CN114805613A - For detecting Fe 3+ Ethyl cellulose base flavonol fluorescent probe and preparation method and application thereof - Google Patents
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Abstract
The invention discloses a method for detecting Fe 3+ The ethyl cellulose base flavonol fluorescent probe and the preparation method and the application thereof. The invention takes 3-hydroxy-4-acetylbiphenyl and 4-formylbenzoic acid as initial raw materials, and HBOB is generated through aldol condensation reaction; preparing HPCB by oxidizing cyclization reaction of HBOB; and esterifying the HPCB with hydroxyl on the ethyl cellulose to obtain the EC-HPCB. DMSO-H of EC-HPCB under 365nm ultraviolet light irradiation 2 Adding Fe into O solution 3+ Then, the fluorescence color of the solution changes from orange yellow to colorless to Fe 3+ Up to 2.65X 10 ‑7 mol/L, response time of 2min, can be used for detecting Fe 3+ The fluorescent probe has good application prospect.
Description
Technical Field
The invention belongs to the technical field of fluorescence detection, and particularly relates to a method for detecting Fe 3+ The ethyl cellulose base flavonol fluorescent probe and the preparation method and the application thereof.
Background
Cellulose is a polysaccharide which is distributed most widely and has the most content in the world, is also a natural high molecular compound with the most abundant reserves in the nature, and has the advantages of good hydrophilicity, low cost, good biodegradability, greenness, no toxicity and the like. China is a large country for agricultural production, cellulose resources are abundant, and the total amount of cellulose generated by crop straws only reaches more than 2.0 hundred million tons every year in China, so that the high-valued utilization of cellulose in China has attracted general attention of the whole society, and particularly, the development and utilization of cellulose-based functional materials become a hot spot of current research. Ethyl Cellulose (EC) is an ethyl ether of cellulose, a long-chain polymer having β -anhydroglucose units linked by acetal, and one of the most widely used water-insoluble cellulose derivatives. Because ethyl cellulose can be dissolved in most organic solvents and can be mixed with resin, oil wax and plasticizer, the ethyl cellulose has good processing performance. Flavonols, also known as 3-hydroxy-2-phenyl-1-benzopyran-4-ones, are a very important class of natural pigments and bioactive substances in nature and are widely distributed in vegetable foods such as fruits and vegetables. Flavonol molecules are easy to generate an Excited State Intramolecular Proton Transfer (ESIPT) effect under the excitation of visible light, so that the flavonol molecules have excellent optical characteristics of good fluorescence intensity, high quantum yield, good light stability, large Stokes shift and the like, and due to the existence of adjacent phenolic hydroxyl groups and oxygen heteroatoms in the structure, the flavonol compounds have good complexing ability, so that the flavonol serving as a fluorescent group with excellent performance is widely applied to the field of fluorescent probes. If the flavonol derivatives are grafted to an ethyl cellulose chain by a chemical synthesis means, the novel cellulose-based flavonol fluorescent probe is synthesized by utilizing the excellent optical characteristics of good fluorescence intensity, good light stability, high quantum yield, large Stokes shift and the like of the flavonol structural units and the physicochemical characteristics of good biodegradability, good biocompatibility, high reaction activity, good processing performance and the like of the ethyl cellulose, and the defects of high cytotoxicity, low quantum yield, poor light stability, poor processing performance and the like of the traditional organic micromolecule fluorescent probe are hopefully overcome. Therefore, the development of various types of ethyl cellulose-based functional materials has very important significance, and the ethyl cellulose-based functional materials have wide application prospects in the fields of biological imaging, detection sensing, information anti-counterfeiting and the like.
Iron being predominantly Fe 2+ And Fe 3+ Is the most abundant essential micronutrient in the body. Wherein, Fe 3+ Plays a crucial role in human respiration and cell metabolism, and maintains Fe 3+ Homeostasis is vital to human health. For example, Fe 3+ Can lead to intracellular hypoxia and many diseases such as liver cancer, gastric adenocarcinoma and anemia. However, some serious complications, such as beta-thalassemia and hereditary hemochromatosis, are also associated with Fe 3+ Too high a level is relevant. In addition, due to Fe 3+ Migration and concentration in the environmental water system can pose a potential health hazard to the food chain. Therefore, Fe is considered 3+ Of interest, development of a highly sensitive monitoring of Fe 3+ The method of (1) is very necessary. Currently, Fe 3+ The detection method mainly comprises a voltammetry method, an inductively coupled plasma mass spectrum, an inductively coupled plasma emission spectrum, an atomic absorption spectrometry method, a spectrophotometry method and the like, and the technologies have the defects of complex operation, low practicability, low sensitivity and the like due to more limiting factors. Fluorescence detection technique for detecting Fe 3+ Has the advantages of convenient operation, high sensitivity and the like.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims to provide a method for detecting Fe 3+ The ethyl cellulose base flavonol fluorescent probe meets the requirement of Fe 3+ Detects the usage requirements. The invention also provides a preparation method of the ethyl cellulose base flavonol fluorescent probe. The invention also aims to solve another technical problem of providing an application of the ethyl cellulose base flavonol fluorescent probe.
