CN113651818A - Condensed heteroaromatic ring organic luminescent material and preparation method and application thereof - Google Patents
Condensed heteroaromatic ring organic luminescent material and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a novel fused heteroaromatic ring organic luminescent material, which has a structure of 11- (diethylamino) benzo [ g ] benzo [4,5] imidazo [1,2-a ] [1,8] naphthyridine-6-Nitrile (NBC). The material is prepared by a one-pot method by taking 2-chloro-7- (diethylamino) quinoline-3-formaldehyde and 2-cyanomethyl benzimidazole as raw materials. In the solution, the NBC has large molar absorption coefficient, high fluorescence quantum yield and large stokes shift value, is sensitive to solvent, environmental pH and viscosity, can be used as a pH and viscosity type probe, and can measure the pH and the solution viscosity in real time and rapidly. In the solid state, the NBC emits light in the near infrared region and has high luminous efficiency. NBC has good luminous performance in solution and solid state, and the double high-efficiency organic materials realize the multi-functionalization of application.
Description
Technical Field
The invention relates to the technical field of organic luminescent materials, in particular to a condensed heteroaromatic ring organic luminescent material and a preparation method and application thereof.
Background
Although the organic luminescent material shows excellent luminescent performance in a solution with good dispersibility, the organic luminescent material shows the reduction of fluorescence and even complete panout in a solution with higher concentration or in an Aggregation state, namely, an Aggregation-quenched Quenching (ACQ) organic luminescent material plays an important role in the fields of chemistry, biology, materials and the like, and is concerned. The traditional organic luminescent materials show excellent luminescent performance in a solution with good dispersibility, but in a solution with higher concentration or in an aggregation state, fluorescence is weakened or even completely quenched, namely, an aggregation quenching effect (ACQ) appears, and the ACQ greatly limits the application of the materials in the field of solid-state luminescence. Aggregate Induced Emission (AIE) materials, which have been rapidly developed in the last two decades, have strong luminescence properties in an aggregate state and a solid state, but they emit little or no luminescence in a solution. Therefore, the design and development of a novel luminescent material which can effectively emit light in both solution and solid state (aggregation state) has important significance and value.
Heterocyclic compounds are various in types, and are mainly divided into five-membered heterocyclic rings and six-membered heterocyclic rings, and the heterocyclic rings are condensed with benzene rings or condensed with heterocyclic rings to form fused heteroaromatic ring compounds. The fused heteroaromatic ring molecules have a large conjugated system, are mostly in a planar configuration, have certain rigidity, have excellent optical performance in a solution, and have easy structure modification, so that the fused heteroaromatic ring compounds have wide application in many aspects such as fluorescent dyes, fluorescent probes, biological imaging and the like. But when they are in high concentration and in the aggregate state, the emission intensity is reduced or even no fluorescence emission is generated due to pi-pi stacking. The invention designs and synthesizes the compound which takes the asymmetric fused heteroaromatic ring structure of quinoline fused pyrimidine as a mother nucleus and is fused with the benzimidazole ring with large steric hindrance and rigidity at the periphery, and the compound has good luminous performance in solution and solid, thereby greatly widening the application range of the compound.
At present, an optical probe becomes one of research hotspots in the field of analytical chemistry, and is widely applied to the fields of biochemical detection, environmental monitoring, disease diagnosis, drug screening and the like. It is also significant to make the application of organic light emitting materials multifunctional. In industrial production, a large amount of strongly acidic industrial wastewater is often generated, which causes great pressure on environmental and ecological protection. Currently, there are few reports of fluorescent probes for use with very acidic (pH < 4). In biological systems, mitochondria become more viscous during apoptosis. The change of the viscosity of mitochondria before and after apoptosis can be detected by the fluorescent probe, and whether the cell is apoptotic or not can be judged by detecting the change of the viscosity of the mitochondria, thereby providing a new direction for researching the apoptosis. Therefore, the development of fluorescent probes of pH type and viscosity is also of great significance.
