CN113278000A - Coumarin-based red light aggregation-induced luminescent material and preparation method thereof - Google Patents
Coumarin-based red light aggregation-induced luminescent material and preparation method thereof Download PDFInfo
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Abstract
A coumarin-based red light aggregation-induced emission material and a preparation method thereof belong to the technical field of organic chemistry and material chemistry. The luminescent material for solving the technical problem has the following structural formula:
the CRTP is named. CRTP synthesis firstly, 4-diethylamino salicylaldehyde, ethyl acetoacetate and piperidine are mixed in absolute ethyl alcohol, reflux heating is carried out to obtain a G-1 product, and then the compound G-1 and 4- (diphenylamine) benzaldehyde with equimolar amount are further catalyzed by piperidine to obtain a final product. The red light aggregation-induced emission material CRTP is prepared by using coumarin and triphenylamine. The raw materials are easy to obtain, and the synthesis is simple and feasible. When the CRTP is aggregated in a poor solvent or a water phase, the CRTP can realize obvious red light emission, can effectively avoid aggregation-induced quenching phenomenon of the traditional organic fluorophore, and hasIs expected to be applied to solid luminescent materials and high-sensitivity fluorescence detection in organisms.
Description
Technical Field
The invention belongs to the technical field of organic chemistry and material chemistry, and particularly relates to a coumarin-based red light aggregation-induced luminescent material and a preparation method thereof.
Background
The aggregation-induced fluorescence quenching property of the traditional organic fluorescent molecules severely limits the application range of the organic fluorescent molecules as a fluorescent sensor, and greatly reduces the detection sensitivity of the organic fluorescent molecules. In order to improve the application of the fluorescent molecules, a series of novel fluorescent molecules with aggregation-induced emission (AIE) property developed by the Tang-Benzhou research group as a lead in recent 20 years have attracted attention, and the molecules are widely applied to the fields of biochemical sensors, fluorescent imaging, organic luminescent materials and the like.
The currently developed aggregation-induced emission materials are mainly based on the tetrastyrene molecule (J.org.chem.2019,84,22, 14498-. In a dilute solution, a benzene ring of the molecule can freely and quickly rotate in the molecule around a single bond, and at the moment, energy from an excited state to a ground state is dissipated in a non-radiation mode; in the aggregation state, the benzene ring is greatly limited in molecular rotation under the influence of physical constraint force, so that the non-radiative inactivation process of a single molecule is strongly inhibited, and finally the benzene ring is shown to be obvious in fluorescence emission characteristics in a solid or aggregation state. This molecular internal Rotation Inhibition (RIR) is considered to be the most dominant mechanism of the AIE phenomenon. Triphenylamine is used as a blue light material with excellent photochemical photo physical properties, is widely applied to electroluminescent materials and fluorescence sensors, is simple in molecular synthesis, easy to obtain raw materials, easy to generate single bond rotation in molecules, has similarity with the internal torsion of tetraphenylethylene, but is far less developed than the aggregation-induced luminescent material based on triphenylamine.
Coumarin derivatives are a fluorophore with excellent luminescence property which is always favored by researchers, but the emission wavelength of the coumarin derivatives is shorter, and the coumarin derivatives are easy to damage when applied in organisms. The coumarin and the triphenylamine with the AIE phenomenon are partially grouped in one organic small molecule, so that the coumarin can be prolonged from high-energy blue light emission to low-energy red light emission, and strong fluorescence emission of red light in an aggregation state can be realized. It is believed that as more and more new AIE materials are synthesized, the fields of biochemical analysis and organic light emitting devices will make the human world more wonderful.
Disclosure of Invention
Aiming at the defects, the invention provides a coumarin-based red light aggregation-induced luminescent material and a preparation method thereof, wherein the luminescent material can also emit strong fluorescent luminescent material in an aggregation state in a solid or poor solvent, so that the fluorescence quenching phenomenon of the traditional organic fluorophore in the aggregation state is avoided.
