CN114853656A - Carbazole derivative with AEE characteristic, preparation method and application - Google Patents
Carbazole derivative with AEE characteristic, preparation method and application Download PDFInfo
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- CN114853656A CN114853656A CN202210512491.2A CN202210512491A CN114853656A CN 114853656 A CN114853656 A CN 114853656A CN 202210512491 A CN202210512491 A CN 202210512491A CN 114853656 A CN114853656 A CN 114853656A
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- 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
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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Abstract
The invention discloses a carbazole derivative with AEE characteristics, which has the following structural formula:
in the formula 1, R is-CHO, -OCH 3 . The compound is prepared by Suzuki coupling and is separated and purified by column chromatography. The carbazole derivative obtained by the invention has excellent AEE effect, the luminous intensity can be respectively improved by 8.2 times and 4 times, a proper measuring solvent of the compound is determined by the solvation effect, and the compound DPC-CHO can be used as a fluorescent probe to have high-efficiency specific identification (the detection limit is 40.8nM) on tryptophan.
Description
Technical Field
The invention relates to an aggregation-induced enhanced emission (AEE) material, in particular to carbazole derivatives with AEE characteristics, and a preparation method and application thereof.
Background
The application range of the traditional fluorescent probe is limited due to aggregation-induced quenching (ACQ) phenomenon caused by pi-pi accumulation among molecules, in 2001, aggregation-induced emission (AIE) concept is proposed for the first time by Tang faith, and intramolecular motion limitation (RIM) is generally considered as the core of AIE working mechanism. In 2022, the Park topic group discovered different phenomena in experiments, the compound cyano-substituted trans-diarylethene emitted light weakly in dilute solution, but emitted light in an aggregation state is enhanced, namely aggregation-induced enhanced emission (AEE), and AEE luminescent materials are widely applied to various research fields, especially research and development of OLED materials and photovoltaic materials due to their special luminescence phenomena. The carbazole fragment can be used as an electron donor unit in a luminophor, is widely used for designing a two-photon excitation fluorophore, and most carbazole derivatives can show aggregation-induced emission properties.
Amino acids, which are important metabolites, are present in various natural substrates, tryptophan (Trp), also known as α -aminoindolpropanic acid, is an essential amino acid involved in various physiological processes, and studies have shown that tumors, infectious diseases and nervous system diseases are accompanied by Trp-related metabolic disorders, and further, tryptophan is an important precursor of melatonin, 5-hydroxytryptamine and nicotinic acid, which are associated with mood, sleep and mental health. Therefore, a simple, high-selectivity and sensitive Trp detection method has important significance in biological research and human health,
the most common method for analyzing amino compounds at present is reverse phase liquid chromatography-tandem mass spectrometry, and certainly, some of the reports on the detection of tryptophan by using probes exist in the literature, but most of fluorescent probes can only identify one part but not one of 20 natural amino acids, so that the discrimination of one specific natural amino acid from other amino acids by using a fluorescence detection means is still a great challenge.
Disclosure of Invention
The invention aims to solve the technical problems in the prior art and provides a carbazole derivative with AEE characteristics, a preparation method and application thereof.
The technical solution of the invention is as follows: a carbazole derivative with AEE characteristics has the following structural formula:
the R is-CHO, -OCH 3 。
A preparation method of the carbazole derivative with AEE characteristics comprises the following synthetic route:
the method comprises the following steps of:
will be provided with
4- (9H-carbazol-9-yl) phenylboronic acid, anhydrous potassium carbonate and Pd (PPh) 3 ) 4 Placing in a bottle, adding 1, 4-dioxane and distilled water or DMSO and distilled water, stirring and heating under the protection of nitrogen until complete reaction; cooling to room temperature after the reaction is finished, extracting with distilled water and dichloromethane, drying with anhydrous sodium sulfate, performing suction filtration, and spinning out the solvent; purifying by column chromatography with petroleum ether/ethyl acetate as eluent, and recrystallizing with ethanol to obtain crystal or powder.
The carbazole derivative prepared by the invention has the characteristics of aggregation-induced enhanced emission (AEE), can be used as a fluorescent probe for identifying biological micromolecules, has high-efficiency specificity on tryptophan, and has the identification detection limit of 40.8 nM.
Drawings
FIG. 1 is a photograph of a compound prepared in example 1 of the present invention 1 H NMR spectrum.
