CN114149369A - Fluorescent probe FAL1 for formaldehyde and pH dual-function detection and preparation method and application thereof - Google Patents
Fluorescent probe FAL1 for formaldehyde and pH dual-function detection and preparation method and application thereof Download PDFInfo
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- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
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Abstract
The invention belongs to the field of chemical detection, relates to a formaldehyde and pH dual-function detection reagent, and particularly relates to a formaldehyde and pH dual-function fluorescent molecule based on a naphthalimide derivative, and a preparation method and application thereof. The recognition performance of the probe FAL1 in DMSO/Tris-HCl for various common analytes was studied by fluorescence spectroscopy. The research result shows that: the probe FAL1 has specific fluorescence recognition performance on formaldehyde, can overcome the interference of other common analytes, and has a wider pH value application range. The lowest detection limit of the probe to formaldehyde is 38 nM, and the probe is successfully applied to detection of formaldehyde in tap water through a labeling recovery test; the probe responds to the fluorescence emission of the pH value within the range of 3-8, is suitable for pH marking in a microenvironment sensitive to the pH value in a living body, and has strong practical application value in the fields of environmental detection and biology.
Description
Technical Field
The invention belongs to the field of chemical detection, relates to a formaldehyde and pH dual-function detection reagent, and particularly relates to a formaldehyde and pH dual-function fluorescent molecule based on a naphthalimide derivative, and a preparation method and application thereof.
Background
Formaldehyde (FA) is a colorless gas and is widely used in wood processing, textile, building, carpet, preservative paper and chemical industries as a synthetic material. Formaldehyde in the environment comes mainly from industrial activities, food preservatives and building materials. Formaldehyde is one of the ubiquitous pollutants in indoor air and, due to its high reactivity and toxicity, is prone to cause DNA damage, tearing, vomiting, sneezing, coughing, lethargy and coma, alzheimer's disease, and even death. According to unequivocal evidence of formaldehyde damage, international agency for research on cancer (IARC) classified it as a class of carcinogens in 2004. However, formaldehyde is also naturally present in human cells and in different organisms. The concentration of endogenous formaldehyde in human blood is about 2-3 mg/L; similar results were also found in the blood of monkeys and rats. Formaldehyde has recently been used as a metabolic intermediate and endogenously produced carbonyl species, released in many biological organisms by protein N-demethylation, DNA/RNA demethylation or metabolite demethylation. For example, formaldehyde concentrations in normal physiological brain range from 0.2 mmol to 0.4 mmol. At this concentration, formaldehyde plays a crucial role in memory formation through DNA demethylation cycles and cognitive abilities. In view of these important effects on human health, there is a need to develop a fast, simple, low cost, high sensitivity method for detecting formaldehyde in environments, foods and biological systems.
The degree of acidity (pH) as an important index of acidity plays a complex and important role in chemistry, biology, physiology and environmental science. Acid-base equilibrium is a key parameter for biological cell survival. For example, higher intracellular pH (. gtoreq.7.4) and lower extracellular pH (. gtoreq.6.7-7.1) in cancer cells form a "reverse" pH gradient with normal cells (. alpha.7.2; pH. minus.7.4) promoting cell proliferation, cancer cell invasion and escape from apoptosis. An abnormal intracellular pH can lead to a homeostatic breakdown of the overall intracellular pH, leading to free radical production, membrane contraction breakdown, apoptosis and necrosis. In addition, acid-base imbalance is a common characteristic of cancer cells and may affect the uptake and efficacy of pH sensitive chemotherapeutic drugs. Therefore, tracking pH fluctuations in acidic organelles is crucial to studying normal cellular function and activity in these chambers.
