CN112480087A - Schiff base with aggregation-induced emission effect and preparation method thereof - Google Patents
Schiff base with aggregation-induced emission effect and preparation method thereof Download PDFInfo
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Abstract
The application belongs to the field of fluorescent probes, and particularly relates to a novel Schiff base with aggregation-induced emission effect and a preparation method thereof. The probe utilizes an intramolecular charge transfer mechanism to coordinate in the presence of copper ions to form a new compound, ultraviolet absorption generates red shift, fluorescence generates red shift and is obviously enhanced.
Description
Technical Field
The invention relates to a Schiff base with aggregation-induced emission effect and a preparation method thereof, the compound has a conjugated and rigid planar structure, shows better fluorescence performance, shows good aggregation-induced emission (AIE) effect, contains C ═ N functional groups, can provide rich coordination modes, and has strong metal coordination ability and good ion selectivity.
Background
Carbazole can be used for producing dyes, pigments, photoconductors, photosensitive materials, special inks and the like. The pigment permanent violet RL produced by the pigment permanent violet RL can be widely used for coloring automobile finish and high-temperature resistant plastics, and has the advantages of high temperature resistance and ultraviolet light resistance. The produced dye sulfuration reduction blue RNX and Haichang blue has excellent fastness indexes, especially excellent fastness to chlorine bleaching. It can also be used to make leather, N-vinyl carbazole plastics, pesticide such as tetranitro carbazole, chlorinated carbazole, and UV-sensitive photographic dry film. In addition, carbazole is increasingly applied in the field of new photoelectric material development, and carbazole can be used for preparing organic nonlinear optical (NLO) materials, Organic Electroluminescence (OEL) materials, photorefractive materials, bifunctional systems containing carbazole chromophore, carbazole-containing photorefractive small molecular glass and the like.
Aggregation-induced emission (AIE) is a phenomenon that was discovered by the team of the down-loyalty college in 2001 occasionally: a silole derivative in the form of a single molecule in solution, which exhibits a gradually increasing fluorescence as the solvent is gradually evaporated. On the basis of this, the subject group has conducted a series of intensive research studies and proposed a novel concept of aggregation-induced emission. Provides a new idea for solving the problems of the traditional ACQ material; it also opens new door for the development of the field of bio-imaging. After more than ten years of effort and development, the AIE material has remarkable advantages in the fields of organelle staining, pathogen recognition, long-period cell tracing, photodynamic therapy and the like. Compared with the traditional ACQ fluorescent material, the AIE material has the advantages that: low background, high signal-to-noise ratio, good sensitivity, strong photobleaching resistance and the like.
The Schiff base is usually formed by condensing amine and active carbonyl, has a special conjugated structure and good chemical coordination performance, and part of metal complexes of the Schiff base have good fluorescence performance, so that the Schiff base can be used as a fluorescent probe to identify metal ions, thereby leading to deeper theoretical and application research of people. Meanwhile, Schiff base compounds and metal complexes thereof are also important in the fields of medicine, catalysis, analytical chemistry, corrosion and photochromism. The characteristics of carbazole compounds and fluorescein are organically combined to prepare the carbazole Schiff base, and the synthesized compound has good specific selectivity on mercury ions, the detection limit reaches the nanometer level, and the carbazole Schiff base has the characteristic of quick response.
The invention content is as follows:
the invention aims to provide Schiff bases with aggregation-induced emission effects, the Schiff bases have special conjugated structures and good chemical coordination performance, and the synthesis process has the advantages of simplicity in operation, high yield, low cost, rapidness in detection and the like.
The invention also aims to provide a preparation method of the Schiff base with the aggregation-induced emission effect.
The invention also aims to provide the application of the Schiff base with the aggregation-induced emission effect.
In order to achieve the purpose, the technical scheme of the invention is as follows:
the compound is mainly applied to the field of materials or sensors;
a preparation method of Schiff base with aggregation-induced emission effect comprises the following steps:
1) weighing N-ethyl carbazole-3-formaldehyde and pyrazine-2-formhydrazide, and dissolving in a solvent;
and stirring the solution at a constant temperature of 60-80 ℃, adding glacial acetic acid, reacting for 3-8 h, distilling under reduced pressure to remove the solvent to obtain a yellow powdery solid, recrystallizing and purifying the yellow powdery solid by using methanol, ethanol, chloroform or ethyl acetate, and drying in vacuum to obtain the Schiff base with the aggregation-induced emission effect.
Preferably, the solvent is one of N, N-dimethylformamide, dimethyl sulfoxide and ethanol;
preferably, the molar ratio of the N-ethylcarbazole-3-formaldehyde to the pyrazine-2-formylhydrazine in the step 1) is 1: 1-1: 1.5; the molar ratio of the N-ethyl carbazole-3-formaldehyde to the solvent is 1: 10-1: 90; the molar ratio of the glacial acetic acid to the solvent is 1: 10-1: 100.
The synthesis route of the Schiff base with aggregation-induced emission effect is as follows:
according to the invention, N-ethyl carbazole-3-formaldehyde and pyrazine-2-formhydrazide are reacted to obtain the novel Schiff base with aggregation-induced emission effect, and the compound has good selectivity on metal copper ions through tests.
