CN115572372A - Pi-conjugated donor-acceptor-based polymer material with similar structure as well as preparation method and application thereof - Google Patents
Pi-conjugated donor-acceptor-based polymer material with similar structure as well as preparation method and application thereof Download PDFInfo
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- CN115572372A CN115572372A CN202211246298.5A CN202211246298A CN115572372A CN 115572372 A CN115572372 A CN 115572372A CN 202211246298 A CN202211246298 A CN 202211246298A CN 115572372 A CN115572372 A CN 115572372A
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- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 239000000463 material Substances 0.000 claims abstract description 19
- 230000005526 G1 to G0 transition Effects 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 14
- -1 5-bromothiophen-2-yl Chemical group 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 10
- 238000005406 washing Methods 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 238000013375 chromatographic separation Methods 0.000 claims description 6
- 239000012043 crude product Substances 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- UKHQRARQNZOXRL-UHFFFAOYSA-N trimethyltin Chemical compound C[SnH](C)C UKHQRARQNZOXRL-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
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- 238000000926 separation method Methods 0.000 description 13
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- 239000000126 substance Substances 0.000 description 6
- NUKZAGXMHTUAFE-UHFFFAOYSA-N methyl hexanoate Chemical compound CCCCCC(=O)OC NUKZAGXMHTUAFE-UHFFFAOYSA-N 0.000 description 4
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 4
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- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 3
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- 239000012159 carrier gas Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
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- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 2
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- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
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- 238000009835 boiling Methods 0.000 description 2
- 229920000547 conjugated polymer Polymers 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
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- YCOZIPAWZNQLMR-UHFFFAOYSA-N pentadecane Chemical compound CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 2
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- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- XKEFYDZQGKAQCN-UHFFFAOYSA-N 1,3,5-trichlorobenzene Chemical compound ClC1=CC(Cl)=CC(Cl)=C1 XKEFYDZQGKAQCN-UHFFFAOYSA-N 0.000 description 1
- FAHUKNBUIVOJJR-UHFFFAOYSA-N 1-(4-fluorophenyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine Chemical compound C1=CC(F)=CC=C1C1C2=CC=CN2CCN1 FAHUKNBUIVOJJR-UHFFFAOYSA-N 0.000 description 1
- KMAQZIILEGKYQZ-UHFFFAOYSA-N 1-chloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1 KMAQZIILEGKYQZ-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical class CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 1
- 241000402754 Erythranthe moschata Species 0.000 description 1
- 239000005640 Methyl decanoate Substances 0.000 description 1
- 239000005641 Methyl octanoate Substances 0.000 description 1
- GLZPCOQZEFWAFX-JXMROGBWSA-N Nerol Natural products CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 1
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- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
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- RECUKUPTGUEGMW-UHFFFAOYSA-N carvacrol Chemical compound CC(C)C1=CC=C(C)C(O)=C1 RECUKUPTGUEGMW-UHFFFAOYSA-N 0.000 description 1
- HHTWOMMSBMNRKP-UHFFFAOYSA-N carvacrol Natural products CC(=C)C1=CC=C(C)C(O)=C1 HHTWOMMSBMNRKP-UHFFFAOYSA-N 0.000 description 1
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- 150000001875 compounds Chemical class 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical compound CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
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- WYXXLXHHWYNKJF-UHFFFAOYSA-N isocarvacrol Natural products CC(C)C1=CC=C(O)C(C)=C1 WYXXLXHHWYNKJF-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
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- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
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- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
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- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
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- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
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- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
- C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
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Abstract
The invention relates to a method based onπA conjugated donor-acceptor (D-A) polymer material with a similar structure, a preparation method and application thereof, belonging to the technical field of functional materials. The structural formula of the polymer material with the similar structure is as follows:
. The invention is based onπ‑The conjugated D-A structural material used as a GC stationary phase shows high selectivity on components with similar properties, and can efficiently separate various component mixtures with different polarities, particularly various isomer mixtures which are difficult to separate. The D-A functional material has stable structure, good thermal stability, good solubility and film forming property in an organic solvent, and is easy to prepare a chromatographic column with high column efficiency. The invention is as describedπ‑Raw materials adopted for preparing conjugated D-A structural materialLow cost, simple synthesis method and high product yield.
