CN110981891B - Methanol fluorescent probe based on viologen derivative, preparation method and application - Google Patents
Methanol fluorescent probe based on viologen derivative, preparation method and application Download PDFInfo
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Abstract
The invention provides a methanol fluorescent probe based on a viologen derivative, a preparation method and application thereof, and the chemical structural formula of the probe is
. The invention can quickly, efficiently and specifically identify the methanol, the ethanol and other alcohols with similar structures do not influence the specific identification of the probe on the methanol, and the fluorescent probe designed by the invention can be used for detecting the methanol in an actual sample.
Description
Technical Field
The invention relates to the technical field of organic small molecule fluorescent probes and biosensing, in particular to a methanol fluorescent probe based on a viologen derivative, a preparation method and application thereof.
Background
Methanol is a very important organic chemical, and can be used as an intermediate for producing other chemical products, such as formic acid, acetic acid, formaldehyde, tert-butyl ether and the like; the method can also be used for preparing clean and environment-friendly methanol gasoline, so that the consumption of fossil fuel can be reduced, and the pollution to the environment can be reduced. However, methanol has toxic effect on human bodies, and people can lose eyesight by taking 10ml of methanol and die by taking 30 ml of methanol. This is because methanol is metabolized into formaldehyde in the liver by the action of alcohol dehydrogenase, formaldehyde is metabolized into formic acid by the action of formaldehyde dehydrogenase, and formic acid can inhibit cytochrome oxidase activity in mitochondria (participating in the last step of the mitochondrial respiratory chain), thereby causing oxygen deficiency in human tissues and leading to human death. Therefore, the development of a detection method with high selectivity and high sensitivity to methanol has important significance on quality control and public safety.
The presently reported methanol fluorescent probe based on the viologen derivative can be used for detecting methanol in white spirit and methanol gasoline. However, water in the actual sample interferes with the detection of methanol, and drying with anhydrous sodium sulfate and distilling off water are required, which is very cumbersome and time-consuming. Secondly, the reaction speed of the probe and methanol is relatively slow, and generally about 15 min is needed. Therefore, the development of a novel fluorescent probe for rapidly, efficiently and specifically identifying methanol is urgently needed.
Disclosure of Invention
The invention provides a methanol fluorescent probe based on a viologen derivative, a preparation method and application, wherein after halogenated dinitrobenzene is introduced on an intermediate (2, 5-di (4-pyridyl) thiazole [5, 4-d ] thiazole), the probe can quickly respond to methanol and is not interfered by water and ethanol with a structure similar to that of the water and the methanol.
The technical scheme for realizing the invention is as follows:
a methanol fluorescent probe based on viologen derivatives has the following structural formula:
the preparation method of the methanol fluorescent probe based on the viologen derivative comprises the following steps:
(1) heating pyridine-4-formaldehyde and erythronic acid in DMF, stirring for reaction, cooling, and washing with water for three times to obtain a light green intermediate;
(2) and (2) heating and reacting the intermediate obtained in the step (1) with halogenated dinitrobenzene, cooling, washing with ethanol/water for three times, and drying in vacuum to obtain the fluorescent probe.
In the step (1), the molar ratio of the pyridine-4-formaldehyde to the erythrosine is (2-4): 1, the heating temperature is 140-.
The molar ratio of the intermediate to the halogenated dinitrobenzene in the step (2) is 1: (42-85).
In the step (2), the heating temperature is 80-100 ℃, and the reaction time is 48-70 h.
The halogenated dinitrobenzene in the step (2) is 2, 4-dinitrofluorobenzene, 2, 4-dinitrochlorobenzene or 2, 4-dinitrobromobenzene.
The fluorescent probe is applied to the specific recognition of methanol.
The application specifically comprises:
respectively testing the changes of the ultraviolet visible spectrum and the fluorescence spectrum before and after the probe storage solution is added into ethanol solutions with different contents of methanol, wherein the excitation wavelength of fluorescence is 435 nm; and observing the change of the ultraviolet and fluorescence spectra.
