CN111944513A - Quinacridone-based low-driving-voltage electrochromic material and preparation method thereof - Google Patents
Quinacridone-based low-driving-voltage electrochromic material and preparation method thereof Download PDFInfo
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Abstract
A quinacridone-based derivative shown in formula (I), a preparation method thereof and a polymer electrochromic material prepared by using the quinacridone-based derivative as a monomer. The quinacridone derivative has a rigid planar structure, quinacridone is used as a weak acceptor, and a strong conjugated structure is formed by the quinacridone and a donor 3, 4-Ethylenedioxythiophene (EDOT), so that a polymer film can generate a color change phenomenon under a lower driving voltage, namely, the polymer film has obvious color change at 0.3V, can realize complete conversion from yellow to blue at 0.9V, has no obvious attenuation after 240 cycles of contrast, and shows excellent electrochemical stability, and therefore, the quinacridone derivative is a novel electrochromic material with a great application prospect.
Description
(I) technical field
The invention relates to a pigment molecule based on quinacridone derivative and an electrochromic material prepared from the pigment molecule as a monomer and having low driving voltage.
(II) background of the invention
The electrochromism means that under the action of an external voltage, due to the injection and the extraction of charges, oxidation-reduction reaction occurs, and simultaneously, along with the doping and the de-doping of electrolyte ions, the optical absorption of the electrochromism changes in a visible light-near infrared region, and macroscopically shows reversible changes in color and transmissivity. Early electrochromic materials mainly comprise inorganic electrochromic materials, but organic electrochromic materials come to the fore due to the advantages of rich structural types, excellent electrochromic comprehensive performance, good processing performance and the like, and show great application values in various fields such as intelligent windows, displays, electronic paper, automobile rearview mirrors, military camouflage, memory storage and the like. However, the driving voltage of the existing conductive polymer electrochromic material is still relatively high (>1V), which relatively increases the energy consumption, thereby limiting the wide application thereof. The poly-3, 4-ethylenedioxythiophene (PEDOT) is one of the research hotspots in the field of electrochromism due to the characteristics of simple synthesis, relatively low driving voltage, excellent cycling stability and the like. But its color change is relatively single. Quinacridone compounds are cheap organic pigments, have good molecular planarity and excellent physicochemical stability, and are easily modified chemically. Based on the method, the novel quinacridone derivative is designed and synthesized by taking quinacridone as a central core and EDOT as a peripheral active group, and the novel quinacridone derivative is used as a monomer to prepare a novel low-driving-voltage electrochromic material by electrochemical polymerization so as to further expand the application of the novel quinacridone derivative.
Disclosure of the invention
In order to overcome the defects of the prior art, the invention aims to provide a novel quinacridone-based low-driving-voltage electrochromic material and a preparation method thereof.
The technical scheme of the invention is as follows:
a quinacridone-based low-driving-voltage electrochromic material is disclosed, monomers of which are shown in a formula (I),
a preparation method of quinacridone-based low driving voltage electrochromic material, comprising the steps of:
(1) quinacridone (II) is subjected to alkylation reaction to obtain quinacridone derivative C10QA (III), the structural formula is respectively as follows:
(2) carrying out bromination reaction on the C10QA (III) and N-bromosuccinimide (NBS) to obtain a brominated product C10QA-2Br (IV), wherein the structural formula of the C10QA-2Br is as follows:
(3)3, 4-Ethylenedioxythiophene (EDOT) reacts with tributyltin chloride to generate stannic EDOT (V), wherein the stannic EDOT has the following structural formula:
(4) c10QA-2Br (IV) and stanned EDOT (V) are subjected to stille coupling reaction to generate a target product C10QA-2EDOT (I);
(5) the C10QA-2EDOT (I) is used as a monomer, and the electrochemical polymerization is adopted to prepare the quinacridone-based low-driving-voltage electrochromic material.
Further, the operation process of the step (1) is as follows:
sequentially adding quinacridone, 1-bromodecane, sodium hydroxide, tetrabutylammonium bromide and dimethyl sulfoxide into a single-mouth bottle, stirring at normal temperature for 24 hours, and carrying out post-treatment to obtain C10 QA;
the amount ratio of the quinacridone to the feed materials of 1-bromodecane, sodium hydroxide and tetrabutylammonium bromide is 1: 3.5-4: 0.4;
the adding volume of the dimethyl sulfoxide is 8-12 mL/g based on the mass of quinacridone;
the reaction post-treatment method comprises the following steps: after the reaction is finished, extracting with water and dichloromethane for three times, concentrating the extract, removing water with anhydrous sodium sulfate, performing column chromatography purification, collecting eluent containing a target compound by taking silica gel as a stationary phase and dichloromethane and petroleum ether as mobile phases, and performing rotary evaporation to remove a solvent and drying;
the volume ratio of the dichloromethane to the petroleum ether is 2-2.5: 1.
