CN113801301B - Isoindigo polymer of fused pyrrole ring type perylene imide with pendant gulf-position and preparation method thereof - Google Patents

Isoindigo polymer of fused pyrrole ring type perylene imide with pendant gulf-position and preparation method thereof Download PDF

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CN113801301B
CN113801301B CN202111191182.1A CN202111191182A CN113801301B CN 113801301 B CN113801301 B CN 113801301B CN 202111191182 A CN202111191182 A CN 202111191182A CN 113801301 B CN113801301 B CN 113801301B
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邓平
蔡洋
夏伟峰
黄源泉
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Abstract

The invention discloses an isoindigo polymer of fused pyrrole ring type perylene imide with pendant gulf position and a preparation method thereof. Firstly, a monomer M1 is prepared by linking gulf-position fused pyrrole rings of perylene imide with isoindigo through a substitution reaction, and then the monomer M1 is heated and polymerized with a methyl tin conjugated monomer M2 to prepare the isoindigo polymer of the side-chain-hung gulf-position fused pyrrole ring type perylene imide. A side chain hanging gulf-position fused pyrrole ring type perylene imide structural unit is introduced into an isoindigo blue polymer donor material to form a novel polymer semiconductor material with a side chain hanging perylene imide derived structural unit. The polymer has good solubility, higher molecular weight and good thermal stability.

