CN113896865A - Naphthalimide polymer semiconductor containing dopamine-derived side chain and preparation method thereof - Google Patents
Naphthalimide polymer semiconductor containing dopamine-derived side chain and preparation method thereof Download PDFInfo
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- CN113896865A CN113896865A CN202111229497.0A CN202111229497A CN113896865A CN 113896865 A CN113896865 A CN 113896865A CN 202111229497 A CN202111229497 A CN 202111229497A CN 113896865 A CN113896865 A CN 113896865A
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- naphthalimide
- dopamine
- polymer
- monomer
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- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 title claims abstract description 58
- 229920000642 polymer Polymers 0.000 title claims abstract description 57
- 229960003638 dopamine Drugs 0.000 title claims abstract description 28
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 239000004065 semiconductor Substances 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 239000000463 material Substances 0.000 claims abstract description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000178 monomer Substances 0.000 claims description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000003960 organic solvent Substances 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 8
- 229940126062 Compound A Drugs 0.000 claims description 8
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
- 239000012300 argon atmosphere Substances 0.000 claims description 6
- 239000003208 petroleum Substances 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- FEDCHNPLDKDTNS-UHFFFAOYSA-N 4,9-dibromoisochromeno[6,5,4-def]isochromene-1,3,6,8-tetraone Chemical compound O=C1OC(=O)C2=C(Br)C=C3C(=O)OC(=O)C4=C3C2=C1C=C4Br FEDCHNPLDKDTNS-UHFFFAOYSA-N 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- 238000000944 Soxhlet extraction Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 239000000741 silica gel Substances 0.000 claims description 5
- 229910002027 silica gel Inorganic materials 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 239000003446 ligand Substances 0.000 claims description 4
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical group [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 claims description 3
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- MBDFUYZNHQSWRD-UHFFFAOYSA-N tert-butyl n-[2-(3,4-dihydroxyphenyl)ethyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCC1=CC=C(O)C(O)=C1 MBDFUYZNHQSWRD-UHFFFAOYSA-N 0.000 claims description 3
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- CSHCPECZJIEGJF-UHFFFAOYSA-N methyltin Chemical compound [Sn]C CSHCPECZJIEGJF-UHFFFAOYSA-N 0.000 claims description 2
- 239000012046 mixed solvent Substances 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 238000001291 vacuum drying Methods 0.000 claims description 2
- 238000010521 absorption reaction Methods 0.000 abstract description 11
- 239000007787 solid Substances 0.000 abstract description 4
- 238000010276 construction Methods 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- 238000009825 accumulation Methods 0.000 abstract description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 229920000547 conjugated polymer Polymers 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002861 polymer material Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- HPJFXFRNEJHDFR-UHFFFAOYSA-N 22291-04-9 Chemical compound C1=CC(C(N(CCN(C)C)C2=O)=O)=C3C2=CC=C2C(=O)N(CCN(C)C)C(=O)C1=C32 HPJFXFRNEJHDFR-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920006254 polymer film Polymers 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- -1 tert-butyl 3, 4-dihydroxybenzene ethylcarbamate Chemical compound 0.000 description 2
- MYMSJFSOOQERIO-UHFFFAOYSA-N 1-bromodecane Chemical compound CCCCCCCCCCBr MYMSJFSOOQERIO-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- 101710134784 Agnoprotein Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102000015554 Dopamine receptor Human genes 0.000 description 1
- 108050004812 Dopamine receptor Proteins 0.000 description 1
- 241000237536 Mytilus edulis Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 238000006619 Stille reaction Methods 0.000 description 1
- 238000004847 absorption spectroscopy Methods 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000020638 mussel Nutrition 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 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
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- 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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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/20—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising organic-organic junctions, e.g. donor-acceptor junctions
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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- 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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- Y02E10/549—Organic PV cells
Abstract
The invention relates to a naphthalimide polymer semiconductor containing dopamine-derived side chains and a preparation method thereof. The naphthalimide polymer containing the dopamine-derived side chain has wide and strong absorption in a visible-near infrared region, is probably due to the increase of the content of the dopamine-derived side chain, improves the solid accumulation effect of polymer molecules, explores new derived side chains, is applied to the design of a novel naphthalimide construction unit, and has positive research significance. The side chain regulates and controls the polymer through the introduced dopamine derivative structural unit, and the flexible side chain can provide good solubility for the material and can be dissolved in solvents such as chloroform, chlorobenzene, toluene and the like, so that the material can be processed by a solution. Therefore, the invention has potential application prospect in organic solar cell devices as a donor material of a semiconductor active layer.