In recent years, small molecule fluorescent probes have been considered as powerful analytical tools for detecting various ions and biomolecules in the environment and biomedicine due to their high selectivity, high sensitivity, and simplicity of operation. Meanwhile, the fluorescent probe also has the advantages of diversity of experimental determination, small damage to a detected object, capability of realizing nondestructive detection and the like. Has been widely applied to the aspects of detecting metal cations, anions, active small molecules in organisms and the like in environment and biological systems. Unlike a single recognition fluorescent probe, the multifunctional fluorescent probe has one or more recognition sites and can recognize a plurality of analytes or dynamically image a specific analyte, and the recognition process is accompanied by fluorescence change and solution color change of a recognition system. The multifunctional fluorescent probe can detect a plurality of targets, thereby being beneficial to improving the efficiency and reducing the cost and becoming a development direction in the field of fluorescent probes. Therefore, the construction of small molecule fluorescent probes suitable for the bifunctional detection of specific formaldehyde and pH in environment, food and medicine has received much attention.
Disclosure of Invention
The invention provides a naphthalimide derivative-based formaldehyde and pH dual-functional fluorescent molecule, and a preparation method and application thereof.
The technical scheme of the invention is realized as follows:
a fluorescent probe FAL1 for formaldehyde and pH dual-function detection has a structural formula as follows:
the technical route of the preparation method of the fluorescent probe FAL1 is as follows:
the method comprises the following steps:
(1) dissolving 4-bromo-1, 8-naphthalic anhydride and dimethyl diamine in ethanol, stirring under reflux condition for reaction, cooling to room temperature, precipitating a large amount of solid, and performing suction filtration to obtain a light yellow solid, namely an intermediate I;
(2) and (2) dissolving the intermediate I obtained in the step (1) and a hydrazine hydrate aqueous solution in an ethylene glycol monomethyl ether solution, completely reacting under a heating reflux condition, cooling to room temperature, pouring the mixed solution into purified water to separate out a large amount of solids, performing suction filtration, and washing the obtained solids with ethylene glycol monomethyl ether to finally obtain an orange solid, namely the fluorescent probe FAL 1.
In the step (1), the mass ratio of the 4-bromo-1, 8-naphthalic anhydride to the dimethyl diamine is 1: (3-10).
In the step (1), the heating reflux reaction time is 4-10 hours, and the yield of the intermediate I is 40-70%.
In the step (2), the mass fraction of the hydrazine hydrate aqueous solution is 80% wt, and the mass ratio of the intermediate I to the hydrazine hydrate is 1: (4-16).
The heating reflux reaction time in the step (2) is 12-24 hours.
The yield of the fluorescent probe FAL1 in the step (2) is 30-60%.
The fluorescent probe FAL1 is applied to specifically recognizing and detecting formaldehyde and pH in environment and biological systems.
The method comprises the following steps: mixing a Tris-HCl buffer solution and dimethyl sulfoxide in equal volume to obtain a solution A, adding 2940 mu L of the solution A and 30 mu L of DMSO solution of probe FAL1 into a fluorescence cuvette, adding 30 mu L of solution to be detected, and detecting the fluorescence emission intensity at 534 nm on a fluorescence spectrometer under the excitation condition at 440 nm.
The Tris-HCl buffer solution had a pH of 7.4 and a concentration of 10 mM, and the DMSO solution of probe FAL1 had a concentration of 1 mM.
The invention has the following beneficial effects:
(1) the molecular structure of the fluorophore naphthalimide derivative selected by the application has a larger conjugated system, and the molecular structure has a large electron absorption-electron supply conjugated system which is easy to be irradiated by light to generate transition, so that strong fluorescence is generated. In addition, after the probe identifies formaldehyde, the fluorescence emission wavelength is in a visible light region, and the Stokes displacement is large (94 nm), so that the fluorescent probe FAL1 has the advantages of low background interference, small light damage to a biological sample, strong sample penetrability, high detection sensitivity and the like.
