CN102993082A - Difluoro monomer with carbazole group and application thereof in preparing polyarylether polymer containing carbazole side group - Google Patents
Difluoro monomer with carbazole group and application thereof in preparing polyarylether polymer containing carbazole side group Download PDFInfo
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- CN102993082A CN102993082A CN2012105279303A CN201210527930A CN102993082A CN 102993082 A CN102993082 A CN 102993082A CN 2012105279303 A CN2012105279303 A CN 2012105279303A CN 201210527930 A CN201210527930 A CN 201210527930A CN 102993082 A CN102993082 A CN 102993082A
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Abstract
The invention belongs to the field of a high molecular material and a preparation technology thereof, and particularly relates to a difluoro monomer 4-(2,6-difluorobenzoyl)phenylpropyl-4-(N-carbazolyl)phenyl ether with a carbazole group and application of the difluoro monomer in preparing a polyarylether polymer containing a carbazole side group. Through the invention, the prepared polyarylether polymer containing the carbazole side group has good heat resistance and chemical stability as well as good properties of photoelectric functional materials, and has wider potential application values in the field of photoelectric polymer materials.
Description
Technical field
The invention belongs to macromolecular material and preparing technical field thereof, be specifically related to a kind of application that has aspect two fluorine monomers of carbazole group and this two fluorine monomer contains the carbazole side group in preparation the polyarylether polymer.
Background technology
Carbazole is a kind of chromophoric group of blue light.No matter the small molecules carbazole compound still contains carbazole polymer, all has the performance of emission blue-fluorescence.During small molecules carbazole compound emitting fluorescence, because fluorescent quenching occurs easily for the gathering of photon, often with it and other materials compound use.
A kind of method that carbazole group is introduced polymkeric substance is that corresponding monomer (the N-vinyl carbazole of buying such as a large amount of commercialization) is prepared the polymkeric substance that side chain contains carbazole by radical polymerization or ionic polymerization, forefathers have synthesized by this method some and have had the material of using value, such as the polyacetylene carbazole, carry out series polymer and the derivative that the Ring-opening metathesis polymerization of norbornylene obtains by the carbazole with the norbornylene modified, and the polymkeric substance that obtains of the carbazole monomers ring-opening polymerization of oxyethyl group oxazole functionalization.In polyarylether material, introduce carbazole group, can make thermotolerance, the good polyarylether material of chemical stability have the advantageous property of photoelectric functional material concurrently, make this class material have potential widely using value at the opto-electrical polymers Material Field.
Summary of the invention
The technical problem to be solved in the present invention is, synthetic a kind of novel two fluorine monomers that contain carbazole and contain the polymkeric substance of carbazole side group based on a class of this monomer preparation.This monomer when having kept the carbazole luminosity, can keep again thermotolerance and the chemical stability of polyarylether material with can introducing in the polymkeric substance for the difluoride group of polyreaction.
The structure of two fluorine monomers that contains carbazole is as follows:
The synthetic method that contains two fluorine monomers of carbazole of the present invention, a minute three-step reaction carries out:
The first step reaction: the preparation of 2,6-, two fluoro-4 '-(1-bromopropyl) benzophenone
Under the ice-water bath condition, methylene dichloride, aluminum trichloride (anhydrous) joined be equipped with in the churned mechanically three-necked flask, afterwards by constant pressure funnel with 2, in the three-necked flask under 6-difluoro benzoyl chloride, 3-hydrocinnamyl bromine slowly splash into successively and stir, wherein 2, the mol ratio of 6-difluoro benzoyl chloride, 3-hydrocinnamyl bromine, aluminum trichloride (anhydrous) is 1: 1～1.1: 1.1～1.2,2, the ratio of 6-difluoro benzoyl chloride and methylene dichloride is 1g: 5～6mL, 4～6 hours reaction times; Reaction system is down to discharging after the room temperature in mass concentration is 10% aqueous hydrochloric acid, organic phase is washed rear separatory successively with aqueous sodium hydroxide solution, the saturated nacl aqueous solution of mass concentration 5%, organic phase dewaters with anhydrous magnesium sulfate, filter, then methylene dichloride is removed in underpressure distillation, product obtains orange 2 with the sherwood oil recrystallization, 6-two fluoro-4 '-(1-bromopropyl) benzophenone solid, and its structural formula is as follows:
Second step reaction: the N-(4-hydroxy phenyl) preparation of carbazole
With carbazole, 4-iodanisol, N, N '-N,N-DIMETHYLACETAMIDE, Red copper oxide join in the round-bottomed flask, carbazole, 4-iodanisol, Red copper oxide three's mol ratio is 1: 1.1～1.2: 1.4～1.5, the solid matter and the N that drop into, the ratio of N '-N,N-DIMETHYLACETAMIDE is about 1g: 3mL is to 1g: 4mL.Mechanical stirring is warming up to N, and N '-N,N-DIMETHYLACETAMIDE refluxes, and reacts 24～36 hours; Reaction system is down to room temperature, filters, and discharging refilters the N-(4-p-methoxy-phenyl that obtains white in methyl alcohol and water volume ratio are 1: 1 mixing solutions) the carbazole crude product.