The specific structure of the luminescent material for solving the technical problems of the invention is named as CRTP.
The reaction route for CRTP is as follows:
CRTP is carried out by the following specific steps:
(1) synthesis of G-1: mixing 4-diethylamino salicylaldehyde with ethyl acetoacetate and piperidine in anhydrous ethanol, heating under reflux for 1.5-2.5 hr, and cooling to room temperature. Filtration under reduced pressure gave the product as a yellow crystalline solid, G-1.
(2) Synthesis of CRTP: and (3) further catalyzing the compound G-1 and 4- (diphenylamine) benzaldehyde by piperidine, stirring in absolute ethyl alcohol at room temperature for 30 minutes, heating to 65 ℃, continuing stirring for reaction, separating out a large amount of solid from a reaction solution, cooling to room temperature, and filtering under reduced pressure to obtain a red solid product.
Further, in the step (1), the molar ratio of the 4-diethylamino salicylaldehyde to the ethyl acetoacetate is 1: 1.42.
further, the absolute ethyl alcohol in the step (1) is added in an amount of 1mmol 4-diethylaminosalicylaldehyde based on 4-diethylaminosalicylaldehyde, and 2-2.5mL of absolute ethyl alcohol is added.
Further, in the step (1), the addition amount of piperidine is 0.05-0.09mL based on 4-diethylaminosalicylaldehyde and 1mmol 4-diethylaminosalicylaldehyde.
Further, the amount of piperidine added in step (2) is based on the compound G-1, and 0.4-06mL of piperidine is added to 1mmol of the compound G-1.
Further, the amount of ethanol added in step (2) is based on the compound G-1, and 10-13mL of ethanol is added to 1mmol of the compound G-1.
The principle is as follows: according to the invention, under the catalysis of piperidine, a carbon-carbon double bond is generated by condensation of an active methyl group of a coumarin derivative and an aldehyde group of triphenylamine through a Knoevenagel reaction, and a triphenylamine molecule is introduced onto a coumarin fluorophore molecule framework, so that on one hand, a conjugated II bond of coumarin is enlarged, the fluorescence emission wavelength of a blue-light coumarin derivative is increased to 600nm, and the coumarin derivative becomes low-energy red fluorescence, and the damage of blue light to organisms is avoided. On the other hand, triphenylamine which is easy to twist is introduced into the polar solvent, so that the triphenylamine can emit strong fluorescence in an aggregation state, fluorescence quenching is avoided, and fluorescent molecules with higher sensitivity are provided for fluorescence detection and organic luminescent materials in organisms.
Has the advantages that: the red light aggregation-induced emission material CRTP is prepared by using coumarin and triphenylamine. The raw materials are easy to obtain, and the synthesis is simple and feasible. When the CRTP is aggregated in a poor solvent or a water phase, the CRTP can realize obvious red light emission, can effectively avoid aggregation-induced quenching of the traditional organic fluorophore, and is expected to be applied to high-sensitivity fluorescence detection in solid luminescent materials and organisms.
Drawings
FIG. 1 shows the nuclear magnetic hydrogen spectrum (deuterated chloroform as solvent) of the AIE fluorescent material CRTP in example 2 of the invention;
FIG. 2 is the nuclear magnetic carbon spectrum (solvent is deuterated chloroform) of the AIE fluorescent material CRTP in example 2 of the invention;
FIG. 3 is the ultraviolet absorption spectra of the AIE fluorescent material CRTP in example 2 of the present invention in various solvents;
FIG. 4A solution of the AIE fluorescent material CRTP at different water contentsUV absorption Spectroscopy in Agents (solvent: MeCN/H)2O, volume percent water varying from 0% to 100%);
FIG. 5 change of ultraviolet absorption intensity at 442 nm of CRTP as a function of water content for AIE fluorescent material (solvent: MeCN/H)2O, volume percent water varying from 0% to 100%);
FIG. 6 change of CRTP fluorescence spectrum of AIE fluorescent material with water content (solvent: MeCN/H)2O, volume percent water varying from 0% to 100%);
FIG. 7 change of maximum fluorescence intensity of AIE fluorescent material CRTP with water content (solvent: MeCN/H)2O, volume percent water varying from 0% to 100%);
FIG. 8 fluorescence spectra of the AIE fluorescent material CRTP in different solvents;
FIG. 9 photograph of the AIE fluorescent material CRTP in different solvents (solvent: MeCN/H)2O, from left to right: the volume percentage of water is changed from 0% to 100% under 345nm ultraviolet lamp irradiation);
FIG. 10 photograph of the AIE fluorescent material CRTP in different solvents (solvent: MeCN/H)2O, from left to right: the volume percentage of water varies from 0% to 100%, under solar irradiation);
FIG. 11 CRTP solid photograph of AIE phosphor (under 345nm UV lamp).