Disclosure of Invention
In view of the above technical problems, the present invention provides a fused heteroaromatic organic light emitting material, which is characterized in that the organic light emitting material is 11- (diethylamino) benzo [ g ] benzo [4,5] imidazo [1,2-a ] [1,8] naphthyridine-6-carbonitrile (NBC), and the specific structural formula is:
the preparation method of the organic luminescent material is characterized by comprising the following steps: adding 2-chloro-7- (diethylamino) quinoline-3-formaldehyde, 2-cyanomethyl benzimidazole, solvent and alkali into a reaction bottle in sequence, refluxing until the reaction is finished (TLC monitors the reaction progress), cooling, performing suction filtration to obtain a solid, and recrystallizing to obtain a product 11- (diethylamino) benzo [ g ] benzo [4,5] imidazo [1,2-a ] [1,8] naphthyridine-6-Nitrile (NBC).
The molar ratio of 2-chloro-7- (diethylamino) quinoline-3-carbaldehyde to 2-cyanomethylbenzimidazole is 1: 0.5 to 2.
The solvent comprises any one of N, N-dimethylformamide, N-dimethylacetamide, dimethyl sulfoxide, acetonitrile, ethanol, propanol and butanol, and preferably N, N-dimethylacetamide.
The alkali comprises any one of potassium carbonate, sodium carbonate, potassium hydroxide, sodium hydroxide, pyridine and triethylamine, and pyridine is preferred.
The application of the organic luminescent material, and the application of the material in pH detection, solvent viscosity detection and fluorescent materials.
The condensed heteroaromatic ring organic luminescent material is applied to detecting the pH value in a solution or being used as a pH detection reagent.
The solution comprises one or more of water, C1-C5 alcohol solvent, and the pH condition is 1< pH <5 solution environment.
The condensed heteroaromatic ring organic luminescent material is applied to detecting the viscosity of a solvent or being used as a solvent viscosity reagent.
The solvent comprises glycerol and/or an alcohol solution, and the alcohol solution comprises one or more of methanol, ethanol, propanol, isopropanol and n-butanol.
The condensed heteroaromatic ring organic luminescent material is applied to a solid luminescent material.
The invention has the beneficial effects that:
1. the invention takes asymmetric fused heteroaromatic ring as a framework, introduces a diethylamino group with a strong electron-donating group (D) and a cyano group with an electron-withdrawing group (A), and designs a novel fused heteroaromatic ring compound 11- (diethylamino) benzo [ g ] benzo [4,5] imidazo [1,2-a ] [1,8] naphthyridine-6-Nitrile (NBC).
2. The organic luminescent material is obtained by directly carrying out one-pot condensation and cyclization on 2-site chlorine atoms and 3-site aldehyde group double high reactivity of quinoline and active methylene of 2-cyanomethyl benzimidazole under the alkaline condition. Has the characteristics of simple synthesis operation, mild reaction condition, high yield and low cost.
3. The organic luminescent material has good optical properties in a solution state, such as large molar absorption coefficient, high fluorescence quantum yield and large stokes shift value, is sensitive to solvent, environmental pH and viscosity, can be used as a pH and viscosity probe, can measure the pH and the solution viscosity in real time and rapidly, and realizes the multifunctionality of application. In a solid state, the material emits strong red fluorescence, and the defect of low luminous efficiency of a common red material is overcome. The organic luminescent material of the invention has good luminescent performance in solution and solid state, and the application range of the luminescent material is greatly expanded.
4. The method has the advantages of original innovation, good social value and good application prospect.
Drawings
FIG. 1 is a photograph of NBC prepared in example 11H-NMR spectrum.
FIG. 2 is a photograph of NBC prepared in example 113C-NMR spectrum.
FIG. 3 is a graph of UV-VIS absorption spectra of NBC prepared in example 1 at various concentrations (chloroform).
FIG. 4 is a fluorescence emission spectrum of NBC prepared in example 1 at different concentrations (chloroform).
FIG. 5 is a UV-VIS spectrum of NBC prepared in example 1 in various solvents.
FIG. 6 shows fluorescence emission spectra of NBC prepared in example 1 in different solvents.
