CN113817142A - Fluorenylcyanoindanone conjugated polymer and preparation method thereof - Google Patents
Fluorenylcyanoindanone conjugated polymer and preparation method thereof Download PDFInfo
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- CN113817142A CN113817142A CN202111192362.1A CN202111192362A CN113817142A CN 113817142 A CN113817142 A CN 113817142A CN 202111192362 A CN202111192362 A CN 202111192362A CN 113817142 A CN113817142 A CN 113817142A
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- fluorenyl
- cyano
- conjugated polymer
- indanone
- monomer
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- 229920000547 conjugated polymer Polymers 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title abstract description 12
- -1 fluorenyl cyano indanone Chemical compound 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 28
- 239000000178 monomer Substances 0.000 claims description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- LYRCQNDYYRPFMF-UHFFFAOYSA-N trimethyltin Chemical compound C[Sn](C)C LYRCQNDYYRPFMF-UHFFFAOYSA-N 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 238000000944 Soxhlet extraction Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000003446 ligand Substances 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 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 2
- 238000006000 Knoevenagel condensation reaction Methods 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 238000007334 copolymerization reaction Methods 0.000 claims description 2
- 239000012046 mixed solvent Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 16
- 230000002349 favourable effect Effects 0.000 abstract description 3
- 230000003287 optical effect Effects 0.000 abstract description 2
- 230000001737 promoting effect Effects 0.000 abstract description 2
- 229920000642 polymer Polymers 0.000 description 57
- 239000010408 film Substances 0.000 description 15
- 238000005227 gel permeation chromatography Methods 0.000 description 12
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
- 239000004065 semiconductor Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 238000004770 highest occupied molecular orbital Methods 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 6
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- MMPZGOUETMIJAS-UHFFFAOYSA-N 2-(9,9-dihexyl-7-thiophen-2-ylfluoren-2-yl)thiophene Chemical compound C1=C2C(CCCCCC)(CCCCCC)C3=CC(C=4SC=CC=4)=CC=C3C2=CC=C1C1=CC=CS1 MMPZGOUETMIJAS-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- 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 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000004847 absorption spectroscopy Methods 0.000 description 2
- QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 238000002484 cyclic voltammetry Methods 0.000 description 2
- 238000006392 deoxygenation reaction Methods 0.000 description 2
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical class Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- OVISMSJCKCDOPU-UHFFFAOYSA-N 1,6-dichlorohexane Chemical compound ClCCCCCCCl OVISMSJCKCDOPU-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- FUKLRRTYUZRVBS-UHFFFAOYSA-N 3-oxo-1,2-dihydroindene-2-carbonitrile Chemical compound C1=CC=C2C(=O)C(C#N)CC2=C1 FUKLRRTYUZRVBS-UHFFFAOYSA-N 0.000 description 1
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
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- 238000010257 thawing Methods 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Abstract
The invention relates to a fluorenyl cyano indanone conjugated polymer and a preparation method thereof. The invention introduces a narrow band gap acceptor material on a fluorenyl cyano indene ketone structure, reduces the optical band gap of the material, has a large pi bond and an alkyl side chain for promoting solubility on the main chain of a conjugated polymer acceptor, has an asymmetric structure, is favorable for forming an amorphous film, and is suitable for an organic solar cell luminescent layer acceptor material.
Description
Technical Field
The invention relates to an organic semiconductor material of a fluorenyl cyano indanone conjugated polymer, belonging to the field of organic photovoltaic semiconductor receptor materials.
Background
Bulk Heterojunction (BHJ) all-polymer solar cells formed by blending P-type conjugated polymer semiconductors and N-type conjugated polymer semiconductors have gained wide attention in the industry due to their characteristics of light weight, good flexibility, easy solution processing, and the like. The P-type conjugated polymer semiconductor material is developed more mature, so that the development of an N-type conjugated polymer semiconductor is an important target for improving the field of all-polymer solar cells.
