CN113880852A - Aggregation-induced emission pyranoquinoline red light material and application thereof - Google Patents
Aggregation-induced emission pyranoquinoline red light material and application thereof Download PDFInfo
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- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
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Abstract
The invention discloses an aggregation-induced emission pyranoquinoline red light material which has a structure of 8- (diethylamino) -2-imino-2HPyrano [2,3-b ]]Quinoline-3-carbonitrile (QPIC). The material takes pyranoquinoline as a fluorophore, and introduces diethylamino and cyano groups with strong electron donating groups to form D-pi-A structural molecules. The QPIC of the red light material has the characteristics of large molar absorption coefficient, large stokes displacement value, Aggregation Induced Emission (AIE), stability in a wide pH (2-11) range and the like. In addition, in the solution state, the material is sensitive to viscosity, can be used as a viscosity probe and can be used as a viscosity probeAn enhanced fluorescent probe for real-time and rapid measurement of solution viscosity.
Description
Technical Field
The invention relates to the technical field of fluorescent materials, in particular to a pyranoquinoline red light material with aggregation-induced emission and a preparation method and application thereof.
Background
The fluorescent material of organic molecules is easy to modify, and can change the conjugation of molecules and the interaction between molecules by changing various chromophores and introducing aromatic rings, olefinic bonds and other functional groups, thereby changing the fluorescent property of the molecules. Therefore, organic molecular fluorescent materials have been developed rapidly and widely. In order to obtain fluorescent materials with good properties, it is necessary to consider: first, molecules of simple structure are preferred because complex structures usually require complex and multiple synthetic steps and yield is very low. Secondly, the practical application environment is aqueous solution or solid state, but most organic chromophores are hydrophobic aromatic compounds, often exist in aggregation state, the emission intensity is generally weakened due to the quenching (ACQ) effect caused by aggregation, and the discovery of aggregation-induced emission (AIE) effect fundamentally overcomes the problem of fluorescence quenching caused by aggregation of the traditional fluorescent materials. Based on the application requirements, the design and development of a simple organic fluorescent material with aggregation-induced emission has important significance and value.
A large number of groups containing aggregation-induced fluorescence properties are used to construct organic light-emitting materials, such as compounds of the class of the tetrastyrenes, the triphenylamines, the quinolines, and the like. In addition, organic red-emitting materials show unique advantages in biomedical imaging, and their structures are generally polycyclic or macrocyclic molecules with extended P-conjugates and planar conformations, some typical donor-acceptor type P-conjugates with strongly distorted intramolecular charge transfer diimines, porphyrins, cyanamides, dipyrrolidines, and the like. The pyranoquinoline compound has a larger structure, a conjugated system is mostly in a planar configuration, has certain rigidity, has excellent optical performance in a solution, and has the advantages of easily-modified structure and physiological activity. Therefore, the pyranoquinoline compound with a slightly distorted structure is designed and synthesized, and a plurality of active sites are designed and formed, so that the application range of the pyranoquinoline compound is widened.
At present, an optical probe becomes one of the 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 realize the multi-functionalization of the application of the organic light-emitting material, and provide more valuable information and higher commercial potential. 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 viscosity-type fluorescent probes is also valuable.
Disclosure of Invention
In order to solve the technical problems, the invention provides a red light material with aggregation-induced emission effect, which is characterized in that the red light material is 8- (diethylamino) -2-imino-2H-pyrano [2,3-b ] quinoline-3-carbonitrile (QPIC), and the specific structural formula is as follows:
the preparation method of the red light material is characterized by comprising the following steps of:
adding 3- (1H-benzo [ d ] imidazole-2-yl) -N, N-diethyl-2-imino-2H-pyrano [2,3-b ] quinoline-8-amine and malononitrile into a reaction bottle in sequence, dissolving the solvent, refluxing until the reaction is finished (TLC monitors the reaction process), cooling, performing suction filtration to obtain a solid, and recrystallizing to obtain the product 8- (diethylamino) -2-imino-2H-pyrano [2,3-b ] quinoline-3-carbonitrile (QPIC).
The preparation method of the red light emitting material is characterized in that the molar ratio of 3- (1H-benzo [ d ] imidazol-2-yl) -N, N-diethyl-2-imino-2H-pyrano [2,3-b ] quinolin-8-amine to malononitrile is 1: 1 to 2.
The preparation method of the red light material is characterized in that the solvent comprises any one of ethylene glycol monomethyl ether, propanol and butanol, preferably ethylene glycol monomethyl ether.
The application of the red light material is characterized in that the material is applied to solvent viscosity detection and fluorescent dyes.
The detection method is characterized in that the mixed solvent comprises glycerol and an alcohol solution, and the alcohol solution comprises one or more of methanol, ethanol, propanol, isopropanol and n-butanol.
