CN110255923B - TiO 22Nanoparticle adsorption perylene bisimide derivative film and application thereof as electrochromic material - Google Patents
TiO 22Nanoparticle adsorption perylene bisimide derivative film and application thereof as electrochromic material Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
- C03C17/34—Surface treatment of glass, not in the form of fibres or filaments, by coating with at least two coatings having different compositions
- C03C17/42—Surface treatment of glass, not in the form of fibres or filaments, by coating with at least two coatings having different compositions at least one coating of an organic material and at least one non-metal coating
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- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C2218/00—Methods for coating glass
- C03C2218/10—Deposition methods
- C03C2218/11—Deposition methods from solutions or suspensions
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- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C2218/00—Methods for coating glass
- C03C2218/10—Deposition methods
- C03C2218/11—Deposition methods from solutions or suspensions
- C03C2218/111—Deposition methods from solutions or suspensions by dipping, immersion
Abstract
The invention discloses a TiO 22The nanometer particle adsorbing perylene bisimide derivative film and the application as electrochromic material, the TiO2The film with the perylene bisimide derivative adsorbed by the nano particles is prepared by mixing N, N' -bis (2-phosphoethyl) -3,4,9, 10-perylene tetracarboxylic acid diimine (PPDI) and TiO2The nanoparticles are obtained by chemisorption. Compared with other existing electrochromic materials, the electrochromic material prepared by the invention has the advantages of reversible color change, high color contrast, relatively fast response time and the like. The material can show color change from red to purple, has optical contrast up to 30.05% and coloring time of 1.62s, and is a potential electrochromic material.
Description
(I) technical field
The invention belongs to the technical field of electrochromic materials, and particularly relates to TiO2The nanometer particle adsorbing perylene bisimide derivative film and the application thereof as an electrochromic material, wherein the electrochromic material can be used in an electrochromic device.
(II) background of the invention
Electrochromism refers to the optical properties of an electroactive material, including the phenomenon that the transmittance, reflectance, color, and the like of the material reversibly change under an applied electric field. The most intuitive change is the change of color under different voltages, and more importantly, the change of the color has reversibility.
According to the different types of electrochromic materials, the electrochromic materials can be divided into inorganic electrochromic materials and organic electrochromic materials, and the inorganic electrochromic materials have higher cycling stability due to the stable molecular structure of the inorganic materials; the molecular structure of the organic electrochromic material is easy to modify, the color is richer, and the response speed is faster.
Perylene imide is one of the most widely studied organic pigment dyes, and the structure of perylene imide is a pi-aggregated electron-deficient aromatic structure, which has good optical and thermal properties, but has limitations in application due to the problems of solubility and film-forming property. Later, people find that the substitution of the electron-withdrawing group at the amide position can effectively adjust the solubility and the photoelectric characteristics of the perylene bisimide derivative in a solvent. For example, the amide position of perylene imide is modified by adopting an electron-withdrawing group such as phosphoric acid or carboxylic acid, and the solubility of perylene imide can be effectively improved. Although the solubility of the perylene imide derivative is well improved, most perylene imide derivatives are difficult to form into films or are easy to fall off after the films are formed, so that the application of the perylene imide derivative as an electrochromic material is limited. TiO 22Is a typical inorganic electrochromic material, can generate reversible oxidation-reduction reaction under negative potential, besides, TiO2And is also considered to be an excellent substrate for semiconductors for mounting and for display materials. By calcining TiO on a layer of ITO2Nanoparticles, recycled TiO2The nano particles and phosphoric acid or carboxylic acid on the organic small molecules form chemical adsorption, so that the film forming problem is solved.
Disclosure of the invention
The invention aims to provide TiO2The film has reversible reduction/oxidation discoloration phenomena, high contrast and short response time.
The technical scheme of the invention is explained in detail as follows:
one of the purposes of the invention is to provide TiO2The nanometer particle adsorbs perylene bisimide derivative film, the TiO2The film with the perylene bisimide derivative adsorbed by the nano particles is prepared by mixing N, N' -bis (2-phosphoethyl) -3,4,9, 10-perylene tetracarboxylic acid diimine (PPDI) and TiO2The nanoparticles are obtained by chemisorption.