(2) The mechanism of the probe FAL1 for identifying formaldehyde is that amino in the molecular structure of the probe FAL1 and formaldehyde are subjected to specific condensation reaction to generate Schiff base, charges in the molecule are rearranged, and fluorescence is released to realize specific identification of formaldehyde. As a contrast, the probe is not easy to be attacked by other common active small molecular substancesThe fluorescence of the solution system is not changed in the raw reaction, thereby realizing the specific recognition of the formaldehyde. The specific recognition reaction mechanism is as follows:
(ii) a The final product of the probe FAL1 after formaldehyde recognition is confirmed by high-resolution mass spectrometry (figure 8), and the experimental result shows that the theoretical calculation value under the FAL1-HCHO positive ion mode is 311.1508, the HR-MS result shows 311.1501, and the high-resolution mass spectrometry experimental result verifies the recognition mechanism.
(3) (the fluorescence emission intensity of an individual probe FAL1 (10 mu M) in a mixed solution A1-A11 with pH values of 3.0, 3.5, 4.0, 4.5, 5.0, 5.5, 6.0, 6.5, 7.0, 7.5 and 8.0 respectively has better linearity at 534 nm under the excitation condition at 440 nm (R 2 = 0.824), the fluorescence emission intensity of the solution system gradually decreases along with the increase of the pH value, and the fact that the probe can be used for accurately detecting the change of the pH value is proved.
(4) The mechanism of response of probe FAL1 to pH in the present application is as follows:
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the drawings without creative efforts.
FIG. 1 shows the hydrogen nuclear magnetic resonance spectrum of the fluorescent probe FAL1 of the present invention.
FIG. 2 is a carbon nuclear magnetic resonance spectrum of FAL1 as a fluorescent probe of the present invention.
FIG. 3 is a high resolution mass spectrum of FAL1 as a fluorescent probe of the present invention.
FIG. 4 is a graph showing fluorescence selectivity of the fluorescent probe FAL1 of the present invention, with an excitation wavelength of 440 nm.
FIG. 5 is a diagram of a competitive experiment for formaldehyde recognition by the fluorescent probe FAL1 of the present invention, wherein the excitation wavelength is 440 nm and the emission wavelength is 534 nm.
FIG. 6 is a fluorescence titration chart of formaldehyde-recognized fluorescence by the fluorescent probe FAL1 of the present invention, with an excitation wavelength of 440 nm.
FIG. 7 is a graph showing the lowest detection limit of formaldehyde recognized by the fluorescent probe FAL1 of the present invention, wherein the excitation wavelength is 440 nm and the emission wavelength is 534 nm.
FIG. 8 is a high-resolution mass spectrometry verification mechanism diagram of formaldehyde recognition by the fluorescent probe FAL1 of the present invention, and the testing solvent is methanol.
FIG. 9 is a graph showing fluorescence emission intensity of the fluorescent probe FAL1 of the present invention recognizing different pH, with an excitation wavelength of 440 nm and an emission wavelength of 534 nm.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to the following embodiments of the present invention, and it should be understood that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be obtained by a person skilled in the art without inventive effort based on the embodiments of the present invention, are within the scope of the present invention.
Example 1
The preparation method of the fluorescent probe FAL1 for the bifunctional detection of formaldehyde and pH comprises the following specific steps:
(1) the preparation method of the intermediate 1 comprises the following steps: dissolving 4-bromo-1, 8-naphthalic anhydride (2.77 g, 10 mmol) and dimethyl diamine (2.644 g, 30 mmol) in ethanol (50 mL), stirring under reflux for 4 hours, cooling to room temperature to precipitate a large amount of solid, and performing suction filtration to obtain 1.384g of light yellow solid, namely the intermediate 1, wherein the yield is 40%;
(2) the preparation method of the probe FAL1 comprises the following steps: dissolving the intermediate 1 (347.2 mg, 1 mmol) and 80% hydrazine hydrate (363 mu L, 6 mmol) in ethylene glycol monomethyl ether (15 mL), reacting for 15 hours under the condition of heating reflux, cooling to room temperature, pouring the mixed solution into purified water to precipitate a large amount of solid, performing suction filtration, and washing the obtained solid with ethylene glycol monomethyl ether to obtain 149 mg of orange solid, namely the fluorescent probe FAL1 for formaldehyde detection, wherein the yield is 50%.