Description
Technical Field
The invention relates to a naphthalimide polymer semiconductor containing dopamine-derived side chains and a preparation method thereof, belonging to the field of organic solar cell materials.
Background
Solar cells are produced within one hundred years after the discovery of photovoltaic effect, so that silicon-based solar cells have entered many fields by virtue of over 20% of industrial photoelectric conversion efficiency, but inorganic silicon solar cells have the disadvantages of high production cost and ecological pollution which cannot be avoided in production. Compared with the organic solar cell, the organic solar cell has many advantages, the organic material has various types, and the structure can be regulated and controlled to optimize the properties of the organic solar cell, such as light absorption capacity, electrochemical energy level, carrier transmission capacity and the like, so that the photovoltaic performance is further optimized. Organic semiconductor materials, particularly polymeric semiconductor materials, can be used in Roll-to-Roll (Roll to Roll) printing of large area devices and in the fabrication of flexible devices.
Naphthalene Diimide (NDI) is an important building block for the construction of polymeric acceptor materials. Among them, the polymer N2200 which is most widely studied and has the best performance is used. N2200 is a high-performance N-type polymer semiconductor material, and has the characteristics of better compatibility, optical absorption complementarity, electrochemical energy level matching property and the like with some high-performance polymer donor materials. Methods for regulating the photoelectric property of the organic semiconductor material are numerous, and one of the methods is to regulate the photoelectric property of the receptor material through molecular side chain engineering. Dopamine, the best known small molecule of hundreds of neurotransmitters in the human brain, binds to dopamine receptors and operates many nerve channels in brain regions, constituting the brain's reward system. Dopamine has found applications in polymer systems because of its unique adhesion, hydrophilicity, biocompatibility, and good film-forming properties in water. In addition, the bisphenol group of dopamine is easy to introduce an auxiliary solubility alkyl chain to form a heterolytic side chain unit, thereby providing good solubility for a polymer material.
Disclosure of Invention
The invention aims to provide a naphthalimide polymer containing a dopamine-derived side chain and a preparation method thereof for the photoelectric conversion efficiency of an organic solar cell. The conjugated polymer has the advantages of simple preparation process, excellent photoelectric property, solution processing and the like, and has great application potential in the field of organic solar cell receptor materials.
The purpose of the invention is realized by the following technical scheme:
in a first aspect, the present invention relates to a naphthalimide polymer semiconductor containing dopamine-derived side chains and a preparation method thereof, wherein the conjugated polymer has a structural formula as follows:
In a second aspect, the present invention relates to a naphthalimide polymer semiconductor containing dopamine-derived side chains and a method for preparing the same, comprising the steps of:
(1) dissolving a monomer M1, a monomer M2, a methyl tin monomer M3, a catalyst and a ligand in an anhydrous organic solvent according to the molar parts; heating and polymerizing under argon atmosphere, purifying by Soxhlet extraction, and vacuum drying to obtain the dark purple naphthalimide polymer containing dopamine-derived side chains.
Preferably, in step (a), the monomer M1 has the following structural formula:
preferably, in step (a), the monomer M2 has the following structural formula:
preferably, in step (a), the monomer M3 has the following structural formula:
preferably, in step (a), the molar ratio of the monomer M1, the monomer M2 and the monomer M3 is 0.3: 0.7: 1.
preferably, in step (a), the anhydrous organic solvent is anhydrous toluene, anhydrous chlorobenzene or tetrahydrofuran.