Still further, the operation process of the step (2) is as follows:
under the protection of nitrogen, sequentially adding alkylated quinacridone C10QA, NBS and N, N-dimethylformamide DMF into a reaction bottle, heating and refluxing, reacting for 24 hours in a dark place, and performing post-treatment to obtain C10QA-2 Br;
the mass ratio of the C10QA to the NBS is 1: 3.5-4;
the adding volume of the DMF is 10-15 mL/g calculated by the mass of the alkylated quinacridone;
the reaction post-treatment method comprises the following steps: after the reaction is finished, extracting with water and dichloromethane for three times, concentrating the extract, removing water with anhydrous sodium sulfate, performing column chromatography purification, collecting the eluent containing the target compound by taking silica gel as a stationary phase and dichloromethane and petroleum ether as mobile phases, and performing rotary evaporation to remove the solvent and drying;
the volume ratio of the dichloromethane to the petroleum ether is 1-1.2: 1.
Further, the operation process of the step (3) is as follows:
under the protection of nitrogen, dissolving EDOT in anhydrous and oxygen-free Tetrahydrofuran (THF), dropwise adding n-hexane solution of n-butyllithium at-78 ℃, keeping the temperature and stirring for 1 hour, then adding tributyltin chloride, keeping the temperature and stirring for 1 hour, naturally heating to normal temperature, stirring for 12 hours, and carrying out aftertreatment on the reaction liquid to obtain stannated EDOT;
the mass ratio of the EDOT, the n-butyl lithium and the tributyl tin chloride is 1: 1.05-1.1: 1.3;
the addition amount of the THF is 9-12 mL/g based on the mass of EDOT;
the reaction post-treatment method comprises the following steps: and after the reaction is finished, collecting eluent containing the target compound by taking aluminum oxide as a stationary phase and dichloromethane as a mobile phase, and removing the solvent by rotary evaporation.
Specifically, the operation process of the step (4) is as follows:
under the protection of nitrogen, adding a bromination product C10QA-2Br, EDOT stannide, palladium tetrakis (triphenylphosphine) and DMF into a reaction bottle, heating and refluxing for 12 hours, and carrying out post-treatment to obtain a target product C10QA-2 EDOT;
the mass ratio of the C10QA-2Br to the stanned EDOT is 1: 3.5-4;
the adding volume of the DMF is 20-30 mL/g calculated by the mass of C10QA-2 Br;
the reaction post-treatment method comprises the following steps: after the reaction is finished, extracting with water and dichloromethane for three times, concentrating the extract, removing water with anhydrous sodium sulfate, performing column chromatography purification, collecting the eluent containing the target compound by taking silica gel as a stationary phase and dichloromethane and petroleum ether as mobile phases, and performing rotary evaporation to remove the solvent and drying;
the volume ratio of the dichloromethane to the petroleum ether is 1-1.4: 1.
Specifically, the operation process of step (5) is as follows:
dissolving C10QA-2EDOT shown in a formula (I) in a mixed solution of chromatographic grade dichloromethane and chromatographic grade acetonitrile, adding tetrabutylammonium hexafluorophosphate serving as a supporting electrolyte, sweeping at the speed of 100mV/s, and electrochemically polymerizing by a cyclic voltammetry to form a film, wherein the voltage range is 0-1.2V, and the number of cycles is 4-12;
the concentration of the C10QA-2EDOT is 0.5-5 mmol/L;
in the mixed solution, the volume ratio of dichloromethane: acetonitrile 9: 1;
the concentration of the tetrabutylammonium hexafluorophosphate is 0.05-0.5 mol/L.