Detailed Description
The present invention will be further described with reference to the following examples.
Example 1
Synthesis of G-1: 4-Diethylaminosalicylaldehyde (1.2g, 6.3mmol), ethyl acetoacetate (1.2g, 9mmol) and piperidine (0.5mL) were mixed in 15mL of anhydrous ethanol, heated at reflux for about 2 hours, and the end of the reaction was determined by thin layer chromatography and cooled to room temperature when the starting materials were completely reacted. Filtration under reduced pressure gave 1.42G of the product G-1 as a yellow crystalline solid in 97% yield. The crude product was directly subjected to the next reaction without further purification.
Example 2
Synthesis of CRTP: putting a compound G-1(100mg, 0.386mmol) and 4- (diphenylamine) benzaldehyde into a round-bottom flask, adding piperidine (0.2ml) into absolute ethyl alcohol (molecular sieve drying), stirring for 30 minutes at room temperature, heating to 65 ℃, continuing stirring for reaction, separating out a large amount of solid from a reaction solution, determining the reaction end point through thin-layer chromatography, cooling to room temperature, filtering under reduced pressure, washing a filter cake with a small amount of ethanol for multiple times, and obtaining a red solid product of 60mg with the yield of 30%.1HNMR(500MHz,CDCl3)δ8.55(s,1H),8.01(d,J＝15.6Hz,1H),7.80(d,J＝15.6Hz,1H),7.53(d,J＝8.6Hz,2H),7.42(d,J＝9.0Hz,1H),7.29(t,J＝7.9Hz,4H),7.14(d,J＝7.6Hz,4H),7.09(t,J＝7.4Hz,2H),7.01(d,J＝8.6Hz,2H),6.63(dd,J＝8.9,2.2Hz,1H),6.49(d,J＝1.9Hz,1H),3.46(q,J＝7.1Hz,4H),1.25(t,J＝7.1Hz,6H).13C NMR(CDCl3,125MHz)δ(ppm):186.38,160.92,158.60,152.80,149.90,148.48,146.96,143.32,131.71,130.05,129.46,128.63,125.38,123.94,122.45,121.71,117.20,109.82,108.75,96.71,45.20,12.49.
Example 3 ultraviolet absorption Spectroscopy of the AIE fluorescent Material CRTP in different solvents
The red light AIE material CRTP in example 2 is weighed and prepared into 10 in different solvents-5Mu m solution, and measuring the ultraviolet absorption spectrum of the solution. As can be seen from FIG. 3, in the toluene solution, the ultraviolet absorption shows two distinct absorption peaks at 433nm and 466nm, and in the polar solution, it mainly shows one absorption peak. This is probably due to the fact that in polar solutions the compound exists mainly in a triphenylamine twisted state, whereas in non-polar solutions both the bond twisted and non-twisted states exist. Weighing red light AIE material CRTP, and preparing into 10 in different acetonitrile and water mixture ratio solutions-5The changes in the violet absorption intensity of the μm solution were observed, and the results of the measurement are shown in FIGS. 4 and 5. A significant decrease in absorption intensity was seen when the proportion of water in the solution was increased, probably due to the solubility of the AIE material CRTP with the water contentThe amount is gradually decreased.