The novel compound can be used as a probe to be applied to the field of ion detection. Although researchers have carried out many reactions by using carbazolyl compounds, the compounds have good specific selectivity to copper ions and the detection limit reaches the nanometer level compared with similar compounds.
Description of the drawings:
(1) FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of Schiff base with aggregation-induced emission effect.
(2) Fig. 2 is a fluorescence spectrum of schiff base selective for metal ions with aggregation-induced emission effect (emission wavelength on abscissa and fluorescence intensity on ordinate).
(3) FIG. 3 is a solid fluorescence spectrum of Schiff base having aggregation-induced emission effect showing AIE effect (abscissa is emission wavelength and ordinate is fluorescence intensity).
In order to better understand the technical solution of the present invention, the following detailed description is given by specific examples.
Example 1
2.23g (10mmol) of N-ethylcarbazole-3-formaldehyde and 1.38g (10mmol) of pyrazine-2-formylhydrazine are weighed, dissolved in 50mL of hot ethanol and added into a 100mL three-neck flask provided with a thermometer and a stirring device. Adding glacial acetic acid 0.63ml (10mmol) into the mixed solution, refluxing at 80 deg.C under stirring for 5 hr, cooling to room temperature to precipitate yellow solid, washing with cold ethanol, and vacuum drying at 50 deg.C for 8 hr to obtain final product compound (Schiff base with aggregation-induced emission effect). Yield: 82 percent.
Example 2
2.23g (10mmol) of N-ethylcarbazole-3-formaldehyde and 1.65g (12mmol) of pyrazine-2-formylhydrazine are weighed, dissolved in 50mL of hot ethanol and added into a 100mL three-neck flask provided with a thermometer and a stirring device. Adding glacial acetic acid 0.63ml (10mmol) into the mixed solution, refluxing at 80 deg.C under stirring for 5 hr, cooling to room temperature to precipitate yellow solid, washing with cold ethanol, and vacuum drying at 50 deg.C for 8 hr to obtain final product compound (Schiff base with aggregation-induced emission effect). Yield: 88 percent.
Example 3
2.23g (10mmol) of N-ethylcarbazole-3-formaldehyde and 1.93g (14mmol) of pyrazine-2-formylhydrazine are weighed, dissolved in 50mL of hot ethanol and added into a 100mL three-neck flask provided with a thermometer and a stirring device. Adding glacial acetic acid 0.63ml (10mmol) into the mixed solution, refluxing at 80 deg.C under stirring for 5 hr, cooling to room temperature to precipitate yellow solid, washing with cold ethanol, and vacuum drying at 50 deg.C for 8 hr to obtain final product compound (Schiff base with aggregation-induced emission effect). Yield: 80 percent.
Example 4
2.23g (10mmol) of N-ethylcarbazole-3-formaldehyde and 2.20g (16mmol) of pyrazine-2-formylhydrazine are weighed, dissolved in 50mL of hot ethanol and added into a 100mL three-neck flask provided with a thermometer and a stirring device. Adding glacial acetic acid 0.63ml (10mmol) into the mixed solution, refluxing at 80 deg.C under stirring for 5 hr, cooling to room temperature to precipitate yellow solid, washing with cold ethanol, and vacuum drying at 50 deg.C for 8 hr to obtain final product compound (Schiff base with aggregation-induced emission effect). Yield: 78 percent.
Example 5
2.23g (10mmol) of N-ethylcarbazole-3-formaldehyde and 2.48g (18mmol) of pyrazine-2-formylhydrazine are weighed, dissolved in 50mL of hot ethanol and added into a 100mL three-neck flask provided with a thermometer and a stirring device. Adding glacial acetic acid 0.63ml (10mmol) into the mixed solution, refluxing at 80 deg.C under stirring for 5 hr, cooling to room temperature to precipitate yellow solid, washing with cold ethanol, and vacuum drying at 50 deg.C for 8 hr to obtain final product compound (Schiff base with aggregation-induced emission effect). Yield: 75 percent.
Example 6
2.23g (10mmol) of N-ethylcarbazole-3-formaldehyde and 2.76g (20mmol) of pyrazine-2-formylhydrazine are weighed, dissolved in 50mL of hot ethanol and added into a 100mL three-neck flask provided with a thermometer and a stirring device. Adding glacial acetic acid 0.63ml (10mmol) into the mixed solution, refluxing at 80 deg.C under stirring for 5 hr, cooling to room temperature to precipitate yellow solid, washing with cold ethanol, and vacuum drying at 50 deg.C for 8 hr to obtain final product compound (Schiff base with aggregation-induced emission effect). Yield: and 69 percent.