Hydrogen nuclear magnetic resonance spectroscopy:1H NMR (DMSO-d 6 , 400 MHz) δ 2.19 (s, 6 H), 3.35 (s, 2 H), 4.10 (s, 2 H), 4.66 (s, 2 H), 7.22 (s, 1 H), 7.60 (s, 1 H), 8.26 (s, 1 H), 8.37 (s, 1 H), 8.58 (s, 1 H), 9.11 (s, 1 H)。
nuclear magnetic resonance carbon spectrum measurement:13C NMR (DMSO-d 6 , 100 MHz) δ 37.62, 45.87, 57.16, 104.42, 107.76, 118.85, 122.12, 124.53, 128.69, 129.75, 131.02, 134.67, 153.63, 163.32, 164.22。
high-resolution mass spectrometry: HR-ESI-MS calcd for C16H19N4O2 +: 299.1508, found 299.1505 [M+H+]+。
Example 2
The preparation method of the fluorescent probe FAL1 for the bifunctional detection of formaldehyde and pH comprises the following specific steps:
(1) the preparation method of the intermediate 1 comprises the following steps: dissolving 4-bromo-1, 8-naphthalic anhydride (2.77 g, 10 mmol) and dimethyl diamine (3.525 g, 40 mmol) in ethanol (50 mL), stirring under reflux for 6 hours, cooling to room temperature to precipitate a large amount of solid, and performing suction filtration to obtain 1.73 g of light yellow solid, namely the intermediate 1, with the yield of 50%;
(2) the preparation method of the probe FAL1 comprises the following steps: dissolving the intermediate 1 (347.2 mg, 1 mmol) and 80% hydrazine hydrate (242 mu L, 4 mmol) in ethylene glycol monomethyl ether (15 mL), reacting under heating reflux for 12 hours, cooling to room temperature, pouring the mixed solution into purified water to precipitate a large amount of solid, performing suction filtration, and washing the obtained solid with ethylene glycol monomethyl ether to obtain 89.4 mg of orange solid, namely the fluorescent probe FAL1 for formaldehyde detection, with the yield of 30%.
Hydrogen nuclear magnetic resonance spectroscopy:1H NMR (DMSO-d 6 , 400 MHz) δ 2.19 (s, 6 H), 3.35 (s, 2 H), 4.10 (s, 2 H), 4.66 (s, 2 H), 7.22 (s, 1 H), 7.60 (s, 1 H), 8.26 (s, 1 H), 8.37 (s, 1 H), 8.58 (s, 1 H), 9.11 (s, 1 H)。
nuclear magnetic resonance carbon spectrum measurement:13C NMR (DMSO-d 6 , 100 MHz) δ 37.62, 45.87, 57.16, 104.42, 107.76, 118.85, 122.12, 124.53, 128.69, 129.75, 131.02, 134.67, 153.63, 163.32, 164.22。
high-resolution mass spectrometry: HR-ESI-MS calcd for C16H19N4O2 +: 299.1508, found 299.1505 [M+H+]+。
Example 3
The preparation method of the fluorescent probe FAL1 for the bifunctional detection of formaldehyde and pH comprises the following specific steps:
(1) the preparation method of the intermediate 1 comprises the following steps: dissolving 4-bromo-1, 8-naphthalic anhydride (2.77 g, 10 mmol) and dimethyl diamine (7.05 g, 80 mmol) in ethanol (50 mL), stirring under reflux for 8 hours, cooling to room temperature to precipitate a large amount of solid, and performing suction filtration to obtain 2.08 g of light yellow solid, namely the intermediate 1, wherein the yield is 60%;
(2) the preparation method of the probe FAL1 comprises the following steps: dissolving the intermediate 1 (347.2 mg, 1 mmol) and 80% hydrazine hydrate (484 mu L, 8 mmol) in ethylene glycol monomethyl ether (15 mL), reacting under heating reflux for 10 hours, cooling to room temperature, pouring the mixed solution into purified water to precipitate a large amount of solid, performing suction filtration, and washing the obtained solid with ethylene glycol monomethyl ether to obtain 119.2 mg of orange solid, namely the fluorescent probe FAL1 for formaldehyde detection, with the yield of 40%.
