CN114933660A - Cellulose-based coumarin fluorescent probe for detecting hydrazine and preparation method and application thereof - Google Patents
Cellulose-based coumarin fluorescent probe for detecting hydrazine and preparation method and application thereof Download PDFInfo
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- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
- C08B15/05—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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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
- 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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- 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"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
Abstract
The invention discloses a cellulose-based coumarin fluorescent probe for detecting hydrazine and a preparation method and application thereof. The invention firstly carries out condensation reaction on 2- (1- (7- (diethylamino) coumarin-3-yl) ethylidene) malononitrile and 4 ' -formylbiphenyl-4-formic acid to prepare 4 ' - (4, 4-dicyano-3- (7-diethylamino-coumarin-3-yl) -1, 3-butadienyl) - [1, 1 ' -biphenyl]-4-carboxylic acid; then the acid-base-modified cellulose acetate is subjected to ring-opening esterification reaction with cellulose acetate glycidyl ether to prepare the ACBC-CA. After hydrazine is added into DMSO/water suspension of ACBC-CA under 365nm ultraviolet light irradiation, the fluorescence color of the solution changes from colorless to yellow, and the detection limit of hydrazine reaches 1.2 x 10 ‑7 mol/L, has good application prospect as a fluorescent probe for detecting hydrazine.
Description
Technical Field
The invention belongs to the technical field of fluorescence detection, and relates to a cellulose-based coumarin fluorescent probe for detecting hydrazine, and a preparation method and application thereof.
Background
Cellulose is a natural polymer which is widely distributed and contains most cellulose in nature. Cellulose is the most extensive and abundant high molecular material, and has the advantages of reproducibility, biocompatibility, biodegradability and nontoxicity. Cellulose is one of important cellulose derivatives, and is formed by esterifying cellulose hydroxyl groups with acetic acid. The cellulose acetate has the advantages of strong flexibility, high mechanical strength, good solubility and the like, and is beneficial to materialization.
Coumarin is one of the most widely used fluorophores, is often used for synthesizing excellent precursors of different fluorescence chemical sensors, is grafted to cellulose macromolecules to obtain cellulose-based fluorescent materials, not only has the excellent performance of the cellulose macromolecules, but also can overcome the limitations of small molecular fluorescent compounds: such as fluorescence quenching due to easy aggregation; difficult to reuse; fluorescent small molecules are difficult to process and mold, and cannot be used for manufacturing devices and the like. Meanwhile, the fluorescent group is connected with the polymer skeleton by a stable chemical bond, so that the problem that the fluorescent micromolecules are easy to lose in the material prepared by physically mixing the fluorescent micromolecules with the polymer can be effectively avoided. Therefore, the development of various cellulose-based functional materials has very important significance and has wide application prospects in the fields of biological imaging, detection sensing, information anti-counterfeiting and the like.
Hydrazine is one of the most common chemical reagents and is widely applied to pesticides,Medicine, textile dye and other industrial fields. Hydrazine is also used as a propellant for missiles and rockets due to its high enthalpy of combustion and flammability. Although the use of hydrazine brings great convenience to us, excess hydrazine is highly toxic and harmful to both humans and animals. In industrial production, the leakage of hydrazine causes environmental pollution. Hydrazine, which is a volatile and highly toxic substance, can enter the human body through the mouth, the nose, the skin and other ways, and cause damage to the lung, the kidney and the central nervous system of the human body, and can cause organ failure in severe cases, thereby threatening the life of the human body. The United states Environmental Protection Agency (EPA) recommends a standard for safe concentrations of hydrazine with a low exposure threshold of 3.03X 10 -7 M (10 ppb). At present, the hydrazine detection method mainly comprises an electrochemical method, a chemical titration method, a spectrophotometry method and the like, and the technologies have the defects of complicated operation, low practicability, low sensitivity and the like due to more limitation factors. The fluorescence detection technology for detecting hydrazine 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 cellulose-based coumarin fluorescent probe for detecting hydrazine, which can meet the use requirement of detecting hydrazine. The invention aims to solve another technical problem of providing a preparation method of the cellulose-based coumarin fluorescent probe. The invention also solves another technical problem of providing an application of the cellulose-based coumarin fluorescent probe in hydrazine detection.