Description
Technical Field
The invention relates to a method based onπA conjugated donor-acceptor similar structure polymer material, a preparation method and application thereof, belonging to the technical field of functional materials.
Background
GC has high separation, qualitative and quantitative analytical properties, and has been widely used for analytical determination of complex sample components in various fields. Among them, the core and key to chromatographic separation analysis is the selectivity and separation performance of the chromatographic stationary phase.
At present, a high-efficiency organic solar cell generally adopts a conjugated polymer with a D-A structure, and the polymer shows good thermal stability and flatness, so that the accumulation of molecules is promoted, the charge transmission between the molecules is effectively promoted, and the polymer can be used as an excellent device and is widely applied to the organic solar cell. As can be seen from the molecular characteristics, on the one hand, PBDB-T type polymers have good chemical and thermal stability. At present, no conjugated polymer with a D-A structure has been reported in chromatographic separation.
Disclosure of Invention
In view of the above, the present invention provides a method for producing a liquid crystal display deviceπWhen the conjugated donor-acceptor (D-A) polymer material with the similar structure is used as a chromatographic stationary phase for gas chromatographic analysis and determination, the functional material shows high selectivity and separation capability for various isomers with similar components and properties, and a chromatographic column prepared by the functional material has good thermal stability, repeatability and reproducibility, and has good application prospect in the aspect of gas chromatographic separation. In addition, the raw materials for preparing the functional material have low cost, the synthesis method is simple, and the product yield is high.
The invention also provides a preparation method of the polymer material with the similar structure.
Another object of the present invention is to provide the use of the above-mentioned structural polymer materials.
The purpose of the invention is realized by the following technical scheme:
the invention provides a method based onπ-a conjugated donor-acceptor like structure polymer material having the formula:
and n is 1-20.
The invention also provides a preparation method of the structure-like polymer material, which comprises the following steps:
(1) Accurately weighing (4, 8-bis (5- (2-ethylhexyl) thiophen-2-yl benzo [1,2-b:4,5-b '] dithiophene-2, 6-diyl) bis (trimethylstannane), 1, 3-bis (5-bromothiophen-2-yl) -5, 7-bis (2-ethylhexyl) -4H and 8H-benzo [1,2-c:4,5-c' ] dithiophene-4, 8-dione and tetratriphenylphosphine palladium respectively, sequentially adding into a eggplant-shaped bottle, dissolving with toluene, ultrasonically shaking, and heating the mixed solution for reaction to obtain a reaction solution;
(2) After the reaction is finished, dripping the reaction solution into methanol, separating out a solid, carrying out suction filtration and drying, then putting the crude product into a Soxhlet extractor, carrying out reflux washing by using methanol, then carrying out reflux washing by using n-hexane, finally dissolving by using chloroform, carrying out rotary evaporation to concentrate the concentration of the sample, then dripping methanol, and slowly separating out the solid to obtain the PBDB-T material.
Further, in the step (1), the mass ratio of the (4, 8-bis (5- (2-ethylhexyl) thiophen-2-ylbenzo [1,2-b:4,5-b '] dithiophene-2, 6-diyl) bis (trimethylstannane), 1, 3-bis (5-bromothiophen-2-yl) -5, 7-bis (2-ethylhexyl) -4H, and 8H-benzo [1,2-c:4,5-c' ] dithiophene-4, 8-dione to palladium tetratriphenylphosphine is from 0.09 to 0.1.
Further, in the step (1), the reaction mixture of the 8H-benzo [1,2-c: the concentrations of 4,5-c' ] dithiophene-4, 8-dione and palladium tetratriphenylphosphine in toluene were 0.6 to 1.2mg/mL.