Description

Isoindigo polymer of fused pyrrole ring type perylene imide with pendant gulf-position and preparation method thereof
Technical Field
The invention belongs to the field of organic synthesis, and relates to an isoindigo polymer of side-chain-hung gulf-position fused pyrrole ring type perylene bisimide and a preparation method thereof.
Background
The perylene bisimide compound is an important small molecule receptor in the field of organic semiconductor materials, the isoindigo compound is an important small molecule donor in the field of organic semiconductor materials, and the introduction of the organic small molecule receptor as a side chain unit into a polymer donor material to form a single-component polymer active layer is an important way for preparing polymer solar cells.
However, the current research work mainly focuses on introducing pendant perylene imide into side chains, and the research on introducing side chains into cross-pendant perylene imide is rare.
Based on the method, a side chain hanging gulf-position fused pyrrole ring type perylene bisimide structural unit is introduced into the isoindigo polymer donor material to form a novel polymer with a side chain hanging perylene bisimide derived structural unit.
Disclosure of Invention
Compared with other isoindigo polymers, the isoindigo polymer has the innovation that perylene imide micromolecule receptors are transversely hung in side chains of donor polymers to form a novel polymer with a side chain hanging structure.
The perylene bisimide has a large plane conjugated system and is a typical construction unit for constructing an organic small molecule receptor. The perylene imide structure is usually designed to be vertically suspended on a main chain as a side chain electron-withdrawing building unit, and an unmodified perylene imide conjugated core is relatively purely applied. By modifying the molecular skeleton, the aggregation state and the physicochemical property of the perylene bisimide structural unit are regulated and controlled, and the possibility that the perylene bisimide structural unit is applied to constructing a single polymer active layer as a side chain receptor is expanded. Therefore, it is of positive interest to study the pendant side chains of perylene imides in other forms from polymers.
The polymer is prepared by introducing the cross-hanging perylene bisimide into the side chain of the polymer, and has the advantages of good chemical stability, higher molecular weight, good solubility and the like.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention aims to protect isoindigo polymer of fused pyrrole ring type perylene imide with pendant gulf position, which has the structural formula:
Figure BDA0003301154950000021
wherein R is1、R2Alkyl chains with different lengths are adopted, and n is more than or equal to 1.
The second purpose of the invention is to protect the isoindigo polymer of the side chain hanging gulf-position condensed pyrrole ring type perylene diimide, which is a preparation method of monomers M1 and M2 and a catalyst tris (dibenzylideneacetone) dipalladium (Pd)2(dba)3) And the ligand tris (o-methylphenyl) phosphorus (P)3) Dissolving in an anhydrous organic solvent, heating, refluxing and polymerizing under the protection of inert gas, purifying by Soxhlet extraction, and drying in vacuum to obtain the polymer;
wherein the structural formula of the monomer M1 is:
Figure BDA0003301154950000022
wherein R is1、R2Alkyl chains with different lengths are adopted, and n is more than or equal to 1. The structure of monomer M2 is:
Figure BDA0003301154950000031
the organic solvent is toluene.
The preparation method of the monomer M1 is as follows:
(1) isoindigo compound A substituted by 1 equivalent of bromoalkyl chain under anhydrous, oxygen-free and argon atmosphere
Figure BDA0003301154950000032
And 2.4 equivalent of gulf-position fused pyrrole ring type perylene diimide compound B
Figure BDA0003301154950000033
Dissolving in organic solvent N, N-dimethylformamide, taking 3 equivalents of potassium carbonate as a catalyst, stirring and reacting at 80 ℃, extracting by ethyl acetate, and purifying by a silica gel chromatography column by taking dichloromethane to petroleum ether with the volume ratio of 7 to 1 as an eluent to obtain the monomer M1.
The polymer preparation method comprises the following steps:
(1) under an anhydrous oxygen-free and argon atmosphere, 1 equivalent of monomer M1
Figure BDA0003301154950000034
And 1 equivalent of monomer M2
Figure BDA0003301154950000035
Dissolving in toluene, an organic solvent, and reacting in the presence of 0.2% equivalent of tris (dibenzylideneacetone) dipalladium (Pd) catalyst2(dba)3) 0.8% equivalent of the ligand tris (o-methylphenyl) phosphorus (P)3) Reacting at 65 deg.C for 5 hr, sequentially extracting with methanol, petroleum ether and chloroform, and vacuum drying to obtain the final productA polymer.
Significant advantages of the invention
(1) The raw materials adopted by the invention are relatively cheap, and the synthesis path is not complex;
(2) the polymer synthesized by the method has good solubility in common organic solvents such as chloroform, tetrahydrofuran, chlorobenzene and the like, is easy to form a film by a dripping or spin coating mode, and has a good light absorption range and good chemical stability.
(3) The polymer synthesized by the invention has excellent thermal stability and can be applied to devices such as polymer solar cells and the like.
Description of the drawings:
FIG. 1 shows the synthetic procedure of this example;
FIG. 2 is a NMR spectrum of monomer M1;
FIG. 3 is a NMR hydrogen spectrum of a polymer;
FIG. 4 is a thermogravimetric analysis curve of a polymer;
FIG. 5 is a gel permeation chromatogram of a polymer;
FIG. 6 is a film UV-VIS absorption spectrum of polymer and monomer M1;
FIG. 7 is a cyclic voltammogram of a polymer.
The specific implementation mode is as follows:
in order to make the present invention more comprehensible, the technical solutions of the present invention are further described below with reference to specific embodiments, but the present invention is not limited thereto.
EXAMPLE 1 preparation of bromoalkyl chain-substituted isoindigo Compound A
Bromoalkyl chain-substituted isoindigo compound a is prepared according to the literature "Brynn p. charron, Michael u. ocheje, Mariia serivanova, et al, Electronic properties of isoindigo-based conjugated polymers bearing-binding and linear alkyl peptides, Journal of Materials Chemistry c.2018, 6, 12070" and has the formula:
Figure BDA0003301154950000051
example 2 bay-position fused pyrrole-ring type perylene imide Compound B
A gulf-fused pyrrole-ring type perylene imide compound B of the formula:
Figure BDA0003301154950000052
example 3 preparation of monomer M1:
compound B (1.69mmol, 1.20g) obtained in example 2, compound A (0.70mmol, 0.52g) obtained in example 1 and potassium carbonate (2.1mmol, 0.29g) were dissolved in a 100mL pressure-resistant tube containing N, N-dimethylformamide (30mL) under an argon atmosphere, reacted with stirring at 80 ℃ and followed by TLC. After 36 hours the reaction was complete and cold water was added. And extracting with ethyl acetate, washing the obtained organic phase with water, collecting the organic phase, drying with anhydrous magnesium sulfate, and removing the solvent from the obtained filtrate under reduced pressure to obtain a crude product. The crude product was purified by column chromatography on silica gel (eluent dichloromethane: petroleum ether in a volume ratio of 7: 1), recrystallized from methanol and dried under vacuum to give a reddish brown solid, monomer M1, in a yield of 1.40g, in a yield of 50%, TLC shift Rf0.48 (developing solvent is dichloromethane: petroleum ether: 7:1, volume ratio).1HNMR(400MHz,CDCl3) δ 8.99(s,8H),8.87(s,2H),8.82(s,4H),6.99(s,2H),6.78(s,2H),5.30(s,4H),4.87(s,4H),3.64(s,4H),2.30(s,8H),2.20(s,4H),1.92(s,8H),1.62(s,4H),1.30(s,58H),0.81(s, 24H). The structure is as follows:
Figure BDA0003301154950000061
example 4 preparation of monomer M2:
monomer M2 was prepared according to the literature "Joonhyong choice, Ki-Yun Kim, Hojeong Yu, Import of Electron Transport instability in Nathalhalene dioxide-Based Polymer accumulators for High-Performance, Additive-Free, All-Polymer Solar Cells, Chemistry of Materials 201527 (15), 5230-5237" and has the structure:
Figure BDA0003301154950000062
example 5 preparation of isoindigo polymer of gulf-position fused pyrrole ring type perylene imide with pendant side chains:
monomer M1(0.1mmol, 200.8mg) and monomer M2(0.1mmol, 49.2mg) were added to a 100mL Schleck reaction tube under argon and 7mL of anhydrous toluene was added. After bubbling deoxygenation for 30 minutes, the catalyst tris (dibenzylideneacetone) dipalladium (Pd) was added2(dba)3) (0.002mmol, 1.9mg), ligand tris (o-methylphenyl) phosphorus (P (o-tolyl)3) (0.008mmol, 2.5mg) and the tube sealed and reacted at 65 ℃ for 5 hours. Cooling the reaction to room temperature, precipitating with methanol to obtain crude product, sequentially performing Soxhlet extraction with methanol, petroleum ether and chloroform, and collecting chloroform extract. After removal of the solvent under reduced pressure, a second precipitation with methanol was carried out, and filtration and vacuum drying were carried out to obtain a black solid as a polymer at a yield of 197mg and a yield of 98%.1H NMR (400MHz, CDCl3) Δ 8.86(s,6H),8.61(s,3H),7.52(s,1H),7.00(s,3H),6.90(s,1H),6.62(s,2H),6.30(s,1H),5.23(s,2H),4.84(s, 1H). The structure is as follows:
Figure BDA0003301154950000071
thermogravimetric analysis, gel permeation chromatography, ultraviolet absorption spectrum and cyclic voltammogram of polymer
FIG. 4 shows the thermogravimetric analysis curve of a polymer at the temperature (T) corresponding to a loss of 5% by weightd) The thermal decomposition temperature of the material is considered. As can be seen from FIG. 4, the thermal decomposition temperature (T) of the polymerd) 375 deg.c, indicating excellent thermal stability. FIG. 5 shows gel permeation of polymersChromatographic GPC curves determined a number average molecular weight of 20866 and a weight average molecular weight of 51234. FIG. 6 shows the UV-visible absorption spectrum of a polymer film and monomer M1, from which FIG. 6 shows the initial absorption (. lamda.) of the polymer filmonset film) At 776nm, the polymer is polymerized from monomer M1, and monomer M1 is a polymer in which two conjugated structural units are bridged by a non-conjugated alkyl chain. The absorption of the polymer is divided into two parts: isoindigo units as comonomer backbone; and the other is perylene diimide side chain unit. When conjugated unit bithiophene is introduced into the conjugated molecular chain, the effective conjugation length of the conjugated molecular chain is obviously improved, the charge transfer effect in the molecular chain is obvious, and the initial absorption wavelength (lambda) of the polymer in a film state is realizedonset film) Compared with the initial absorption wavelength of M1 under the same condition, the absorption wavelength is increased by about 200nm, which expands the absorption range of the polymer to visible light and contributes to the improvement of the utilization rate of the light. FIG. 7 shows a cyclic voltammogram of a polymer, characterizing the electrochemical properties of the polymer, and the cyclic voltammetry test was performed on a PGSTAT302N type electrochemical workstation. Three-electrode system: the working electrode is a platinum electrode, the auxiliary electrode is a platinum wire electrode, and the reference electrode is an Ag/AgCl electrode. The electrolyte is 0.1M tetrabutylammonium hexafluorophosphate solution (the solvent is anhydrous acetonitrile). Under the nitrogen atmosphere, the scanning speed is 100mV/s, ferrocene is used as an external standard before and after a test sample, and during the test, the polymer is dissolved and then is dripped on a platinum disk electrode to form a film, and then the electrochemical test is carried out.