In order to solve the technical problems, the invention adopts the technical scheme that:
for detecting Fe 3+ The ethyl cellulose base flavonol fluorescent probe is EC-HPCB, and the structural formula is as follows:
the preparation method of the ethyl cellulose base flavonol fluorescent probe comprises the following steps:
(1) carrying out aldol condensation reaction on 3-hydroxy-4-acetylbiphenyl and 4-formylbenzoic acid to prepare 2 '-hydroxy-4' -phenyl-4-carboxyl chalcone (HBOB); HBOB is subjected to oxidative cyclization reaction to prepare 3-hydroxy-7-phenyl-4' -carboxyl flavonol (HPCB);
(2) esterification of HPCB with hydroxyl groups on Ethyl Cellulose (EC) produces EC-HPCB.
In the step (1), the preparation steps of HPCB are as follows:
1) taking 5-10 mmol of 3-hydroxy-4-acetylbiphenyl, 5-10 mmol of 4-formylbenzoic acid and 30-60 mL of ethanol, carrying out ultrasonic treatment for 10min, adding 5-10 mL of 20% potassium hydroxide aqueous solution, reacting at room temperature for 24-48 h, and monitoring the reaction process by using thin layer chromatography; after the reaction is finished, pouring the reaction solution into ice water, then acidifying with 20% hydrochloric acid, generating a precipitate, filtering, recrystallizing in ethanol, and drying to obtain yellow HBOB;
2) dissolving 3-6 mmol of HBOB in 15-30 mL of ethanol in an ice bath, adding 10-20 mmol of sodium hydroxide, dropwise adding 5-10 mL of 30% hydrogen peroxide, and stirring for 5 hours. After the reaction was completed, the reaction mixture was poured into ice water, neutralized with 20% hydrochloric acid, and the resulting precipitate was filtered, recrystallized from ethanol, and dried to obtain HPCB.
In the step (2), the preparation steps of the EC-HPCB are as follows:
1) adding 1.0-2.0 mmol of ethyl cellulose, 0.2-0.4 mmol of 4- (N, N-dimethyl) aminopyridine, 0.5-1.0 mmol of HPCB and 20-40 mL of DMF into a round-bottom flask, and degassing for 20min under the protection of nitrogen; dropwise adding 1.0-2.0 mmol of N, N' -dicyclohexylcarbodiimide dissolved in DMF into the solution at 0 ℃, and reacting for 24-48 h at room temperature;
2) and after the reaction is finished, pouring the reaction solution into 100-200 mL of pure water, carrying out suction filtration on the precipitate, washing the precipitate with DMF/water, and carrying out vacuum drying at 45 ℃ for 24-36 h to obtain the EC-HPCB.
The ethyl cellulose base flavonol fluorescent probe is used for detecting Fe 3+ The use of (1).
The application is that DMSO/H of EC-HPCB is irradiated by 365nm ultraviolet light 2 Adding Fe into O solution 3+ After that, the fluorescence color of the solution changed from orange yellow to colorless.
The ethyl cellulose base flavonol fluorescent probe is used for detecting Fe in preparation 3+ The fluorescent probe of (1).
Has the advantages that: compared with the prior art, the invention has the following main advantages:
1) according to the application, the cellulose-based fluorescent probe obtained by grafting HPCB (HPCB) to the cellulose macromolecules has excellent performance of the cellulose macromolecules, and simultaneously overcomes a plurality of limitations of small molecular fluorescent compounds. Has the characteristics of good luminous performance, stable structure and the like.
2) The application is proved through experiments: DMSO/H of EC-HPCB under 365nm ultraviolet light irradiation 2 O(DMSO∶H 2 O1: 9, v/v) solution with Fe 3+ Then, the fluorescence color of the solution changes from orange yellow to colorless to Fe 3+ Up to 2.65X 10 -7 M, response time 2min, as detecting Fe 3+ Of (5) isThe optical probe has good application prospect.
Drawings
FIG. 1 is a chart of (a) the infrared spectrum of HPCB, (b) the infrared spectrum of EC, and (c) the infrared spectrum of EC-HPCB;
FIG. 2 is DMSO/H of EC-HPCB 2 O(DMSO∶H 2 O1: 9, v/v) solution with Fe 3+ Front and back fluorescence spectra;
FIG. 3 is DMSO/H of EC-HPCB 2 O(DMSO∶H 2 O1: 9, v/v) solution, adding fluorescence spectrograms of different metal ions;
FIG. 4 is DMSO/H of EC-HPCB 2 O(DMSO∶H 2 O1: 9, v/v) solution with different concentrations of Fe 3+ Fluorescence spectrum of (2).
