CN114085206A - 2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base and preparation method and application thereof - Google Patents
2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base and preparation method and application thereof Download PDFInfo
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- CN114085206A CN114085206A CN202111417836.8A CN202111417836A CN114085206A CN 114085206 A CN114085206 A CN 114085206A CN 202111417836 A CN202111417836 A CN 202111417836A CN 114085206 A CN114085206 A CN 114085206A
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- 239000002262 Schiff base Substances 0.000 title claims abstract description 54
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- OTMRXENQDSQACG-UHFFFAOYSA-N thiophene-2,5-dicarbaldehyde Chemical compound O=CC1=CC=C(C=O)S1 OTMRXENQDSQACG-UHFFFAOYSA-N 0.000 claims abstract description 11
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910001431 copper ion Inorganic materials 0.000 claims abstract description 9
- ZMXYNJXDULEQCK-UHFFFAOYSA-N 2-amino-p-cresol Chemical compound CC1=CC=C(O)C(N)=C1 ZMXYNJXDULEQCK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000001514 detection method Methods 0.000 claims abstract description 5
- 238000001035 drying Methods 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 238000005406 washing Methods 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- -1 2, 5-thiophene-dicarboxaldehyde 2-amino-4-methylphenol Schiff base Chemical class 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 2
- 150000004753 Schiff bases Chemical class 0.000 abstract description 12
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 238000012512 characterization method Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000002189 fluorescence spectrum Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 238000000695 excitation spectrum Methods 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000002284 excitation--emission spectrum Methods 0.000 description 1
- 238000001506 fluorescence spectroscopy Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
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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
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- 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 2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base and a preparation method and application thereof, belonging to the technical field of organic synthesis. The Schiff base is prepared by taking 2, 5-thiophene-dicarbaldehyde and 2-amino-4-methylphenol as raw materials, reacting at 45-55 ℃ in the presence of an organic solvent according to the molar ratio of 1: 2, and after the reaction is finished, separating, washing and drying the obtained product. The 2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base compound is Schiff base with a novel structure, is simple in preparation method and can be used for copper ion detection.
Description
Technical Field
The invention relates to the technical field of organic synthesis, in particular to 2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base and a preparation method and application thereof.
Background
Schiff bases mainly refer to a class of organic compounds containing imine or azomethine groups, and are generally formed by condensing compounds containing active carbonyl groups and primary amines. In recent years, schiff bases have better biological activity and pharmaceutical activity, enzyme-like catalysis, photoelectric property and fluorescence property, such as antibacterial, anticancer, antioxidant, antiviral and the like, so that the schiff bases are more and more emphasized by researchers. At present, Schiff bases reported in documents are mainly single Schiff bases, and aromatic ring bis-Schiff bases are synthesized less.
Two aldehyde groups in the 2, 5-thiophene-dicarbaldehyde are easy to perform condensation reaction with amine compounds, and the 2, 5-thiophene-dicarbaldehyde is widely used for water treatment and organic synthesis catalysts and is also used in dye and medicine industries, so that the study on the chemical properties and the activity of the Schiff base based on the 2, 5-thiophene-dicarbaldehyde has wide application prospects in synthesis materials, catalysis and related fields.
Disclosure of Invention
The invention aims to provide 2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base and a preparation method and application thereof, and the Schiff base is Schiff base with a novel structure and can be used for detecting copper ions.
In order to achieve the purpose, the invention provides the following scheme:
one of the technical schemes of the invention is to provide 2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base, and the Schiff base has the following structure:
the second technical scheme of the invention is to provide a preparation method of the 2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base, which comprises the following steps:
reacting 2, 5-thiophene-dicarbaldehyde with 2-amino-4-methylphenol at a molar ratio of 1: 2 at 45-55 ℃ in the presence of an organic solvent, and after the reaction is finished, separating, washing and drying the product to obtain the 2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base.
Further, the organic solvent is ethanol.
Further, the reaction time is 1.5-3 h.
The third technical scheme of the invention is to provide the application of the 2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base in the aspect of copper ion detection.
The invention discloses the following technical effects:
the invention takes 2, 5-thiophene-dicarbaldehyde and 2-amino-4-methylphenol as reaction raw materials, synthesizes the 2, 5-thiophene-dimethylaldehyde 2-amino-4-methylphenol Schiff base compound with a novel structure by a simple preparation method, and the Schiff base compound can be used for copper ion detection.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings needed in the embodiments will be briefly described below, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and it is obvious for those skilled in the art to obtain other drawings without creative efforts.
