CN112079840B - Indole derivative-thiophene compound and preparation and application thereof - Google Patents
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Abstract
The invention provides an indole derivative-thiophene compound, and a preparation method and application thereof, wherein the indole derivative is used as a central core, thiophene is used as a peripheral group, and the structure is shown as a formula (1). The invention has the following main effects: (1) The indole derivative-thiophene compound has a reticular space structure, and is subjected to electrochemical polymerization to form a film, so that the obtained film has a large specific surface area and good electrochemical properties such as electrochromic; (2) The film prepared by taking the compound as a monomer through electrochemistry can realize arbitrary switching from yellow to green, has an optical contrast of 20-50%, and a response time of 0.5-9 s, shows relatively good spectroelectrochemical stability in any wave band, and is a potential electrochromic material capable of being used for military camouflage.
Description
Field of the art
The invention relates to an indole derivative-thiophene compound, and a preparation method and application thereof.
(II) background art
With the rapid consumption of global energy and the continuous deterioration of the environment. Energy-saving and environment-friendly materials attract wide attention of people. Electrochromic materials are one such new type of functional materials that can change the human production lifestyle and contribute to the rational utilization of energy. The material has the advantages of rich sources, simple device preparation process, low working voltage and the like, and can be widely applied to the fields of intelligent windows, electronic paper, displays and the like. The conductive polymer-based electrochromic material is the most potential substance in the electrochromic material due to easy modification of structure, higher coloring efficiency, shorter response time, higher optical contrast and richer color conversion.
Currently, electrochromic conductive polymers are mainly linear polymers, and network electrochromic conductive polymers are rarely reported.
(III) summary of the invention
The invention aims to provide a reticular electrochromic conductive high molecular compound, namely an indole derivative-thiophene compound, and a preparation method and application thereof.
The technical scheme adopted by the invention is as follows:
an indole derivative-thiophene compound takes the indole derivative as a central core, thiophene as a peripheral group, and the structure is shown as a formula (1):
the invention also relates to a method for preparing the indole derivative-thiophene compound, which comprises the following steps:
(1) Thiophene is dissolved in anhydrous tetrahydrofuran, n-butyllithium solution (with the concentration of 1-3 mol/L) is dropwise added under nitrogen protection at the temperature of minus 78 ℃, tributyltin chloride hexane solution (with the concentration of 1-5 g/mL) is added after stirring for 0.3-1 h, tributyltin chloride is recovered to room temperature after the addition is finished, stirring is carried out for 6-24 h, and the obtained reaction solution A is subjected to post-separation and purification to obtain a compound shown in a formula 2; the mass ratio of the thiophene to the n-butyllithium to the tributyl tin chloride is 1:1-1.1:1-1.6;
(2) Under the nitrogen atmosphere, mixing a compound shown in a formula 1, a catalyst and a compound shown in a formula 2, dissolving in anhydrous DMF, heating to 120+/-20 ℃, stirring and refluxing for 6-16 hours, and separating and purifying the obtained reaction solution B to obtain an indole derivative-thiophene compound shown in the formula (1); the ratio of the amount of the compound shown in the formula 1 to the amount of the catalyst and the material fed by the compound shown in the formula 2 is 1:0.001 to 0.01:4.0 to 6.0; the catalyst is tetra (triphenylphosphine) palladium or palladium acetate.
Preferably, the tetrahydrofuran in the step (1) is used in an amount of 10-50 mL/g thiophene.
Preferably, the anhydrous DMF in step (2) is used in an amount of 50 to 70mL/g of the compound of formula 1.
Specifically, the separation and purification method in the step (1) is as follows: concentrating the reaction solution A under reduced pressure to obtain neutral Al 2 O 3 Eluting with stationary phase and dichloromethane as mobile phase, collecting eluent containing target product, and concentrating under reduced pressure to obtain compound shown in formula 2.
Specifically, the separation and purification method in the step (2) is as follows: cooling the reaction liquid B to room temperature, pouring the reaction liquid B into water, filtering to obtain yellow solid, continuously extracting with dichloromethane and water, collecting an organic phase, drying with anhydrous sodium sulfate, concentrating under reduced pressure, further purifying with a chromatographic column, eluting with 300-400 mesh silica gel as a stationary phase and petroleum ether/dichloromethane mixed liquid with a volume ratio of 1.5-5:1 as a mobile phase, collecting eluent containing a target compound, and concentrating under reduced pressure to obtain an indole derivative-thiophene compound shown in a formula (1).