The change in fluorescence spectrum was: when the fluorescent material is excited by 435 nm light, methanol with different concentrations is gradually added, the fluorescence intensity is gradually enhanced, and the logarithmic value of the fluorescence is in direct proportion to the concentration range of the methanol.
And (3) actual sample detection:
diluting the purchased red star Erguotou twice, adding the probe storage solution into diluted red star Erguo solutions with different contents of methanol, and observing the change of a fluorescence spectrum to detect the selectivity and the sensitivity of the probe to the methanol.
The change in fluorescence spectrum was: when the fluorescent material is excited by 435 nm light, methanol with different concentrations is gradually added, the fluorescence intensity is gradually enhanced, and the logarithmic value of the fluorescence is in direct proportion to the concentration range of the methanol.
The invention has the beneficial effects that: (1) the probe is very simple to synthesize and convenient to operate; (2) the invention can realize the specificity detection and the rapid identification of the methanol, and the ethanol and other alcohols with similar structures do not interfere the identification of the probe to the methanol; (3) the invention can realize the detection of methanol in white spirit and methanol gasoline.
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 probe of example 11H NMR spectrum.
FIG. 2 shows the probe of example 113C NMR spectrum.
FIG. 3 is the reaction of 2 μ M probe with different polar solvents in different polar solvent systems with the probe of example 1.
FIG. 4 is the reaction of 2 μ M probe with alcohol in an alcohol system with the probe of example 1.
FIG. 5 is the time kinetics of the probe of example 1 in methanol.
FIG. 6 a) is a fluorescence spectrum of 2 μ M probe of example 1 in ethanol with gradual addition of methanol at different concentrations; b) is a linear relationship between the log of the fluorescence intensity of the probe at 510 nm and the methanol concentration.
FIG. 7 a) is a fluorescence spectrum of 2 μ M probe of example 1 in water with gradual addition of methanol at different concentrations; b) is a linear relationship between the log of the fluorescence intensity of the probe at 510 nm and the methanol concentration.
FIG. 8 is a 2 μ M fluorescent titration spectrum of the probe of example 1 in a red star Erguon twice diluted with water in the presence of different concentrations of methanol twice with water. (a) Fluorescence titration spectra of the probe 1 in the presence of methanol of different concentrations; b) is a linear relationship between the log of the fluorescence intensity of the probe at 510 nm and the methanol concentration.
Fig. 9 a) is a fluorescence spectrum of a 2 μ M probe in simulated methanol gasoline consisting of petroleum ether (50%) and alcohol (50%) with ethanol and ethanol containing 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 100% methanol; b) is a linear relationship between the logarithmic value of the fluorescence intensity at 510 nm and the methanol concentration for the probe of example 1.
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
Prepared by heating pyridine-4-carbaldehyde (0.58 g, 5.4 mmol) and erythronic acid (0.32 g, 2.7 mmol) in 10mL DMF to 150 mLoC stirring and reacting for 6H, cooling and then using 50 mL of H2O washing three times to obtain light green intermediate, taking the intermediate (0.3 g, 1 mmol) and 10mL of 2, 4-dinitrofluorobenzene, and heating to 80 DEGoC, reacting for 60 hours, cooling, washing with 50 mL of ethanol/water (1: 1) for three times, and drying in vacuum for 5 hours to obtain the product.
Example 2
Prepared by heating pyridine-4-carbaldehyde (0.87 g, 8.1 mmol) and erythronic acid (0.32 g, 2.7 mmol) in 10mL DMF to 140oC stirring for inverse 10H, cooling, and adding 50 mL of H2O washes three times to give a pale green intermediate, and the intermediate (0.3 g, 1 mmol) and 2, 4-dinitrofluorobenzene (42 mmol) are heated to 100 deg.CoC, reacting for 48 hours, cooling, washing with 50 mL of ethanol/water (1: 1) for three times, and drying in vacuum for 5 hours to obtain the product.