FIG. 2 shows the compound prepared in example 1 of the present invention in THF/C 2 H 5 Fluorescence spectra and trend plots of fluorescence in OH mixtures.
FIG. 3 is a graph showing fluorescence spectra of the compound prepared in example 1 of the present invention in various solvents.
FIG. 4 is a fluorescence spectrum of the interaction of the compound prepared in example 1 of the present invention with different amino acids as a fluorescent probe.
FIG. 5 is a PL diagram of the interaction of the compound prepared in example 1 of the present invention as a fluorescent probe with tryptophan at various concentration gradients.
FIG. 6 is a graph showing the tendency of fluorescence intensity of the compound prepared in example 1 of the present invention as a fluorescent probe.
FIG. 7 is a graph showing the fluorescence spectrum of a compound prepared in example 1 of the present invention as a competitive assay for amino acids as a fluorescent probe.
FIG. 8 is a photograph of a compound prepared in example 2 of the present invention 1 H NMR spectrum.
FIG. 9 shows the compound prepared in example 2 of the present invention in THF/C 2 H 5 Fluorescence spectra and trend plots of fluorescence in OH mixtures.
Detailed Description
Example 1:
the preparation method of the carbazole derivative (DCP-CHO) with AEE characteristics is sequentially carried out according to the following steps:
4- (9H-carbazol-9-yl) phenylboronic acid (1.09g,3.79mmol), 3, 5-dibromobenzaldehyde (0.5g,1.89mmol), anhydrous potassium carbonate (1.75g,12.7mmol), Pd (PPh) 3 ) 4 (0.1g,0.087mmol) is placed in a two-mouth bottle, a small amount of dichloromethane is used for completely dissolving the mixture, 125mL of DMSO and 25mL of distilled water are added into the mixture, and the mixture is stirred and heated to 100 ℃ under the protection of nitrogen for 24 hours to react;after the reaction is finished, cooling to room temperature, extracting with 50mL of distilled water and 30mL of dichloromethane, drying with anhydrous sodium sulfate, carrying out suction filtration, and spinning out the solvent; column chromatography purification using petroleum ether/ethyl acetate (100/1.5, v/v) as eluent gave 0.21g of white needle crystals, yield: 18.8 percent.
Preparation of the compound 1 The H NMR spectrum is shown in figure 1, and the structural formula is as follows:
experiment 1: AEE Performance testing of the Compounds prepared in example 1
Although the compounds are highly soluble in most organic solvents, many substances are not soluble in ethanol. To examine the AEE activity of the compound prepared in example 1, ethanol was added to the THF solution to prepare THF-C at various concentrations ranging from 0% to 90% in volume fraction 2 H 5 The PL spectrum of the OH solution, recorded mixture, is shown in FIG. 2 (A). As shown in FIG. 2(B), the compound DPC-CHO emits strong fluorescence in the pure THF solution, the fluorescence intensity gradually increases with the increase of the ethanol content, and the emission intensity reaches the highest value up to 70% which is 8.2 times higher than the original value. The compounds are capable of emitting fluorescence in pure solution, while the fluorescence intensity in mixed solution is enhanced, which is characterized by a typical aggregation-induced enhanced emission (AEE) effect.
Experiment 2: solvent Effect of DPC-CHO
The emission behaviour of compound DPC-CHO in different solvents was tested in order to select the appropriate solvent. As shown in fig. 3, the emission behaviors of 10 μ M compounds in different solvents are different, 10 solvents (N-hexane, toluene, ethyl acetate, tetrahydrofuran, 1, 4-dioxane, acetone, ethanol, N-dimethylformamide, acetonitrile, dimethyl sulfoxide) are selected in this experiment, and in general, the polarity of the solvent is increased, the energy difference Δ E required for pi → pi transition is small, the transition probability is increased, the fluorescence wavelength is red-shifted, and the intensity is also enhanced, but the dispersion state of the probe in DMF is good, the interaction is stronger, and Δ E is smaller, so the probe shows higher fluorescence intensity in DMF, and DMF solvent is selected in the next test.