The invention has the beneficial effects
1. The invention takes a pyranoquinoline ring as a framework, introduces diethylamino with an electron-donating group (D) and cyano with an electron-withdrawing group (A) to synthesize a red light material with a slightly distorted structure, forms a plurality of active sites, and can be used as a good synthetic intermediate.
2. The red light material is synthesized under the condition of no catalyst. Has the characteristics of simple synthesis operation, high yield and low cost.
3. The red light material has the characteristics of large molar absorption coefficient, large stokes shift value, Aggregation Induced Emission (AIE), stability in a wide pH (2-11) range and the like. In addition, in the solution state, the material is sensitive to viscosity, can be used as a viscosity probe, and can be used as an enhanced fluorescent probe for measuring the viscosity of the solution in real time and rapidly.
4. The method has the advantages of original innovation, good social value and good application prospect.
Drawings
FIG. 1 shows QPIC prepared in example 11H-NMR spectrum.
FIG. 2 shows QPIC prepared in example 113C-NMR spectrum.
FIG. 3 shows the UV-VIS absorption spectrum (left) and fluorescence emission spectrum (right) of QPIC prepared in example 1 at different concentrations (chloroform).
FIG. 4 shows the UV-visible absorption spectrum (left) and fluorescence emission spectrum (right) of QPIC prepared in example 1 in different solvents.
FIG. 5 is the stokes shift versus solvent polarity parameter Δ f for the QPIC prepared in example 1.
FIG. 6 shows the UV-VIS absorption spectrum (left) and the change of absorption value (right) of QPIC prepared in example 1 under different pH environments.
FIG. 7 shows the fluorescence spectrum (left) and fluorescence intensity (right) of QPIC prepared in example 1 under different pH conditions.
FIG. 8 shows the THF/H at different water contents of QPIC prepared in example 12Fluorescence spectra in O-mix solution (left) and EtOH/H at different water contents2Fluorescence spectrum in O mixed solution (right).
FIG. 9 is the fluorescence spectrum (left) of QPIC prepared in example 1 at different viscosities and the linear relationship between the fluorescence intensity (right) of QPIC and different viscosities (right).
FIG. 10 is a spectrum (left) and a picture (right) of QPIC prepared in example 1 with the milled solid.
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
8- (diethylamino) -2-imino-2H-pyrano [2,3-b ] quinoline-3-carbonitrile (QPIC)
To a 50mL single-necked flask was added 3- (1H-benzo [ d ] in sequence]Imidazol-2-yl) -N, N-diethyl-2-imino-2H-pyrano [2,3-b]1.00g (2.6mmol) of quinolin-8-amine, 0.25g (3.9mmol) of malononitrile and 20mL of ethylene glycol monomethyl ether. The reaction was refluxed for 3h (TLC check). The reaction solution was cooled to room temperature, filtered under reduced pressure, recrystallized from methanol, and dried to give 0.80g of a dark red solid with a yield of 70%.1H NMR(400MHz,DMSO-d6)δ:11.69(s,1H),8.55(s,1H),8.08(s,1H),7.52(d,J＝8.8Hz,1H),6.78(dd,J＝9.2,2.0Hz,1H),6.44(s,1H),3.48(q,J＝6.8Hz,4H),1.17(t,J＝6.8Hz,6H).13C NMR(100MHz,DMSO-d6)δ:160.81,153.79,153.16,144.66,142.25,132.96,116.25,115.57,114.98,111.19,110.43,94.18,73.70,45.08,12.96.
The steps of the above example 1 are adopted to perform adjustment optimization, specifically as follows:
EXAMPLE 2 preparation of test solutions
(1) Preparation procedure of stock solution:
the QPIC prepared in example 1 was weighed and added to a 10mL cuvette to prepare a mixture having a concentration of 1.0X 10- 3The chloroform solution of mol/L is diluted by 10 times, 100 times, 1000 times and 10000 times respectively to prepare the QPIC 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 × 10-3Adding the QPIC solution of mol/L into 12 colorimetric tubes of 10mL, 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 QPIC by using the mol/L solution and taking rhodamine B as a standard reference substance.
(2) QPIC concentration dependent test:
2mL of QPIC chloroform solutions with different concentrations are respectively taken to carry out the tests of ultraviolet absorption spectrum and fluorescence emission spectrum. In the UV-visible spectrum, a chloroform solution of QPIC shows a single peak at 520nm, and the absorption value gradually increases with the increase of the concentration. In the fluorescence spectrum, the fluorescence intensity at 560nm gradually increased with the increase of the concentration, and when the concentration increased to 5X 10-5At mol/L, the QPIC fluorescence intensity decreases and the maximum emission wavelength red shifts to 580 nm. As shown in fig. 3. QPIC has a concentration-induced aggregation effect, probably as QPIC forms aggregates in chloroform with increasing concentration; the probability of collisions between solute molecules increases, resulting in energy loss.