Preferably, in step (a), the catalyst is tris (dibenzylideneacetone) dipalladium and the ligand is tris (o-methylphenyl) phosphorus.
Preferably, in the step (a), the heating is specifically: reacting for 48 hours at 100 ℃; the solvents adopted in sequence in the Soxhlet extraction are methanol, petroleum ether and chloroform.
(2) The monomer M1 in step (1) is prepared by the following steps:
a. adding 1 part of tert-butyl 3, 4-dihydroxyphenethylcarbamate, 2.4 parts of brominated hydrocarbon and 2.1 parts of potassium carbonate into an organic solvent according to molar parts, and reacting at 80 ℃ for 12 hours; after the reaction is finished, an intermediate compound A is obtained after extraction and drying, and the structural formula of the intermediate compound A is as follows:
b. adding 1 part of intermediate compound A into an organic solvent according to molar weight parts, and reacting for 4 hours at room temperature; after the reaction is finished, purifying and drying the intermediate compound B by a silica gel column to obtain an intermediate compound B, wherein the structural formula of the intermediate compound B is as follows:
c. adding 1 part of 2, 6-dibromonaphthalene-1, 4,5, 8-tetracarboxylic dianhydride (CAS:83204-68-6) and 2.5 parts of intermediate compound B into an organic solvent according to molar parts, and reacting at 120 ℃ for 12 hours; after the reaction is finished, the monomer M1 is obtained after silica gel column extraction and drying.
Preferably, in step a, the organic solvent is N, N-dimethylformamide, and the brominated hydrocarbon is a C1-C30 brominated alkane.
Preferably, in step b, the organic solvent is a mixed solvent of dichloromethane and trifluoroacetic acid.
Preferably, in step c, the organic solvent is acetic acid.
The invention has the following remarkable advantages:
(1) the naphthalimide n-type polymer containing dopamine derived side chains synthesized by the invention adopts classical Stille coupling polycondensation to synthesize a series of polymers with ultrahigh number average molecular weight.
(2) The raw materials used in the invention are all easily available and low in price, and the synthesis process is simple and mature, and overall, the synthesis cost is low.
(3) The main chain of the conjugated polymer prepared by the invention has a large pi conjugated structure of a rigid plane, and the introduction of the dopamine side chain forms a heterosis side chain unit, so that good solubility is provided for a polymer material, and the polymer material has the potential of being used as an organic field solar cell device.
(4) The polymer of the invention has a large light absorption range and good chemical stability and thermal stability.
Drawings
FIG. 1 is a scheme showing the synthesis of polymer P in example 1 of the present invention.
FIG. 2 shows the NMR spectrum of monomer M1 in example 1 of the present invention.
FIG. 3 shows the NMR carbon spectrum of monomer M1 in example 1 of the present invention.
FIG. 4 shows the NMR spectrum of a polymer P in example 1 of the present invention.
FIG. 5 shows a film UV-Vis spectrum of the polymer P in example 2 according to the invention.
FIG. 6 is a CV curve of polymer P in example 2 of the present invention.
FIG. 7 is a thermogravimetric plot of polymer P in example 2 of the present invention.
Detailed Description
The present invention will be described in detail with reference to specific examples. The following examples will assist those skilled in the art in further understanding the invention, but are not intended to limit the invention in any way. It should be noted that variations and modifications can be made by persons skilled in the art without departing from the spirit of the invention. All falling within the scope of the present invention.
Example 1 preparation of a Naphthylimide Polymer semiconductor containing dopamine-derived side chains
This example provides 1 kind of naphthalimide polymer containing dopamine derivative side chain, whose structural formula is shown in the following figure, and its synthetic route is shown in fig. 1.