Experiment 3: interaction experiment of DPC-CHO as fluorescent probe and different amino acids
The concentration is 10 by taking DMF as a solvent -5 M, excitation wavelength of 300nm determined by uv test, slit width 5: 5, 100. mu.M of different amino acids, tryptophan (Trp), leucine (Leu), serine (Ser), methionine (Met), alanine (Ala), isoleucine (Ile), threonine (Thr), proline (Pro), arginine (Arg), lysine (Lys), aspartic acid (Asp), glutamic acid (Glu), tyrosine (Tyr), phenylalanine (Phe), valine (Val), cysteine (Cys), histidine (His), glycine (Gly), were added to the sensor, and fluorescence emission spectrometry was performed, and the fluorescence spectrum was shown in FIG. 4. The results show that: the fluorescence intensity was significantly increased only with the addition of tryptophan, whereas no significant fluorescence response was observed with the addition of other amino acids under the same conditions.
Experiment 4: interaction experiment of DCP-CHO as fluorescent probe and tryptophan with different concentration gradients
The response range of the probe to the tryptophan is measured by adding tryptophan (0,10,20, … … 280 mu M) with different concentration gradients into a probe solution with a certain concentration, as shown in FIG. 5, the fluorescence intensity is gradually increased along with the increase of the amino acid concentration, a linear relation graph (as shown in FIG. 6) of the tryptophan detected by the probe is obtained through linear fitting, the detection limit is 40.8nM through calculation according to the formula LOD (3 sigma/k), and the detection limit on the nanometer level is lower, so that the probe can better realize trace detection of the tryptophan.
Experiment 5: competitive experiment of DCP-CHO as fluorescent probe for amino acid
In order to determine whether a compound specifically and selectively recognizes tryptophan, fluorescence spectra were examined for the presence of leucine (Leu), serine (Ser), methionine (Met), alanine (Ala), isoleucine (Ile), threonine (Thr), proline (Pro), arginine (Arg), lysine (Lys), aspartic acid (Asp), glutamic acid (Glu), tyrosine (Tyr), phenylalanine (Phe), valine (Val), cysteine (Cys), histidine (His), glycine (Gly), and tryptophan (Trp), respectively, as shown in fig. 7.
The results show that: as shown in FIG. 7, 20. mu.M of other amino acids and Trp were alternately added (2 times each) to a probe solution, and the fluorescence intensity was measured, and it was found that the influence of the addition of other amino acids on the fluorescence intensity was small, and the intensity sharply increased after the addition of the coloring acid. According to the molecular structure of tryptophan, Trp is used as a group with stronger electron donating ability, the electron donating ability of the Trp is reduced due to the combination with the probe, the photoinduced electron transfer Process (PET) is blocked, and the excited electrons in the fluorophore return to the ground state in a radiation transition mode, so that the fluorescence emission is enhanced.
Example 2:
the carbazole derivative (DCP-OCH) with AEE characteristics 3 ) The preparation method comprises the following steps in sequence:
4- (9H-carbazol-9-yl) phenylboronic acid (1.08g,3.76mmol), 3, 5-dibromoanisole (0.5g,1.88mmol), anhydrous potassium carbonate (1.75g,12.7mmol), Pd (PPh) 3 ) 4 (0.1g,0.087mmol) is placed in a two-neck flask, 125mL of 1, 4-dioxane and 25mL of distilled water are added, and the mixture is stirred and heated to 90 ℃ under the protection of nitrogen to react for 24 hours; after the reaction is finished, cooling to room temperature, extracting with 50mL of distilled water and 30mL of dichloromethane, drying with anhydrous sodium sulfate, carrying out suction filtration, and spinning out the solvent; column chromatography purification using petroleum ether/ethyl acetate (100/1, v/v) as eluent, recrystallization from dichloromethane and absolute ethanol gave 0.89g of a white powder, yield: 80.18 percent.
Preparation of the compound 1 The H NMR spectrum is shown in FIG. 8, and the structural formula is as follows:
experiment 1: to investigate whether the compound prepared in example 2 has AEE properties, an ethanol solution was also added to the combinationThe THF solutions of the compounds are prepared into THF-C with different volume fractions 2 H 5 The PL spectrum of the OH solution, recorded mixture, is shown in FIG. 9 (A). As shown in FIG. 9(B), the compound in the original THF solution can emit fluorescence, the aggregation degree of the compound is gradually increased with the increase of the ethanol content, the fluorescence intensity is also increased, the fluorescence intensity is highest when the ethanol content reaches 80% and is 4 times higher than the original value, and the fluorescence characteristic also accords with the aggregation-induced enhanced emission (AEE) characteristic.