Further, in the step (1), the time of the ultrasonic oscillation is 10 to 15 min; the reaction is carried out at the temperature of 100 to 120 ℃ for 10 to 15 hours.
Further, in the step (2), the time for refluxing and washing the methanol is 5 to 10 hours; the time for the reflux flushing of the n-hexane is 6 to 10 hours.
The invention also provides application of the polymer material with the structure as a stationary phase for gas chromatographic separation in gas chromatographic analysis.
The material molecule provided by the invention has better planarity, good planarity and a special accumulation mode, so that PBDB-T molecules can form effective accumulation in a tube, and can effectively perform selective adsorption when mixed gas passes through. In addition, PBDB-T is oneπSemiconductor material of the type which has, in itself, electron-donating properties, which for some haveMolecules with strongly electron-withdrawing groups should be significantly selective to allow efficient separation of analytes of a certain type.
The invention has the beneficial effects that:
(1) The invention is based onπ-The conjugated D-A structural material is used as a GC stationary phase, shows high selectivity to components with similar properties, and can efficiently separate various component mixtures with different polarities, particularly various isomer mixtures which are difficult to separate.
(2) The D-A functional material has stable structure, good thermal stability, good solubility and film forming property in an organic solvent, and is easy to prepare a chromatographic column with high column efficiency.
(3) The invention is as describedπ-The conjugated D-A structural material has the advantages of low cost of raw materials, simple synthesis method and high product yield.
Drawings
FIG. 1 is a GPC chart of PBDB-T material prepared.
FIG. 2 is a chromatogram of a mixed sample of alkane and ester mixture separated by using PBDB-T as a stationary phase; wherein substances corresponding to No. 1 to No. 14 chromatographic peaks are as follows in sequence: nonane, methyl hexanoate, decane, methyl heptanoate, undecane, methyl octanoate, dodecane, methyl nonanoate, tridecane, methyl decanoate, tetradecane, methyl undecanoate, pentadecane and methyl dodecanoate.
FIG. 3 is a separation chromatogram of a mixture of prepared PBDB-T as a fixed relative phenolic isomer; wherein substances corresponding to No. 1 to No. 9 chromatographic peaks are as follows in sequence: phenol, 2, 6-xylenol, o-cresol, p-cresol, m-cresol, 2, 5-xylenol, 2, 3-xylenol, 3, 5-xylenol, and 3, 4-xylenol.
FIG. 4 is a chromatogram of separated chloronitrobenzene isomers with PBDB-T as the stationary phase; wherein substances corresponding to chromatographic peaks No. 1 to No. 3 in the figure are as follows in sequence: m-chloronitrobenzene, p-chloronitrobenzene, and o-chloronitrobenzene.
FIG. 5 is a chromatogram for separating PBDB-T from a mixture of isomers of trimethylbenzene and trichlorobenzene fixed relative to aromatic species; wherein substances corresponding to chromatographic peaks of 1 to 6 are as follows in sequence: 1,3, 5-trimethylbenzene, 1,2, 4-trimethylbenzene, 1,2, 3-trimethylbenzene, 1,3, 5-trichlorobenzene, 1,2, 4-trichlorobenzene and 1,2, 3-trichlorobenzene.
FIG. 6 is a chromatogram of separated neryl geraniol muscariol isomer using PBDB-T prepared as stationary phase; wherein substances corresponding to chromatographic peaks No. 1 to No. 4 in the figure are as follows in sequence: nerol, geraniol, thymol and carvacrol.
Detailed Description
The invention is further illustrated with reference to the following figures and detailed description, wherein the processes are conventional unless otherwise specified, and the starting materials are commercially available from a disclosure unless otherwise specified.
