CN111944513B - Low-driving voltage electrochromic material based on quinacridone and preparation method thereof - Google Patents
Low-driving voltage electrochromic material based on quinacridone and preparation method thereof Download PDFInfo
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Abstract
A quinacridone-based derivative shown in a formula (I), a preparation method thereof and a polymer electrochromic material prepared by taking the quinacridone-based derivative as a monomer. The quinacridone derivative has a rigid planar structure, takes quinacridone as a weak receptor, forms a very strong conjugated structure with donor 3, 4-Ethylenedioxythiophene (EDOT), causes a polymer film to generate a color change phenomenon under lower driving voltage, namely has obvious color change at 0.3V, can realize complete conversion from yellow to blue at 0.9V, has no obvious attenuation of 240 cycle contrast, shows excellent electrochemical stability, and is a novel electrochromic material with huge application prospect.
Description
Field of the art
The invention relates to a pigment molecule based on a quinacridone derivative and an electrochromic material prepared by using the pigment molecule as a monomer.
(II) background art
Electrochromic refers to the fact that under the action of an applied voltage, oxidation-reduction reaction occurs due to charge injection and extraction, and meanwhile, the optical absorption of electrolyte ions changes in the visible light-near infrared region, and the change is macroscopically represented by reversible changes of color and transmittance. The early electrochromic materials mainly comprise inorganic electrochromic materials, but the organic electrochromic materials have the advantages of abundant structural types, excellent electrochromic comprehensive performance, good processing performance and the like, and later have great application value 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), and the energy consumption is relatively increased, so that the wide application of the conductive polymer electrochromic material is limited. Poly (3, 4-ethylenedioxythiophene) (PEDOT) is one of the research hot spots in the electrochromic field due to the characteristics of simple synthesis, relatively low driving voltage, excellent cycling stability and the like. But its color change is relatively single. The quinacridone compound is an inexpensive organic pigment, has good molecular planeness and excellent physicochemical stability, and is easy to modify chemically. Based on the above, the invention designs and synthesizes a novel quinacridone derivative by taking quinacridone as a central core and EDOT as a peripheral active group, and prepares a novel low-driving-voltage electrochromic material by taking the quinacridone derivative as a monomer and adopting electrochemical polymerization so as to further expand the application of the novel low-driving-voltage electrochromic material.
(III) summary of the invention
In order to overcome the defects in the prior art, the invention aims to provide a novel low-driving voltage electrochromic material based on quinacridone and a preparation method thereof.
The technical scheme of the invention is as follows:
a low-driving voltage electrochromic material based on quinacridone, the monomer of which is shown as a formula (I),
a method of preparing a quinacridone-based low drive voltage electrochromic material, the method comprising the steps of:
(1) The quinacridone (II) is subjected to alkylation reaction to obtain a quinacridone derivative C10QA (III), wherein the structural formulas are respectively as follows:
(2) Bromination reaction of C10QA (III) and N-bromosuccinimide (NBS) is carried out 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 produce a stannized EDOT (V), wherein the structural formula of the stannized EDOT is as follows:
(4) C10QA-2Br (IV) and tin-treated EDOT (V) are subjected to a stinlle coupling reaction to generate a target product C10QA-2EDOT (I);
(5) The low-driving voltage electrochromic material based on quinacridone is prepared by electrochemical polymerization by taking C10QA-2EDOT (I) as a monomer.
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 performing post-treatment to obtain C10QA;
the ratio of the amounts of the materials added into the quinacridone, the 1-bromodecane, the sodium hydroxide and the tetrabutylammonium bromide is 1:3.5-4:3.5-4:0.4;
the adding volume of the dimethyl sulfoxide is 8-12 mL/g based on the mass of the quinacridone;
the post-reaction treatment method comprises the following steps: extracting with water and dichloromethane for three times after the reaction is finished, 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 mobile phases, collecting eluent containing target compounds, removing solvent by rotary evaporation, and drying;
the volume ratio of the dichloromethane to the petroleum ether is 2-2.5:1.