Claims (10)

1. The utility model provides an isoindigo polymer of fused pyrrole ring type perylene imide of gulf position of side chain suspension which characterized in that, its structure is:
Figure FDA0003301154940000011
in the formula R1、R2Alkyl chains with different lengths are adopted, and n is more than or equal to 1.
2. The preparation method of the isoindigo polymer of the side-chain-suspended gulf-position fused pyrrole ring type perylene diimide of claim 1, characterized in that monomers M1 and M2 and a catalyst are dissolved in an anhydrous organic solvent, heated and refluxed under inert gas for polymerization, and then purified and dried at high temperature in vacuum to obtain the polymer; wherein the structural formula of the monomer M1 is:
Figure FDA0003301154940000012
wherein R is1、R2Alkyl chains of different lengths;
the structure of monomer M2 is:
Figure FDA0003301154940000021
3. the method for preparing the isoindigo polymer of the side-chain-suspended gulf-position fused pyrrole-ring type perylene imide according to claim 2, which is characterized by comprising the following steps:
(1) carrying out substitution reaction on isoindigo compound A substituted by bromoalkyl chain and gulf-position fused pyrrole ring type perylene diimide compound B in an organic solvent to obtain a monomer M1;
(2) the monomer M1 and the methyl tin conjugated monomer M2 are subjected to polymerization reaction in an anhydrous organic solvent under the action of a catalyst and a ligand, and the polymer is obtained through soxhlet extraction.
4. The method for preparing isoindigo polymer of fused pyrrole ring type perylene imide with pendant gulf position according to claim 3, wherein the bromoalkyl chain substituted isoindigo compound A in the step (1) has the structural formula:
Figure FDA0003301154940000022
wherein R is2Are alkyl chains of different lengths.
5. The method for preparing the side-chain-suspended gulf-position fused pyrrole-ring perylene imide isoindigo polymer according to claim 3, wherein the gulf-position fused pyrrole-ring perylene imide compound B in the step (1) has a structural formula as follows:
Figure FDA0003301154940000023
wherein R is1Are alkyl chains of different lengths.
6. The preparation method of the side-chain-suspended gulf-position fused pyrrole ring type perylene imide isoindigo polymer according to claim 3, wherein the specific method of the step (1) is as follows: under the atmosphere of anhydrous oxygen-free and argon gas, 1 equivalent of isoindigo compound A substituted by bromoalkyl chain and 2.4 equivalents of gulf-position fused pyrrole ring type perylene diimide compound B react by taking 3 equivalents of potassium carbonate as a catalyst and N, N-dimethylformamide as a reaction medium; extracting, and purifying by a silica gel chromatographic column to obtain the monomer M1.
7. The preparation method of the side-chain-hung gulf-position fused pyrrole-ring type perylene imide isoindigo polymer according to claim 6, wherein the extracting agent is ethyl acetate for extraction; the eluent for purifying the silica gel chromatographic column is the eluent with the volume ratio of dichloromethane to petroleum ether being 7 to 1.
8. The method for preparing the side-chain-suspended gulf-position fused pyrrole ring type perylene imide isoindigo polymer according to claim 6, wherein the specific reaction temperature is 80 ℃ and the reaction time is 36 hours.
9. The preparation method of the side-chain-suspended gulf-position fused pyrrole ring type perylene imide isoindigo polymer according to claim 3, wherein the specific method of the step (2) is as follows: 1 equivalent of monomer M1 and 1 equivalent of 5,5 '-bis (trimethylstannyl) -2,2' -bithiophene monomer M2 were dissolved in anhydrous toluene in an anhydrous oxygen-free and argon atmosphere, and 2% equivalent of catalyst tris (dibenzylideneacetone) dipalladium Pd was dissolved at 65 ℃ in an anhydrous toluene atmosphere2(dba)3And 8% equivalent of ligand III(o-methylphenyl) phosphorus P (o-tolyl)3Reacting under the action of the alcohol, sequentially performing Soxhlet extraction by using methanol, petroleum ether and chloroform, and performing vacuum drying to obtain the polymer.
10. The method for preparing the perylene ring type perylene imide isoindigo polymer with pendant gulf sites according to claim 9, wherein the reaction time is 5 hours.
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苝二酰亚胺悬挂型非平面聚合物受体材料的合成及光伏性能研究;汪赵镜;《中国优秀硕士学位论文全文数据库 工程科技I辑》;20200115(第01期);全文 *
苝二酰亚胺类衍生物的制备及光电性能研究;于昌仕;《中国优秀硕士学位论文全文数据库 工程科技II辑》;20190115(第12期);38-40 *

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