Further, the invention also provides TiO shown as the formula (I)2The preparation method of the film with the perylene bisimide derivatives adsorbed by the nano particles comprises the following steps:
(1) adding TiO into the mixture2Dispersing the nano particles in deionized water to obtain TiO2Nano-dispersion, then adding to said TiO2Adding acetic acid into the nano dispersion liquid, placing the nano dispersion liquid into a reaction kettle for full reaction at the temperature of 140-180 ℃, then adding polyethylene glycol, uniformly stirring until the reaction liquid is viscous paste, then uniformly coating the reaction liquid on a conductive substrate in a spinning way, placing the conductive substrate in a drying oven for drying, placing the conductive substrate in a muffle furnace for heat treatment after drying, and forming TiO on the surface of the conductive substrate2A nanoparticle film; the TiO is2The mass ratio of the nanoparticles to the water is 1: 10; the concentration of the acetic acid is 0.05-0.2 mol/L; the volume ratio of the water to the acetic acid is 2-4: 1; the polyethylene glycol and TiO2The mass ratio of the nano particles is 0.3-0.5: 1;
(2) coating the TiO obtained in the step (1)2Immersing a conductive base material of the nano-particle film in N, N' -bis (2-phosphoethyl) -3,4,9, 10-perylenetetracarboxylic acid diimine (PPDI) water solution, standing for 24-48 h at room temperature, and allowing TiO on the conductive base material to stand2The nano particles can form chemical bonds with hydroxyl (-OH) in N, N' -bis (2-phosphoethyl) -3,4,9, 10-perylenetetracarboxylic acid diimine (PPDI) aqueous solution to obtain a target product TiO2The nanometer particles adsorb the perylene bisimide derivative film.
Still further, in the step (1), the TiO is2The diameter of the nanoparticles is 5-100 nm.
Still further, in the step (1), the conductive substrate is indium tin oxide conductive glass or fluorinated doped tin oxide glass.
And (2) in the step (1), the reaction time is 8-15 h.
And (2) further, in the step (1), the drying temperature is 60-80 ℃, and the drying time is 3-6 hours.
And (2) in the step (1), the calcining temperature is 400-500 ℃, and the calcining time is 1-2 hours.
And (2) further, in the step (1), the stirring time is 6-12 h.
And (3) in the step (2), the concentration of the N, N' -bis (2-phosphoethyl) -3,4,9, 10-perylenetetracarboxylic acid diimine (PPDI) aqueous solution is 5-20 mmol/L.
Further, specifically, the preparation method of the N, N' -bis (2-phosphoethyl) -3,4,9, 10-perylenetetracarboxylic acid diimine (PPDI) comprises the following steps:
(1) synthesis of N, N' -bis (2-phosphobisimidazoleethyl) -3,4,9, 10-perylenetetracarboxylic acid diimine: mixing perylene-3, 4,9, 10-tetracarboxylic dianhydride, 2-aminoethyl phosphonic acid and imidazole, reacting at 130-150 ℃, and separating and purifying a reactant a obtained after full reaction to obtain N, N' -bis (2-phosphodiimidazole ethyl) -3,4,9, 10-perylene tetracarboxylic acid diimine;
(2) synthesis of N, N' -bis (2-bissodiumethyl phosphate) -3,4,9, 10-perylenetetracarboxylic acid diimine: adding a sodium hydroxide aqueous solution into N, N '-bis (2-phosphoimidazole ethyl) -3,4,9, 10-perylene tetracarboxylic acid diimine, and separating and purifying a reactant b obtained after fully stirring to obtain N, N' -bis (2-phosphodisodium ethyl) -3,4,9, 10-perylene tetracarboxylic acid diimine;
(3) synthesis of PPDI: and (3) acidifying the N, N' -bis (2-sodium phosphate ethyl) -3,4,9, 10-perylene tetracarboxylic acid diimine by using excessive hydrochloric acid, and separating, purifying and drying a reactant c obtained after full reaction to obtain PPDI.
Further, in the step (1), the ratio of the amounts of the perylene-3, 4,9, 10-tetracarboxylic dianhydride, 2-aminoethylphosphonic acid and imidazole is 1: 2: 18.
further, in the step (1), the reaction time is 15-30 min.
Further, in the step (1), the separation and purification steps of the reactant a are as follows: after the reaction, the reaction mixture was cooled, washed with (V ethanol: V2mol/L HCl 1: 1), (V ethanol: V water 1: 1) and an ethanol solution, and filtered, and the filtrate was filtered off and dried under vacuum to obtain N, N' -bis (2-phosphobisimidazolylethyl) -3,4,9, 10-perylenetetracarboxylic acid diimine.
Further, in the step (2), the ratio of the amount of the sodium hydroxide to the amount of the N, N' -bis (2-phosphodiimidazole ethyl) -3,4,9, 10-perylenetetracarboxylic acid diimine is 4: 1-5: 1.
further, in the step (2), the temperature is room temperature, and the stirring time is 10-20 min.