The invention also relates to application of the indole derivative-thiophene compound in preparation of electrochromic materials. The indole derivative-thiophene compound can be used as an electrochromic monomer, and is formed into a film by adopting an electrochemical method, and the film can be used as an electrochromic material in the fields of intelligent windows, electronic paper, displays and the like.
The electrochemical polymerization film forming process can be as follows:
dissolving an indole derivative-based compound represented by formula (1) in methylene chloride/acetonitrile volume ratio 1:1, tetrabutylammonium perchlorate (TBAP) is added as electrolyte, the sweeping speed is 100mV/s, and the film is formed by electrochemical polymerization by a cyclic voltammetry of 0-1.2V (pTTIT film).
The volume usage amount of the dichloromethane is 1-2 mL/mg of the compound shown in the formula (1).
The dosage of the tetrabutylammonium perchlorate is 0.1mol/L methylene dichloride.
The invention has the following main effects: (1) The indole derivative-thiophene compound has a reticular space structure, and is subjected to electrochemical polymerization to form a film, so that the obtained film has a large specific surface area and good electrochemical properties such as electrochromic; (2) The film prepared by taking the compound as a monomer through electrochemistry can realize arbitrary switching from yellow to green, has an optical contrast of 20-50%, and a response time of 0.5-9 s, shows relatively good spectroelectrochemical stability in any wave band, and is a potential electrochromic material capable of being used for military camouflage.
(IV) description of the drawings
FIG. 1 is a CV polymerization curve of pTTIT film according to the embodiment of the invention;
FIG. 2 is a graph showing ultraviolet absorption spectra of pTTIT film at various voltages in the examples of the present invention.
FIG. 3 shows the dynamic stability of pTTIT film at 633nm band in the examples of the present invention.
FIG. 4 shows the optical contrast and response time of pTTIT film at 633nm band in the examples of the present invention.
(fifth) detailed description of the invention
The present invention will be described in further detail with reference to the following specific examples, which are only for the purpose of illustrating the invention and are not to be construed as limiting the scope of the invention.
Example 1:
step (1) Synthesis of Compound 2 tributyl (2-thienyl) tin:
thiophene (15 mmol,1.26 g) was dissolved in 100mL anhydrous tetrahydrofuran and placed in a 250mL single neck round bottom flask and the vacuum and nitrogen cycles were performed three times. A solution of n-butyllithium (1.6 mol/L,15mmol, 9.4 mL) was slowly added dropwise under nitrogen at-78deg.C, and after stirring at this temperature for 0.5h, a solution of tributylstannyl chloride in hexane (1.2 g/mL,20mmol,5.5 mL) was slowly added dropwise. Stirring at-78℃for 0.5h, and returning to room temperature and stirring for 8h.
After the reaction is finished, the reaction liquid is decompressed and concentrated, and Al is used for 2 O 3 The packing layer is a stationary phase, dichloromethane is a mobile phase for eluting, all eluents are collected, and the transparent liquid compound shown in the formula 2 is obtained after decompression and concentration, and the yield is 90%.
Step (2) synthesis of compound (1) TTIT:
compound 1 (1.07 g,1.6 mmol) (synthetic reference to Compound 1: angew.chem. 2020,132,1-6) was placed in a 100mL double-neck, double-bottom flask, and catalyst Pd (pph) was rapidly added 3 ) 4 (18.5 mg,0.016 mmol) was circulated three times with nitrogen under vacuum. The compound (2.61 g,7 mmol) shown in the formula 2 obtained in the step (1) and 30mL of anhydrous DMF are added in sequence under the nitrogen protection condition, the temperature is quickly raised to 120+/-20 ℃, and the mixture is stirred and refluxed for 14 hours.
After the reaction is finished, after the reaction liquid is cooled to room temperature, pouring the reaction liquid into water, filtering to obtain yellow solid, continuously extracting with dichloromethane and water, collecting an organic phase, drying with anhydrous sodium sulfate, concentrating under reduced pressure, further purifying with a chromatographic column, eluting with 300-400 mesh silica gel as a stationary phase and petroleum ether/dichloromethane mixed solution with the volume ratio of 1.5-5:1 as a mobile phase, determining part of eluent containing target compounds by TLC, collecting eluent containing target compounds, concentrating under reduced pressure to obtain a target product TTIT with the yield of 60%.
1H NMR(500MHz，CDCl3)δ8.31(d，J＝8.2Hz，3H)，7.86(d， J＝1.0Hz，3H)，7.65(dd，J＝8.3，1.1Hz，3H)，7.48(d，J＝2.7Hz， 3H)，7.35(d，J＝4.7Hz，3H)，7.18(dd，J＝5.0，3.6Hz，3H)，5.05 (m，J＝6.9Hz，6H)，1.67(t，J＝6.6Hz，9H).