The polymer taking the cyanoindanone as the structural unit develops rapidly in a polymer receptor material, is relatively simple for the non-condensed ring type micromolecule receptor structural unit, is a good photosensitive material, has good stability and high molar extinction coefficient, and has specific advantages in the aspects of synthesis steps and synthesis cost. The invention constructs a conjugated polymer receptor based on the fluorenylcyano indanone micromolecule receptor derivative unit, and the polymer has good solubility and is a material suitable for a light-emitting layer receptor of an organic solar cell.
Disclosure of Invention
The invention introduces a narrow band gap acceptor material on a fluorenyl cyano indene ketone structure, reduces the optical band gap of the material, has a large pi bond and an alkyl side chain for promoting solubility on the main chain of a conjugated polymer acceptor, has an asymmetric structure, is favorable for forming an amorphous film, and is suitable for an organic solar cell luminescent layer acceptor material.
The purpose of the invention is realized by the following technical scheme:
in a first aspect, the present invention relates to a conjugated polymer of fluorenyl cyano indanone, wherein the conjugated polymer has a structural formula shown in formula (I):
or
(I); wherein R1 and R2 are C6～C29Alkyl, n is more than or equal to 1.
In a second aspect, the present invention relates to a method for preparing the above-mentioned fluorenyl cyanoindanone conjugated polymer, comprising the steps of:
a. and carrying out Knoevenagel reaction on the intermediate A and the intermediate B in an organic solvent to obtain the fluorenyl cyano indanone monomer M1.
b. Copolymerizing a monomer M1 of fluorenyl cyano-indene ketone group with a trimethyl tin conjugated monomer C or a trimethyl tin conjugated monomer D in an anhydrous organic solvent under the action of a catalyst and a ligand, and performing Soxhlet extraction to obtain the conjugated polymer.
Preferably, in step a, the intermediate A has a structural formula shown in formula (II):
the structural formula of the intermediate B is shown as the formula (III):
the structural formula of the monomer M1 is shown as the formula (IV):
Preferably, in step b, the structural formula of the trimethyltin conjugated monomer C is shown as formula (V):
Preferably, in the step b, the structural formula of the trimethyltin conjugated monomer D is shown as the formula (VI):
Preferably, the step a specifically comprises: taking an organic solvent as a medium, and carrying out reflux reaction on the intermediate A and the intermediate B for 2-18 hours under the action of alkali; recrystallization from a methanol/dichloromethane mixed solvent gave the fluorenyl cyano indanone monomer M1.
Further preferably, the organic solvent is chloroform, and the base is pyridine.
The fluorenyl cyano indolone monomer M1 has good solubility in common solvents; the common solvent is chloroform, toluene or dichlorobenzene.
Preferably, in the step b, the copolymerization reaction time is 0.5-18 hours, and the reaction temperature is 60-120 ℃.
Preferably, in step b, the anhydrous organic solvent is anhydrous toluene, anhydrous chlorobenzene or tetrahydrofuran.
Preferably, in step b, the catalyst is tris (dibenzylideneacetone) dipalladium and the ligand is tri-o-tolylphosphine.
Preferably, in step b, the solvents adopted in sequence by soxhlet extraction are methanol, acetone, n-hexane and chloroform.
Preferably, in the step b, the trimethyltin conjugated monomer C and the trimethyltin conjugated monomer D are commercial products and do not need to be synthesized.
In a third aspect, the invention relates to the use of the aforementioned fluorenyl cyano indanone based conjugated polymer as a semiconductor organic layer in an organic solar device for the preparation of an organic solar cell device.
The invention has the following beneficial effects: the synthesis method disclosed by the invention is simple and effective; the raw materials are easy to synthesize and prepare, the synthesis cost is low, and the purity of the obtained target compound is high; the main chain of the fluorenyl cyano group indeno-ketone semiconductor polymer has a large pi conjugated system and a side chain is a flexible dissolution-promoting alkyl chain, and the asymmetric structure of the structure is favorable for forming an amorphous film, so that the fluorenyl cyano group indeno-ketone semiconductor polymer is a material suitable for a light-emitting layer receptor of an organic solar cell.