The invention has the beneficial effects that: the pigment molecular quinacridone is introduced into the field of electrochromism, and a novel electrochromism material based on the quinacridone is provided. The quinacridone derivative takes quinacridone as a weak acceptor, and forms a strong conjugated structure with a donor 3, 4-Ethylenedioxythiophene (EDOT), so that a polymer film can generate a color change phenomenon under a lower driving voltage, namely, the color change is obvious at 0.3V, the complete conversion from yellow to blue can be realized at 0.9V, and the contrast is not obviously attenuated after 240 cycles, so that the quinacridone derivative shows excellent electrochemical stability, and is a novel electrochromic material with a great application prospect.
(IV) description of the drawings
FIG. 1 is a scheme for the synthesis of quinacridone derivatives according to the present invention;
FIG. 2 is a graph of the electrochemical polymerization of quinacridone derivatives according to the present invention;
FIG. 3 is a graph of the UV-VIS absorption spectra of quinacridone based polymer films according to the present invention at different voltages;
fig. 4 is an illustration of the electrochromic properties of quinacridone based polymer films according to the present invention.
(V) detailed description of the preferred embodiments
The technical solution of the present invention is further illustrated by the following specific examples, but the scope of the present invention is not limited thereto:
example 1: synthesis of C10QA
Quinacridone 3.12g (0.01mol), 1-bromodecane 8.84g (0.04mol), sodium hydroxide 1.6g (0.04mol), tetrabutylammonium bromide 1.3g (0.004mol) and dimethyl sulfoxide 30mL are sequentially added into a 100mL single-neck flask, stirred at normal temperature for 24 hours, after the reaction is finished, water and dichloromethane are extracted for three times, the extract liquid is concentrated and then dehydrated by anhydrous sodium sulfate, column chromatography purification is carried out, silica gel is used as a stationary phase, dichloromethane and petroleum ether are used as mobile phases, the eluent containing the target compound is collected, and the solvent is removed by rotary evaporation and dried to obtain an orange-red solid C10QA with the yield of 85%. The characteristic structure of the confirmed substances is as follows:1H NMR(500MHz，CDCl3)8.82(s，2H)，8.61(dd，2H)，7.80(td，2H)，7.56(d，2H)，7.30(t，2H)，4.55(m，4H)，2.0(m，4H)，1.64(m，4H)，1.47(m，4H)，1.42-1.20(m，20H)，0.90(t，6H)。
example 2: synthesis of C10QA-2Br
C10QA 1.19.19 g (0.002mol), NBS 1.25g (0.007mol) were added toAdding 10mL of N, N-Dimethylformamide (DMF) into a 100mL double-mouth bottle under the protection of nitrogen, heating and refluxing, reacting for 24 hours in a dark place, extracting for three times by using water and dichloromethane after the reaction is finished, concentrating the extract, removing water by using anhydrous sodium sulfate, carrying out column chromatography purification, collecting eluent containing a target compound by using silica gel as a stationary phase and dichloromethane and petroleum ether as mobile phases, removing a solvent by rotary evaporation, and drying to obtain an orange-red solid C10QA-2Br with the yield of 80%. The characteristic structure of the confirmed substances is as follows:1H NMR(500MHz,CDCl3)8.78(s，2H)，8.70(s，2H)，7.85(d，2H)，7.45(d，2H)，4.55(m，4H)，2.0(m，4H)，1.64(m，4H)，1.47(m，4H)，1.42-1.20(m，20H)，0.90(t，6H)。
example 3: synthesis of stanned EDOT
Under nitrogen protection, 2g (0.014mol) of EDOT was dissolved in 20mL of anhydrous and oxygen-free Tetrahydrofuran (THF), 6.16mL (0.0148mol, 2.4M) of an n-hexane solution of n-butyllithium was added dropwise at-78 ℃ and stirred under heat for 1 hour, 5.9g (0.018mol) of tributyltin chloride was added thereto and stirred under heat for 1 hour, followed by naturally increasing to room temperature and stirring for 12 hours. And after the reaction is finished, collecting eluent containing the target compound by using aluminum oxide as a stationary phase and dichloromethane as a mobile phase, and evaporating the solvent to obtain liquid-state tin EDOT.