Hydrogen nuclear magnetic resonance spectroscopy:1H NMR (DMSO-d 6 , 400 MHz) δ 2.19 (s, 6 H), 3.35 (s, 2 H), 4.10 (s, 2 H), 4.66 (s, 2 H), 7.22 (s, 1 H), 7.60 (s, 1 H), 8.26 (s, 1 H), 8.37 (s, 1 H), 8.58 (s, 1 H), 9.11 (s, 1 H)。
nuclear magnetic resonance carbon spectrum measurement:13C NMR (DMSO-d 6 , 100 MHz) δ 37.62, 45.87, 57.16, 104.42, 107.76, 118.85, 122.12, 124.53, 128.69, 129.75, 131.02, 134.67, 153.63, 163.32, 164.22。
high-resolution mass spectrometry: HR-ESI-MS calcd for C16H19N4O2 +: 299.1508, found 299.1505 [M+H+]+。
Example 4
The preparation method of the fluorescent probe FAL1 for the bifunctional detection of formaldehyde and pH comprises the following specific steps:
(1) the preparation method of the intermediate 1 comprises the following steps: dissolving 4-bromo-1, 8-naphthalic anhydride (2.77 g, 10 mmol) and dimethyl diamine (8.813 g, 100 mmol) in ethanol (50 mL), stirring under reflux for 10 hours, cooling to room temperature to precipitate a large amount of solid, and performing suction filtration to obtain 2.42 g of light yellow solid, namely the intermediate 1, wherein the yield is 70%;
(2) the preparation method of the probe FAL1 comprises the following steps: dissolving the intermediate 1 (347.2 mg, 1 mmol) and 80% hydrazine hydrate (968 mu L, 16 mmol) in ethylene glycol monomethyl ether (15 mL), reacting under heating reflux for 24 hours, cooling to room temperature, pouring the mixed solution into purified water to precipitate a large amount of solid, performing suction filtration, and washing the obtained solid with ethylene glycol monomethyl ether to obtain 178.8 mg of orange solid, namely the fluorescent probe FAL1 for formaldehyde detection, with the yield of 60%.
Hydrogen nuclear magnetic resonance spectroscopy:1H NMR (DMSO-d 6 , 400 MHz) δ 2.19 (s, 6 H), 3.35 (s, 2 H), 4.10 (s, 2 H), 4.66 (s, 2 H), 7.22 (s, 1 H), 7.60 (s, 1 H), 8.26 (s, 1 H), 8.37 (s, 1 H), 8.58 (s, 1 H), 9.11 (s, 1 H)。
nuclear magnetic resonance carbon spectrum measurement:13C NMR (DMSO-d 6 , 100 MHz) δ 37.62, 45.87, 57.16, 104.42, 107.76, 118.85, 122.12, 124.53, 128.69, 129.75, 131.02, 134.67, 153.63, 163.32, 164.22。
high-resolution mass spectrometry: HR-ESI-MS calcd for C16H19N4O2 +: 299.1508, found 299.1505 [M+H+]+。
Examples of the effects of the invention
Fluorescence selectivity experiments:
Tris-HCl buffer solution with pH 7.4 and concentration 10 mM was prepared, mixed solution A was prepared with the above buffer solution and dimethyl sulfoxide (DMSO) in a volume ratio of 1:1, and probe FAL1 solution was prepared with DMSO at concentration 1 mM. The selectivity of probe FAL1 for formaldehyde and other common small molecule analytes in mixed solution A was examined using fluorescence spectroscopy. As shown in FIG. 4, the individual probe FAL1 (10 μ M) had a weak fluorescence emission intensity at 534 nm under excitation conditions at 440 nm in the mixed solution A and at room temperature. Under the same condition, after formaldehyde (100 mu M) is added, the fluorescence emission intensity at 534 nm is obviously enhanced, but when other active small molecules (various aldehydes, amino acids, peroxides and the like) (100 mu M) are added, the fluorescence emission intensity of the solution system is not obviously changed compared with the fluorescence emission intensity of a single probe system. The experimental results show that the probe FAL1 has good fluorescence specificity selectivity on formaldehyde in the mixed solution A.
