CN110872229A - Pyrenyl derivative ionic complex and preparation method and application thereof - Google Patents
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Abstract
The invention discloses a pyrenyl derivative ionic complex and a preparation method and application thereof, wherein the pyrenyl derivative ionic complex is represented by a formula (IV):
wherein: r+＝R′2(CH3)2N+(ii) a R' is a linear, branched or cyclic alkyl chain having from 16 to 18 carbon atomsAn alkyl group. The pyrenyl derivative ionic complex has high luminous efficiency, the solid fluorescence quantum yield is higher than 60%, and the luminous performance is excellent; the invention has the advantages of simple preparation method, high yield, easy purification, low cost and the like; the pyrenyl derivative ionic complex forms supermolecule organic luminescent gel in a solvent, and the luminescent performance is excellent.
Description
Technical Field
The invention belongs to the technical field of organic luminescent materials, and particularly relates to a pyrenyl derivative ionic complex with high luminescent performance, a preparation method and application of the pyrenyl derivative ionic complex in preparation of supramolecular organic luminescent gel.
Background
In recent years, aromatic compounds having delocalized large pi bonds have been widely used in the fields of molecular probes, optical sensors, nonlinear optics, molecular electronics, and the like, due to their many unique characteristics. Pyrene and its derivatives are one of the compounds that has been studied more often because of their excellent fluorescent properties such as blue light emission, high fluorescent quantum efficiency, long fluorescent lifetime, and good thermal stability. Pyrenyl fluorescent molecular probes have been widely used in structural studies, DNA recognition and lipid membrane studies of proteins/polypeptides. Pyrene is sensitive to changes in the microenvironment and is also used to detect environmental factors such as temperature, pressure, pH, etc. Meanwhile, the material can also detect the existence of substances such as gas, organic matters, metal and the like in the environment. Besides molecular probes, pyrene and its derivatives are also widely used in the field of photovoltaics. Flat aromatic compounds, such as 1,3,6, 8-tetraphenylpyrene based on pyrenyl derivatives, are widely used in field effect transistors or as electroluminescent components in organic light emitting field effect transistors. However, pyrene easily forms pi aggregates or excimers, resulting in red shift of the emission spectrum, and stacking easily results in quenching, so that the light emitting effect of these materials is not good. The reduction of the luminous efficiency makes a large amount of energy converted into heat energy without being converted into light energy, so that the temperature of the device rises, and finally the luminous device has low efficiency and reduced service life, and therefore, the improvement of the luminous performance is an important task. In addition, the development of pyrenyl luminescent materials at present mainly depends on a chemical synthesis method (namely, functional groups are connected through covalent bonds), the preparation process is complex, the time period is long, the yield is low, and the product is not easy to purify.
Ion self-assembly is a new method for preparing organic functional materials by connecting functional groups together through ionic bonds by utilizing electrostatic interaction. Compared with a chemical synthesis method, the ion self-assembly method is simpler, more convenient and faster to prepare the functional material, higher in freedom degree of assembly of functional groups, low in cost and higher in yield, and more importantly, a special aggregate structure can be formed by means of phase separation, so that the photoelectric material with more excellent light-emitting performance is obtained.
The low molecular weight organogelators can self-assemble in a solvent to form a three-dimensional network structure through the synergistic interaction of hydrogen bonds, pi-pi stacking, van der waals forces, and other non-covalent bonds, so that the solvent molecules are gelled. Due to the non-covalent bond function between molecules, the gel realizes reversible conversion between a sol state and a gel state under the stimulation of certain conditions. Therefore, the method has application value in the fields of intelligent materials, pharmaceutical science, life science and the like.
However, no report on the pyrenyl derivative ionic complex, the preparation method and the application of the pyrenyl derivative ionic complex is available at present.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a pyrenyl derivative ion complex with excellent luminescence property.
The second purpose of the invention is to provide a preparation method of the pyrenyl derivative ion complex, which overcomes the defects of complex synthetic steps, low yield and the like in the prior art, and has simple steps and high yield.
The third purpose of the invention is to provide the application of the pyrenyl derivative ionic complex.
The technical scheme of the invention is summarized as follows:
a pyrenyl derivative ionic complex represented by formula (IV):
wherein: r+＝R′2(CH3)2N+；
Wherein R' is a straight chain alkyl group, a branched alkyl group or an alkyl group with a cyclic alkyl chain having 16 to 18 carbon atoms.