1.1 preparation of monomer M1
The preparation of the monomer M1 specifically comprises the following steps:
(a) synthesis of intermediate Compound A
The structural formula of the intermediate compound A is
Under an argon atmosphere, tert-butyl 3, 4-dihydroxybenzene ethylcarbamate (14.84mmol), decyl bromide (35.62mmol), potassium carbonate (31.17mmol) and N, N-dimethylformamide (20mL) were added to a two-necked flask. After the reaction mixture was stirred at 80 ℃ for 12 hours, it was cooled to room temperature, extracted with ethyl acetate, and the resulting organic phase was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Methanol was added and the resulting precipitate was collected by filtration and dried under vacuum to give intermediate compound a as a white solid (yield 30%).1H NMR(600MHz,CDCl3):δ6.81(d,J＝8.0Hz,1H),6.72–6.67(m,2H),4.52(s,1H),3.96(td,J＝6.7,4.2Hz,4H),3.34(d,J＝6.3Hz,2H),2.71(t,J＝6.8Hz,2H),1.84–1.75(m,4H),1.51–1.38(m,12H),1.40–1.09(m,28H),0.91–0.86(m,6H).
Among these references for the synthesis of tert-butyl 3, 4-dihydroxyphenethylcarbamate: maerten C, Garnier T, Lupatelli P, et al, Morphogen electrochemical sampled Self-Construction of Polymeric Films Based on Mussel-induced Chemistry [ J ]. Langmuir the Acs Journal of surfaces & Colloids 2015: 13385.
(b) Synthesis of intermediate Compound B
The structural formula of the intermediate compound B is
Under an argon atmosphere, intermediate compound a (4.8mmol) and a mixture of compounds represented by volume ratio 6: a mixture of dichloromethane and trifluoroacetic acid (7mL) in a 1 ratio configuration was added to the two-necked flask. The reaction mixture was reacted at room temperature for 4 hours, the reaction mixture was quenched with 20mL of a 5% aqueous solution of sodium hydroxide, extracted with dichloromethane, and the resulting organic phase was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. Purification through flash silica gel column (eluent petroleum ether: ethyl acetate 7:1 by volume) afforded intermediate compound B as a white solid after drying in vacuo (83% yield).1H NMR(600MHz,CDCl3):δ6.81(d,J＝8.1Hz,1H),6.74–6.69(m,2H),3.97(dt,J＝8.8,6.7Hz,4H),2.94(t,J＝6.8Hz,2H),2.68(t,J＝6.8Hz,2H),1.82–1.77(m,4H),1.49–1.43(m,4H),1.34–1.21(m,24H),0.90–0.86(m,6H).
(c) Synthesis of monomer M1
The monomer M1 has a structural formula
Under an argon atmosphere, 2, 6-dibromonaphthalene-1, 4,5, 8-tetracarboxylic dianhydride (CAS:83204-68-6) (1.57mmol), intermediate compound B (3.94mmol), and anhydrous acetic acid (25ml) were added to a two-necked flask. Reacting at 120 deg.C for 12 hr, cooling the reactant to room temperature, adding100ml of cold water was added. The precipitate was collected by filtration and washed with methanol to give the crude product. Purification by column chromatography (eluent dichloromethane: petroleum ether 5:1 by volume) dissolved in dichloromethane, added the appropriate amount of petroleum ether, frozen (-18 ℃) and filtered gave monomer M1 as a white solid (10.1%).1H NMR(600MHz,CDCl3):δ9.00(s,2H),6.88(d,J＝2.0Hz,2H),6.85(dd,J＝8.1,2.0Hz,2H),6.81(d,J＝8.1Hz,2H),4.42–4.37(m,4H),3.98(dt,J＝18.9,6.7Hz,8H),2.98–2.94(m,4H),1.80(ddt,J＝14.7,12.6,6.3Hz,8H),1.49–1.43(m,8H),1.39–1.23(m,48H),0.91–0.85(m,12H).13C NMR(101MHz,Chloroform-d)δ160.67,147.98,139.07,130.63,121.22,114.72,114.16,69.45,69.34,42.94,33.58,31.95,29.70,29.67,29.64,29.62,29.50,29.48,29.41,29.39,26.10,26.07,22.72,14.16.