And (3) interference resistance experiment:
Tris-HCl buffer solution with pH 7.4 and concentration 10 mM was prepared, mixed solution A was prepared with the above buffer solution and dimethyl sulfoxide (DMSO) in a volume ratio of 1:1, and probe FAL1 solution was prepared with DMSO at concentration 1 mM. The competition selectivity experiment of the probe FAL1 on formaldehyde in the mixed solution A under the condition of the existence of other active small molecules is examined by a fluorescence spectrometer. 2940 μ L of the mixed solution a and 30 μ L of the DMSO solution of the probe FAL1 were added to 20 clean fluorescence cuvettes, 10 molar equivalents of formaldehyde and 10 molar equivalents of other analytes (various aldehydes, amino acids, peroxides, etc.) were added, detected on a fluorescence spectrometer, and histograms of 534 nm fluorescence intensities corresponding to the different analytes were plotted under excitation conditions at 440 nm, to obtain fluorescence emission histograms (fig. 5).
Experiments prove that the probe FAL1 is not interfered by other analytes in the mixed solution A for identifying the formaldehyde, and has better anti-interference performance.
Minimum detection limit experiment:
good detection limit is one of the important criteria for determining whether a fluorescent probe has practical application value. Tris-HCl buffer solution with pH 7.4 and concentration 10 mM was prepared, mixed solution A was prepared with the above buffer solution and dimethyl sulfoxide (DMSO) in a volume ratio of 1:1, and probe FAL1 solution was prepared with DMSO at concentration 1 mM. The concentration of the fixed probe FAL1 is 10 mu M, the fluorescence emission response intensity of the fixed probe FAL1 to formaldehyde with different concentrations is measured, the fluorescence emission intensity of the system is continuously enhanced at 534 nm along with the increase of the formaldehyde concentration (figure 6), and the research shows that the fluorescence emission intensity of the solution is linear between 0.1 and 0.7 mu M of the formaldehyde concentration (the concentration is linear in the range of (the concentration is less than or equal to the concentration of the formaldehyde) (the concentration is less than or equal to the concentration is equal to the concentration of the formaldehyde: (the concentration is less than or equal to the concentration is less than or equal to the concentration of the concentration is less than the concentration of the concentration is less than or less than the concentration of the concentration is less than the concentration of the fluorescence emission intensity of the fluorescence emission) of the fluorescence emission intensity of the fluorescence emission intensity of the fluorescence emission intensity of the fluorescence emission ofR 2 = 0.995) (fig. 7), and the detection limit of the probe molecule for formaldehyde was calculated to be 38 nM (3 σ/k).