In order to solve the technical problems, the invention adopts the technical scheme that:
the cellulose-based coumarin fluorescent probe for detecting hydrazine is ACBC-CA, and the structural formula of the cellulose-based coumarin fluorescent probe is as follows:
the preparation method of the cellulose-based coumarin fluorescent probe for detecting hydrazine comprises the following steps:
(1) carrying out condensation reaction on 2- (1- (7- (diethylamino) coumarin-3-yl) ethylidene) malononitrile (DCM for short) and 4 ' -formylbiphenyl-4-formic acid (FBC for short) to prepare 4 ' - (4, 4-dicyano-3- (7-diethylamino-coumarin-3-yl) -1, 3-butadienyl) - [1, 1 ' -biphenyl ] -4-formic acid (ACBC for short);
(2) cellulose acetate glycidyl ether (GCA for short) and a compound ACBC are subjected to ring-opening esterification reaction to prepare the ACBC-CA.
In the step (1), the specific preparation steps of the ACBC are as follows:
1) sequentially adding 1-2 mmol of DCM, 1-2 mmol of FBC and 20-50 mL of ethanol into a 50mL three-neck flask with a stirrer, a thermometer and a reflux condenser, adding 3-6 drops of piperidine, and reacting for 24-36 h at 80 ℃ under the protection of nitrogen;
2) after the reaction is finished, evaporating the solvent to obtain an ACBC crude product, and purifying by silica gel column chromatography to obtain the compound ACBC.
In the step (2), the specific preparation steps of the ACBC-CA are as follows:
1) dissolving 0.5-1 mmol of ACBC in 10-20 mL of DMSO, adding 0.50-1 mmol of N, N' -carbon-based diimidazole, reacting at 80 ℃ for 20-30 min, adding 0.1-0.2 g of GCA, and continuing to react for 24-36 h;
2) and cooling the reaction liquid to room temperature, adding 20-30 mL of distilled water to separate out the ACBC-CA, filtering, washing with ethanol, and drying in vacuum at 45 ℃ for 24-36 h to obtain the product ACBC-CA.
Under 365nm ultraviolet irradiation, adding the ACBC-CA before and after hydrazine in DMSO/H 2 The fluorescence color of the suspension of O (v: v ═ 9: 1) changed from colorless to yellow, and it was used as a fluorescent probe for detecting hydrazine.
Has the advantages that: compared with the prior art, the invention has the following advantages:
cellulose acetate is a cellulose derivative prepared by taking cellulose as a raw material, and the cellulose is a natural polymer which is widely distributed in the nature, and has the characteristics of wide source and low price. The cellulose-based fluorescent probe prepared by grafting the compound ACBC to a cellulose acetate macromolecule not only has the excellent performance of the cellulose macromolecule, but also overcomes the defects of a plurality of places of small-molecule fluorescent compoundsAnd (4) limitation. The prepared ACBC-CA fluorescent probe has the characteristics of good luminous performance, stable structure and the like. Under 365nm ultraviolet irradiation, suspension prepared by ACBC-CA in DMSO/water changes the fluorescence color of the solution from colorless to yellow before and after hydrazine is added, and the detection limit of hydrazine reaches 1.2 multiplied by 10 -7 M, as a fluorescent probe for detecting hydrazine, has good application prospect.
Drawings
FIG. 1 is an infrared spectrum of a compound wherein a is ACBC, b is GCA, and c is ACBC-CA;
FIG. 2 is a graph of fluorescence spectra of ACBC-CA before and after hydrazine addition in DMSO/water;
FIG. 3 is a graph of the fluorescence spectra of ACBC-CA in DMSO/water with various hydrazine derivatives and amino acid derivatives added;
FIG. 4 is a graph of the fluorescence spectra of ACBC-CA in DMSO/water with various concentrations of hydrazine added.