Further, in the step (2), the separation and purification steps of the reactant b are as follows: after stirring, filtering, and filtering out solids to obtain the N, N' -bis (2-disodium ethyl phosphate) -3,4,9, 10-perylene tetracarboxylic acid diimine.
Further, in the step (3), the concentration of hydrochloric acid is 12-16 mol/L.
Further, in the step (3), the reaction temperature is room temperature, and the reaction time is 48-72 hours.
Further, in the step (3), the separation and purification steps of the reactant c are as follows: after the acidification was completed, washing with ethanol solution and filtering, filtering off the filtrate, and drying under vacuum to obtain PPDI. The second object of the present invention is to provide TiO2The film with the perylene bisimide derivatives adsorbed by the nano particles can be used as an electrochromic material, and the color is changed from red to purple along with the application of voltage from zero to negative; when the voltage gradually returns to zero, the color changes back to red.
The electrochromic material provided by the invention has reversible reduction/oxidation discoloration phenomena, high contrast and short response time.
Compared with the prior art, the invention has the advantages that:
(1) the invention introduces phosphate group at the imine site of perylene bisimide and adopts TiO2The method for adsorbing the perylene bisimide derivative by the nano particles successfully prepares the electrochromic film, and solves the problems that organic dye perylene bisimide is poor in solubility and difficult to form the film.
(2) Compared with other existing electrochromic materials, the electrochromic material prepared by the invention has the advantages of reversible color change, fast response time, good stability and the like. The contrast ratio can reach 30.05%, and the coloring response time is 1.62 s.
Drawings
FIG. 1TiO2The structure of the perylene bisimide derivative film adsorbed by the nano particles is shown schematically.
FIG. 2 is TiO2Nanoparticles and their TiO2Scanning electrode of PPDI film adsorbed by nano particlesA mirror photograph.
FIG. 3 is TiO2Nanoparticles and their TiO2Cyclic voltammogram of a PPDI film adsorbed by nanoparticles.
FIG. 4 is TiO2Nanoparticles and their TiO2The nano-particles adsorb the PPDI biological film under different voltages and the ultraviolet-visible absorption spectrum is obtained.
FIG. 5 is TiO2Contrast and response time curves of the nano-particle adsorbed PPDI film at different wavebands.
Detailed Description
The technical solution of the present invention is further illustrated by the following examples, but the scope of the present invention is not limited thereto.
Example 1: synthesis of PPDI
(1) Synthesis of N, N' -bis (2-phosphodiimidazoleethyl) -3,4,9, 10-perylenetetracarboxylic acid diimine
Perylene-3, 4,9, 10-tetracarboxylic dianhydride (157mg, 0.40mmol), 2-aminoethylphosphonic acid ((100mg, 0.80 mmol) and imidazole ((0.5g, 7.35mmol) were added in sequence to a 50mL single-neck flask which had been previously dried, after they were mixed well, the temperature was raised to 135 deg.c, at the moment, imidazole is melted into liquid, the reaction is carried out for 15min, the heating device is closed when the reaction end point is reached, and the solid crude product is obtained after the reaction is cooled to room temperature, wherein the solid crude product is prepared by respectively using (ethanol: 2mol/L HCl ═ 1: 1), (ethanol: water 1: 1) and ethanol solution and filtering, filtering the filtrate, drying under vacuum gave 200mg of N, N' -bis (2-phosphobisimidazoleethyl) -3,4,9, 10-perylenetetracarboxylic acid diimine in 74.3% yield as a dark red solid.
(2) Synthesis of N, N' -bis (2-disodium ethyl phosphate) -3,4,9, 10-perylene tetracarboxylic acid diimine
The prepared N, N '-bis (2-bisimidazolylethyl phosphate) -3,4,9, 10-perylenetetracarboxylic acid diimine (200mg) is added into a 50mL beaker which is dried in advance, a sodium hydroxide aqueous solution (1.6mmol) is added into the beaker, the mixture is fully stirred, the mixed solution is filtered, and solids are filtered off to obtain the N, N' -bis (2-bisodiumlethyl phosphate) -3,4,9, 10-perylenetetracarboxylic acid diimine, wherein the product is a dark red solution.
1H NMR(500MHz,D2O)δ7.84(d,J＝158.8Hz,8H),4.31(s, 4H),1.90(s,4H).
(3) Synthesis of PPDI
Adding the prepared N, N' -bis (2-disodium ethyl phosphate) -3,4,9, 10-perylene tetracarboxylic acid diimine into a surface dish which is dried in advance, taking 50mL of concentrated hydrochloric acid from a 100mL beaker, putting the perylene bisimide derivative sodium salt and the concentrated hydrochloric acid together into a closed container for acidification, and standing for 48 hours at room temperature. After the acidification was complete, it was washed with ethanol solution and filtered, the filtrate was filtered off and dried under vacuum to give PPDI150mg in 42% yield as a dark red solid.