Experiment of pH value action range:
Tris-HCl buffer solutions with pH values of 3.0, 3.5, 4.0, 4.5, 5.0, 5.5, 6.0, 6.5, 7.0, 7.5 and 8.0 respectively at a concentration of 10 mM are prepared, and mixed solutions A1, A2, A3, A4, A5, A6, A7, A8, A9, A10 and A11 at a volume ratio of 1:1 are prepared by using the buffer solutions and DMSO, and probe FAL1 solutions with a concentration of 1mM are prepared by using DMSO. The fluorescence emission intensity of the individual probe FAL1 (10. mu.M) in the mixed solution A1-A11 was examined by a fluorescence spectrometer. As shown in FIG. 9, under the excitation condition at 440 nm, the single probe FAL1 (10 μ M) has better linearity of fluorescence emission intensity at 534 nm in the mixed solution A1-A11 with pH values of 3.0, 3.5, 4.0, 4.5, 5.0, 5.5, 6.0, 6.5, 7.0, 7.5 and 8.0 respectively (the wavelength of the fluorescence emission intensity at 534 nmR 2 = 0.824), the fluorescence emission intensity of the solution system gradually decreases along with the increase of the pH value, and the fact that the probe can be used for accurately detecting the change of the pH value is proved.
Actual in-water analytical applications
In order to further examine the application value of the probe FAL1 in actual samples, the probe is applied to city tap water for a standard recovery test. Controlling the experimental conditions to be consistent, adding formaldehyde (0.8 mu M, 1.0 mu M and 1.2 mu M) with different concentrations into a tap water sample respectively, and figuring out corresponding formaldehyde concentrations (0.651 mu M, 0.836 mu M and 0.948 mu M) through a working curve, wherein the recovery rate is between 80% and 120% (see table 1):
TABLE 1 results of formaldehyde addition recovery test in tap water
Mean ± standard deviation
The detection result fully reflects the practical application value of the probe in detecting formaldehyde in practical urban tap water samples.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (10)
1. A fluorescent probe FAL1 for formaldehyde and pH dual-function detection has a structural formula as follows:
2. the method for preparing the fluorescent probe FAL1 as claimed in claim 1, which comprises the following steps:
(1) dissolving 4-bromo-1, 8-naphthalic anhydride and dimethyl diamine in ethanol, stirring under reflux condition for reaction, cooling to room temperature, precipitating a large amount of solid, and performing suction filtration to obtain a light yellow solid, namely an intermediate I;
(2) and (2) dissolving the intermediate I obtained in the step (1) and a hydrazine hydrate aqueous solution in an ethylene glycol monomethyl ether solution, completely reacting under a heating reflux condition, cooling to room temperature, pouring the mixed solution into purified water to separate out a large amount of solids, performing suction filtration, and washing the obtained solids with ethylene glycol monomethyl ether to finally obtain an orange solid, namely the fluorescent probe FAL 1.
3. The method of claim 2, wherein: in the step (1), the mass ratio of the 4-bromo-1, 8-naphthalic anhydride to the dimethyl diamine is 1: (3-10).
4. The method of claim 2, wherein: the heating reflux reaction time in the step (1) is 4-10 hours.
5. The method of claim 2, wherein: in the step (2), the mass fraction of the hydrazine hydrate aqueous solution is 80% wt, and the mass ratio of the intermediate I to the hydrazine hydrate is 1: (4-16).
6. The method of claim 2, wherein: the heating reflux reaction time in the step (2) is 12-24 hours.
7. Use of the fluorescent probe FAL1 according to claim 1 for specifically recognizing and detecting formaldehyde and pH in environmental and biological systems.
8. Use according to claim 7, characterized by the steps of: mixing the Tris-HCl buffer solution and dimethyl sulfoxide in equal volume to obtain a solution A, adding 2940 mu L of the solution A and 30 mu L of DMSO solution of the probe FAL1 into a fluorescence cuvette, adding 30 mu L of solution to be detected, and detecting the fluorescence emission intensity at 534 nm on a fluorescence spectrometer under the excitation condition at 440 nm.
9. Use according to claim 8, characterized in that: the Tris-HCl buffer solution has a pH of 7.4 and a concentration of 10 mM.
10. Use according to claim 8 or 9, characterized in that: the concentration of the probe FAL1DMSO solution was 1 mM.
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