FIG. 7 is a plot of the stokes shift versus the solvent polarity parameter Δ f for NBC prepared in example 1.
Fig. 8 is a graph (a) of the uv-vis absorption spectrum of NBC prepared in example 1 under different pH environments and a graph (B) of the change in the absorption value under different pH environments.
FIG. 9 is a fluorescence spectrum (A) of NBC prepared in example 1 under different pH environments and a change in fluorescence intensity (B) under different pH environments.
FIG. 10 is a fluorescence spectrum (A) of NBC prepared in example 1 at different viscosities and a linear relationship (V) of the fluorescence intensity of NBC with different viscosities.
FIG. 11 is a spectrum of NBC prepared in example 1, NBC after milling, and NBC after recrystallization.
Detailed Description
The invention is further illustrated by the following examples, but the scope of the invention as claimed is not limited to the scope of the examples.
Example 1
N11- (diethylamino) benzo [ g ] benzo [4,5] imidazo [1,2-a ] [1,8] naphthyridine-6-carbonitrile (NBC)
To a 50mL two-necked flask were added 1.00g (3.8mmol) of 2-chloro-7- (diethylamino) quinoline-3-carbaldehyde, 0.50g (3.2mmol) of 2-cyanomethylbenzimidazole and 10mL of N, N-dimethylformamide in this order, and then 0.5mL of pyridine was added, followed by stirring with heating. The resulting mixture was then stirred at 85 ℃ until the reaction was complete (TLC detection). Naturally cooling to room temperature, adding 30mL of water into the reaction solution, precipitating an orange solid, performing suction filtration under reduced pressure, performing silica gel column chromatography, and purifying with petroleum ether, ethyl acetate 5: 1.05g of an orange solid are obtained, with a yield of 70%.1H NMR(400MHz,DMSO-d6)δ:9.36(d,J＝8.0Hz,1H),8.74(d,J＝23.2Hz,1H),8.02-7.93(m,2H),7.65–7.57(m,2H),7.36(dd,J＝9.2,2.0Hz,1H),7.20(s,1H),3.64(q,J＝7.2Hz,4H),1.26(t,J＝6.8Hz,6H).13C NMR(100MHz,DMSO)δ:152.07,150.80,146.70,146.27,143.97,140.92,139.79,131.33,131.23,125.61,124.12,119.86,118.68,117.68,116.38,112.04,103.45,100.00,97.69,44.74,13.09.
The technical scheme for optimizing the conditions by using the preparation method of the embodiment 1 is as follows:
EXAMPLE 2 preparation of test solutions
(1) Preparation procedure of stock solution:
NBC prepared in example 1 was weighed and added to a 10mL colorimetric tube to prepare a mixture having a concentration of 1.0X 10-3Using a chloroform solution of mol/L as a stock solution, and then respectively diluting NBC stock solution by 10, 100, 1000 and 10000 times to prepare the NBC stock solution with the concentration of 1.0 multiplied by 10-4mol/L、1.0×10-5mol/L、1.0×10-6mol/L、1.0×10-7A chloroform solution of mol/L. Respectively taking 10 μ L of the extract at a concentration of 1.0 × 10-5Adding the mol/L NBC solution into 12 10mL colorimetric tubes, diluting to 10mL with different solvents to obtain a solution with a concentration of 1.0 × 10-6And (3) determining the fluorescence quantum yield of the NBC by using the rhodamine B as a standard reference substance by using the solution in mol/L.
(2) NBC concentration dependent test:
2mL of NBC chloroform solution with different concentrations are respectively taken for testing the ultraviolet-visible absorption spectrum and the fluorescence emission spectrum. As shown in fig. 3, the absorption value of the NBC solution at 480nm gradually increases with the increase of the NBC concentration, and the color of the solution gradually changes from colorless to yellow; meanwhile, the fluorescence intensity of the NBC solution is gradually enhanced, the maximum emission wavelength is gradually red-shifted, the maximum emission wavelength is red-shifted by 15nm within the tested concentration gradient change range, and the solution is gradually changed from colorless to bright yellow under an ultraviolet lamp, as shown in FIG. 4. The above results indicate that the NBC luminescence properties depend on its concentration.