(3) QPIC solvent effect:
2mL of different solvents (including dioxane, chloroform, toluene, ethyl acetate, tetrahydrofuran, dichloromethane, acetone, ethanol, methanol, acetonitrile, N-dimethylformamide and dimethyl sulfoxide) were added to 20. mu.L of the stock solution, and after shaking uniformly, the spectrum test was performed, and the results are shown in FIGS. 4 and 5. In the ultraviolet-visible spectrum, the maximum absorption wavelength of QPIC in 1, 4-dioxane is 497nm, the maximum absorption wavelength in dimethyl sulfoxide is 512nm, and the red shift is 15 nm; in the fluorescence spectrum, the QPIC has a maximum emission wavelength of 546nm in toluene and a maximum emission wavelength of 591nm in dimethyl sulfoxide, which are red-shifted by 45 nm. The Stokes shift value of NBC increased from 41nm to 79 nm. Solvents with different polarities have little influence on the ultraviolet-visible spectrum of QPIC and have great influence on the fluorescence spectrum. With the increase of the polarity of the solvent, the maximum absorption wavelength of the QPIC does not change greatly, the emission wavelength is red-shifted, the stokes shift of the QPIC is gradually increased, the molar absorption coefficient is reduced, and the larger the epsilon value is, the stronger the absorption capacity of the QPIC to the light with the wavelength is, the more sensitive the color reaction is, and the higher the sensitivity of measuring the light-absorbing substance by using an absorptiometry is reflected; while the corresponding fluorescence quantum yield of QPI is increased. The stokes shift increases gradually as the polarity of the solvent increases. The stokes shift has a certain linear relationship with the solvent polarity parameter Δ f. With the increase of the polarity of the solvent, the maximum emission wavelength of the QPIC is significantly red-shifted, and the QPIC shows a certain solvation effect, and there may be intramolecular charge transfer.
Table 1 shows the photophysical data of QPIC prepared in example 1 in different solvents.
(4) Effect of pH on QPIC fluorescence Properties
2mL of methanol/water (4: 1, v/v) solutions at different pH values were added to 20. mu.L of the stock solution and subjected to spectroscopic measurements, the results of which are shown in FIGS. 6 and 7. In an environment of 0.9< pH <2.86, both the absorbance and fluorescence intensity of QPIC increased gradually; in an environment of 2.86< pH <10.41, the absorption and fluorescence intensity of QPIC do not change much, in an environment of pH >10.41, the absorption of QPIC at 480nm decreases and with increasing pH the maximum absorption wavelength blueshifts to 430nm, blueshifting by 50 nm; and the fluorescence intensity of QPIC at 590nm decreased significantly and with increasing pH the maximum emission wavelength gradually blueshifted to 510nm, with a blue shift of 80 nm. These phenomena indicate that QPIC is stable over a wide range of pH (2-11).
(5) Aggregation-induced emission Effect of QPIC
2mL of THF/H with different water contents were taken2O mixed solution or EtOH/H2The solution was mixed with O, 20. mu.L of the stock solution was added, and the spectrum test was performed, and the result is shown in FIG. 8. In THF/H2In the O mixed solution, with the water content fwIncrease, fluorescence intensity of QPIC increases when the water content fwUp to 80%, the fluorescence intensity of QPIC was lower than that of QPIC in 100% THF, and the maximum emission wavelength was gradually blue-shifted; in EtOH/H2In O mixed solution, there is a similar law with the water content fwIncrease, fluorescence intensity of QPIC increases when the water content fwWhen the fluorescence intensity of the fluorescence intensity is increased to 70%, the fluorescence intensity of the QPIC is lower than 100%Fluorescence intensity of QPIC in EtOH, and gradually blue-shifted in maximum emission wavelength. The reason for the change in the emission spectrum may be: when the water content is more than a certain value, the dispersed monomer molecules slowly form crystalline aggregates to promote fluorescence enhancement, and when the water content is too large, the molecules rapidly aggregate into particles and amorphous aggregates, resulting in fluorescence reduction. Thus, QPIC has aggregation-induced emission (aggregation-induced emission) properties. (6) Effect of viscosity on QPIC fluorescence Properties
2mL of glycerol/methanol solutions of different ratios were added to 20. mu.L of the stock solution and subjected to spectroscopic measurements. In the fluorescence spectrum, as the viscosity of the mixed solution increases, the QPIC 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. 9. It is shown that QPIC can be used for quantitative determination of viscosity in mixed solvents.