Drawings
FIG. 1 is a scheme showing the synthesis of Compound M1 of example 1;
FIG. 2 is a scheme for the synthesis of polymers P1 and P2 of example 1;
FIG. 3 is a gel permeation chromatography GPC of polymer P1 (tetrahydrofuran as eluent);
FIG. 4 is a gel permeation chromatography GPC of polymer P2 (tetrahydrofuran as eluent);
FIG. 5 is a thermogravimetric analysis curve of Polymer P1 and Polymer P2;
FIG. 6 is a cyclic voltammogram of polymer P1;
FIG. 7 is a cyclic voltammogram of polymer P2;
FIG. 8 is a UV absorption spectrum of polymer P1 in chloroform and as a film;
FIG. 9 shows an ultraviolet absorption spectrum of polymer P2 in chloroform and during film formation.
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 fluorenyl cyanoindolone based conjugated Polymer
This example provides 2 soluble conjugated polymers of benzopyrrole group, the structural formula of which is shown in table 1 (wherein, n ≧ 1), and the synthetic route thereof is shown in fig. 1.
TABLE 1
1.1 preparation of Compounds P1 and P2
The synthetic scheme of the fluorenylcyanoindanone-containing polymers (P1 and P2) is shown in FIG. 2, and the preparation method comprises the following steps:
(a) synthesis of intermediate Compound A
The structural formula of the intermediate compound A is
(b) Intermediate compound B
The structural formula of the intermediate compound B is
The detailed preparation method comprises the following steps: 2, 7-bis (2-thienyl) -9, 9-dihexylfluorene (2.00mmol,1.00g) and 1, 6-dichlorohexane (50mL) were added to a two-necked flask under argon. N, N-dimethylformamide (12mL) was pre-formulated with phosphorus oxychloride (20.00mmol,1.86mL) as Vilsmeier reagent (orange). The Vilsmeier reagent was slowly dropped into the reaction under ice bath conditions. After heating to 65 ℃ and reacting for 17 hours, the reaction solution was cooled to room temperature. Quenching the reaction by using ice water, stirring for half an hour, and adjusting the pH value of the solution to be neutral by using sodium carbonate powder. It was extracted with dichloromethane, washed with water and saturated brine. Dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Most of the impurities were removed by silica gel column chromatography (dichloromethane/petroleum ether) to obtain crude product. The crude product was purified by recrystallization from methanol to give a yellow-green solid, i.e., intermediate compound B (yield: 1.05g, yield: 95%).
1H NMR(400MHz,CDCl3):δ9.92(s,2H),7.79–7.74(m,4H),7.70(d,J＝6.9Hz,2H), 7.64(s,2H),7.49(d,J＝3.9Hz,2H),2.07–2.01(m,4H),1.09(dd,J＝14.8,8.5Hz,12H), 0.76(t,J＝6.7Hz,6H),0.72–0.62(m,4H).
13C NMR(101MHz,CDCl3):δ182.72,154.80,152.26,142.26,141.64,137.46,132.43, 125.75,124.07,120.78,120.71,77.36,77.04,76.72,55.56,40.27,31.42,29.58,23.78,22.54, 13.97
The structural formula of the 2, 7-di (2-thienyl) -9, 9-dihexylfluorene is as follows:
a detailed preparation method thereof is described in Promarak, V., Pankvuang, A. & Ruchirawat, S.Synthesis and characterization of novel N-carbazole end-capped oligothiophene-fluorene, tetrahedron Lett.48, 1151-1154 (2007)
(c) Intermediate compound C
The structural formula of the intermediate compound C is
CAS: 1632459-72-3, 98% pure, purchased from Zheng Zhou Cheng Ke Biotechnology Ltd.