A preparation method of pyrenyl derivative ionic complex comprises the following steps:
(1) putting the compound (II) into a potassium hydroxide aqueous solution with the concentration of 0.015-0.025mol/L, wherein the molar ratio of potassium hydroxide to the compound (II) is 4.2-6: 1, stirring for 2-3h under the condition of water bath at 40-50 ℃ to obtain a solution containing a compound (III), and cooling to room temperature;
(2) r 'at 40-50℃'2(CH3)2N+BrˉDissolving in ethanol-water mixed solvent to obtain solution with concentration of 0.011-0.017mol/L, R'2(CH3)2N+BrˉThe molar ratio to the compound (II) is 4.2 to 5: 1, wherein the volume ratio of ethanol to water in the ethanol-water mixed solvent is 3: 1 to 25;
(3) dropping a solution containing the compound (III) into the solution obtained in the step (2) under stirring at 40-50 ℃, stirring until a precipitate is formed, filtering, and adding a solvent in a volume ratio of 3: washing the precipitate with a mixed solvent of 1-25 ethanol and water, and drying in vacuum to obtain a pyrenyl derivative ionic complex (IV);
the reaction equation is as follows:
wherein: r+＝R′2(CH3)2N+；
R' is a straight-chain alkyl group, a branched-chain alkyl group or an alkyl group with a cyclic alkyl chain having 16 to 18 carbon atoms.
The application of the pyrenyl derivative ionic complex in preparing supermolecule organic luminescent gel.
The application comprises the following steps: adding the pyrenyl derivative ionic complex into a solvent to enable the concentration to be at least 2mg/mL, heating to dissolve, standing and cooling to room temperature to obtain the supramolecular organic luminescent gel.
The concentration of the pyrenyl derivative ion complex added to the solvent is preferably 10 to 50mg/mL, and may be 50mg/mL or more.
The solvent is toluene or o-xylene.
The invention has the beneficial effects that:
(1) the pyrenyl derivative ionic complex has high luminous efficiency, the solid fluorescence quantum yield is higher than 60%, and the luminous performance is excellent;
(2) according to the method, the pyrenyl derivative and the cationic surfactant are connected by ionic bonds through electrostatic interaction by adopting an ionic self-assembly method, and compared with the traditional chemical synthesis method, the method has the advantages of simple preparation method, high yield, easiness in purification, low cost and the like;
(3) the pyrenyl derivative ionic complex can form supermolecule organic luminescent gel in partial solvent (such as toluene), and has excellent luminescent performance.
Drawings
FIG. 1 is a scheme of the ionic complex Py-DOAB1H NMR spectrum;
FIG. 2 is an infrared spectrum of the ionic complex Py-DOAB;
FIG. 3 shows the fluorescence emission spectra of Py-DOAB in ethanol-water mixed solvents of different water contents, the excitation wavelength of the spectra is 380 nm;
FIG. 4 is a photograph of Py-DOAB under 365nm UV light (a: 0% water content mixed solution of Py-DOAB in ethanol-water solution b: 90% water content mixed solution of Py-DOAB in ethanol-water solution);
FIG. 5 is a photograph of a solution and gel of Py-DOAB in toluene (A: toluene solution B of Py-DOAB: Py-DOAB toluene gel formed by heating, standing and cooling to room temperature C: Py-DOAB toluene gel under irradiation of 365nm wavelength ultraviolet lamp)
The specific implementation mode is as follows:
the invention will be further illustrated with reference to specific examples:
the present invention is a known technique for producing the compound (II) from 1,3,6, 8-tetrakis (4-carboxyphenyl) pyrene (II), and the present invention is exemplified to enable a person skilled in the art to better understand the present invention, but is not limited to the production of the compound (II).
The experiment adopts Swiss BrAVANCE III 400M model liquid NMR spectrometer manufactured by uker company for detecting products1H NMR spectrum, solvent is deuterated Methanol (Methanol-d4), Tetramethylsilane (TMS) is internal standard. In the experiment, an infrared spectrum of a product is obtained by a Bio-Rad FTS-6000 infrared spectrometer produced by Hercules company in America and tabletting by KBr. The fluorescence spectrum of the product is measured by using an F-2500 type fluorescence spectrophotometer produced by Hitachi company, a quartz cuvette with the wavelength of 1 multiplied by 1cm is used as a sample cell, the excitation wavelength is 380nm, the test collection wavelength range is 375-750nm, and the purity of the solvent used in the fluorescence spectrum test is chromatographic purity. In the experiment, the solid fluorescence quantum yield of the products Py-DOAB and Py-DHAB is measured by using an FLS 920P type steady state/transient state fluorescence spectrometer produced by Edinburgh company in England and taking 380nm as the optimal excitation wavelength, and the solid fluorescence quantum yield is used for representing the luminescence properties of the pyrenyl derivative ion complex and the gel thereof.