Using the preparation prepared in the examplesπThe preparation method of the capillary chromatographic column by using the conjugated D-A material as the stationary phase comprises the following steps:
taking a quartz capillary column with a certain length (5 m to 30 m) and an inner diameter of 0.25 mm, washing the quartz capillary column with dichloromethane for 20 min, and then aging the quartz capillary column at 260 ℃ for 3 h under a nitrogen atmosphere; then, under the pressure of nitrogen, continuously introducing a saturated solution of sodium chloride and methanol into the capillary column until the effluent liquid is turbid, discharging the solution in the capillary column, and keeping the temperature of the capillary column at 200 ℃ for 3 hours under the nitrogen; the PBDB-T material prepared in the embodiment is dissolved in dichloromethane to be prepared into a material with proper concentration (0.10 mg/mL-0.50 mg/mL,w/v) After 5 min of ultrasonic treatment, the stationary phase solution is led into a capillary column, one end of the capillary column is sealed, the other end of the capillary column is connected with a vacuum pump, the solvent is evaporated in a water bath at 40 ℃, the stationary phase is deposited on the inner wall of the capillary column, and then the capillary column is aged under the following conditions: the temperature is kept for 30 min at 40 ℃, then the temperature is increased to 180 ℃ at the heating rate of 1 ℃/min and kept for 6 h, and the aged capillary column is the chromatographic column which can be used for GC analysis and determination.
Example 1
The specific preparation steps of the D-A compound PBDB-T are as follows:
(1) Accurately weighed 90.46 mg of (4, 8-bis (5- (2-ethylhexyl) thiophen-2-ylbenzo [1,2-b:4,5-b '] dithiophene-2, 6-diyl) bis (trimethylstannane), 0.0766g of 1, 3-bis (5-bromothiophen-2-yl) -5, 7-bis (2-ethylhexyl) -4H and 6 mg of 8H-benzo [1,2-c:4,5-c' ] dithiophene-4, 8-dione and palladium tetratriphenylphosphine were sequentially added to a 10 mL single-necked eggplant-shaped bottle, dissolved with 6 mL of toluene, ultrasonically shaken for 10 min, the gas in the mixed solution was discharged, and the mixed solution was heated to 110 ℃ for 12 hours.
(2) After the reaction is finished, dripping the solution into 40 mL of methanol, separating out a solid, carrying out suction filtration and drying, then putting the crude product into a Soxhlet extractor, firstly carrying out reflux washing on the crude product for 6 h by using methanol, then carrying out reflux washing on the crude product for 6 h by using n-hexane, finally dissolving the crude product by using chloroform, and carrying out rotary evaporation to concentrate the concentration of the sample. Then, 40 mL of methanol was added dropwise to precipitate a solid slowly (yield: 71%). Determined by GPC, m.w. = 7148, molecular weight distribution PDI = 1.16, see fig. 1 for GPC diagram. M.w. = 7148 was chosen because of the lower solubility of higher molecular weight pi-conjugated materials in DCM.