(d) Intermediate compound D
The structural formula of the intermediate compound D is
CAS:1252555-61-5, 98% pure, purchased from Zheng Zhou Cheng Ke Biotech, Inc.
(e) Synthesis of Compound M1
The structural formula of the compound M1 is
The detailed preparation method comprises the following steps: chloroform (50mL) was bubbled in a two-necked flask under argon for deoxygenation for 15 minutes, and then intermediate A (1mmol,554.8mg) and intermediate B (3mmol,819.3mg) were added to the flask. After the drug substance had dissolved, pyridine (2mL) was added. The reaction was heated to 65 ℃ and protected from light for 18 hours. Stopping heating, and quenching the reaction by using ice water after the system naturally falls to the normal temperature. Extraction with dichloromethane, washing with water, drying over anhydrous magnesium sulfate, concentration under reduced pressure gave a crude product, which was recrystallized by adding methanol and a small amount of dichloromethane to collect M1 as a black solid (yield: 0.88g, yield: 83%).
1H NMR(400MHz,CDCl3):δ8.94–8.93(m,2H),8.86–8.57(m,2H),8.09–8.08(m, 1H),7.94(dd,J＝5.8,4.1Hz,2H),7.91(ddd,J＝8.4,3.8,1.7Hz,2H),7.87(dt,J＝7.9,1.4 Hz,2H),7.84–7.81(m,3H),7.78(dd,J＝2.1,1.1Hz,2H),7.64(dt,J＝4.2,1.1Hz,2H), 2.12(d,J＝8.6Hz,4H),1.09(dd,J＝14.8,8.5Hz,12H),0.76(d,J＝6.7Hz,6H),0.72–0.62 (m,4H).
(f) Synthesis of polymers P1 and P2
The detailed preparation method comprises the following steps: under the protection of nitrogen, M1(0.15mmol,164.6mg), commercial monomer C (0.15mmol, 178.1mg), Pd2(dba)3(0.003mmol,2.8mg)，P(o-tolyl)3(0.012mmol,3.7mg) and dry toluene (6mL) were charged into a 100mL Schlenk reaction tube. The operation is carried out for three times by circulation of liquid nitrogen mixed ethyl acetate freezing, vacuum pumping and argon filling (external methanol thawing). After stirring the reaction mixture at 120 ℃ for 3 hours, the reaction mixture was cooled to room temperature. Adding a certain amount of methanol for precipitation, filtering out a solid, sequentially performing Soxhlet extraction with methanol, petroleum ether, acetone and chloroform, collecting a chloroform solution, performing spin drying, and precipitating with methanol to obtain the polymer P1 with metallic luster (yield: 261mg, yield: 96%).
1H NMR(400MHz,CDCl3):δ8.85(br,6H)7.81–7.57(br,16H),4.13(br,4H),2.13 (m,4H),1.97(m,2H),1.28–1.23(br,80H),0.85(br，18H)。
M1(0.1mmol,106.4mg) and commercial monomer D (0.1mmol,125.8mg) were charged with toluene (4mL) in a 100mL Schlenk tube under nitrogen. Bubbling for deoxygenation, adding Pd2(dba)3(0.002 mmol,1.9mg), ligand P (o-tolyl)3(0.008mmol,2.5 mg). The reaction was carried out at 90 ℃ for 1 hour, and the heating was stopped. Cooling to room temperature, adding a certain amount of methanol for precipitation, filtering to obtain solid, sequentially extracting with methanol, petroleum ether, acetone, and chloroform by Soxhlet extraction, collecting chloroform solution, and spin dryingThen, methanol was added thereto to precipitate a black polymer P2 (yield: 175.5mg, yield 97%).