Example 1
The preparation method of the 1,3,6, 8-tetra (4-carboxyphenyl) pyrene (II) comprises the following steps:
(1)N2under protection, 0.5g (0.97mmol) of 1,3,6, 8-tetrabromopyrene, 1.04g (5.80mmol) of 4-methoxycarbonylphenylboronic acid and 1.1g (5.30mmol) of anhydrous potassium phosphate were sequentially added to a 250ml two-necked flask, and 100ml of 1, 4-dioxane (Diox) was added thereto, followed by stirring at room temperature for 30 min. Adding 100mg (0.08mmol) of tetrakis (triphenylphosphine) palladium (0) under the condition of keeping out of the light for refluxing for 10h, cooling, adding the same amount of tetrakis (triphenylphosphine) palladium, and continuing to react for 48h to obtain a mixture. After the reaction is finished, the solvent is removed by rotary evaporation, the residue is fully dissolved by dichloromethane, and insoluble substances are removed by vacuum filtration. Extracting the filtrate with saturated saline solution for three times, collecting an organic phase, drying with anhydrous sodium sulfate, performing rotary evaporation on the obtained filtrate to remove the solvent, recrystallizing the residue with toluene, performing suction filtration to obtain a yellow compound (I), and performing vacuum drying to obtain the yield of 53.3%;
(2) weighing 0.606g (0.82mmol) of the compound (I), heating and dissolving in 10mL tetrahydrofuran, then adding ethanol with the same volume as the tetrahydrofuran, adding 0.56g (10mmol) of potassium hydroxide, heating and refluxing, and enabling the solution to become turbid; slowly dripping deionized water until the turbid liquid becomes transparent, and continuously refluxing for 4 h; removing solvent tetrahydrofuran and ethanol by rotary evaporation, adjusting the solution to pH 2 with hydrochloric acid to obtain yellow precipitate, filtering, washing the precipitate with deionized water, and vacuum drying to obtain compound (II) with yield of 87.2%;
the reaction equation is as follows:
example 2
A preparation method of pyrenyl derivative ionic complex comprises the following steps:
(1) 0.069g (0.1mmol) of compound (II) was added to 28mL of an aqueous solution of potassium hydroxide having a molar concentration of 0.015mol/L, in a molar ratio of potassium hydroxide to compound (II) of 4.2: 1, stirring for 3 hours in a water bath condition at 40 ℃ to obtain a solution containing a compound (III), and cooling to room temperature for later use;
(2) 0.265g (0.42mmol) of dioctadecyldimethylammonium bromide (DOAB) was dissolved in 38mL of an ethanol-water mixed solvent at 40 ℃ to give a solution of DOAB having a molar concentration of 0.011mol/L and a molar ratio of DOAB to compound (II) of 4.2: 1, mixing an ethanol-water mixed solvent with a volume ratio of 3: 1 of ethanol and water;
(3) dropping a solution containing the compound (III) into the DOAB solution obtained in the step (2) at a rate of 5 drops/min with stirring at 40 ℃, stirring for 24 hours, causing a precipitate to be formed, filtering, and adding a solvent in a volume ratio of 3: 1, washing the precipitate with a mixed solvent of ethanol and water, and drying in vacuum to obtain a pyrenyl derivative ionic complex (IV-1) named as Py-DOAB, wherein the yield is 97.5%;
the reaction equation is as follows:
wherein: r+＝(C18H37)2(CH3)2N+；
The molecular weight of Py-DOAB is 2882.91, the structure is characterized by nuclear magnetic hydrogen spectrum and infrared spectrum, and it is confirmed that tetraphenylpyrene is connected with DOAB through ionic bond, as shown in figure 1 and figure 2.
