CN106700037A - Dithienyl pyrrolo-pyrroledione broad-absorption conjugated polymer and preparation method thereof - Google Patents
Dithienyl pyrrolo-pyrroledione broad-absorption conjugated polymer and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a dithienyl pyrrolo-pyrroledione broad-absorption conjugated polymer and a preparation method thereof and relates to the field of synthesis of organic conjugated polymers, in particular to an organic conjugated polymer based on a dithienyl pyrrolo-pyrroledione dual-tin monomer and 2,7-dibromo-N-9-(ethylhexyl)carbazole and a preparation method thereof. The novel organic conjugated polymer synthetized by the preparation method has a relatively wide absorption range, the involved visible light even extends into a near infrared region; furthermore, the novel organic conjugated polymer has favorable solubility in common organic solvents and can be applied to the organic photovoltaic field as an optical absorption material.
Description
Technical field
The present invention relates to conjugatd polymerses synthesis field, it is related to a kind of new conjugatd polymerses and its synthesis side
Method.
Background technology
Conjugatd polymerses with lightweight, flexible and low cost and other advantages due to being widely used in organic light
Volt device.At present, most study is donor (Donor, D)-acceptor (Acceptor, A) in main chain in conjugatd polymerses
The conjugated polymer being alternately arranged, this is because the mutual push-and-pull action of electronics between D and A enhances intramolecular and intermolecular
Active force, can be used to the optical absorption ranges of conjugated polymer.In numerous receptor units, pyrrolo-pyrrole-dione
(DPP) unit has good coplanarity and stronger electron-withdrawing power, and it is low to be widely used for synthesis as receptor unit
Band gap polymer, its optical absorption ranges can reach near-infrared region.But based on DPP conjugated polymers intramolecular and molecule
Between too strong push-and-pull electronic action make its optical absorption ranges narrower；On the other hand, too strong push-and-pull electronic action can also be reduced
The dissolubility of polymer, weakens the film forming ability of polymer.Therefore, the new low band-gap of design and synthesis high comprehensive performance
Conjugated polymer material has very important significance to improving organic photovoltaic devices performance.According to former document report,
π units (herein referring to Dithiophene group) formation D- π-A structures are introduced between D-A units can be effectively improved the light of conjugated polymer
Learn absorption region；Meanwhile, can be used to adjust the film forming ability of polymer by changing the alkyl side chain in polymer.The present invention
Synthesized it is a kind of it is new based on DPP be acceptor, carbazole be donor, di- thiophene for bridged group D- π-A types have suction wider
The low band-gap conjugated polymer of scope is received, organic photovoltaic devices can be used for.
The content of the invention
It is an object of the invention to provide a kind of low band-gap conjugated polymers with absorption region wider of solution processable
Thing and preparation method thereof.
The present invention is achieved by the following technical solutions：
A kind of low band-gap conjugated polymer with absorption region wider, described conjugated polymer is based on di- thiophene
The low band-gap conjugated polymer of the double tin monomers of fen pyrrolo-pyrrole-dione and 2,7- bis- bromo- N-9- (2- ethylhexyls) carbazole.
The structural formula of the conjugated polymer is：
Wherein 15>n>8.
A kind of preparation method of the low band-gap conjugated polymer with absorption region wider, is carried out as steps described below：
With the double tin monomers of di- thiophene pyrrole and pyrroledione and 2,7- bis- bromo- N-9- (2- ethylhexyls) carbazole monomers for raw material, with
Three (dibenzalacetone) two palladium is catalyst, under three (o-methyl-phenyl) phosphorus are for the system of part, using Shi Dile
(Stille) cross-coupling reaction obtains described conjugatd polymerses.
Described cross-coupling reaction temperature is 85-120 DEG C.
The described cross-coupling reaction time is 48-72 hours.
Described di- thiophene pyrrole and the double tin monomers of pyrroledione, 2,7- bis- bromo- N-9- (2- ethylhexyls) carbazole list
Body, three (dibenzalacetone) two palladium, the consumption mol ratio of three (o-methyl-phenyl) phosphorus are 1:1:0.06:0.12.
It is an advantage of the invention that：D- π-A type conjugatd polymerses the present invention relates to synthesize have rigid copline
Structure, while having absworption peak wide, covering visible light simultaneously extends to near-infrared field；Side chain is the deliquescent alkyl of promotion
Chain, belongs to the conjugation low band gap polymers of solution processable.