(3) NBC solvent effect:
2mL of different solvents (including dioxane, chloroform, toluene, ethyl acetate)Tetrahydrofuran, dichloromethane, acetone, ethanol, methanol, acetonitrile, N-dimethylformamide, and dimethyl sulfoxide) was added to 20. mu.L of a stock solution (1.0X 10)-3NBC chloroform solution in mol/L) and after shaking uniformly, performing spectrum test. As shown in fig. 5 and 7, NBC shows strong absorption performance with a large molar extinction coefficient in various solvents; but its maximum absorption peak wavelength gradually red-shifts with increasing polarity of the solvent. The maximum absorption peak wavelength of NBC is 456nm as in 1, 4-dioxane; the maximum absorption peak wavelength of NBC in dimethylsulfoxide was 490nm, which was red-shifted by 34 nm. The fluorescence emission showed similar changes, and the results are shown in FIG. 6 and Table 1. Among 12 tested solvents, NBC emits strong fluorescence, and the fluorescence quantum yield is high; but as the polarity of the solvent is increased, the corresponding emission peak wavelength is gradually red-shifted, and the fluorescence quantum yield is slightly reduced. For example, in toluene with a small polarity, the emission peak wavelength of NBC was 521nm, and in dimethyl sulfoxide with a large polarity, the emission peak wavelength of NBC was 567nm, which was red-shifted by 46 nm. The Stokes shift of NBC increases from 49nm to 71nm with increasing solvent polarity, and the Stokes shift has a linear relationship with the solvent polarity parameter Δ f, and the results are shown in FIG. 7, showing significant solvation effect.
Table 1 shows photophysical data of NBC prepared in example 1 in different solvents.
(4) Effect of pH on NBC fluorescence Performance
2mL of methanol/water (4: 1, v/v) solutions at different pH were added to 20. mu.L of stock solution (1.0X 10)-3mol/L NBC in chloroform) for spectroscopic testing. The results are shown in FIGS. 8 and 9. In the UV-visible spectrum, at pH>2.37 Environment, NBC has substantially unchanged absorbance at 480nm and pH<2.37, the absorbance of NBC at 480nm decreased slightly and the maximum absorption wavelength gradually red-shifted to 540nm, red-shifted by 60nm, with decreasing pH. In fluorescence spectrum, at pH>3.04 in the environment, the fluorescence intensity of NBC at 560nm is substantially unchanged at pH<3.04 in the environmentThe fluorescence intensity of NBC at 560nm decreases and the maximum emission wavelength gradually red-shifts to 610nm as the pH decreases. At 0.9<pH<4.21, the absorption value and fluorescence intensity of NBC have a certain linear relation with pH; at 4.21<pH<13.03, the absorbance and fluorescence intensity of NBC were substantially stable. Therefore, NBC can serve as a strongly acidic pH colorimetric probe and a fluorescent probe.
(5) Effect of viscosity on NBC fluorescence Properties
Adding 2mL of glycerol/methanol solution (99/1, 90/10, 80/20, 70/30, 60/40, 50/50, 40/60, 30/70, 20/80, 10/90, 0) at different ratios into 20 μ L of stock solution (1.0 × 10)-3mol/L NBC in chloroform) for spectroscopic testing. In the fluorescence spectrum, as the viscosity of the mixed solution increases, the fluorescence intensity gradually increases, and the maximum emission wavelength red shifts to 560 nm. The fluorescence intensity was plotted as a log of the viscosity and was found to be linear, as shown in FIG. 10. It was shown that NBC can be used for quantitative determination of viscosity in mixed solvents.
(6) Solid state fluorescence properties of NBC
A certain amount of NBC solid was taken and subjected to spectroscopic testing. The emission spectrum of NBC in the different solid states is shown in FIG. 11.