Elemental analysis (CNOP), calculated for C28H20N2O10P2(theoretical) 58.07% C (57.33%); 5.67% N (4.78%); 26.97% O (27.3%); 9.29% P (10.58%).
Example 2: TiO 22Preparation of nanoparticle-adsorbed PPDI film
Adding TiO with the diameter of 20nm into a 25mL beaker which is subjected to drying treatment in advance2Uniformly mixing nano particles (1g), deionized water (10mL) and 0.1mol/L acetic acid (5mL), putting the mixture into a reaction kettle, placing the reaction kettle into a drying oven at 150 ℃ and keeping the temperature for 12 hours, pouring the treated mixed solution into a 25mL beaker subjected to drying treatment in advance, adding 0.4g of polyethylene glycol, stirring the mixture at room temperature for 8 hours to obtain viscous paste, rotating the viscous paste on cleaned ITO at the rotating speed of 1000rmb/min, drying the coated ITO in the drying oven at 80 ℃, drying the ITO for 1 hour, putting the ITO into a muffle furnace at 450 ℃ for heat treatment, and treating the ITO for 1 hour to obtain transparent TiO with a certain thickness2A nanoparticle film. Treated TiO2The ITO of the nano-particle film is put into 5mmol/L PPDI water solution and stands for 36h under the condition of room temperature, and then TiO on the ITO2The nanoparticles will form a chemical bond with-OH in PPDI, thereby adsorbing a layer of PPDI thereon. To obtain TiO2The nanometer particles adsorb the perylene bisimide derivative film.
We observed TiO with a scanning electron microscope2And TiO thereof2The microscopic morphology of the PPDI film adsorbed by the nanoparticles, as shown in FIG. 2The TiO can be seen from the surface appearance2Nanoparticles are uniformly attached to the ITO surface, the diameter of the nanoparticles is about 20nm, PPDI is tightly adsorbed on the ITO surface, the film shows uniform distribution, a small amount of pores exist, and the thickness of the self-assembled film depends on TiO spin-coated on ITO according to the cross-sectional morphology2The thickness of the nanoparticle particles was about 366 nm.
Example 3: TiO 22Electrochromic property of nano-particle adsorbed PPDI film
The ITO glass-coated TiO prepared in example 22Putting the PPDI film adsorbed by the nano particles into a three-electrode electrolytic cell, and taking a solution dissolved with 0.2 mol/L1-butyl-3 methyl-imidazole trifluoromethanesulfonate/propylene carbonate as an electrolytic solution, wherein the working electrode is attached with TiO2The nano particles adsorb ITO glass of the PPDI film, the counter electrode is a platinum wire, and the reference electrode is a silver-silver chloride electrode. Scanning for 10 weeks at a scanning voltage of 0-1.3V and a scanning speed of 100mV/s by adopting cyclic voltammetry. The film can be observed with naked eyes to change the color from red to purple along with the decrease of the negative voltage, and the color changes to red again after the negative voltage is increased, and the steps are repeated. The redox peak on the cyclic voltammogram was recorded as a function of the film color (see table 1). Furthermore, it can be seen from FIG. 3 that TiO is present under these conditions2The nanoparticles do not have redox properties, so TiO2The oxidation reduction peaks of the nanoparticles adsorbing PPDI are all attributed to PPDI.
TABLE 1 relationship between Redox Peak and film color
| |
0～-0.9V | -0.9V～-1.3V |
| Colour(s) | Red colour | Purple color |
Example 4: response speed and contrast ratio of PPDI self-assembled film
The ITO glass-coated TiO prepared in example 22Putting the PPDI film adsorbed by the nano particles into a three-electrode electrolytic cell, and taking a solution dissolved with 0.2 mol/L1-butyl-3 methyl-imidazole trifluoromethanesulfonate/propylene carbonate as an electrolyte solution, wherein a working electrode is attached with TiO2The nano-particle ITO glass adsorbing the PPDI film is characterized in that a counter electrode is a platinum wire, and a reference electrode is a silver-silver chloride electrode. The method adopts a combined technology of an electrochemical workstation and an ultraviolet spectrometer, wherein the electrochemical workstation is set to be a constant potential electrolysis method, the ultraviolet spectrum is set to be ultraviolet visible absorption, and the scanning range is 1100-350 nm. The finally obtained data are shown in FIG. 4, and FIG. 4 shows that under the condition of a neutral state of 0V, a strong absorption peak exists at 480nm of the PPDI self-assembly film, the intensity of the peak is gradually reduced along with the increase of negative voltage, and new absorption peaks appear at 725 nm, 811 nm and 978nm, which indicates that PPDI is reduced to generate an anion free radical form; as the negative voltage continued to increase, a new absorption peak appeared at 630nm and the intensity of the absorption peak at 524nm increased, with no more absorption peak at 480nm, indicating further reduction of the PPDI radical anion to the dianion form. In addition, it can be seen from the figure that TiO is present under these conditions2The nano-particles have no absorption in all bands and show higher transmittance (70%), so TiO2The ultraviolet absorption of PPDI adsorbed by the nanoparticles is attributed to PPDI.