Example 4 fluorescence emission Spectroscopy of the AIE fluorescent Material CRTP in different solvents
Weighing the red-light AIE material CRTP prepared in the example 1, and preparing the red-light AIE material CRTP into 10 parts in different acetonitrile and water mixture solutions-5The change of the fluorescence spectrum of the solution of μm was measured, and the test results are shown in fig. 6 and 7, in which the fluorescence intensity was significantly decreased as the water content was increased, but when the volume percentage of water reached 80%, the fluorescence intensity was significantly increased. The fluorescence intensity appeared to be at a maximum when the volume percentage of water reached 90%. This indicates that, when the water content is low, the fluorescence of the compound is weak due to the decrease of the solubility of the compound, but when the water content reaches above 70%, the aggregation-induced emission phenomenon is obvious, which indicates that the compound can indeed realize the fluorescence emission in the aggregation state, and avoid the fluorescence quenching phenomenon of the traditional solvent in the aggregation state with high water content. At the same time, a significant red fluorescence emission was observed under 365nm uv illumination, as shown in fig. 9. When the fluorescence emission of CRTP was observed in different polar organic solvents, it can be seen (as shown in fig. 8) that CRTP fluoresces very weakly in polar solvents and strongly in non-polar solvents. This is probably due to the fact that CRTP is more prone to single bond twisting in polar solvents, thereby dissipating its excited to ground state energy in a non-radiative manner and weakening fluorescence.
EXAMPLE 5 pictures of the AIE fluorescent Material CRTP
Weighing the red-light AIE material CRTP prepared in the example 2, and preparing the red-light AIE material CRTP into 10 in different acetonitrile and water mixture ratio solutions-5In the μm solution, as shown in fig. 9 and 10, when the compound CRTP is excited by an ultraviolet lamp of 345nm, it can be seen that the fluorescence of the compound CRTP is weak when the water content is 0-70%, but the fluorescence is significantly enhanced when the water content reaches 80%, which indicates that the compound CRTP has a significant aggregation-induced emission property. When viewed in sunlight, the compound can be seen to appear noticeably yellow, but after the water content reaches 80%, the yellow color can be seen noticeably weaker, which is consistent with the weakening of the absorption intensity observed in the ultraviolet absorption spectrum. As shown in FIG. 11, fluorescence of solid CRTP under 345nm UV lightThe optical picture shows that the compound has obvious fluorescence in the solid state.
The ultraviolet absorption spectrum and the fluorescence emission spectrum of the red light aggregation luminescent material CRTP can be observed, the CRTP fluorescence emission is obvious in acetonitrile solution, after a small amount of water is added, the fluorescence is quenched, when the water content is continuously increased to 80% (volume percentage, in a mixed solvent of acetonitrile and water), the fluorescence emission spectrum is obviously enhanced, when the water volume percentage is 90%, the fluorescence has the strongest value, and the ultraviolet absorption intensity of the compound is obviously reduced, which shows that the red light aggregation luminescent material CRTP is stacked due to poor solubility in poor solvents, and the specific triphenylamine structure of the CRTP enables the CRTP to have torsion at a certain angle, so that the phenomenon that the CRTP is stacked and quenched like a traditional organic fluorophore is avoided, and the CRTP can also emit obvious red fluorescence in an aggregation state.
The foregoing examples are provided for illustration and description of the invention only and are not intended to limit the invention to the scope of the described examples. Furthermore, it will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, and that many variations and modifications may be made in accordance with the teachings of the present invention, which variations and modifications are within the scope of the present invention as claimed.