Example 4: synthesis of C10QA-2EDOT
0.6g (0.8mmol) of C10QA-2Br, a small amount of tetrakis (triphenylphosphine) palladium and a 100mL two-necked flask were charged, and 1.4g (3.2mmol) of stannated EDOT and 20mL and 10mL of DMF were added under nitrogen and heated under reflux for 12 hours. After the reaction is finished, extracting with water and dichloromethane for three times, concentrating the extract, removing water with anhydrous sodium sulfate, performing column chromatography purification, collecting eluent containing a target compound by using silica gel as a stationary phase and dichloromethane and petroleum ether as mobile phases, removing the solvent by rotary evaporation, and drying to obtain a rose-red solid C10QA-2EDOT with the yield of 65%. The characteristic structure of the confirmed substances is as follows:1H NMR(500MHz，CDCl3)8.91(d，J＝2.3Hz，2H)，8.81(s，2H)，8.15(dd，J＝9.1，2.3Hz，2H)，7.55(d，J＝9.2Hz，2H)，6.35(s，2H)，4.55(t，4H)，4.40(m，J＝4.1Hz，4H)，4.32(m，4H)，2.25(m，4H)，1.60(m，4H)，1.52-1.25(m，24H)，0.90(t，6H)。
example 5: electrochemical polymerization of C10QA-2EDOT
The monomer C10QA-2EDOT 8.73mg (0.5mmol/L) and the electrolyte tetrabutylammonium hexafluorophosphate 0.387g (0.1mol/L) are added into a 10mL volumetric flask, the volume is fixed by a mixed solution (volume ratio is 9:1) of chromatographic grade dichloromethane and chromatographic grade acetonitrile, ultrasonic treatment is carried out for 3min, electrochemical polymerization is carried out after complete dissolution, and the electrochemical polymerization curve is shown in figure 2. ITO glass (0.9 x 4cm) is used as a working electrode, a platinum sheet is used as a counter electrode, Ag/AgCl is used as a reference electrode, a film is formed by polymerization through cyclic voltammetry, the voltage range is 0-1.2V, and the number of cycles is 10. The membrane was dedoped in a blank solution (0.387g tetrabutylammonium hexafluorophosphate dissolved in 10mL acetonitrile) for 1min, and then the electrolyte and oligomers on the membrane surface were washed off with a mixture of dichloromethane and acetonitrile.
Example 6: performance testing based on quinacridone electrochromic materials
Adding 0.387g (0.1mol/L) of tetrabutylammonium hexafluorophosphate into a 10mL volumetric flask, carrying out constant volume by using chromatographic grade acetonitrile, taking the obtained solution as a blank solution, taking ITO glass covered with a polymer film as a working electrode and Ag/AgCl as a reference electrode, and carrying out electrochemical, optical and electrochromic performance tests. As a result, it was found that: the film has obvious color change at 0.3V, and can realize complete conversion from yellow to blue at 0.9V, and the ultraviolet absorption of the film is shown in figure 3; the coloring time at 457nm, 707nm and 1100nm are respectively 4.10s, 2.79s and 2.74s, the fading time is respectively 1.53s, 2.22s and 2.15s, the contrast is respectively 16%, 19% and 41%, as shown in figure 4, and the contrast is not obviously attenuated after 240 cycles, thereby showing excellent electrochemical stability.
Claims (7)
1. A quinacridone-based low driving voltage electrochromic material is characterized in that a monomer is shown as a formula (I):
2. the preparation method of quinacridone-based low driving voltage electrochromic material according to claim 1, characterized in that said preparation method comprises the following steps:
(1) quinacridone (II) is subjected to alkylation reaction to obtain quinacridone derivative C10QA (III), the structural formula is respectively as follows:
(2) carrying out bromination reaction on the C10QA (III) and N-bromosuccinimide (NBS) to obtain a brominated product C10QA-2Br (IV), wherein the structural formula of the C10QA-2Br is as follows:
(3)3, 4-Ethylenedioxythiophene (EDOT) reacts with tributyltin chloride to generate stannic EDOT (V), wherein the stannic EDOT has the following structural formula:
(4) c10QA-2Br (IV) and stanned EDOT (V) are subjected to stille coupling reaction to generate a target product C10QA-2EDOT (I);
(5) the C10QA-2EDOT (I) is used as a monomer, and the electrochemical polymerization is adopted to prepare the quinacridone-based low-driving-voltage electrochromic material.