Nuclear magnetic analysis (nuclear magnetic spectrum is shown in figure 1) of the compound of the final product:
as shown in figure 1, the total of 14 hydrogen of the compound is obtained by analyzing the structural formula and nuclear magnetic resonance hydrogen spectrogram of the novel Schiff base with aggregation-induced emission effect. The signal peak(s) appearing in the vicinity of 12.26ppm was the signal peak of proton 10, whose peak area was 1.00; the signal peak appearing in the vicinity of 9.32ppm was that of proton 12, and its peak area was 0.88; the signal peaks appearing in the vicinity of 8.88ppm were those of protons 11, 13, and 14, and the peak area thereof was 3.01; the signal peak appearing around 8.50ppm is the signal peak of proton 9, and the peak area thereof is 1.02; a signal peak of proton 1, which appears near 8.29ppm and whose peak area is 1.05; the signal peak appearing around 7.95ppm is the signal peak of proton 8; its peak area is 1.02; the signal peaks appearing around 7.72ppm were for protons 4 and 7, whose peak area was 2.08; the signal peak appearing in the vicinity of 7.53ppm was that of proton 3, and its peak area was 1.02; the signal peak appearing around 7.29ppm is the signal peak of proton 2, and the peak area thereof is 1.03; the signal peak appearing in the vicinity of 4.52ppm was that of proton 5, the peak area of which was 2.04; the signal peak appearing in the vicinity of 1.37ppm was that of proton 6, and its peak area was 3.11. Therefore, the nuclear magnetic resonance hydrogen spectrogram of the compound well accords with the structure of the compound, namely the novel Schiff base with the aggregation-induced emission effect.
Application of copper ion fluorescent probe
Experimental example 1
The novel Schiff base with aggregation-induced emission effect prepared in example 1 was dissolved in DMSO solution to prepare 1X 10-5mol/L solution. Using F-4600 fluorescenceThe spectrophotometer measures the fluorescence excitation wavelength of the compound and measures the fluorescence spectrum of the compound. Then adding different metal ions Ag with equivalent weight into the solution respectively+,Co2+,Cd2+,Na+,Cu2+,Ni2+,Fe2+,Pb2+,Cr3+,Al3+,Zn2+,Hg2+K+and Fe3+Measuring the fluorescence emission spectrum of the fluorescent probe molecule in the presence of each metal ion (see the result in figure 2);
we found that the fluorescence intensity of the compound itself is so weak that it is difficult to observe in the figure without addition of metal ions, only when Cu is added2+And then, the fluorescence spectrum generates very remarkable enhancement, the characteristic has important significance for rapidly identifying metal copper ions, and the synthesized fluorescent probe has better selectivity on the copper ions (II).
As seen from FIG. 2, the probe has good selectivity for copper ions, and can rapidly show differences from other particles.
As seen from FIG. 3, the probe has aggregation-induced emission effect, and the solid has good fluorescence intensity.
Claims (5)
1. A schiff base having an aggregation-induced emission effect, wherein: the structural formula is as follows:
2. use of a schiff base having an aggregation-induced emission effect according to claim 1, wherein: the method is applied to the field of materials or the field of sensors.
3. A method of preparing a schiff base having an aggregation-induced emission effect according to claim 1, wherein: the method comprises the following specific steps:
1) weighing N-ethyl carbazole-3-formaldehyde and pyrazine-2-formhydrazide, and dissolving in a solvent;
and stirring the solution at a constant temperature of 60-80 ℃, adding glacial acetic acid, reacting for 3-8 h, distilling under reduced pressure to remove the solvent to obtain a yellow powdery solid, recrystallizing and purifying the yellow powdery solid by using methanol, ethanol, chloroform or ethyl acetate, and drying in vacuum to obtain the Schiff base with the aggregation-induced emission effect.
4. A method for preparing Schiff base with aggregation-induced emission effect according to claim 3, wherein the solvent is N, N-dimethylformamide or dimethyl sulfoxide or ethanol.
5. The method for preparing Schiff base with aggregation-induced emission effect according to claim 3, wherein the molar ratio of N-ethylcarbazole-3-formaldehyde to pyrazine-2-formhydrazide in the step 1) is 1:1 to 1: 1.5; the molar ratio of the glacial acetic acid to the solvent is 1: 10-1: 100; the molar ratio of the N-ethyl carbazole-3-formaldehyde to the solvent is 1: 10-1: 90.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113105467A (en) * | 2020-11-27 | 2021-07-13 | 齐鲁工业大学 | Xanthene-based near-infrared fluorescent probe and preparation method thereof |
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Non-Patent Citations (3)
| Title |
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| DAOXUE LI等: ""A carbazole-based "turn-on" two-photon fluorescent probe for biological Cu2+ detection vis Cu2+-promoted hydrolysis"", 《DYES AND PIGMENTS》, vol. 125, 31 December 2016 (2016-12-31) * |
| 无: "STN检索记录", 《STN》, 28 November 2000 (2000-11-28), pages 3 - 4 * |
| 汤立军等: ""一种基于咔唑的荧光探针对铜(II)离子的荧光增强识别"", 《化学研究与应用》, vol. 25, no. 7, 31 December 2013 (2013-12-31), pages 947 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113105467A (en) * | 2020-11-27 | 2021-07-13 | 齐鲁工业大学 | Xanthene-based near-infrared fluorescent probe and preparation method thereof |
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Application publication date: 20210312 |