1.2 Synthesis of Polymer P
The structural formula of the polymer P is
The invention optimizes the reaction condition of the conjugated polymer for many times, firstly optimizes the solvent used for polymerization, and selects o-xylene, 2-methyltetrahydrofuran and the like as the solvent. In addition, the amount of catalyst is also optimized. The final optimization results were as follows:
under the argon atmosphere, adding monomer M1(0.06mmol), monomer M2(0.14mmol), monomer M3(0.2mmol) and anhydrous toluene (0.4mL) into a pressure-resistant tube, stirring and dissolving, adding tris (dibenzylideneacetone) dipalladium (0.002mmol) and tris (o-methylphenyl) phosphine (0.008mmol), deoxidizing on the liquid for 10min, and sealing the tube. Reacting at 100 ℃ for 48 hours, cooling the reactant to room temperature, adding methanol, and filtering under reduced pressure to obtain a crude product. The crude product was subjected to soxhlet extraction with methanol, petroleum ether and chloroform in this order, and chloroform-extracted fractions were collected, the solvent was removed under reduced pressure, methanol was added to obtain a precipitate, which was filtered and vacuum-dried to obtain the objective polymer P (99.8%).1H NMR(400MHz,Chloroform-d)δ8.83(s,1H),8.51(s,1H),7.34(s,4H),6.82(s,1.8H),4.38(s,1.2H),4.13(s,2.8H),3.96(s,2.4H),2.95(s,1.2H),1.25(s,64H),0.85(s,12H).Mn＝127.6kDa，Mw＝345.6kDa，PDI＝2.70。
Wherein monomer M2 was purchased from Aladdin (CAS: 1100243-35-3); monomer M3 was purchased from Aladdin (CAS: 86134-26-1).
Example 2 ultraviolet absorption Spectroscopy, electrochemical Properties and thermal stability of Polymer P
2.1 ultraviolet absorption Spectrum of Polymer P
FIG. 5 shows the UV absorption spectra of polymer P in chlorobenzene solutions and films. Comparing the film absorption and solution absorption properties, it can be seen that the absorption peaks of both do not show significant broadening, which is associated with good molecular stacking of the material. The polymer film absorbs in the long wavelength absorption range of 450-850 nm, and has stronger absorption characteristic compared with solution absorption. The results show that the accumulation of molecules in each polymer film is stronger, and the charge transfer effect in the molecules is more obvious. The polymer P has high absorption strength in the visible light region and wide absorption peak, which is probably related to the introduction of the most dopamine-derived side chains. Initial absorption wavelength (λ onset) of polymer P filmfilm) At around 863nm, the Eg can be calculated from thisfilm＝1.44eV(Egfilm＝1240/λonsetfilmeV), indicating that the polymer is a narrow bandgap polymer.
2.2 electrochemical Properties of Polymer P
Ag/AgNO with platinum sheet as working electrode and platinum wire as counter electrode3The electrode was the reference electrode, 0.1M tetrabutylammonium hexafluorophosphate acetonitrile solution was the electrolyte, ferrocene was the calibration, the scan rate was 60mV/s, and the polymer was tested on a platinum sheet. Figure 6 shows the electrochemical curves of the polymers obtained from the tests. The energy level and the energy gap can be calculated according to the formula: eLUMO＝﹣(Ere onset+4.33)eV，Eg＝ELUMO－EHOMOIn which Ere onsetIs the initial reduction potential.
As can be seen from FIG. 6, E of Polymer Pre onsetIs-0.54 eV. According to a given formula, the calculation of the convergenceThe LUMO level of compound P was-3.79 eV. It can act as an acceptor material from the point of view of its energy level.