Detailed Description
In order to make the aforementioned objects, features and advantages of the present invention comprehensible, specific embodiments accompanied with examples are described in detail below.
Example 1
The synthesis of ACBC-CA, the reaction formula is as follows:
the preparation process comprises the following steps:
sequentially adding 1mmol of DCM compound, 1mmol of FBC compound and 20mL of ethanol into a 50mL three-neck flask with a stirrer, a thermometer and a reflux condenser, adding 3 drops of piperidine, and reacting for 24 hours at 80 ℃ under the protection of nitrogen; after the reaction was completed, the ethanol solvent was distilled off to obtain crude ACBC, which was purified by silica gel column chromatography (dichloromethane: methanol 50: 1, v/v) to obtain compound ACBC. 1 H NMR(600MHz，DMSO-d 6 )δ(ppm)：10.05(s，1H)，8.62(s，1H)，8.03(d，J＝1.4Hz，2H)，7.91-7.89(m，2H)，7.87(d，J＝4.6Hz，2H)，7.85(m，2H)，7.72(d，J＝7.8Hz，2H)，6.83(dd，J＝8.4，2.5Hz，1H)，6.62(d，J＝2.4Hz，1H)，3.52(q，J＝7.0Hz，4H)，1.16(t，J＝7.1Hz，6H). 13 C NMR(150MHz，DMSO-d 6 )δ(ppm)：185.85，170.87，168.75，166.25，161.86，160.43，158.73，154.30，153.51，152.79，150.74，148.93，141.56，140.00，133.26，132.86，130.50，130.47，129.57，127.97，127.26，125.91，116.39，110.71，108.43，97.70，67.29，44.94，30.47，18.26，14.01，12.83.
Dissolving 0.50mmol of compound ACBC in 20mL of DMSO, adding 0.50mmol of N, N' -carbon-based diimidazole, reacting at 80 ℃ for 30min, adding 0.1g of glycidol-based cellulose acetate (GCA for short), and continuing to react for 24 h; and cooling the reaction liquid to room temperature, adding 20mL of distilled water to separate out the ACBC-CA, filtering, washing with ethanol, and drying in vacuum at 45 ℃ for 24h to obtain the product ACBC-CA.
The structure of the cellulose-based coumarin derivative is analyzed by FT-IR. In FIG. 1, (a), (b) and (c) are the infrared spectra of ACBC, GCA and ACBC-CA, respectively. As can be seen from FIG. 1, after GCA and ACBC react, the infrared spectrum of GCA has changed significantly, which is 3200- -1 The peak intensity is enhanced due to the stretching vibration of hydroxyl group H-O generated after the ring opening esterification of epoxy ring, 1720cm -1 Is the C ═ O stretching vibration peak on the ester group, 1602cm -1 The stretching vibration peak of C ═ C on a benzene ring indicates that the GCA and the ACBC have ring-opening esterification reaction, and the ACBC is successfully grafted to the cellulose acetate macromolecule.
Example 2
The prepared probe was added to a DMSO/water (v: 9: 1, the same applies below) solution to prepare a suspension of 1.0mg/mL, and the fluorescence emission spectrum in DMSO/water was measured as shown in FIG. 2. The result shows that in a DMSO/water system, when hydrazine is not added, the fluorescence intensity is weak, after the hydrazine is added, the fluorescence intensity is rapidly enhanced, and the maximum emission wavelength is 547nm (the excitation wavelength is 400nm, the excitation slit broadband is 15nm, and the emission slit broadband is 4.5 nm).