Example 3
A preparation method of pyrenyl derivative ionic complex comprises the following steps:
(1) 0.069g (0.1mmol) of compound (II) was added to 24mL of an aqueous potassium hydroxide solution having a molar concentration of 0.025mol/L, and the molar ratio of the potassium hydroxide to compound (II) was 6: 1, stirring for 2 hours in a water bath condition at 50 ℃ to obtain a solution containing a compound (III), and cooling to room temperature for later use;
(2) 0.287g (0.5mmol) of dicetyldimethylammonium bromide (DHAB) was dissolved in 29mL of an ethanol-water mixed solvent at 50 ℃ to give a DHAB solution with a molar concentration of 0.017mol/L, the molar ratio of DHAB to compound (II) was 5: 1, mixing an ethanol-water mixed solvent with a volume ratio of 3: 25 of ethanol and water;
(3) dropping a solution containing the compound (III) into the DHAB solution obtained in the step (2) at a rate of 5 drops/min with stirring at 50 ℃, stirring for 24 hours, causing a precipitate to be formed, filtering, and adding a solvent in a volume ratio of 3: washing the precipitate with 25 parts of mixed solvent of ethanol and water, and drying in vacuum to obtain pyrenyl derivative ion complex (IV-2) named as Py-DOAB with the yield of 97.5%;
the reaction equation is as follows:
wherein: r+＝(C16H33)2(CH3)2N+；
The molecular weight of Py-DHAB is 2658.48.
By using
Compound (IV-3) was prepared in the same manner as in this example except that bis (10-butyltetradecyl) dimethylammonium bromide was used instead of bis-hexadecyldimethylammonium bromide in this example.
By using
Compound (IV-4) was prepared in the same manner as in this example except that bis (12-cyclohexyldodecyl) dimethylammonium bromide was used instead of dicetyl dimethylammonium bromide in this example.
Example 4
A preparation method of a pyrenyl derivative ionic complex supramolecular organic luminescent gel comprises the following specific steps:
Py-DOAB is added into toluene to make the content of the gel be 30mg/mL, the solution is heated to 100 ℃ to be dissolved, and the solution is stood and cooled to room temperature to obtain the supermolecule organic luminescent gel.
The gel has thermal reversibility, namely, the gel is completely dissolved after being heated, and can form opaque gel after being cooled to room temperature, and the process can be repeated for many times;
the o-xylene is used for replacing toluene in the embodiment, and other materials can also obtain the supermolecule organic luminescent gel in the same embodiment;
the compounds IV-2, IV-3 and IV-4 were used in place of Py-DOAB in this example, and a supramolecular organic luminescent gel was obtained in the same manner as in this example.
Experiments prove that: adding Py-DOAB into toluene to make the content of Py-DOAB respectively be 2mg/mL, 10mg/mL or 50mg/mL, heating to 100 deg.C to make it dissolve, standing and cooling to room temperature to obtain the supermolecule organic luminescent gel with thermal reversibility.
FIG. 3 shows the fluorescence emission spectra of Py-DOAB in ethanol-water mixed solvents of different water contents.
As can be seen from the figure, when fwWhen the content of water in the poor solvent is relatively low, most of Py-DOAB molecules are dissolved in the mixed solvent in a monomolecular state, the fluorescence signal of the solution is strong, and the maximum emission wavelength is about 444 nm; when f iswWhen the content of the poor solvent water is more than or equal to 40 percent, the Py-DOAB molecules begin to gather in the mixed solvent, the solution strength is obviously weakened, the phenomenon of red shift occurs, and the maximum emission wavelength red shifts to 473 nm. Indicating that the Py-DOAB ion complex in the aggregated state results in a significant fluorescence reduction with a red shift in emission wavelength.
The luminescence property of the pyrenyl derivative ion complex in the solid state is tested by a solid fluorescence quantum yield experiment. The solid fluorescence quantum yield of Py-DOAB at room temperature was 69%, and that of Py-DHAB at room temperature was 63%.
Experiments prove that: the solid fluorescence quantum yields of the compound (IV-3) and the compound (IV-4) at room temperature were similar to those of Py-DHAB at room temperature.
The pyrenyl derivative ionic complex disclosed by the invention has excellent luminescence property.