To detect TiO2The response speed and contrast of the PPDI film adsorbed by the nanoparticles are realized by adopting a combined technology of an electrochemical workstation and an ultraviolet spectrometer, wherein the electrochemical workstation is set to be a multi-potential step method: the initial potential is 0V, the final potential is-1.2V, the potential pulse width is 10s, and the scanning time is 200 s; ultraviolet spectrum is set as spectral dynamics and wavelengths are respectivelyThe settings were 524nm and 630 nm. The resulting data is shown in FIG. 5. from FIG. 5, it can be seen that at 524nm, TiO is present2The contrast of PPDI adsorbed by the nanoparticles is 17.258%, the coloring time is 2.2s, and the fading time is 7.00 s; at 630nm, TiO2The contrast of the nanoparticles adsorbing PPDI was 30.05%, the coloration time was 1.62s, and the fade time was 8.07 s.
Claims (9)
1. TiO 22The film with the perylene bisimide derivative adsorbed by the nano particles is characterized in that: the TiO is2The film with the perylene bisimide derivatives adsorbed by the nano particles is prepared by the following method:
(1) adding TiO into the mixture2Dispersing the nano particles in deionized water to obtain TiO2Nano-dispersion, then adding to said TiO2Adding acetic acid into the nano dispersion liquid, placing the nano dispersion liquid into a reaction kettle for full reaction at the temperature of 140-180 ℃, then adding polyethylene glycol, uniformly stirring until the reaction liquid is viscous paste, then uniformly coating the reaction liquid on a conductive substrate in a spinning way, placing the conductive substrate in a drying oven for drying, then placing the conductive substrate in a muffle furnace at the temperature of 400-500 ℃ for heat treatment, and forming TiO on the surface of the conductive substrate2A nanoparticle film; the TiO is2The mass ratio of the nanoparticles to the water is 1: 10; the concentration of the acetic acid is 0.05-0.2 mol/L; the volume ratio of the water to the acetic acid is 2-4: 1; the polyethylene glycol and TiO2The mass ratio of the nano particles is 0.3-0.5: 1;
(2) coating the TiO obtained in the step (1)2Immersing a conductive base material of the nano-particle film in an N, N' -bis (2-phosphoethyl) -3,4,9, 10-perylene tetracarboxylic acid diimine aqueous solution, and standing for 24-48 h at room temperature to obtain a target product TiO2The nanometer particles adsorb the perylene bisimide derivative film.
2. The TiO of claim 12The film with the perylene bisimide derivative adsorbed by the nano particles is characterized in that: in the step (1), the TiO is2The diameter of the nanoparticles is 5-100 nm.
3. Such as rightThe TiO of claim 12The film with the perylene bisimide derivative adsorbed by the nano particles is characterized in that: the conductive substrate is indium tin oxide conductive glass or fluorinated doped tin oxide glass.
4. The TiO of claim 12The film with the perylene bisimide derivative adsorbed by the nano particles is characterized in that: in the step (1), the reaction time is 8-15 h.
5. The TiO of claim 12The film with the perylene bisimide derivative adsorbed by the nano particles is characterized in that: in the step (1), the drying temperature is 60-80 ℃, and the drying time is 3-6 h.
6. The TiO of claim 12The film with the perylene bisimide derivative adsorbed by the nano particles is characterized in that: in the step (1), the time of the heat treatment is 1-2 h.
7. The TiO of claim 12The film with the perylene bisimide derivative adsorbed by the nano particles is characterized in that: in the step (1), the stirring time is 6-12 h.
8. The TiO of claim 12The film with the perylene bisimide derivative adsorbed by the nano particles is characterized in that: in the step (2), the concentration of the N, N' -bis (2-phosphoethyl) -3,4,9, 10-perylene tetracarboxylic acid diimine aqueous solution is 5-20 mmol/L.
9. The TiO of claim 12The application of the nanometer particle adsorbing perylene bisimide derivative film as an electrochromic material.
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