The probe was added to DMSO/water to prepare a DMSO suspension having a concentration of 1.0mg/mL, wherein 1 part was used as a blank, and cysteine, homocysteine, glutathione, glutamic acid, tryptophan, glutamic acid, lysine, histidine, serine, leucine, butyryl hydrazide, nicotinyl hydrazide, valeryl hydrazide, isoniazid, benzenesulfonyl hydrazide, formyl hydrazine, 2-furancarbohydrazide, benzoyl hydrazine, hydrazine hydrochloride, and phenylhydrazine were added to the other parts, and the fluorescence emission spectrum of the solution was measured, and the results are shown in FIG. 3. As can be seen from FIG. 3, the maximum emission wavelength of the solution after the addition of hydrazine was 547nm, and the fluorescence intensity of the solution was significantly enhanced. While the fluorescence intensity of the solution changes very little when other analytes are added. This indicates that the probe has good selectivity for hydrazine.
The probes were added to DMSO/water to prepare DMSO suspensions at concentrations of 1.0mg/mL, and fluorescence emission spectra were measured after the addition of various concentrations of hydrazine. As shown in fig. 4. The results show that the fluorescence signal intensity of the probe at 547nm is gradually increased along with the gradual increase of the hydrazine concentration, which indicates that the probe can be used for detecting the hydrazine concentration in the solution, and the detection limit of the hydrazine reaches 1.2 multiplied by 10 -7 M。
Claims (6)
1. A cellulose-based coumarin fluorescent probe for detecting hydrazine is characterized in that the structural formula is as follows:
2. the method for preparing the cellulose-based coumarin fluorescent probe for detecting the hydrazine as claimed in claim 1, which is characterized by comprising the following steps:
(1) carrying out condensation reaction on DCM and FBC to prepare ACBC;
(2) and carrying out ring-opening esterification reaction on GCA and a compound ACBC to prepare the ACBC-CA.
3. The method for preparing the cellulose-based coumarin fluorescent probe for detecting the hydrazine according to claim 2, wherein the preparation of the ACBC in the step (1) comprises the following steps:
1) sequentially adding 1-2 mmol of DCM, 1-2 mmol of FBC and 20-50 mL of ethanol into a 50mL three-neck flask with a stirrer, a thermometer and a reflux condenser, adding 3-6 drops of piperidine, and reacting for 24-36 h at 80 ℃ under the protection of nitrogen;
2) after the reaction is finished, the solvent is evaporated to obtain an ACBC crude product, and the crude product is purified by silica gel column chromatography (eluent is supplemented) to obtain the compound ACBC.
4. The method for preparing the cellulose-based coumarin fluorescent probe for detecting hydrazine according to claim 2, wherein the preparation of the ACBC-CA in the step (2) comprises the following steps:
1) dissolving 0.5-1 mmol of ACBC in 10-20 mL of DMSO, adding 0.50-1 mmol of N, N' -carbon-based diimidazole, reacting at 80 ℃ for 20-30 min, adding 0.1-0.2 g of GCA, and continuing to react for 24-36 h;
2) and cooling the reaction liquid to room temperature, adding 20-30 mL of distilled water to separate out the ACBC-CA, filtering, washing with ethanol, and drying in vacuum at 45 ℃ for 24-36 h to obtain the product ACBC-CA.
5. The application of the cellulose-based coumarin fluorescent probe in the detection of hydrazine according to claim 1.
6. The use according to claim 5, wherein the DMSO/water suspension of the cellulose-based coumarin fluorescent probe does not fluoresce under 365nm ultraviolet light, and the solution changes its fluorescent color from colorless to yellow upon the addition of hydrazine.
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Cited By (3)
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| CN115677864A (en) * | 2022-11-11 | 2023-02-03 | 南京林业大学 | Cellulose-based coumarin fluorescent probe for detecting cyanide ions and preparation method and application thereof |
| CN115894293A (en) * | 2022-12-15 | 2023-04-04 | 枣庄学院 | Ratiometric near-infrared fluorescent probe for detecting hydrazine, and synthetic method and application thereof |
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| CN115677864B (en) * | 2022-11-11 | 2023-08-29 | 南京林业大学 | Cellulose coumarin fluorescent probe for detecting cyanide ions and preparation method and application thereof |
| CN115894293A (en) * | 2022-12-15 | 2023-04-04 | 枣庄学院 | Ratiometric near-infrared fluorescent probe for detecting hydrazine, and synthetic method and application thereof |
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