1H NMR(400MHz,CDCl3):δ8.94–8.93(m,2H),8.86–8.57(m,2H),8.09–8.08(m, 1H),7.94(dd,J＝5.8,4.1Hz,2H),7.91(ddd,J＝8.4,3.8,1.7Hz,2H),7.87(dt,J＝7.9,1.4 Hz,2H),7.84–7.81(m,3H),7.78(dd,J＝2.1,1.1Hz,2H),7.64(dt,J＝4.2,1.1Hz,2H), 2.12(d,J＝8.6Hz,4H),1.09(dd,J＝14.8,8.5Hz,12H),0.76(d,J＝6.7Hz,6H),0.72–0.62 (m,4H).
Example 2 gel permeation chromatography, UV absorption Spectroscopy, electrochemical Properties and thermal stability of Polymer P1
2.1 gel permeation chromatography of Polymer P1
FIG. 3 shows that the polymer P1 has a number average molecular weight of 10.48kDa, a weight average molecular weight of 35.72kDa and a distribution coefficient PDI of 3.41, as determined by gel permeation chromatography GPC.
2.2 ultraviolet absorption Spectrum of Polymer P1
FIG. 8 shows the UV absorption spectrum of polymer P1 in chloroform and a thin film, which has a wide and strong UV-visible absorption range. Initial absorption of the film (. lamda. onset)film) At 831nm, according to the formula Egfilm＝1240/λonsetfilmEg calculated from eVfilm1.49eV, indicating that the polymer is a narrow bandgap polymer.
2.3 electrochemical Properties of Polymer P1
The electrochemical performance of the polymer is tested by taking a platinum sheet as a working electrode, a platinum wire as a counter electrode and a saturated calomel electrode as a reference electrode. The polymer was tested on a platinum sheet in an anhydrous acetonitrile solvent with tetrabutylammonium hexafluorophosphate as electrolyte at a concentration of 0.1mol/L and a scanning speed of 100mV/s, and the electrochemical curve of the polymer is given, see FIG. 6. We derive the HOMO and LUMO and energy gaps of the polymer according to the following equations. EHOMO＝﹣(Eox onset+4.36)eV，ELUMO＝﹣(Ere onset+4.36)eV，Eg＝ELUMO－EHOMO，Eox onseIs the initial oxidation potential, Ere onsetIs the initial reduction potential。
As can be seen from the graph, the initial reduction potential and oxidation potential of the polymer were-0.80V and 0.71V, respectively. The HOMO level and LUMO level of the polymer were calculated to be-5.42 eV and-3.91 eV, respectively, based on the above formula. From the point of view of its energy level, can become a solar receptor material.
2.4 thermal stability of Polymer P1
Thermogravimetric test conditions: the temperature was raised from room temperature to 540 ℃ at a temperature raising rate of 20 ℃/min under a nitrogen atmosphere. As shown in FIG. 5, Td of the polymer P1 was 350 ℃. The polymers are proved to have excellent thermal stability, and meet the thermal stability requirements of devices such as polymer solar cells and the like.
Gel permeation chromatography, ultraviolet absorption spectroscopy, electrochemical properties and thermal stability of example 3, Polymer P2
3.1 gel permeation chromatography of Polymer P2
FIG. 4 shows that the polymer P2 has a number average molecular weight of 6.97kDa, a weight average molecular weight of 12.93kDa and a distribution coefficient PDI of 1.86 as determined by gel permeation chromatography GPC.
3.2 ultraviolet absorption Spectrum of Polymer P2
FIG. 9 shows the UV absorption spectrum of polymer P2 in chloroform and film, and it can be seen that the two absorption peaks of the polymer have almost the same absorption intensity. Initial absorption of the film (. lamda. onset)film) At 698nm, according to the formula Egfilm＝1240/λonsetfilmEg calculated from eVfilm1.77eV, indicating that the polymer is a narrow bandgap polymer.