A certain amount of NBC solid was taken and subjected to spectroscopic testing. The emission spectrum of NBC in the different solid states is shown in FIG. 11. The solvent was evaporated in example 1 to give NBC powder (unmilled NBC) having an emission peak of 638nm showing red fluorescence; the powder is ground for 0.5h at room temperature, the position of the emission peak of the obtained ground powder is not changed remarkably, but the intensity of the emission peak is increased; and (2) adding 0.3g of NBC powder into a small test tube, dropwise adding about 5mL of solvent, heating to 80 ℃, stopping heating after complete dissolution, naturally cooling to separate out 0.18g of brownish red needle-shaped crystals, and performing suction filtration under reduced pressure to obtain the NBC crystals recrystallized by using N, N-dimethylformamide, wherein the maximum emission wavelength of the NBC crystals is shifted to 683nm, the NBC crystals belong to a deep infrared light-emitting area, and the fluorescence intensity is remarkably enhanced (16 times of that in the solution). The common defect of low luminous efficiency of a red light material is overcome in deep infrared luminous intensity, and the red light material can emit light in different solid states, and the characteristics show the potential application of NBC in the aspect of solid luminous materials, particularly red light.
Claims (10)
1. The fused heteroaromatic ring organic luminescent material is characterized in that the organic luminescent material is 11- (diethylamino) benzo [ g ] benzo [4,5] imidazo [1,2-a ] [1,8] naphthyridine-6-Nitrile (NBC), and the specific structural formula is as follows:
2. the method for preparing the fused heteroaromatic ring organic light-emitting material according to claim 1, comprising the following steps:
adding 2-chloro-7- (diethylamino) quinoline-3-formaldehyde, 2-cyanomethyl benzimidazole, solvent and alkali into a reaction bottle in sequence, refluxing until the reaction is finished, cooling, performing suction filtration to obtain a solid, and performing column chromatography to obtain a product 11- (diethylamino) benzo [ g ] benzo [4,5] imidazo [1,2-a ] [1,8] naphthyridine-6-Nitrile (NBC).
3. The method of claim 2, wherein the molar ratio of 2-chloro-7- (diethylamino) quinoline-3-carbaldehyde to 2-cyanomethylbenzimidazole is 1: 0.5 to 2.
4. The method for preparing a fused heteroaromatic organic light emitting material as claimed in claim 2, wherein the solvent comprises any one of N, N-dimethylformamide, N-dimethylacetamide, dimethylsulfoxide, acetonitrile, ethanol, propanol and butanol.
5. The method for preparing the condensed heteroaromatic organic light-emitting material according to claim 2, wherein the base comprises any one of potassium carbonate, sodium carbonate, potassium hydroxide, sodium hydroxide, pyridine and triethylamine.
6. The use of the fused heteroaromatic organic light emitting material of claim 1 in detecting pH in a solution or as a pH detection reagent.
7. The use of claim 6, wherein said solution comprises a mixture of one or more of water, a C1-C5 alcohol solvent, and said pH conditions are in a solution environment of 1< pH < 5.
8. The use of the fused heteroaromatic organic light emitting material of claim 1 as a solvent viscosity detection agent.
9. The use according to claim 8, wherein the solvent comprises glycerol and/or an alcohol solution comprising one or more of methanol, ethanol, propanol, isopropanol, n-butanol.
10. The use of the fused heteroaromatic ring organic light emitting material of claim 1 as a solid light emitting material.
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| CN116535405A (en) * | 2023-02-13 | 2023-08-04 | 武汉轻工大学 | Benzimidazole fused pyrimidoquinoline fluorescent molecule, and preparation method and application thereof |
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| CN106800548A (en) * | 2017-01-17 | 2017-06-06 | 三峡大学 | 8 benzimidazole quinoline Ratio-type pH probes and its preparation method and application |
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| CN116535405A (en) * | 2023-02-13 | 2023-08-04 | 武汉轻工大学 | Benzimidazole fused pyrimidoquinoline fluorescent molecule, and preparation method and application thereof |
| CN116535405B (en) * | 2023-02-13 | 2024-05-17 | 武汉轻工大学 | Benzimidazole fused pyrimidoquinoline fluorescent molecule, and preparation method and application thereof |
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