Detailed Description
In order to make the aforementioned objects, features and advantages of the present invention more comprehensible, specific embodiments thereof are described in detail below with reference to examples of the specification.
Example 1
Synthesizing an ethyl cellulose base flavonol fluorescent probe, wherein the reaction formula is as follows:
the preparation method comprises the following specific steps:
1) a50 mL flask was charged with 5mmol of 3-hydroxy-4-acetylbiphenyl, 5mmol of 4-formylbenzoic acid and 30mL of ethanol, sonicated for 10min, and 5mL of 20% aqueous potassium hydroxide was added, reacted at room temperature for 48h, and the progress of the reaction was monitored by thin layer chromatography. After the reaction is finished, the reaction solution is poured into ice water, the ice water is acidified by hydrochloric acid with the concentration of 20%, and the generated precipitate is filtered, recrystallized and dried to obtain yellow HBOB.
2) Under the ice-bath condition, 3mmol HBOB is dissolved in 15mL ethanol, 10mmol sodium hydroxide is added, 5mL hydrogen peroxide with the concentration of 30% is dripped, and the mixture is stirred for 5 hours. After the reaction was completed, the reaction solution was poured into ice water, neutralized with a 20% hydrochloric acid aqueous solution, and the resulting precipitate was filtered and recrystallized in ethanol to obtain HPCB.
3) Adding 1.0mmol of ethyl cellulose, 0.2mmol of 4- (N, N-dimethyl) aminopyridine, 0.5mmol of HPCB and 20mL of DMF into a round-bottom flask, and degassing for 20min under the protection of nitrogen; 1.0mmol of N, N' -dicyclohexylcarbodiimide dissolved in DMF was added dropwise to the solution at 0 ℃ and reacted at room temperature for 48 hours. After the reaction, the reaction mixture was poured into 100mL of purified water, precipitated, filtered, and the filter cake was washed with DMF/water (DMF/water 1: 1, v/v) and dried under vacuum at 45 ℃ for 24h to obtain EC-HPCB.
The structure of an ethyl cellulose base flavonol fluorescent probe (EC-HPCB) is analyzed by FT-IR. FIG. 1 is an infrared spectrum of HPCB, EC and EC-HPCB, respectively. The infrared spectrum of EC-HPCB appears at 3500cm -1 And 3300cm- 1 Two peaks of (2) are O-H stretching vibration absorption peaks on EC and HPCB, 2982cm -1 And 2923cm -1 The absorption peak is asymmetric and symmetric stretching vibration absorption peak of C-H of methyl and methylene in the molecule, 1743cm -1 The C ═ O stretching shock absorption peak indicates that HPCB was successfully grafted onto the ethylcellulose molecular backbone.
Example 2
Adding EC-HPCB to DMSO/H 2 O(DMSO∶H 2 O1: 9, v/v) was prepared in a concentration of 0.1mg/mL, and measured on a fluorescence spectrophotometer by fluorescence spectrometry in DMSO/H 2 O(DMSO∶H 2 O1: 9, v/v) fluorescence emission spectrum in solution, as shown in fig. 2. The results show that in DMSO/H 2 O(DMSO∶H 2 O1: 9, v/v) solution without addition of Fe 3+ When the solution fluoresces orange yellow, Fe is added 3+ Then, the fluorescence intensity was sharply reduced, and the maximum emission wavelength was 565nm (excitation wavelength was 365nm, excitation slit broad band was 12.0nm, and emission slit broad band was 3.8 nm).
Adding EC-HPCB to DMSO/H 2 O(DMSO∶H 2 O1: 9, v/v) solution to a concentration of 0.1mg/mL, 1 part of which was used as a blank, and the other parts were each added with Fe 3+ ，Zn 2+ ，Mg 2+ ，Pb 2+ ，Hg 2+ ，Ca 2+ ，Ag + ，Al 3+ ，Co 2+ ，Cd 2+ ，Ba 2+ ，K + ，Ni 2+ ，Mn 2+ ，Cr 3+ ，La 3+ ，Cu 2+ And Fe 2+ The fluorescence emission spectrum of the solution was measured on a fluorescence spectrophotometer by fluorescence spectrometry, and the result is shown in FIG. 3. As can be seen from FIG. 3, Fe was added 3+ The maximum emission wavelength of the solution was then 565nm, and the fluorescence intensity of the solution decreased significantly. While the fluorescence intensity of the solution changes very little when other analytes are added. This indicates that EC-HPCB is on Fe 3+ Has good selectivity.