Claims (8)
1. A coumarin-based red light aggregation-induced emission material is characterized in that the structural formula of the emission material is as follows, and the emission material is named as CRTP:
2. a method for preparing a luminescent material according to claim 1, characterized in that the method is prepared by the following steps:
the preparation steps of CRTP are as follows:
s1.G-1 synthesis: mixing 4-diethylamino salicylaldehyde, ethyl acetoacetate and piperidine in absolute ethyl alcohol, heating for 1.5-2.5 hours under reflux, and cooling to room temperature; filtering under reduced pressure to obtain a yellow crystal solid G-1 product;
s2, CRTP synthesis: and (3) further catalyzing the compound G-1 and 4- (diphenylamine) benzaldehyde with an equal molar amount by piperidine, stirring the mixture for 30 minutes in absolute ethyl alcohol at room temperature, heating the mixture to 65 ℃, continuing stirring the mixture for reaction, separating out a large amount of solid from a reaction solution, cooling the reaction solution to the room temperature, and filtering the reaction solution under reduced pressure to obtain a red solid product.
3. The method for preparing the coumarin-based red light aggregation-induced emission material according to claim 2, wherein in the step S1, the molar ratio of the 4-diethylamino salicylaldehyde to the ethyl acetoacetate is 1: 1.42.
4. the method of claim 2, wherein the absolute ethanol is added in step S1 in an amount of 1mmol 4-diethylamino salicylaldehyde based on 4-diethylamino salicylaldehyde, and the absolute ethanol is added in an amount of 2-2.5 mL.
5. The method as claimed in claim 2, wherein the amount of piperidine added in step S1 is 0.05-0.09mL based on 4-diethylaminosalicylaldehyde and 1mmol 4-diethylaminosalicylaldehyde.
6. The method for preparing the coumarin-based red light aggregation-induced emission material as claimed in claim 2, wherein the amount of piperidine added in step S2 is 0.4-06mL piperidine to 1mmol compound G-1 based on compound G-1.
7. The method for preparing the coumarin-based red light aggregation-induced emission material according to claim 2, wherein the ethanol is added in the step S2 in an amount of 10-13mL of ethanol based on 1mmol of the compound G-1.
8. Use of a luminescent material according to claim 1 in the field of solid-state luminescent materials.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114685530A (en) * | 2022-03-30 | 2022-07-01 | 湖南科技大学 | Isoquinoline-based aggregation-induced emission molecule and preparation method thereof |
| CN115093737A (en) * | 2022-06-06 | 2022-09-23 | 中国船舶集团有限公司系统工程研究院 | Underwater object cavity leak point optical indication material, method and cavity structure |
| CN115417846A (en) * | 2022-09-21 | 2022-12-02 | 安徽科技学院 | Coumarin-based two-state high-fluorescence material and synthesis method and application thereof |
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| CN108440475A (en) * | 2018-03-16 | 2018-08-24 | 济南大学 | A kind of Ratiometric fluorescent probe and its preparation method and application for distinguishing opposed polarity fat drips |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108440475A (en) * | 2018-03-16 | 2018-08-24 | 济南大学 | A kind of Ratiometric fluorescent probe and its preparation method and application for distinguishing opposed polarity fat drips |
Cited By (6)
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| CN114685530A (en) * | 2022-03-30 | 2022-07-01 | 湖南科技大学 | Isoquinoline-based aggregation-induced emission molecule and preparation method thereof |
| CN114685530B (en) * | 2022-03-30 | 2023-11-14 | 湖南科技大学 | Aggregation-induced emission molecule based on isoquinoline and preparation method thereof |
| CN115093737A (en) * | 2022-06-06 | 2022-09-23 | 中国船舶集团有限公司系统工程研究院 | Underwater object cavity leak point optical indication material, method and cavity structure |
| CN115093737B (en) * | 2022-06-06 | 2024-02-09 | 中国船舶集团有限公司系统工程研究院 | Optical indication material and method for leakage point of cavity of underwater object and cavity structure |
| CN115417846A (en) * | 2022-09-21 | 2022-12-02 | 安徽科技学院 | Coumarin-based two-state high-fluorescence material and synthesis method and application thereof |
| CN115417846B (en) * | 2022-09-21 | 2023-05-26 | 安徽科技学院 | Coumarin-based bimodal high-fluorescence material and synthesis method and application thereof |
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