With the N-(4-p-methoxy-phenyl) carbazole crude product, methylene dichloride join in the three-necked flask, mechanical stirring under the ice-water bath, slowly splash into boron tribromide in the three-necked flask, the N-(4-p-methoxy-phenyl) mol ratio of carbazole, boron tribromide is 1: 1.5, the N-(4-p-methoxy-phenyl) ratio of carbazole and methylene dichloride is 1g: 15～25mL, continues ice-water bath 10～20 hours; Add the distilled water cancellation reaction of about 1/5th methylene chloride volume, the organic phase washing, dry behind the separatory, revolve steaming, purifying with silica gel column chromatography obtains white N-(4-hydroxy phenyl) the carbazole solid, its structural formula is:
Three-step reaction:
In three-necked flask, with 2,6-two fluoro-4 '-(1-bromopropyl) benzophenone, N-(4-hydroxy phenyl) carbazole and potassium hydroxide is dissolved in the ethanol, 2,6-, two fluoro-4 '-(1-bromopropyl) benzophenone, N-(4-hydroxy phenyl) mol ratio of carbazole, potassium hydroxide is 1: 1: 1～1.1, the N-(4-hydroxy phenyl) ratio of carbazole and ethanol is 1g: 20～40mL, pass into nitrogen, mechanical stirring is heated to alcohol reflux, reacts 10 hours; Reaction system is down to room temperature, and removal of solvent under reduced pressure with the methylene dichloride dissolving, is filtered, and methylene dichloride is removed in decompression; Purify with silica gel column chromatography, obtain the white needles solid with the sherwood oil recrystallization again, namely contain two fluorine monomer 4-(2 of carbazole group, the 6-difluoro benzoyl) hydrocinnamyl-4-(N-carbazyl) phenyl ether, its structural formula is:
The synthetic carbazole side group polymkeric substance that contains of polycondensation:
With 4-(2, the 6-difluoro benzoyl) hydrocinnamyl-4-(N-carbazyl) phenyl ether, two halogen monomers (4,4 '-difluoro benzophenone, 4,4 '-difluorodiphenyl sulfone, or 4,4 '-dichloro diphenyl sulfone), biphenol monomer (2,2 '-two (4-hydroxy phenyl)-HFC-236fa or 2,2 '-two (hydroxy phenyl) propane) be reactant, Anhydrous potassium carbonate is salt forming agent, tetramethylene sulfone is solvent, toluene or dimethylbenzene are azeotropy dehydrant, 4-(2, the 6-difluoro benzoyl) hydrocinnamyl-4-(N-carbazyl) phenyl ether, two halogen monomers, biphenol monomer, the mol ratio of Anhydrous potassium carbonate is m: 1-m: 1: 1.1～1.2,0＜m≤1, the mass ratio of tetramethylene sulfone and all reactants is 2.5～3: 1, and the volume ratio of tetramethylene sulfone and azeotropy dehydrant is 1.5: 1～5: 1; Above-mentioned reactant, salt forming agent, solvent, azeotropy dehydrant adding are equipped with in the churned mechanically there-necked flask, being heated to azeotropy dehydrant under nitrogen protection refluxes, keep temperature to steam unnecessary azeotropy dehydrant after 2～3 hours, 210 ℃～220 ℃ continuation react sticky to reaction system, namely obtain the polymkeric substance crude product; The polymkeric substance crude product is poured into water, pulverizes, filter; Boil, filter with distilled water again, repeat 5～6 times; Then boil, filter with ethanol, repeat 5～6 times; Namely obtain containing the polyarylether polymer of carbazole side group after the oven dry.