In conclusion, the pyrenyl derivative ion complex is prepared by adopting an ion self-assembly method through electrostatic interaction, and compared with a chemical synthesis method, the preparation method has the advantages of simplicity, high yield, easiness in purification, low cost and the like, and can be popularized for large-scale production and application. Most importantly, the pyrenyl derivative ionic complex disclosed by the invention has excellent luminescence performance, the maximum solid fluorescence quantum yield can reach 69%, meanwhile, a supramolecular organic luminescent gel can be formed in toluene/o-xylene, and the pyrenyl derivative ionic complex also has good luminescence performance. Therefore, the preparation method of the pyrenyl derivative ionic complex and the supramolecular organic light-emitting gel formed by the preparation method have wide application prospects in the aspects of light-emitting devices such as organic light-emitting diodes and liquid crystal displays.
Claims (6)
1. A pyrenyl derivative ionic complex characterized by being represented by formula (IV):
wherein: r+＝R′2(CH3)2N+；
Wherein R' is a straight chain alkyl group, a branched alkyl group or an alkyl group with a cyclic alkyl chain having 16 to 18 carbon atoms.
2. The method for preparing pyrenyl derivative ionic complexes of claim 1, characterized by comprising the steps of:
(1) putting the compound (II) into a potassium hydroxide aqueous solution with the concentration of 0.015-0.025mol/L, wherein the molar ratio of potassium hydroxide to the compound (II) is 4.2-6: 1, stirring for 2-3h under the condition of water bath at 40-50 ℃ to obtain a solution containing a compound (III), and cooling to room temperature;
(2) r 'at 40-50℃'2(CH3)2N+BrˉDissolving in ethanol-water mixed solvent to obtain solution with concentration of 0.011-0.017mol/L, R'2(CH3)2N+BrˉThe molar ratio to the compound (II) is 4.2 to 5: 1, wherein the volume ratio of ethanol to water in the ethanol-water mixed solvent is 3: 1 to 25;
(3) dropping a solution containing the compound (III) into the solution obtained in the step (2) under stirring at 40-50 ℃, stirring until a precipitate is formed, filtering, and adding a solvent in a volume ratio of 3: washing the precipitate with 1-25% ethanol-water mixed solvent, and vacuum drying to obtain pyrenyl derivative ionic complex (IV);
the reaction equation is as follows:
wherein: r+＝R′2(CH3)2N+；
R' is a straight-chain alkyl group, a branched-chain alkyl group or an alkyl group with a cyclic alkyl chain having 16 to 18 carbon atoms.
3. Use of the pyrenyl derivative ionic complexes of claim 1 for the preparation of supramolecular organic light emitting gels.
4. Use according to claim 3, characterized in that it comprises the following steps: adding the pyrenyl derivative ionic complex into a solvent to enable the concentration to be at least 2mg/mL, heating to dissolve, standing and cooling to room temperature to obtain the supramolecular organic luminescent gel.
5. The use according to claim 4, characterized in that the pyrenyl derivative ionic complex is added to the solvent at a concentration of 10-50 mg/mL.
6. Use according to claim 4 or 5, characterized in that the solvent is toluene or o-xylene.
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|---|---|---|---|---|
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102858911A (en) * | 2010-03-01 | 2013-01-02 | 香港科技大学 | Light emitting tetraphenylene derivatives, its method for preparation and light emitting device using the same derivatives |
| CN106318380A (en) * | 2016-08-14 | 2017-01-11 | 天津大学 | Tetraphenyl ethylene derivative ion complex and preparation method thereof |
| CN107188801A (en) * | 2017-05-15 | 2017-09-22 | 天津大学 | Bivalent cupric ion fluorescence probe and Preparation method and use based on tetraphenylethylene ionic complex |
-
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102858911A (en) * | 2010-03-01 | 2013-01-02 | 香港科技大学 | Light emitting tetraphenylene derivatives, its method for preparation and light emitting device using the same derivatives |
| CN106318380A (en) * | 2016-08-14 | 2017-01-11 | 天津大学 | Tetraphenyl ethylene derivative ion complex and preparation method thereof |
| CN107188801A (en) * | 2017-05-15 | 2017-09-22 | 天津大学 | Bivalent cupric ion fluorescence probe and Preparation method and use based on tetraphenylethylene ionic complex |
Non-Patent Citations (1)
| Title |
|---|
| JINGYUN YE 等: "Organic Linker Effect on the Growth and Diffusion of Cu Clusters in a Metal-Organic Framework", 《JOURNAL OF PHYSICAL CHEMISTRY C》 * |
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| CN115232327B (en) * | 2022-09-22 | 2023-02-14 | 吉林中科研伸科技有限公司 | Metal organic framework material and preparation method and application thereof |
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