Brief description of the drawings
Fig. 1 is based on di- thiophene pyrrole and the double tin monomers of pyrroledione and 2,7- bis- bromo- N-9- (2- ethylhexyls) click
The synthesis path schematic diagram of the conjugatd polymerses (PCDTDPP) of azoles monomer；
Fig. 2 is the synthesis path schematic diagram of di- thiophene pyrrole and the double tin monomers of pyrroledione；
Fig. 3 is the synthesis path schematic diagram of 2,7- bis- bromo- N-9- (2- ethylhexyls) carbazole monomers；
Fig. 4 is the uv-visible absorption spectroscopy figure of the conjugatd polymerses PCDTDPP of solution processable
Specific embodiment
Embodiments of the invention are elaborated below in conjunction with the accompanying drawings：The present embodiment is with technical solution of the present invention as preceding
Put and implemented, combine detailed implementation method and specific operating process, but protection scope of the present invention is not limited to down
The embodiment stated.
As shown in figure 1, the present invention is with di- thiophene pyrrole and the double tin monomers of pyrroledione and bromo- N-9- (the 2- second of 2,7- bis-
Base hexyl) carbazole monomers copolymerization under the conditions of Stille cross-coupling reactions, with methanol extraction, then sequentially pass through methyl alcohol, just
Hexane, chloroform surname extraction, obtain subject polymer.
The conjugated polymer that absorbs wide of solution processable of the invention has following structure：
Wherein 15>n>8.
Preparation method to each monomer is illustrated, as follows：
The synthesis path schematic diagram of di- thiophene pyrrole and the double tin monomers of pyrroledione is as shown in Fig. 2 preparation method is referred to
Document report (Journal of Materials Chemistry A, 2014,2,6589-6597).Monomer has following structure：
The synthesis path schematic diagram of 2,7- bis- bromo- N-9- (2- ethylhexyls) carbazole monomers is as shown in figure 3, preparation method is joined
Examine document report (Chemistry of Materials, 2005,17,3031-3039).Monomer has following structure：
Embodiment 1, synthetic polymer PCDTDPP
The synthesis path of polymer PC DTDPP is as shown in figure 1, concretely comprise the following steps：Under argon gas protection, by di- thiophene pyrrole
Cough up and double tin monomer (350mg, 0.34mmol) of pyrroledione and 2,7- bis- bromo- N-9- (2- ethylhexyls) carbazole monomers
(148mg, 0.34mmol), the palladium (18.7mg, 6mol%) of catalyst three (dibenzalacetone) two, part three (o-methyl-phenyl)
Phosphorus (12.4mg, 12mol%), dry toluene (15mL) is added in three mouthfuls of reaction bulbs.Then reaction bulb is freezed with liquid nitrogen, is vacuumized
After 30 minutes, argon gas is poured, repeat this operation three times.Slowly it is warmed up to 110 DEG C to react 72 hours, reaction solution is cooled to room
Temperature, pours into 400mL methyl alcohol and precipitates, and filters out solid.Respectively with methyl alcohol and n-hexane surname extraction to after colourless, then use chloroform
Surname extraction collects chloroformic solution to colourless, finally rotates liquid, and methanol extraction obtains dark green polymer.
The double tin monomers of embodiment 2, synthon di- thiophene pyrrole and pyrroledione
The synthesis path of monomer di- thiophene pyrrole and the double tin monomers of pyrroledione is as shown in Fig. 2 concretely comprise the following steps：Yu Gan
1.6mL diisopropylamines and 18mL anhydrous tetrahydro furans are added in dry tri- mouthfuls of reaction bulbs of 100mL, is frozen reaction system with liquid nitrogen
Firmly.Vacuumized through three times change argon gas replace three times after, reduce the temperature to -78 DEG C, be added dropwise over 4.8mL n-BuLis
(11.44mmol, 2.4M hexane solution), is kept for -78 DEG C after one hour by temperature, is slowly warmed up to -15 DEG C.By fresh preparation
Diisopropylamino lithium (LDA) be added dropwise to be reduced to -78 DEG C di- thiophene pyrrole and pyrroledione (916.4mg,
Anhydrous tetrahydrofuran solution 1.33mmol), system maintained -78 DEG C after two hours, is slowly warmed up to -20 DEG C and remains three small
When.System temperature is cooled to -78 DEG C, (tetrahydrofuran of 4.7mmol, 1M is molten to rapidly join 4.7mL trimethyl ammonia chlorides solution of tin
Liquid).Mixture is warming up to room temperature, is stirred overnight.Reactant is entered into row temper with 30mL deionized waters to go out, deionization is then used
Water, dichloromethane are extracted three times.Organic extraction solution washes three times with water, then with anhydrous sodium sulfate drying overnight.Vacuum is done
Darkviolet solid (1.06g, yield 94%) is obtained after dry.