Claims (3)
1. A carbazole derivative with AEE characteristics is characterized in that the structural formula is as follows:
wherein R is-CHO, -OCH 3 。
2. A process for the preparation of carbazole derivatives having AEE characteristics according to claim 1, characterized by the following successive steps:
will be provided with
4- (9H-carbazol-9-yl) phenylboronic acid, anhydrous potassium carbonate and Pd (PPh) 3 ) 4 Placing in a bottle, adding 1, 4-dioxane and distilled water or DMSO and distilled water, stirring and heating under the protection of nitrogen until complete reaction; cooling to room temperature after the reaction is finished, extracting with distilled water and dichloromethane, drying with anhydrous sodium sulfate, performing suction filtration, and spinning out the solvent; purifying by column chromatography with petroleum ether/ethyl acetate as eluent, and recrystallizing with ethanol to obtain crystal or powder.
3. The application of carbazole derivatives with AEE characteristics as fluorescent probes for identifying small molecular substances is characterized in that: the application of the fluorescent probe for identifying tryptophan.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115925683A (en) * | 2022-11-25 | 2023-04-07 | 郑州大学 | Dendritic carbazole pyridine formaldehyde compound, preparation method and application |
Citations (7)
| 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 |
| CN103896825A (en) * | 2014-04-17 | 2014-07-02 | 东南大学 | 9,10-diarylethene anthracene (CPASA) aggregation-induced light emitting molecule and preparation method thereof |
| CN104498025A (en) * | 2015-01-21 | 2015-04-08 | 武汉大学 | Polyphenyl benzene structured cyanogroup-containing luminescent molecule and preparation method and purpose thereof |
| CN106986876A (en) * | 2017-03-20 | 2017-07-28 | 北京理工大学 | A kind of fluorescence probe for targetting mark eye lens epithelial cell, its preparation and application |
| CN107011244A (en) * | 2017-04-20 | 2017-08-04 | 北京理工大学 | Benzocyclobutane diene with AEE effects and azole derivatives and its preparation |
| CN108794382A (en) * | 2018-06-29 | 2018-11-13 | 华南师范大学 | A kind of multi-functional aggregation-induced emission enhancement compound and the preparation method and application thereof |
| CN113336622A (en) * | 2021-04-09 | 2021-09-03 | 辽宁师范大学 | Fluorene derivative with AIE characteristic, preparation method and application |
-
2022
- 2022-05-12 CN CN202210512491.2A patent/CN114853656B/en active Active
Patent Citations (7)
| 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 |
| CN103896825A (en) * | 2014-04-17 | 2014-07-02 | 东南大学 | 9,10-diarylethene anthracene (CPASA) aggregation-induced light emitting molecule and preparation method thereof |
| CN104498025A (en) * | 2015-01-21 | 2015-04-08 | 武汉大学 | Polyphenyl benzene structured cyanogroup-containing luminescent molecule and preparation method and purpose thereof |
| CN106986876A (en) * | 2017-03-20 | 2017-07-28 | 北京理工大学 | A kind of fluorescence probe for targetting mark eye lens epithelial cell, its preparation and application |
| CN107011244A (en) * | 2017-04-20 | 2017-08-04 | 北京理工大学 | Benzocyclobutane diene with AEE effects and azole derivatives and its preparation |
| CN108794382A (en) * | 2018-06-29 | 2018-11-13 | 华南师范大学 | A kind of multi-functional aggregation-induced emission enhancement compound and the preparation method and application thereof |
| CN113336622A (en) * | 2021-04-09 | 2021-09-03 | 辽宁师范大学 | Fluorene derivative with AIE characteristic, preparation method and application |
Non-Patent Citations (3)
| Title |
|---|
| CHAO WU ET AL.: "Versatile Donor−π−Acceptor-Type Aggregation-Enhanced Emission Active Fluorophores as Both Highly Efficient Nondoped Emitter and Excellent Host", 《ACS APPLIED MATERIALS & INTERFACES》, vol. 9, pages 32946 * |
| DEFANG XU ET AL.: "Aggregation-induced enhanced emission-type cruciform luminophore constructed by carbazole exhibiting mechanical force-induced luminescent enhancement and chromism", 《RSC ADVANCES》, vol. 10, pages 12025 * |
| QING WAN ET AL.: "Feasible structure-modification strategy for inhibiting aggregation-caused quenching effect and constructing exciton conversion channels in acridone-based emitters", 《PHYS. CHEM. CHEM. PHYS.》, vol. 21, pages 9837 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115925683A (en) * | 2022-11-25 | 2023-04-07 | 郑州大学 | Dendritic carbazole pyridine formaldehyde compound, preparation method and application |
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