Description of drawings
Fig. 1: the nucleus magnetic hydrogen spectrum figure (imaging reagent is deuterochloroform) of carbazole two fluorine monomers of the embodiment of the invention 1 preparation and the ownership at each hydrogen atom peak;
Fig. 2: the nucleus magnetic hydrogen spectrum figure of the polymkeric substance that contains the carbazole side group of the m=0.4 of the embodiment of the invention 2 preparations, the integral area at each peak of nuclear magnetic spectrogram can mate with each component ingredient proportion;
Fig. 3: the DSC curve of the polymkeric substance that contains the carbazole side group of the m=0.4 of the embodiment of the invention 2 preparations; The T that records
gIt is 158 ℃;
Fig. 4: the Infrared Characterization spectrogram of two fluorine monomers that contain carbazole of the embodiment of the invention 1 preparation; 3050cm wherein
-1About be the C-H peak of phenyl ring, 2930cm
-1About be the C-H peak of methylene radical, at 1250cm
-1About locate the peak of C-O key;
Fig. 5: the Infrared Characterization spectrogram of the polymkeric substance that contains the carbazole side group of the m=0.6 of the embodiment of the invention 3 preparations; Can see that the infrared absorption peak in the monomer has embodiment, 1250cm in polymkeric substance
-1The peak at place significantly strengthens, and is because produced a large amount of C-O keys after generating polymkeric substance;
Fig. 6: the ultraviolet-visible absorption spectroscopy spectrogram of two fluorine monomers that contain carbazole of the embodiment of the invention 1 preparation; Can see at the 343nm place obvious absorption peak is arranged;
Fig. 7: the ultraviolet-visible absorption spectroscopy spectrogram of the polymkeric substance that contains the carbazole side group of the m=0.4 of the embodiment of the invention 2 preparations; Can see at the 343nm place obvious uv-absorbing is also arranged;
Fig. 8: the fluorescence emission spectrum spectrogram of the polymkeric substance that contains the carbazole side group of the m=0.4 of example 2 preparations of the present invention; Spectrogram shows that maximum emission wavelength is 463nm, and polymkeric substance sends blue-greenish colour fluorescence.
Embodiment
Embodiment 1: synthetic two fluorine monomers that contain carbazole
The first step, under ice-water bath, in the 500mL three-necked flask that the mechanical stirring oar is housed, add the 200mL methylene dichloride, 31.85g(0.24mol) aluminum trichloride (anhydrous), afterwards by constant pressure funnel with 35.20g(0.2mol) 2,6-difluoro benzoyl chloride, 43.78g(0.22mol) 3-hydrocinnamyl bromine slowly splashes into successively and stirs in the lower three-necked flask, and ice bath reacted 4 hours; After the question response system is down to room temperature, reaction solution is poured in the aqueous hydrochloric acid of mass concentration 10%, organic phase is washed with sodium hydroxide solution, the saturated nacl aqueous solution of mass concentration 5%, get with the separating funnel separatory and to add anhydrous magnesium sulfate after the organic phase and dewater, filter, methylene dichloride is removed in underpressure distillation, product sherwood oil recrystallization, thereby obtain orange solids 2,6-two fluoro-4 '-(1-bromopropyl) benzophenone 50.90g, productive rate 75%.
Second step, in the 100mL three-necked flask of mechanical stirring oar is housed, add 3.1g(18.3mmol) carbazole, 5.2g(22.1mmol) the 4-iodanisol, 6.6g(45.8mmol) Red copper oxide, the N of 50mL, N '-N,N-DIMETHYLACETAMIDE, mechanical stirring is warming up to N, and N '-N,N-DIMETHYLACETAMIDE refluxes, back flow reaction 24 hours, reaction system is down to room temperature, filter, with the mixture discharging in methyl alcohol and volume of water are 1: 1 mixing solutions, filtration obtains white solid N-(4-p-methoxy-phenyl) the thick product 4.5g of carbazole, productive rate 89%.