Embodiment 3, synthesizes 2,7- bis- bromo- N-9- (2- ethylhexyls) carbazole monomers
Monomer 2, the synthesis path of 7- bis- bromo- N-9- (2- ethylhexyls) carbazole is as shown in figure 3, concretely comprise the following steps：In argon
Under gas shielded, by 1.0g 2, the bromo carbazoles of 7- bis- (3.07mmol) is added in three mouthfuls of reaction bulbs equipped with 12mL acetone, then is added
Enter 368.3mg (6.14mmol) powdered potassium hydroxide, 1.2g (6.14mmol) 2- ethyl hexyl bromides, 0.1g tetrabutyl hydrogen sulfates
Ammonium.After reaction solution is heated slowly into backflow, react 12 hours.Then extracted three times with deionized water, dichloromethane.Organic extraction
Take solution and wash three times with water, then with anhydrous sodium sulfate drying overnight.Crude product is obtained after vacuum drying, crude product passes through silica gel
Column chromatography, using petroleum ether and chloroform (1:1, v/v) mixed solvent is obtained as eluant, eluent after vacuum drying
Solid recrystallizing methanol, obtains white needle-like crystals 1.2g (yields：88%).
Fig. 4 gives the abosrption spectrogram of polymer PC DTDPP, absorption region covering visible light, and extends to near-infrared
Region.
In sum, new conjugatd polymerses of the present invention have rigid coplanar structure, polymer tool
There are good dissolubility and optical absorption ability, organic photovoltaic field can be applied to as optical absorbing material.
Claims (5)
1. the low band-gap conjugated polymer with absorption region wider of a kind of solution processable, it is characterised in that described to have
The structural formula of machine conjugated polymer is：
Wherein 15>n>8.
2. the preparation method of a kind of low band-gap conjugated polymer with absorption region wider according to claim 1,
It is characterized in that carrying out as steps described below：With di- thiophene pyrrole and the double tin monomers of pyrroledione and the bromo- N-9- (2- of 2,7- bis-
Ethylhexyl) carbazole monomers are raw material, be catalyst with three (dibenzalacetone) two palladium, three (o-methyl-phenyl) phosphorus are part
System under, described conjugatd polymerses are obtained using Shi Dile (Stille) cross-coupling reaction.
3. the preparation method of a kind of low band-gap conjugated polymer with absorption region wider according to claim 1,
It is characterized in that described cross-coupling reaction temperature is 85-120 DEG C.
4. the preparation method of a kind of low band-gap conjugated polymer with absorption region wider according to claim 1,
It is characterized in that the cross-coupling reaction time is 48-72 hours.
5. the preparation method of a kind of low band-gap conjugated polymer with absorption region wider according to claim 1,
It is characterized in that described di- thiophene pyrrole and the double tin monomers of pyrroledione, 2,7- bis- bromo- N-9- (2- ethylhexyls) carbazoles
Monomer, three (dibenzalacetone) two palladium, the consumption mol ratio of three (o-methyl-phenyl) phosphorus are 1:1:0.06:0.12.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108192084A (en) * | 2018-01-17 | 2018-06-22 | 合肥工业大学 | A kind of organic semiconductor conjugated polymer and its synthetic method |
| CN108285527A (en) * | 2018-01-17 | 2018-07-17 | 合肥工业大学 | A kind of A-D-A types semiconductive conjugated polymer and its synthetic method |
| CN114773580A (en) * | 2022-04-29 | 2022-07-22 | 太原理工大学 | Irregular ternary conjugated polymer photocatalytic material and preparation method and application thereof |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108192084A (en) * | 2018-01-17 | 2018-06-22 | 合肥工业大学 | A kind of organic semiconductor conjugated polymer and its synthetic method |
| CN108285527A (en) * | 2018-01-17 | 2018-07-17 | 合肥工业大学 | A kind of A-D-A types semiconductive conjugated polymer and its synthetic method |
| CN114773580A (en) * | 2022-04-29 | 2022-07-22 | 太原理工大学 | Irregular ternary conjugated polymer photocatalytic material and preparation method and application thereof |
| CN114773580B (en) * | 2022-04-29 | 2024-04-30 | 太原理工大学 | Irregular ternary conjugated polymer photocatalytic material and preparation method and application thereof |
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