2.3 thermal stability of Polymer P
FIG. 7 shows that the thermal decomposition temperature of the polymer P is above 400 ℃ and shows that the polymer P has good thermal stability.
2.4 solubility of Polymer P
The polymer P has better solubility in solvents such as chloroform, chlorobenzene and the like at room temperature, and guarantees the treatment of soluble solution of the polymer P.
The above description is only a preferred embodiment of the present invention, and all equivalent changes and modifications made in accordance with the claims of the present invention should be covered by the present invention.
Claims (10)
1. A naphthalimide polymer containing dopamine-derived side chains, characterized in that the structural formula of the polymer is as follows:
2. The method of preparing a naphthalimide polymer having dopamine-derived side chains according to claim 1, comprising the steps of:
dissolving a monomer M1, a monomer M2, a methyl tin monomer M3, a catalyst and a ligand in an anhydrous organic solvent; heating and polymerizing under argon atmosphere, purifying by Soxhlet extraction, and vacuum drying to obtain the dark purple naphthalimide polymer containing dopamine-derived side chains.
3. The method for preparing a naphthalimide polymer containing dopamine-derived side chains according to claim 2, wherein the monomer M1 has the following structural formula:
4. The preparation method of the naphthalimide polymer containing the dopamine-derived side chain according to claim 3, wherein the monomer M1 is prepared by the following steps:
a. adding 1 part of tert-butyl 3, 4-dihydroxyphenethylcarbamate, 2.4 parts of brominated hydrocarbon and 2.1 parts of potassium carbonate into an organic solvent according to molar parts, and reacting at 80 ℃ for 12 hours; after the reaction is finished, an intermediate compound A is obtained after extraction and drying, and the structural formula of the intermediate compound A is as follows:
b. Adding 1 part of intermediate compound A into an organic solvent according to molar weight parts, and reacting for 4 hours at room temperature; after the reaction is finished, purifying and drying the intermediate compound B by a silica gel column to obtain an intermediate compound B, wherein the structural formula of the intermediate compound B is as follows:
c. Adding 1 part of 2, 6-dibromonaphthalene-1, 4,5, 8-tetracarboxylic dianhydride and 2.5 parts of intermediate compound B into an organic solvent according to molar parts, and reacting at 120 ℃ for 12 hours; after the reaction is finished, the monomer M1 is obtained after silica gel column extraction and drying.
5. The method for preparing the dopamine-derived pendant-containing naphthalimide polymer of claim 4, wherein the organic solvent of step a is N, N-dimethylformamide, and the brominated hydrocarbon is a C1-C30 brominated alkane; the organic solvent in the step b is a mixed solvent of dichloromethane and trifluoroacetic acid; the organic solvent in the step c is acetic acid.
6. The method for preparing a naphthalimide polymer containing dopamine-derived side chains according to claim 2, wherein the monomer M2 has the following structural formula:
7. The method for preparing a naphthalimide polymer containing dopamine-derived side chains according to claim 2, wherein the monomer M3 has the following structural formula:
8. the method of claim 2, wherein the catalyst is tris (dibenzylideneacetone) dipalladium and the ligand is tris (o-methylphenyl) phosphorus; the anhydrous organic solvent is anhydrous toluene, anhydrous chlorobenzene or tetrahydrofuran; the molar ratio of the monomer M1 to the monomer M2 to the monomer M3 is 0.3: 0.7: 1.
9. the method for preparing a naphthalimide polymer containing dopamine-derived side chains according to claim 2, wherein the heating is specifically: reacting for 48 hours at 100 ℃; the solvents adopted in sequence in the Soxhlet extraction are methanol, petroleum ether and chloroform.
10. The application of the naphthalimide polymer semiconductor containing the dopamine-derived side chain according to claim 1, wherein the naphthalimide polymer containing the dopamine-derived side chain is applied as a donor material of a semiconductor active layer in an organic solar cell device.
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