Example 2:
the product TTIT (6.8 mg,1 mM), TBAP (3411 mg, 0.1M) was used as electrolyte, added to a volumetric flask, added to 10mL of a mixed solution of acetonitrile and dichloromethane (volume ratio 1:1), sonicated for 3min, and after complete dissolution, used for electrochemical polymerization. ITO is used as a working electrode, a platinum sheet (0.9 x 4 cm) is used as a counter electrode, ag/AgCl is used as a reference electrode, cyclic voltammetry is used for forming a film at 0-1.2V, the film is dedoping is carried out for 1min in a blank solution (0.1M TBAP is dissolved in acetonitrile), and the prepared film is dried in an oven at 60 ℃ for 1 hour and then subjected to electrochemical, optical and electrochromic performance tests in TBAP/acetonitrile. All films were prepared by cyclic voltammetry 10 cycles in a mixed solution of acetonitrile and dichloromethane containing TBAP under the test conditions of the acetonitrile solution containing TBAP.
The CV polymerization graph of the pTTIT film is shown in FIG. 1, the ultraviolet absorption spectrum of the pTTIT film at various voltages is shown in FIG. 2, the dynamic stability of the pTTIT film at 633nm band is shown in FIG. 3, and the optical contrast and response time of the pTTIT film at 633nm band are shown in FIG. 4. As can be seen, the film exhibits good redox performance, shows a change in color from yellow to green at a voltage step of 0 to 1.4V, has an optical contrast of 36% at 633nm, and has a coloration and fade time of 1.93s and 0.52s, respectively, at 633nm, indicating that such materials are potentially electrochromic materials useful for military camouflage. Compared with the benzene-thiophene polymer electrochromic material, the compound forms a stable polymer film with a cross-linked structure through electrochemical polymerization, and the electrochromic stability is improved to a certain extent.
Claims (7)
1. An indole derivative-thiophene compound takes the indole derivative as a central core, thiophene as a peripheral group, and the structure is shown as a formula (1):
2. a process for preparing an indole derivative-thiophene compound according to claim 1, the process comprising:
(1) Dissolving thiophene in anhydrous tetrahydrofuran, dropwise adding n-butyllithium solution under nitrogen protection at the temperature of minus 78 ℃, stirring for 0.3-1 h, adding tributyl stannic chloride hexane solution, recovering to room temperature after the addition of tributyl stannic chloride is completed, stirring for 6-24 h, and separating and purifying the obtained reaction solution A to obtain a compound shown in a formula 2; the mass ratio of the thiophene to the n-butyllithium to the tributyl tin chloride is 1:1-1.1:1-1.6;
(2) Under the nitrogen atmosphere, mixing a compound shown in a formula 1, a catalyst and a compound shown in a formula 2, dissolving in anhydrous DMF, heating to 120+/-20 ℃, stirring and refluxing for 6-16 hours, and separating and purifying the obtained reaction solution B to obtain an indole derivative-thiophene compound shown in the formula (1);
the ratio of the amount of the compound shown in the formula 1 to the amount of the catalyst and the material fed by the compound shown in the formula 2 is 1:0.001 to 0.01:4.0 to 6.0; the catalyst is tetra (triphenylphosphine) palladium or palladium acetate.
3. The process according to claim 2, wherein tetrahydrofuran is used in step (1) in an amount of 10 to 50mL/g thiophene.
4. The process according to claim 2, wherein in step (2) anhydrous DMF is used in an amount of 50 to 70mL/g of the compound of formula 1.
5. The method according to claim 2, wherein the separation and purification method in step (1) is as follows: concentrating the reaction solution A under reduced pressure to obtain neutral Al 2 O 3 Eluting with stationary phase and dichloromethane as mobile phase, collecting eluent containing target product, and concentrating under reduced pressure to obtain compound shown in formula 2.
6. The method according to claim 2, wherein the separation and purification method in step (2) is as follows: cooling the reaction liquid B to room temperature, pouring the reaction liquid B into water, filtering to obtain yellow solid, continuously extracting with dichloromethane and water, collecting an organic phase, drying with anhydrous sodium sulfate, concentrating under reduced pressure, further purifying with a chromatographic column, eluting with 300-400 mesh silica gel as a stationary phase and petroleum ether/dichloromethane mixed liquid with a volume ratio of 1.5-5:1 as a mobile phase, collecting eluent containing a target compound, and concentrating under reduced pressure to obtain an indole derivative-thiophene compound shown in a formula (1).
7. The use of an indole derivative-thiophene compound according to claim 1, for preparing electrochromic materials.
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