(7) Solid state fluorescence properties of QPIC
Taking a certain amount of QPI crystals, grinding the QPI crystals into powder, and carrying out spectrum test on the crystals and the powder. The QPIC maximum emission wavelength was found to blue shift to 540nm with a slight increase in fluorescence intensity, with the fluorescence color still red, with no noticeable change, see figure 10. These features indicate the potential application of QPIC in solid red materials.
Claims (7)
1. A pyranoquinoline red light material capable of aggregation-induced emission is characterized in that the red light material is 8- (diethylamino) -2-imino-2H-pyrano [2,3-b ] quinoline-3-nitrile, and the specific structural formula is as follows:
2. the method for preparing the aggregation-induced emission pyranoquinoline red material according to claim 1, comprising the following steps: adding 3- (1H-benzo [ d ] imidazole-2-yl) -N, N-diethyl-2-imino-2H-pyrano [2,3-b ] quinoline-8-amine and malononitrile into a reaction bottle in sequence, dissolving the mixture by a solvent, carrying out reflux reaction, monitoring the reaction progress by TLC until the reaction is finished, cooling, carrying out suction filtration to obtain a solid, and recrystallizing to obtain the product 8- (diethylamino) -2-imino-2H-pyrano [2,3-b ] quinoline-3-carbonitrile.
3. The method for preparing an aggregation-induced emission pyranoquinoline red-light material according to claim 2, wherein the molar ratio of 3- (1H-benzo [ d ] imidazol-2-yl) -N, N-diethyl-2-imino-2H-pyrano [2,3-b ] quinolin-8-amine to malononitrile is 1: 1 to 2.
4. The method for preparing an aggregation-induced emission pyranoquinoline red light-emitting material according to claim 2, wherein the solvent comprises any one of ethylene glycol monomethyl ether, propanol and butanol.
5. Use of the aggregation-induced emission pyranoquinoline red material according to claim 1 for detecting the viscosity of a solvent.
6. The use of claim 5, wherein the solvent comprises glycerol and an alcohol solution to form a mixed solvent, the alcohol solution comprising one or more of methanol, ethanol, propanol, isopropanol, and n-butanol.
7. Use of the aggregation-induced emission pyranoquinoline red material according to claim 1 as a fluorescent dye.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5759729A (en) * | 1995-12-05 | 1998-06-02 | Xerox Corporation | Photochromic electrostatic toner compositions |
| WO2011066804A1 (en) * | 2009-12-03 | 2011-06-09 | 大连理工大学 | Fluorescent probe compounds, preparation method and use thereof |
| CN109879884A (en) * | 2019-03-12 | 2019-06-14 | 济南大学 | A kind of fluorescence probe and its preparation method and application detecting viscosity |
| CN112390790A (en) * | 2020-11-30 | 2021-02-23 | 西北师范大学 | Methyl quinoline-benzopyrylium derivative and preparation method and application thereof |
| CN112480134A (en) * | 2020-12-17 | 2021-03-12 | 河南大学 | Pair of isomers, preparation method and application thereof |
| CN112625024A (en) * | 2020-11-26 | 2021-04-09 | 华东理工大学 | Amphiphilic fluorescent probe for rapid wash-free imaging of cell membrane |
-
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- 2021-09-08 CN CN202111052176.8A patent/CN113880852B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5759729A (en) * | 1995-12-05 | 1998-06-02 | Xerox Corporation | Photochromic electrostatic toner compositions |
| WO2011066804A1 (en) * | 2009-12-03 | 2011-06-09 | 大连理工大学 | Fluorescent probe compounds, preparation method and use thereof |
| CN109879884A (en) * | 2019-03-12 | 2019-06-14 | 济南大学 | A kind of fluorescence probe and its preparation method and application detecting viscosity |
| CN112625024A (en) * | 2020-11-26 | 2021-04-09 | 华东理工大学 | Amphiphilic fluorescent probe for rapid wash-free imaging of cell membrane |
| CN112390790A (en) * | 2020-11-30 | 2021-02-23 | 西北师范大学 | Methyl quinoline-benzopyrylium derivative and preparation method and application thereof |
| CN112480134A (en) * | 2020-12-17 | 2021-03-12 | 河南大学 | Pair of isomers, preparation method and application thereof |
Non-Patent Citations (3)
| Title |
|---|
| BHAWANA SINGH等: "Rapid, clean and efficient one-pot synthesis of thiopyrano[2,3-b]quinolines via domino Michael addition/cyclization reactions", 《TETRAHEDRON LETTERS》 * |
| DOKYOUNG KIM等: "Synthesis of Benzocoumarins and Characterization of Their Photophysical Properties", 《ASIAN J. ORG. CHEM.》 * |
| 朱清雅等: "用于活细胞成像的黏度荧光探针研究进展", 《武汉大学学报（理学版）》 * |
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