FIG. 1 is a UV-VIS absorption spectrum of 2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base;
FIG. 2 is a graph showing a fluorescence excitation spectrum and an emission spectrum of 2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base; wherein, the graph A is an excitation spectrum graph, and the graph B is an emission spectrum graph;
FIG. 3 is an infrared spectrum of 2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base;
FIG. 4 is a fluorescence spectrum of copper ions of different concentrations added with 2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base.
Detailed Description
Reference will now be made in detail to various exemplary embodiments of the invention, the detailed description should not be construed as limiting the invention but as a more detailed description of certain aspects, features and embodiments of the invention.
It is to be understood that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. Further, for numerical ranges in this disclosure, it is understood that each intervening value, between the upper and lower limit of that range, is also specifically disclosed. Every smaller range between any stated value or intervening value in a stated range and any other stated or intervening value in a stated range is encompassed within the invention. The upper and lower limits of these smaller ranges may independently be included or excluded in the range.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although only preferred methods and materials are described herein, any methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present invention. All documents mentioned in this specification are incorporated by reference herein for the purpose of disclosing and describing the methods and/or materials associated with the documents. In case of conflict with any incorporated document, the present specification will control.
It will be apparent to those skilled in the art that various modifications and variations can be made in the specific embodiments of the present disclosure without departing from the scope or spirit of the disclosure. Other embodiments will be apparent to those skilled in the art from consideration of the specification. The description and examples are intended to be illustrative only.
As used herein, the terms "comprising," "including," "having," "containing," and the like are open-ended terms that mean including, but not limited to.
Example 12 preparation of 5, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base Compound:
weighing 0.140g of 2, 5-thiophene-diformaldehyde, dissolving in 20.0mL of absolute ethyl alcohol to prepare a 2, 5-thiophene-diformaldehyde solution, weighing 0.246g of 2-amino-4-methylphenol, dissolving in 20.0mL of absolute ethyl alcohol to prepare a 2-amino-4-methylphenol solution, dropwise adding the 2-amino-4-methylphenol solution into the 2, 5-thiophene-diformaldehyde solution, reacting for 2 hours at 50 ℃, forming crystals, performing suction filtration, washing with ethanol, naturally drying to obtain crystals, washing with 50.0mL of absolute ethyl alcohol, and drying for 1 hour at 50 ℃ to obtain orange yellow crystals.
The crystal is 2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base which is formed by condensing one molecule of 2, 5-thiophene-dicarbaldehyde and two molecules of 2-amino-4-methylphenol.
Characterization of 2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base:
ultraviolet-visible absorption spectrum characterization: and adjusting the base line by using anhydrous methanol, wherein the scanning wavelength range is 200-800 nm, and performing ultraviolet-visible absorption spectrum analysis on the 2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base.
FIG. 1 shows the UV-VIS absorption spectrum of 2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base. As can be seen, there is a strong absorption peak at 206nm, which is mainly due to the pi → pi transition of the C ═ N double bond; while the absorption peak at 416nm is mainly due to the N → pi transition of the C ═ N double bond and red-shifted, the conjugated absorption band is broadened due to the elongation of thiophene and benzene rings.
And (3) fluorescence spectrum characterization: the fluorescence excitation spectrum and emission spectrum of 2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base in anhydrous methanol were measured at room temperature, and the results are shown in FIG. 2. FIG. 2A shows that the fluorescence intensity of 2, 5-thiophene-dimethyl-acetal 2-amino-4-methylphenol Schiff base is the greatest at an excitation wavelength of 460nm, so 460nm is selected as the optimal excitation wavelength of 2, 5-thiophene-dimethyl-acetal 2-amino-4-methylphenol Schiff base for fluorescence emission spectroscopy detection; FIG. 2B shows that 2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base has two obvious fluorescence emission peaks at 487nm and 525 nm.
Fourier transform infrared spectroscopy characterization (FT-IR): characterizing the 2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base by a Fourier transform infrared spectrometer, taking a proper amount of dried sample powder and KBr, uniformly grinding in an agate mortar, tabletting and characterizing.
The infrared spectrum of 2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base is shown in figure 3. The infrared spectrum of the Schiff base compound has a characteristic absorption peak of C-N and a characteristic absorption peak of hydroxyl at the same time, which indicates the formation of the Schiff base. The compound has the presence of C ═ N (1600 cm) in the infrared pattern-1)，-OH(3352cm-1) In addition, at 1456cm-1、1503cm-1The characteristic peak of benzene ring appears at 799cm-1、859cm-1、1222cm-1The characteristic peak of thiophene appears, but-CHO (1670 cm) does not appear-1) and-NH2(3377cm-1) The characteristic peak of (A) can prove the generation of the large base.