Still further, the operation procedure 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, carrying out light-shielding reaction for 24 hours, and carrying out aftertreatment to obtain C10QA-2Br;
the ratio of the amounts of the materials fed into the C10QA and the NBS is 1:3.5-4;
the DMF addition volume is 10-15 mL/g based on the mass of the alkylated quinacridone;
the post-reaction treatment method comprises the following steps: extracting with water and dichloromethane for three times after the reaction is finished, 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 mobile phases, collecting eluent containing target compounds, removing solvent by rotary evaporation, 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 the EDOT in anhydrous and anaerobic Tetrahydrofuran (THF), then dropwise adding n-hexane solution of n-butyllithium at the temperature of-78 ℃, carrying out heat preservation and stirring for 1 hour, then adding tributyltin chloride, continuing to carry out heat preservation and stirring for 1 hour, then naturally heating to normal temperature, stirring for 12 hours, and carrying out post-treatment on the reaction solution to obtain the tin EDOT;
the ratio of the amounts of the materials added into EDOT, n-butyllithium and tributyl tin chloride is 1:1.05-1.1:1.3;
the addition amount of THF is 9-12 mL/g based on the mass of EDOT;
the post-reaction treatment method comprises the following steps: after the reaction is finished, taking aluminum oxide as a stationary phase and methylene dichloride as a mobile phase, collecting eluent containing a target compound, 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, tin EDOT, tetra (triphenylphosphine) palladium and DMF into a reaction bottle, heating and refluxing for 12 hours, and performing post-treatment to obtain a target product C10QA-2EDOT;
the ratio of the amounts of the materials added into the C10QA-2Br and the tin-added EDOT is 1:3.5-4;
the added volume of the DMF is 20-30 mL/g based on the mass of C10QA-2Br;
the post-reaction treatment method comprises the following steps: extracting with water and dichloromethane for three times after the reaction is finished, 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 mobile phases, collecting eluent containing target compounds, removing solvent by rotary evaporation, and drying;
the volume ratio of the dichloromethane to the petroleum ether is 1-1.4:1.
Specifically, the operation procedure of the step (5) is as follows:
c10QA-2EDOT shown in a formula (I) is dissolved in a mixed solution of chromatographic grade dichloromethane and chromatographic grade acetonitrile, tetrabutylammonium hexafluorophosphate is added as a supporting electrolyte, the sweeping speed is 100mV/s, and electrochemical polymerization is carried out to form a film by a cyclic voltammetry, the voltage range is 0-1.2V, and the cycle number 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: pigment molecules quinacridone are introduced into the field of electrochromic, and a novel electrochromic material based on quinacridone is provided. The quinacridone derivative takes quinacridone as a weak receptor, forms a very strong conjugated structure with donor 3, 4-Ethylenedioxythiophene (EDOT), so that a polymer film can generate a color change phenomenon under 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 color change is not obviously attenuated by 240 cycles, so that the quinacridone derivative shows excellent electrochemical stability, and is a novel electrochromic material with great application prospect.
(IV) description of the drawings
FIG. 1 is a synthetic route to quinacridone derivatives according to the invention;
FIG. 2 is a graph of electrochemical polymerization of quinacridone derivatives according to the invention;
FIG. 3 is a graph of the ultraviolet-visible absorption spectra of quinacridone based polymer films according to the invention at different voltages;
fig. 4 is an electrochromic profile of a quinacridone based polymer film according to the invention.
(fifth) detailed description of the invention
The following describes the technical scheme of the present invention with specific examples, but the scope of the present invention is not limited thereto:
example 1: synthesis of C10QA
3.12g (0.01 mol) of quinacridone, 8.84g (0.04 mol) of 1-bromodecane, 1.6g (0.04 mol) of sodium hydroxide, 1.3g (0.004 mol) of tetrabutylammonium bromide and 30mL of dimethyl sulfoxide are sequentially added into a 100mL single-neck flask, stirring is carried out for 24 hours at normal temperature, water and dichloromethane are used for extraction three times after the reaction is finished, the extract is concentrated and 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, eluent containing a target compound is collected, solvent is removed by rotary evaporation, and drying is carried out, thus obtaining orange-red solid C10QA with the yield of 85%. The characterization structure of the validation material is as follows: 1 H NMR(500MHz，CDCl 3 )δ8.82(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 1.19g (0.002 mol) and NBS 1.25g (0.007 mol) are added into a 100mL double-mouth bottle, 10mL of N, N-Dimethylformamide (DMF) is added under the protection of nitrogen, heating reflux and light-shielding reaction are carried out for 24 hours, after the reaction is finished, water and dichloromethane are used for extraction for three times, anhydrous sodium sulfate is used for removing water after the concentration of extract liquid, column chromatography purification is carried out, silica gel is used as stationary phase, dichloromethane and petroleum ether are used as mobile phase, eluent containing target compounds is collected, solvent is removed by rotary evaporation and drying is carried out, and orange-red solid C10QA-2Br is obtained, and the yield is 80%. The characterization structure of the validation material is as follows: 1 H NMR(500MHz,CDCl 3 )δ8.78(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 tin EDOT
EDOT 2g (0.014 mol) was dissolved in 20mL anhydrous and anaerobic Tetrahydrofuran (THF) under nitrogen protection, then 6.16mL (0.0148 mol, 2.4M) of n-hexane solution of n-butyllithium was added dropwise at-78℃and stirred for 1 hour under heat preservation, then 5.9g (0.018 mol) of tributyltin chloride was added and stirring was continued for 1 hour under heat preservation, followed by natural rising to normal temperature and stirring for 12 hours. After the reaction is finished, taking aluminum oxide as a stationary phase and methylene dichloride as a mobile phase, collecting eluent containing a target compound, and evaporating a solvent to obtain liquid tin EDOT.