With the N-(4-p-methoxy-phenyl) the thick product 5.3g(20.4mmol of carbazole), the 100mL methylene dichloride adds in the 250mL three-necked flask, mechanical stirring under the ice-water bath slowly splashes into 7.3g(29.1mmol) boron tribromide, continued ice-water bath 15 hours, add 20mL distilled water cancellation reaction, the organic phase washing, dry behind the separatory, revolve steaming, obtain white N-(4-hydroxy phenyl with the silica gel column chromatography purification) carbazole solid 4.6g, productive rate 92%
In the 3rd step, in the 100mL three-necked flask of mechanical stirring oar is housed, add 1g(3.9mmol) the N-(4-hydroxy phenyl) carbazole, 0.238g(4.2mmol) potassium hydroxide, 30mL ethanol passes into nitrogen, mechanical stirring, be heated to alcohol reflux, add 1.308g(3.9mmol after 30 minutes) 2,6-two fluoro-4 '-(1-bromopropyl) benzophenone, continue to reflux 10 hours, system is down to room temperature, and removal of solvent under reduced pressure is dissolved with methylene dichloride, filter, methylene dichloride is removed in decompression.Purify with silica gel column chromatography, obtain white, needle-shaped crystals 4-(2 with the sherwood oil recrystallization afterwards, the 6-difluoro benzoyl) hydrocinnamyl-4-(N-carbazyl) phenyl ether 1.40g, productive rate 70%.
Embodiment 2: the synthetic carbazole side group polymkeric substance (m=0.4) that contains
The two fluorine monomer 0.4140g(0.8mmol that embodiment 1 is made), 4,4 '-difluoro benzophenone 0.2618g(1.2mmol), 2,2 '-two (4-hydroxy phenyl)-HFC-236fa 0.6725g(2mmol), Anhydrous potassium carbonate 0.3036g(2.2mmol), tetramethylene sulfone 3.21mL(4.04g), toluene 2mL adds and is equipped with in the 25mL three-necked flask of water-taker, is warming up to refluxing toluene under the nitrogen atmosphere, band water is after 3 hours, steam except toluene, heat up, continue to react to system thickness (about 6 hours) under 200 ℃.The polymkeric substance crude product is poured into water, pulverizes, filter; Boil, filter with distilled water again, repeat 5～6 times; Then boil, filter with ethanol, repeat 5～6 times and obtain polymkeric substance.Polymkeric substance is at 343nm
-1Excitation wavelength under send blue-greenish colour fluorescence.Embodiment 3: the synthetic carbazole side group polymkeric substance (m=0.6) that contains
Method changes the difluoro monomeric charge that makes into 1.2mmol with embodiment 2, and 4,4 '-difluoro benzophenone feeds intake and changes 0.8mmol into, and in 8 hours reaction times, other conditions are constant.Then can obtain the polymkeric substance of m=0.6 ratio.
Embodiment 4: the synthetic carbazole side group polymkeric substance (m=0.4) that contains
Method is with embodiment 2, with 4,4 '-difluoro benzophenone changes 4 into, 4 '-difluorodiphenyl sulfone or 4,4 '-dichloro diphenyl sulfone is with 2,2 '-two (4-hydroxy phenyl)-HFC-236fa change 2 into, 2 '-two (4-hydroxy phenyl)-propane, mole number is constant, can obtain equally the similar polymkeric substance that contains the carbazole side group.
Claims (3)
1. two fluorine monomer 4-(2 that contain carbazole, the 6-difluoro benzoyl) hydrocinnamyl-4-(N-carbazyl) phenyl ether, its structural formula is as follows:
2. two fluorine monomer 4-(2 claimed in claim 1, the 6-difluoro benzoyl) hydrocinnamyl-4-(N-carbazyl) application of phenyl ether aspect the preparation structural formula polyarylether polymer that contains the carbazole side group as follows,
3. two fluorine monomer 4-(2 as claimed in claim 2, the 6-difluoro benzoyl) hydrocinnamyl-4-(N-carbazyl) phenyl ether contains the application aspect the polyarylether polymer of carbazole side group in preparation, it is characterized in that: with 4-(2, the 6-difluoro benzoyl) hydrocinnamyl-4-(N-carbazyl) phenyl ether, two halogen monomers, biphenol monomer is reactant, Anhydrous potassium carbonate is salt forming agent, tetramethylene sulfone is solvent, toluene or dimethylbenzene are azeotropy dehydrant, 4-(2, the 6-difluoro benzoyl) hydrocinnamyl-4-(N-carbazyl) phenyl ether, two halogen monomers, biphenol monomer, the mol ratio of Anhydrous potassium carbonate is m:1-m:1:1.1～1.2,0＜m≤1, the mass ratio of tetramethylene sulfone and all reactants is 2.5～3:1, and the volume ratio of tetramethylene sulfone and azeotropy dehydrant is 1.5: 1～5: 1; Above-mentioned reactant, salt forming agent, solvent, azeotropy dehydrant are heated to azeotropy dehydrant under nitrogen protection reflux, keep temperature to steam unnecessary azeotropy dehydrant after 2～3 hours, 210 ℃～220 ℃ continuation react sticky to reaction system, namely obtain the polymkeric substance crude product; The polymkeric substance crude product is poured into water, pulverizes, filter; Boil, filter with distilled water again, repeat 5～6 times; Then boil, filter with ethanol, repeat 5～6 times; Namely obtain containing the polyarylether polymer of carbazole side group after the oven dry; Wherein two halogen monomers are 4, and 4 '-difluoro benzophenone, 4,4 '-difluorodiphenyl sulfone or 4,4 '-dichloro diphenyl sulfone, biphenol monomer are 2,2 '-two (4-hydroxy phenyl)-HFC-236fa or 2,2 '-two (hydroxy phenyl) propane.