Example 3
Prepared by heating pyridine-4-carbaldehyde (1.2 g, 10.8 mmol) and erythronic acid (0.32 g, 2.7 mmol) in 10mL DMF to 150 mLoC stirring and reacting for a certain time, cooling and then using 50 mLH2O washing three times to obtain light green intermediate, taking intermediate (0.3 g, 1 mmol) and 2, 4-dinitrofluorobenzene (60 mmol), and heating to 60%oC, reacting for 72 hours, cooling, washing with 50 mL of ethanol/water (1: 1) for three times, and drying in vacuum for 5 hours to obtain the product.
Example 4
Prepared by heating pyridine-4-carbaldehyde (0.58 g, 5.4 mmol) and erythronic acid (0.32 g, 2.7 mmol) in 10mL DMF to 150 mLoC stirring and reacting for 6H, cooling and then using 50 mL of H2O washing three times to obtain light green intermediate, taking the intermediate (0.3 g, 1 mmol) and 5 mL of 2, 4-dinitrofluorobenzene, and heating to 80 DEGoC, reacting for 60 hours, cooling, washing with 50 mL of ethanol/water (1: 1) for three times, and drying in vacuum for 5 hours to obtain the product.
Example 5
Prepared by heating pyridine-4-carbaldehyde (0.58 g, 5.4 mmol) and erythronic acid (0.32 g, 2.7 mmol) in 10mL DMF to 150 mLoC stirring and reacting for 6H, cooling and then using 50 mL of H2O washing three times to obtain a light green intermediate, taking the intermediate (0.3 g, 1 mmol) and 8 mL of 2, 4-dinitrofluorobenzene, and heating to 80 DEGoC, reacting for 60 hours, cooling, washing with 50 mL of ethanol/water (1: 1) for three times, and drying in vacuum for 5 hours to obtain the product.
Example 6
Prepared by heating pyridine-4-carbaldehyde (0.58 g, 5.4 mmol) and erythronic acid (0.32 g, 2.7 mmol) in 10mL DMF to 140oC stirring and reacting for a certain time, cooling and then using 50 mL of H2O washing three times to obtain light green intermediate, taking the intermediate (0.3 g, 1 mmol) and 10mL of 2, 4-dinitrofluorobenzene, and heating to 80 DEGoC, reacting for 60 hours, cooling, washing with 50 mL of ethanol/water (1: 1) for three times, and drying in vacuum for 5 hours to obtain the product.
Example 7
Prepared by heating pyridine-4-carbaldehyde (0.58 g, 5.4 mmol) and erythronic acid (0.32 g, 2.7 mmol) in 10mL DMF to 160 mLoC stirring and reacting for a certain time, cooling and then using 50 mL of H2Washing with O for three times to obtain light green intermediate, heating intermediate (0.3 g, 1 mmol) and a certain amount of 2, 4-dinitrofluorobenzene to 80%oC, reacting for 60 hours, cooling, washing with 50 mL of ethanol/water (1: 1) for three times, and drying in vacuum for 5 hours to obtain the product.
Example 8
Prepared by heating pyridine-4-carbaldehyde (0.58 g, 5.4 mmol) and erythronic acid (0.32 g, 2.7 mmol) in 10mL DMF to 150 mLoC stirring and reacting for 6H, cooling and then using 50 mL of H2Washing with O for three times to obtain light green intermediate, heating the intermediate (0.3 g, 1 mmol) and a certain amount of 2, 4-dinitrochlorobenzene to 80%oC, reacting for 60 hours, cooling, washing with 50 mL of ethanol/water (1: 1) for three times, and drying in vacuum for 5 hours to obtain the product.
Example 9
Prepared by mixing pyridine-4-carbaldehyde (0.58 g, 5.4 mmol) andred amino acid (0.32 g, 2.7 mmol) was heated to 160 mL DMFoC stirring and reacting for a certain time, cooling and then using 50 mL of H2Washing with O for three times to obtain light green intermediate, heating intermediate (0.3 g, 1 mmol) and a certain amount of 2, 4-dinitrobromobenzene to 80%oC, reacting for 60 hours, cooling, washing with 50 mL of ethanol/water (1: 1) for three times, and drying in vacuum for 5 hours to obtain the product.