Adding EC-HPCB to DMSO/H 2 O(DMSO∶H 2 O1: 9, v/v) solution, preparing a solution with the concentration of 0.1mg/mL, and measuring the addition of Fe with different concentrations on a fluorescence spectrophotometer by adopting a fluorescence spectrum titration method 3+ Fluorescence emission spectra after ionization. As shown in fig. 4. The results show that with Fe 3+ The gradual increase of the concentration and the gradual decrease of the fluorescence signal intensity of the EC-HPCB at 565nm indicate that the EC-HPCB can be used for detecting Fe in the solution 3+ Concentration of, to Fe 3+ Up to 2.65X 10 -7 M。
Claims (7)
1. For detecting Fe 3+ The ethyl cellulose base flavonol fluorescent probe is characterized in that the structural formula is as follows:
2. the method for preparing an ethylcellulose-based flavonol fluorescent probe as claimed in claim 1, which is characterized by comprising the following steps:
(1) carrying out aldol condensation reaction on 3-hydroxy-4-acetylbiphenyl and 4-formylbenzoic acid to prepare HBOB; preparing HPCB by oxidizing cyclization reaction of HBOB;
(2) and esterifying the HPCB and hydroxyl on the EC to obtain the EC-HPCB.
3. The method for preparing an ethylcellulose-based flavonol fluorescent probe according to claim 2, wherein in the step (1), the preparation steps of HPCB are as follows:
1) taking 5-10 mmol of 3-hydroxy-4-acetylbiphenyl, 5-10 mmol of 4-formylbenzoic acid and 30-60 mL of ethanol, carrying out ultrasonic treatment for 10min, adding 5-10 mL of 20% potassium hydroxide aqueous solution, reacting at room temperature for 24-48 h, and monitoring the reaction process by using thin layer chromatography; after the reaction is finished, pouring the reaction solution into ice water, then acidifying with 20% hydrochloric acid, generating a precipitate, filtering, recrystallizing in ethanol, and drying to obtain yellow HBOB;
2) dissolving 3-6 mmol of HBOB in 15-30 mL of ethanol in an ice bath, adding 10-20 mmol of sodium hydroxide, dropwise adding 5-10 mL of 30% hydrogen peroxide, and stirring for 5 hours. After the reaction was completed, the reaction mixture was poured into ice water, neutralized with 20% hydrochloric acid, and the resulting precipitate was filtered, recrystallized from ethanol, and dried to obtain HPCB.
4. The method for preparing an ethylcellulose-based flavonol fluorescent probe according to claim 2, wherein in the step (2), the EC-HPCB is prepared by the following steps:
1) adding 1.0-2.0 mmol of ethyl cellulose, 0.2-0.4 mmol of 4- (N, N-dimethyl) aminopyridine, 0.5-1.0 mmol of HPCB and 20-40 mL of DMF into a round-bottom flask, and degassing for 20min under the protection of nitrogen; dropwise adding 1.0-2.0 mmol of N, N' -dicyclohexylcarbodiimide dissolved in DMF into the solution at 0 ℃, and reacting for 24-48 h at room temperature;
2) and after the reaction is finished, pouring the reaction solution into 100-200 mL of pure water, carrying out suction filtration on the precipitate, washing the precipitate with DMF/water, and carrying out vacuum drying at 45 ℃ for 24-36 h to obtain the EC-HPCB.
5. The ethylcellulose-based flavonol fluorescent probe as claimed in claim 1 for detecting Fe 3+ The use of (1).
6.Use according to claim 5, characterized in that the DMSO/H of the EC-HPCB is under 365nm UV irradiation 2 Adding Fe into O solution 3+ After that, the fluorescence color of the solution changed from orange yellow to colorless.
7. The method for detecting Fe by using the ethylcellulose-based flavonol fluorescent probe as claimed in claim 1 3+ The fluorescent probe of (1).
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| CN116217753A (en) * | 2023-01-04 | 2023-06-06 | 齐鲁工业大学(山东省科学院) | Preparation method and application of xylan viscosity fluorescent probe |
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| CN113979984A (en) * | 2021-11-23 | 2022-01-28 | 南京林业大学 | Preparation method and application of water-soluble flavonoid aluminum ion fluorescent probe |
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| CN105542754A (en) * | 2015-12-31 | 2016-05-04 | 深圳大学 | Flavone-based fluorescent molecular probe and preparation method and application thereof |
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| CN116217753A (en) * | 2023-01-04 | 2023-06-06 | 齐鲁工业大学(山东省科学院) | Preparation method and application of xylan viscosity fluorescent probe |
| CN116217753B (en) * | 2023-01-04 | 2024-02-23 | 齐鲁工业大学(山东省科学院) | Preparation method and application of xylan viscosity fluorescent probe |
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