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| CN104860808A (en) * | 2015-06-03 | 2015-08-26 | 吉林大学 | Difluoro monomer containing tetraphenylethylene groups and application of difluoro monomer for preparing polyaryletherketone polymers |
| CN105130774A (en) * | 2015-09-09 | 2015-12-09 | 吉林大学 | Hexaphenylbenzene structure-containing difluo monomer, preparation method and application of difluo monomer in preparation of polyarylether |
| CN105440279A (en) * | 2016-01-21 | 2016-03-30 | 吉林大学 | Polyarylether containing 3, 6-bi(triphenyl) methyl-9-hydrogen carbazole side base and preparation method of polyarylether |
| CN105461613A (en) * | 2015-12-17 | 2016-04-06 | 吉林大学 | Carbazole derivative graft monomer, preparing method and application of carbazole derivative graft monomer to polyarylether polymer |
| CN105482119A (en) * | 2016-01-25 | 2016-04-13 | 吉林大学 | Difluoro monomer with photoelectric activity and application to preparation of polyarylether sulphone high-molecular polymer |
| CN110423343A (en) * | 2019-08-08 | 2019-11-08 | 吉林大学 | A kind of polyarylether polymer containing photoelectric functional group, preparation method and applications |
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Cited By (12)
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| CN103923311A (en) * | 2014-04-22 | 2014-07-16 | 吉林大学 | Carbazole-containing side chain type polyether sulfone, and preparation method and applications |
| CN103923311B (en) * | 2014-04-22 | 2016-02-03 | 吉林大学 | Side chain type polyether sulphone containing carbazole, preparation method and application |
| CN104860808A (en) * | 2015-06-03 | 2015-08-26 | 吉林大学 | Difluoro monomer containing tetraphenylethylene groups and application of difluoro monomer for preparing polyaryletherketone polymers |
| CN104860808B (en) * | 2015-06-03 | 2016-09-07 | 吉林大学 | Two fluorine monomers containing tetraphenyl ethylene group and be used for preparing poly aryl ether ketone polymer |
| CN105130774A (en) * | 2015-09-09 | 2015-12-09 | 吉林大学 | Hexaphenylbenzene structure-containing difluo monomer, preparation method and application of difluo monomer in preparation of polyarylether |
| CN105461613A (en) * | 2015-12-17 | 2016-04-06 | 吉林大学 | Carbazole derivative graft monomer, preparing method and application of carbazole derivative graft monomer to polyarylether polymer |
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| CN105440279A (en) * | 2016-01-21 | 2016-03-30 | 吉林大学 | Polyarylether containing 3, 6-bi(triphenyl) methyl-9-hydrogen carbazole side base and preparation method of polyarylether |
| CN105440279B (en) * | 2016-01-21 | 2017-06-09 | 吉林大学 | Polyarylether containing the hydrogen carbazole side base of 3,6 2 (triphenyl) methyl 9 and preparation method thereof |
| CN105482119A (en) * | 2016-01-25 | 2016-04-13 | 吉林大学 | Difluoro monomer with photoelectric activity and application to preparation of polyarylether sulphone high-molecular polymer |
| CN110423343A (en) * | 2019-08-08 | 2019-11-08 | 吉林大学 | A kind of polyarylether polymer containing photoelectric functional group, preparation method and applications |
| CN110423343B (en) * | 2019-08-08 | 2021-04-13 | 吉林大学 | Polyarylether polymer containing photoelectric functional group, preparation method and application thereof |
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