Application of the fluorescent Probe prepared in example 1
1. Change in fluorescence intensity of probe in response to solvents of different polarity
Weighing probes, dissolving the probes by DMSO (dimethyl sulfoxide), and accurately preparing 2 mM probe stock solution; after 2mL of solvents with different polarities are added to each cuvette, 2 muL of probe stock solution with the concentration of 2 mM is added for fluorescence spectrum test. As shown in FIG. 3, the probe emits strong fluorescence in methanol, and does not fluoresce in other solvents with different polarities.
2. Change in fluorescence intensity of probe in response to different alcohols
After 2mL of different alcohols were added to each cuvette, 2 μ L of a probe stock solution with a concentration of 2 mM was added to perform a fluorescence spectrum test. As shown in FIG. 4, the probe emits strong fluorescence in methanol, and does not emit fluorescence in any other alcohol.
As can be seen from fig. 5, the probe responds faster to methanol.
3. The fluorescence intensity of the probe in response to methanol varied with the methanol concentration in different solutions
Keeping the total volume of each cuvette to be 2mL, gradually adding methanol (methanol accounts for 0%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 100% of the volume ratio of ethanol) with different concentrations into ethanol, water, a red star Erguotou diluted twice with water and methanol gasoline, adding 2 muL of a probe storage solution with a concentration of 2 mM, and carrying out fluorescence spectrum test.
As shown in FIG. 6, the fluorescence intensity gradually increases with the increase of the methanol concentration, and ethanol and other alcohols with similar structures do not influence the specific recognition of the methanol by the probe.
As can be seen from FIG. 7, the probe of the present invention is able to detect methanol in water without interference.
As can be seen from FIG. 8, the probe of the present invention can rapidly detect methanol in practical sample spirit without interference.
As can be seen from FIG. 9, the probe of the present invention is also capable of detecting methanol in gasoline rapidly and efficiently.
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 (7)
1. A methanol fluorescent probe based on viologen derivatives is characterized in that the structural formula is as follows:
2. the method for preparing the viologen derivative-based methanol fluorescent probe as claimed in claim 1, which is characterized by comprising the following steps:
(1) heating pyridine-4-formaldehyde and erythronic acid in DMF, stirring for reaction, cooling, and washing with water for three times to obtain a light green intermediate;
(2) and (2) heating and reacting the intermediate obtained in the step (1) with halogenated dinitrobenzene, cooling, washing with ethanol/water for three times, and drying in vacuum to obtain the fluorescent probe.
3. The method for preparing a methanol fluorescent probe based on a viologen derivative as claimed in claim 2, wherein the method comprises the following steps: in the step (1), the molar ratio of the pyridine-4-formaldehyde to the erythrosine is (2-4): 1, the heating temperature is 140-.
4. The method for preparing a methanol fluorescent probe based on a viologen derivative as claimed in claim 2, wherein the method comprises the following steps: the molar ratio of the intermediate to the halogenated dinitrobenzene in the step (2) is 1: (42-85).
5. The method for preparing a methanol fluorescent probe based on a viologen derivative as claimed in claim 2, wherein the method comprises the following steps: in the step (2), the heating temperature is 80-100 ℃, and the reaction time is 48-70 h.
6. The method for preparing a methanol fluorescent probe based on a viologen derivative as set forth in any one of claims 2 to 5, wherein: the halogenated dinitrobenzene in the step (2) is 2, 4-dinitrofluorobenzene, 2, 4-dinitrochlorobenzene or 2, 4-dinitrobromobenzene.
7. The use of the fluorescent probe of claim 1 for specifically identifying methanol in white spirit and methanol gasoline.
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Non-Patent Citations (2)
| Title |
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| A π-Conjugation Extended Viologen as a Two-Electron Storage Anolyte for Total Organic Aqueous Redox Flow Batteries;Jian Luo，等;《Angew. Chem. Int. Ed.》;20171213;第57卷;全文 * |
| Thiazolothiazole Fluorophores Exhibiting Strong Fluorescence and Viologen-Like Reversible Electrochromism;Alexis N. Woodward，等;《J. Am. Chem. Soc.》;20170308;第139卷;全文 * |
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