The prepared 2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base is used for detecting copper ions in water:
3.5mg of 2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base is dissolved in 10mL of anhydrous methanol to prepare 1mM 2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base solution. Then 5 μ L of 1mM 2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base solution is added with 1mM CuSO respectively4Aqueous 5. mu.L, 10. mu.L, 30. mu.L and 50. mu.L of water and 10mM CuSO4Adding pure water to 50 μ L of the aqueous solution, adding pure water to complement, and mixing uniformly to obtain 100 μ L of mixed solution, wherein the concentration of 2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base is 50 μ M, and the concentration of Cu is2+The concentrations were 50. mu.M, 100. mu.M, 300. mu.M, 500. mu.M and 5mM, respectively. Scanning fluorescence emission spectrum of the mixed liquid within the range of 465-500 nm by taking 460nm as an excitation wavelength.
FIG. 4 is a fluorescence spectrum of copper ions of different concentrations added with 2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base. As can be seen from FIG. 4, the fluorescence intensity of 2, 5-thiophene-dimethyl-acetal 2-amino-4-methylphenol Schiff base gradually decreases as the concentration of copper ions increases.
The above-described embodiments are merely illustrative of the preferred embodiments of the present invention, and do not limit the scope of the present invention, and various modifications and improvements of the technical solutions of the present invention can be made by those skilled in the art without departing from the spirit of the present invention, and the technical solutions of the present invention are within the scope of the present invention defined by the claims.
Claims (5)
1. A2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base, which is characterized by having the following structure:
2. the process for the preparation of 2, 5-thiophene-dicarboxaldehyde 2-amino-4-methylphenol Schiff base according to claim 1, comprising the steps of:
reacting 2, 5-thiophene-dicarbaldehyde with 2-amino-4-methylphenol at a molar ratio of 1: 2 at 45-55 ℃ in the presence of an organic solvent, and after the reaction is finished, separating, washing and drying the product to obtain the 2, 5-thiophene-dimethyl acetal 2-amino-4-methylphenol Schiff base.
3. The process for the preparation of 2, 5-thiophene-dicarboxaldehyde 2-amino-4-methylphenol Schiff base according to claim 2, wherein the organic solvent is ethanol.
4. The method for preparing 2, 5-thiophene-dicarboxaldehyde 2-amino-4-methylphenol Schiff base according to claim 2, wherein the reaction time is 1.5-3 hours.
5. The use of the 2, 5-thiophene-dicarboxaldehyde 2-amino-4-methylphenol Schiff base of claim 1 for the detection of copper ions.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE58904709D1 (en) * | 1988-09-16 | 1993-07-22 | Ciba Geigy Ag | OPTICAL BRIGHTENERS. |
| CN105820180A (en) * | 2016-04-14 | 2016-08-03 | 新疆大学 | Preparation and biological activity of pyrazolone thiophene hydrazide copper complex |
| CN107314991A (en) * | 2017-05-16 | 2017-11-03 | 西北农林科技大学 | Schiff base compound as cyanide ion and copper ion fluorescence probe application |
| CN110950854A (en) * | 2019-12-16 | 2020-04-03 | 温州医科大学 | Off-on molecular fluorescent probe CMTAH and preparation method and application thereof |
-
2021
- 2021-11-21 CN CN202111417836.8A patent/CN114085206A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE58904709D1 (en) * | 1988-09-16 | 1993-07-22 | Ciba Geigy Ag | OPTICAL BRIGHTENERS. |
| CN105820180A (en) * | 2016-04-14 | 2016-08-03 | 新疆大学 | Preparation and biological activity of pyrazolone thiophene hydrazide copper complex |
| CN107314991A (en) * | 2017-05-16 | 2017-11-03 | 西北农林科技大学 | Schiff base compound as cyanide ion and copper ion fluorescence probe application |
| CN110950854A (en) * | 2019-12-16 | 2020-04-03 | 温州医科大学 | Off-on molecular fluorescent probe CMTAH and preparation method and application thereof |
Non-Patent Citations (5)
| Title |
|---|
| BISWAJIT CHOWDHURY: "Salen Type Ligand as a Selective and Sensitive Nickel(II) ion Chemosensor: A Combined Investigation with Experimental and Theoretical Modelling", 《SENSORS AND ACTUATORS B: CHEMICAL》 * |
| UDHAYAKUMARI, DURAISAMY: "Naked eye sensing of toxic metal ions in aqueous medium using thiophene-based ligands and its application in living cells", 《JOURNAL OF MOLECULAR RECOGNITION》 * |
| 戴寰等: "铜(Ⅱ)与2,5-噻吩二甲醛Schiff碱配合物的合成及表征", 《高等学校化学学报》 * |
| 谢昕等: "《食品仪器分析技术》", 31 January 2019, 国家图书馆出版社 * |
| 金奎励等: "《当代煤及有机岩研究新技术》", 31 March 1997, 地质出版社 * |
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