Example 4: synthesis of C10QA-2EDOT
0.6g (0.8 mmol) of C10QA-2Br, a small amount of tetrakis (triphenylphosphine) palladium was added to a 100mL double-necked flask, and 1.4g (3.2 mmol) of tinned 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, taking silica gel as a stationary phase, dichloromethane and petroleum ether as mobile phases, collecting eluent containing target compounds, removing the solvent by rotary evaporation, and drying to obtain the rose solid C10QA-2EDOT with the yield of 65%. The characterization structure of the validation material is as follows: 1 H NMR(500MHz，CDCl 3 )δ8.91(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
Monomer C10QA-2EDOT 8.73mg (0.5 mmol/L) and electrolyte tetrabutylammonium hexafluorophosphate 0.387g (0.1 mol/L) are added into a 10mL volumetric flask, the volume is fixed by chromatographic grade dichloromethane and chromatographic grade acetonitrile mixed solution (volume ratio is 9:1), ultrasonic treatment is carried out for 3min, after complete dissolution, electrochemical polymerization is carried out, and an electrochemical polymerization curve is shown in figure 2. ITO glass (0.9 x 4 cm) is used as a working electrode, a platinum sheet is used as a counter electrode, ag/AgCl is used as a reference electrode, and the ITO glass is polymerized into a film by adopting a cyclic voltammetry, wherein the voltage range is 0-1.2V, and the number of cycles is 10. The membrane was dedoped in a blank solution (0.387 g 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
Tetrabutylammonium hexafluorophosphate (0.387 g, 0.1 mol/L) was added to a 10mL volumetric flask, the volume was determined using chromatographic grade acetonitrile, which was used as a blank solution, ITO glass covered with a polymer film was used as a working electrode, ag/AgCl was used as a reference electrode, and electrochemical, optical and electrochromic performance tests were performed. The result shows that: the film had a clear color change at 0.3V and a complete transition from yellow to blue at 0.9V, with uv absorption as shown in fig. 3; the coloring times at 457nm, 707nm and 1100nm are respectively 4.10s, 2.79s and 2.74s, the fading times are respectively 1.53s, 2.22s and 2.15s, the contrast is respectively 16%, 19% and 41%, as shown in FIG. 4, and the contrast is not obviously attenuated after 240 cycles, and the excellent electrochemical stability is shown.
Claims (7)
1. A low-driving voltage electrochromic material based on quinacridone is characterized in that the monomer is shown as a formula (I):
2. the method for preparing the quinacridone-based low driving voltage electrochromic material according to claim 1, wherein the preparation method comprises the following steps:
(1) The quinacridone (II) is subjected to alkylation reaction to obtain a quinacridone derivative C10QA (III), wherein the structural formulas are respectively as follows:
(2) Bromination reaction of C10QA (III) and N-bromosuccinimide (NBS) is carried out 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 produce a stannized EDOT (V), wherein the structural formula of the stannized EDOT is as follows:
(4) C10QA-2Br (IV) and tin-treated EDOT (V) are subjected to a stinlle coupling reaction to generate a target product C10QA-2EDOT (I);
(5) The low-driving voltage electrochromic material based on quinacridone is prepared by electrochemical polymerization by taking C10QA-2EDOT (I) as a monomer.