The prepared PBDB-T is dissolved in dichloromethane to prepare a stationary phase solution with the concentration of 1.0 mg/mL, and a quartz capillary chromatographic column (5 m) is prepared. The combined sample is used for separation, and the separation result is shown in figures 2 to 6 in detail; wherein, the chromatographic parameters of the No. 2 to No. 6 are as follows in sequence: nitrogen is used as carrier gas, and the flow rate of the carrier gas is as follows: 1 mL/min, wherein the flow rates are the flow rate and the split ratio of carrier gas to flow rate 50; FIG. 2 is a temperature programming of 60 deg.C (2 min) -10 deg.C/min-150 deg.C; FIG. 3 shows a temperature program 90 o C (1 min)-5 o C /min-150 o C; FIG. 4 is a temperature program 40 o C -5 o C /min-150 o C; FIG. 5 shows temperature program 70 o C（2 min）-10 o C /min-150 o C; FIG. 6 shows a constant temperature 80 o C. As can be seen from FIGS. 2 to 6, the chromatographic peak shape obtained by gas chromatography separation using PBDB-T as the stationary phase has good symmetry and shows good chromatographic separation performance. Each pair of adjacent alkanes and fatty esters in FIG. 2 have very close boiling points, e.g., nonane (150.8 ℃) and methyl hexanoate (149.8 ℃) have boiling points that differ by only 1 ℃ which presents a challenge to the separation performance of the column. The PBDB-T chromatographic column achieves baseline separation for each pair of adjacent alkane and ester components; the analytes in FIG. 3 are cresol and xylenol isomer mixtures, their separations anddetection is very important for the field as an important raw material in the fields of medicine and dyes. The phenol isomers have higher polarity, are easy to adsorb on a chromatographic column, cause tailing or signal reduction, but have symmetrical peak shapes and good separation degree on the stationary phase; in FIGS. 4 to 6 we have selected different polar isomers to further investigate the column, these isomers encompassing medium polarity chloronitrobenzene, non-polar trimethylbenzene and mixtures of medium polarity trichlorobenzenes and polar nergeraniol musk carvacrol isomers. From the figure we can see that both non-polar and polar isomers give good separation on the column.
In summary, the above description is only a preferred embodiment of the present invention, and is not intended to limit the scope of the present invention. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (7)
1. Based onπ-a conjugated donor-acceptor structure-like polymer material, wherein the structure of the structure-like polymer material is:
and n is 1-20.
2. A method of making the structure-like polymeric material of claim 1, comprising the steps of:
(1) Accurately weighing (4, 8-bis (5- (2-ethylhexyl) thiophen-2-yl benzo [1,2-b:4,5-b '] dithiophene-2, 6-diyl) bis (trimethylstannane), 1, 3-bis (5-bromothiophen-2-yl) -5, 7-bis (2-ethylhexyl) -4H and 8H-benzo [1,2-c:4,5-c' ] dithiophene-4, 8-dione and tetratriphenylphosphine palladium respectively, sequentially adding into a eggplant-shaped bottle, dissolving with toluene, ultrasonically shaking, and heating the mixed solution for reaction to obtain a reaction solution;
(2) After the reaction is finished, dripping the reaction solution into methanol, separating out a solid, carrying out suction filtration and drying, then putting the crude product into a Soxhlet extractor, carrying out reflux washing by using methanol, then carrying out reflux washing by using n-hexane, finally dissolving by using chloroform, carrying out rotary evaporation to concentrate the concentration of the sample, then dripping methanol, and slowly separating out the solid to obtain the PBDB-T material.
3. The production method according to claim 2, characterized in that, in step (1), the mass ratio of the (4, 8-bis (5- (2-ethylhexyl) thiophen-2-ylbenzo [1,2-b:4,5-b '] dithiophene-2, 6-diyl) bis (trimethylstannane), 1, 3-bis (5-bromothiophen-2-yl) -5, 7-bis (2-ethylhexyl) -4H, and 8H-benzo [1,2-c:4,5-c' ] dithiophene-4, 8-dione to palladium tetratriphenylphosphine is from 0.09 to 0.1.
4. The production method according to claim 2 or 3, wherein in the step (1), the ratio of the 8H-benzo [1,2-c: the concentrations of 4,5-c' ] dithiophene-4, 8-dione and palladium tetratriphenylphosphine in toluene were 0.6 to 1.2mg/mL.
5. The method according to any one of claims 2 to 4, wherein in the step (1), the time of the ultrasonic oscillation is 10 to 15 min; the reaction is carried out at 100 to 120 ℃ for 10 to 15 hours.
6. The preparation method according to claim 2, wherein in the step (2), the time for the methanol reflux washing is 5 to 10 hours; the time for the reflux flushing of the n-hexane is 6 to 10 hours.
7. Use of the structurally analogous polymeric material of claim 1 as a stationary phase for gas chromatographic separations in gas chromatographic analysis.
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