl azodicarboxylate (5mol%) and 2mL DMF, reaction flask clogs with the turned welt plug, good seal, and drum nitrogen deoxygenation was placed in 70 ℃ of oil baths and reacted 24 hours in 40 minutes.Reaction is cooled off with ice bath after finishing.Polymkeric substance is used the methyl alcohol sedimentation, and the suction filtration final vacuum is dry, obtains polymkeric substance 58mg, and monomer conversion is 44.6%.The GPC characterization result is following: Mn=21000, PDI=1.26.Referring to Fig. 8.
Claims (8)
1. one type of vinyl polymer with absorbancy-temperature response characteristics, its side group of described vinyl polymer contains the triarylimidazoles group shown in the general formula 1, and general formula 1 is:
General formula 1
Said solutions of vinyl polymers or polymeric film are at optical wavelength 220-450nm, and temperature is in 20-90 ℃ of scope, and the absorbancy of polymers soln and polymeric film presents linear change with temperature variation; Polymericular weight is at 1000-10
6In the g/mol scope, molecular weight distributing index is in the 1-50 scope; Polymers soln is to be solvent with N or DMSO 99.8MIN., and polymer film thickness is 8-300nm; R in the general formula 1
1, R
2, R
3Be hydrogen.
2. vinyl polymer according to claim 1 is characterized in that, (COO-), (CO-), (O-), (Ph-), naphthyl, substituted-phenyl or heterocyclic group are connected with the phenyl ring a of triarylimidazoles group phenyl ether ketone group main polymer chain through ester group; Described heterocyclic group is
3. vinyl polymer according to claim 1 is characterized in that described polymkeric substance has following structure: n=2～2000
4. one type of preparation with vinyl polymer of absorbancy-temperature response characteristics; It is characterized in that; To have and contain polymerisable vinyl group simultaneously in the monomer structure shown in formula 2 or the formula 3 and the triarylimidazoles group is selected corresponding polyreaction synthetic polymer according to monomer character, selected polyreaction comprises Raolical polymerizable, activity or controlled radical polymerization, ionic polymerization reaction or polycoordination reaction:
Formula 2 formulas 3
R in the general formula 1
1, R
2, R
3Be hydrogen
X is ester group (COO-), ketone group (CO-), ether (O-), phenyl (Ph-), naphthyl, substituted-phenyl or a heterocyclic group
5. like the preparation of the said polymkeric substance of claim 4, the preparation process comprises solution polymerization, letex polymerization, suspension polymerization or solid state polymerization.
6. like the preparation of the said polymkeric substance of claim 4, it is characterized in that resulting polymkeric substance can be formula 2, formula 3 said monomeric homopolymer, or formula 2, formula 3 said monomeric multipolymers.
7. like the preparation of the said polymkeric substance of claim 4, it is characterized in that described multipolymer comprises binary, ternary and tetrapolymer, multipolymer is formed and can be regulated arbitrarily.
8. like the preparation of the said polymkeric substance of claim 4; It is characterized in that; Said solutions of vinyl polymers or polymeric film are at optical wavelength 220-450nm, and temperature is in 20-90 ℃ of scope, and the absorbancy of polymers soln and polymeric film presents linear change with temperature variation; Polymers soln is with N or dimethyl sulfoxide solvent, and polymer film thickness is 8-300nm; Polymericular weight is at 1000-10
6In the g/mol scope, MWD is in the 1-50 scope.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6569978B2 (en) * | 2000-12-19 | 2003-05-27 | Kwangju Institute Of Science And Technology | Anionic polymerization of functionalized styrene derivatives containing carbazole |
| CN1699362A (en) * | 2005-06-02 | 2005-11-23 | 上海交通大学 | Thienyl substituted hexa-aryl bis-imidazole and method for preparing same |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6569978B2 (en) * | 2000-12-19 | 2003-05-27 | Kwangju Institute Of Science And Technology | Anionic polymerization of functionalized styrene derivatives containing carbazole |
| CN1699362A (en) * | 2005-06-02 | 2005-11-23 | 上海交通大学 | Thienyl substituted hexa-aryl bis-imidazole and method for preparing same |
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