3. The method of claim 2, wherein the step (1) is performed 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 performing post-treatment to obtain C10QA; the ratio of the amounts of the materials added into the quinacridone, the 1-bromodecane, the sodium hydroxide and the tetrabutylammonium bromide is 1:3.5-4:3.5-4:0.4; the adding volume of the dimethyl sulfoxide is 8-12 mL/g based on the mass of the quinacridone; the post-reaction treatment method comprises the following steps: after the reaction is finished, extracting with water and dichloromethane for three times, concentrating the extract, removing water by using anhydrous sodium sulfate, performing column chromatography purification, taking silica gel as a stationary phase, taking dichloromethane and petroleum ether as mobile phases, collecting eluent containing target compounds, removing solvent by rotary evaporation, and drying.
4. The method of claim 2, wherein the step (2) is performed as follows: under the protection of nitrogen, sequentially adding C10QA, NBS and N, N-dimethylformamide DMF into a reaction bottle, heating and refluxing, carrying out light-shielding reaction for 24 hours, and carrying out post-treatment to obtain a brominated product C10QA-2Br; the ratio of the amounts of the materials fed into the C10QA and the NBS is 1:3.5-4; the DMF adding volume is 10-15 mL/g based on the mass of C10QA; the post-reaction treatment method comprises the following steps: after the reaction is finished, extracting with water and dichloromethane for three times, concentrating the extract, removing water by using anhydrous sodium sulfate, performing column chromatography purification, taking silica gel as a stationary phase, taking dichloromethane and petroleum ether as mobile phases, the volume ratio of the dichloromethane to the petroleum ether is 1-1.2:1, collecting eluent containing target compounds, removing solvent by rotary evaporation, and drying.
5. The method of claim 2, wherein the step (3) is performed as follows: under the protection of nitrogen, dissolving the EDOT in anhydrous and anaerobic tetrahydrofuran THF, then dropwise adding n-hexane solution of n-butyllithium at the temperature of minus 78 ℃, carrying out heat preservation and stirring for 1 hour, then adding tributyltin chloride, continuing to carry out heat preservation and stirring for 1 hour, then naturally heating to normal temperature, stirring for 12 hours, and carrying out post-treatment on the reaction solution to obtain the tin EDOT; the ratio of the amounts of the materials added into EDOT, n-butyllithium and tributyl tin chloride is 1:1.05-1.1:1.3; the addition amount of THF is 9-12 mL/g based on the mass of EDOT; the post-reaction treatment method comprises the following steps: after the reaction is finished, taking aluminum oxide as a stationary phase and methylene dichloride as a mobile phase, collecting eluent containing a target compound, and removing the solvent by rotary evaporation.
6. The method of claim 2, wherein the step (4) is performed as follows: under the protection of nitrogen, adding C10QA-2Br, tin EDOT, tetra (triphenylphosphine) palladium and DMF into a reaction bottle, heating and refluxing for 12 hours, and performing post-treatment to obtain a target product C10QA-2EDOT; the ratio of the amounts of the materials added into the C10QA-2Br and the tin-added EDOT is 1:3.5-4; the added volume of the DMF is 20-30 mL/g based on the mass of C10QA-2Br; the post-reaction treatment method comprises the following steps: after the reaction is finished, extracting with water and dichloromethane for three times, concentrating the extract, removing water by using anhydrous sodium sulfate, performing column chromatography purification, taking silica gel as a stationary phase, taking dichloromethane and petroleum ether as mobile phases, wherein the volume ratio of the dichloromethane to the petroleum ether is 1-1.4:1, collecting eluent containing target compounds, removing the solvent by rotary evaporation, and drying to obtain a target product C10QA-2EDOT.
7. The method of claim 2, wherein the step (5) is performed as follows: c10QA-2EDOT shown in a formula (I) is dissolved in a mixed solution of dichloromethane and acetonitrile, tetrabutylammonium hexafluorophosphate is added as a supporting electrolyte, the sweeping speed is 100mV/s, and the membrane is formed by electrochemical polymerization by a cyclic voltammetry, wherein the voltage range is 0-1.2V, and the cycle number 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=9:1; the concentration of the tetrabutylammonium hexafluorophosphate is 0.05-0.5 mol/L.
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