3.3 electrochemical Properties of Polymer P2
The electrochemical performance of the polymer is tested by taking a platinum sheet as a working electrode, a platinum wire as a counter electrode and a saturated calomel electrode as a reference electrode. The polymer was tested on a platinum sheet in an anhydrous acetonitrile solvent with tetrabutylammonium hexafluorophosphate as electrolyte at a concentration of 0.1mol/L and a scanning speed of 100mV/s, and the electrochemical curve of the polymer is given, see FIG. 7. We derive the HOMO and LUMO and energy gaps of the polymer according to the following equations. EHOMO＝﹣(Eox onset+4.36)eV，ELUMO＝﹣(Ere onset+4.36)eV，Eg＝ELUMO－EHOMO，Eox onseIs the initial oxidation potential, Ere onsetIs the initial reduction potential.
As can be seen from the graph, the initial reduction potential and oxidation potential of the polymer were-0.80V and 0.75V, respectively. The HOMO level and LUMO level of the polymer were calculated to be-5.46 eV and-3.91 eV, respectively, based on the above formula. From the point of view of its energy level, can become a solar receptor material.
3.4 thermal stability of Polymer P2
Thermogravimetric test conditions: the temperature was raised from room temperature to 540 ℃ at a temperature raising rate of 20 ℃/min under a nitrogen atmosphere. T of Polymer P2, shown in FIG. 5dRespectively at 404 ℃. The polymers are proved to have excellent thermal stability, and meet the thermal stability requirements of devices such as polymer solar cells and the like.
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 fluorenyl cyano indanone conjugated polymer is characterized in that the conjugated polymer has a structural formula shown in a formula (I):
or
(I); wherein R1 and R2 are C6～C29Alkyl, n is more than or equal to 1.
2. A method of preparing the fluorenyl cyanoindanone conjugated polymer of claim 1 comprising the steps of:
a. carrying out Knoevenagel reaction on the intermediate A and the intermediate B in an organic solvent to obtain a fluorenyl cyano indanone monomer M1;
b. and copolymerizing a fluorenyl cyano indanone monomer M1 and a trimethyl tin conjugated monomer C or a trimethyl tin conjugated monomer D in an anhydrous organic solvent under the action of a catalyst and a ligand, and performing Soxhlet extraction to obtain the conjugated polymer.
3. The method for preparing the fluorenyl cyano indanone based conjugated polymer according to claim 2, wherein in the step a, the structural formula of the intermediate A is shown as the formula (II):
the structural formula of the intermediate B is shown as the formula (III):
the structural formula of the monomer M1 is shown as the formula (IV):
4. The method for preparing a fluorenyl cyano indanone based conjugated polymer according to claim 2, wherein in the step b, the structural formula of the trimethyl tin conjugated monomer C is shown as the formula (V):
5. The method for preparing the fluorenyl cyano indanone based conjugated polymer according to claim 2, wherein in the step b, the structural formula of the trimethyl tin conjugated monomer D is shown as the formula (VI):
6. The method for preparing a fluorenyl cyano indanone based conjugated polymer according to claim 2, wherein the step a specifically comprises: taking an organic solvent as a medium, and carrying out reflux reaction on the intermediate A and the intermediate B for 2-18 hours under the action of alkali; recrystallization from a methanol/dichloromethane mixed solvent gave the fluorenyl cyano indanone monomer M1.
7. The method of claim 6, wherein the organic solvent is chloroform and the base is pyridine.
8. The method for preparing the fluorenyl cyano indanone based conjugated polymer according to claim 2, wherein in the step b, the reaction time of the copolymerization is 0.5 to 18 hours, and the reaction temperature is 60 to 120 ℃.
9. The method of claim 2, wherein in step b, the catalyst is tris (dibenzylideneacetone) dipalladium and the ligand is tris (o-tolyl) phosphine.
10. The method for preparing a fluorenyl cyano indanone based conjugated polymer according to claim 2, wherein in the step b, the anhydrous organic solvent is anhydrous toluene, anhydrous chlorobenzene or tetrahydrofuran; the Soxhlet extraction sequentially adopts solvents of methanol, petroleum ether, acetone and chloroform.
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