3. The method according to claim 2, wherein the step (1) is performed by:
sequentially adding quinacridone, 1-bromodecane, sodium hydroxide, tetrabutylammonium bromide and dimethyl sulfoxide into a single-mouth bottle, stirring at normal temperature for 24 hours, and carrying out post-treatment to obtain C10 QA; the amount ratio of the quinacridone to the feed materials of 1-bromodecane, sodium hydroxide and tetrabutylammonium bromide is 1: 3.5-4: 0.4; the adding volume of the dimethyl sulfoxide is 8-12 mL/g based on the mass of quinacridone; the reaction post-treatment method comprises the following steps: after the reaction is finished, extracting with water and dichloromethane for three times, concentrating the extract, removing water with anhydrous sodium sulfate, performing column chromatography purification, taking silica gel as a stationary phase, dichloromethane and petroleum ether as a mobile phase, wherein the volume ratio of dichloromethane to petroleum ether is 2-2.5: 1, collecting eluent containing the target compound, performing rotary evaporation to remove the solvent, and drying.
4. The method according to claim 2, wherein the step (2) is performed by: under the protection of nitrogen, sequentially adding C10QA, NBS and N, N-dimethylformamide DMF into a reaction bottle, heating and refluxing, reacting for 24 hours in a dark place, and performing post-treatment to obtain a brominated product C10QA-2 Br; the mass ratio of the C10QA to the NBS is 1: 3.5-4; the adding volume of the DMF is 10-15 mL/g by the mass of C10 QA; the reaction post-treatment method comprises the following steps: after the reaction is finished, extracting with water and dichloromethane for three times, concentrating the extract, removing water with anhydrous sodium sulfate, performing column chromatography purification, taking silica gel as a stationary phase, dichloromethane and petroleum ether as a mobile phase, wherein the volume ratio of dichloromethane to petroleum ether is 1-1.2: 1, collecting eluent containing the target compound, removing the solvent by rotary evaporation, and drying.
5. The method according to claim 2, wherein the step (3) is performed by: under the protection of nitrogen, dissolving EDOT in anhydrous and oxygen-free tetrahydrofuran THF, dropwise adding n-butyl lithium n-hexane solution at-78 ℃, keeping the temperature and stirring for 1 hour, then adding tributyltin chloride, keeping the temperature and stirring for 1 hour, then naturally heating to the normal temperature, stirring for 12 hours, and carrying out aftertreatment on the reaction liquid to obtain stannated EDOT; the mass ratio of the EDOT, the n-butyl lithium and the tributyl tin chloride is 1: 1.05-1.1: 1.3; the addition amount of the THF is 9-12 mL/g based on the mass of EDOT; the reaction post-treatment method comprises the following steps: and after the reaction is finished, collecting eluent containing the target compound by taking aluminum oxide as a stationary phase and dichloromethane as a mobile phase, and removing the solvent by rotary evaporation.
6. The method according to claim 2, wherein the step (4) is performed by: under the protection of nitrogen, adding C10QA-2Br, stanned EDOT, tetrakis (triphenylphosphine) palladium and DMF into a reaction bottle, heating and refluxing for 12 hours, and carrying out post-treatment to obtain a target product C10QA-2 EDOT; the mass ratio of the C10QA-2Br to the stanned EDOT is 1: 3.5-4; the adding volume of the DMF is 20-30 mL/g calculated by the mass of C10QA-2 Br; the reaction post-treatment method comprises the following steps: after the reaction is finished, extracting with water and dichloromethane for three times, concentrating the extract, removing water with anhydrous sodium sulfate, performing column chromatography purification, taking silica gel as a stationary phase, dichloromethane and petroleum ether as a mobile phase, wherein the volume ratio of dichloromethane to petroleum ether is 1-1.4: 1, collecting eluent containing a target compound, removing the solvent by rotary evaporation, and drying to obtain a target product C10QA-2 EDOT.
7. The method according to claim 2, wherein the step (5) is performed by: dissolving C10QA-2EDOT shown in the formula (I) in a mixed solution of dichloromethane and acetonitrile, adding tetrabutylammonium hexafluorophosphate serving as a supporting electrolyte, sweeping at the speed of 100mV/s, electrochemically polymerizing by a cyclic voltammetry to form a film, wherein the voltage range is 0-1.2V, and the number of cycles is 4-12; the concentration of the C10QA-2EDOT is 0.5-5 mmol/L; in the mixed solution, the volume ratio of dichloromethane to acetonitrile is 9: 1; the concentration of the tetrabutylammonium hexafluorophosphate is 0.05-0.5 mol/L.
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| CN114409647B (en) * | 2021-12-07 | 2022-12-30 | 浙江工业大学 | Bifunctional electrochromic material based on quinacridone and preparation method thereof |
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