CN115433126B - Functionalized quinoline analog color ion probe and synthesis method and application thereof - Google Patents

Functionalized quinoline analog color ion probe and synthesis method and application thereof Download PDF

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CN115433126B
CN115433126B CN202210971373.8A CN202210971373A CN115433126B CN 115433126 B CN115433126 B CN 115433126B CN 202210971373 A CN202210971373 A CN 202210971373A CN 115433126 B CN115433126 B CN 115433126B
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hdqno
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CN115433126A (en
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佘远斌
陈铭
车思莹
付海燕
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Zhejiang University of Technology ZJUT
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    • C07—ORGANIC CHEMISTRY
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    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/24—Oxygen atoms attached in position 8
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
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    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
    • G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
    • G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
    • G01N21/33—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using ultraviolet light
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • 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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    • G01—MEASURING; TESTING
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    • 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
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
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Abstract

The invention discloses a functionalized quinoline analog color ion probe and a synthesis method and application thereof, and the invention designs and synthesizes a nitro-modified 8-hydroxyquinoline ionic liquid ([ HDQNO) shown in a formula (I) through a simple acid-base proton exchange reaction 2 ][P 66614 ]) The method comprises the steps of carrying out a first treatment on the surface of the Due to Fe 3+ And [ HDQNO ] 2 ][P 66614 ]Complexing the [ HDQNO ] by oxygen atom 2 ][P 66614 ]The color of the fluorescent probe is changed from pale yellow to dark green, and the designed and synthesized fluorescent probe has the advantages of good stability (120 days), short response time (2 s), good specificity and the like, particularly when the fluorescent probe is applied to Fe in actual samples 3+ During detection of (2), fe can be realized by simple pretreatment 3+ Is the quantitative detection of Fe in complex matrix 3+ Provides a new idea for the convenient detection;

Description

Functionalized quinoline analog color ion probe and synthesis method and application thereof
Technical Field
The invention relates to a functionalized quinoline analog color ion probe and a synthesis method thereof, and Fe in an actual sample 3+ Application in visual rapid detection.
Background
Iron is one of the essential elements necessary for the human body and is also one of the metal ions most relevant to biological physiological activities. Wherein Fe is 3+ Is the main component of myoglobin peroxidase and cytochrome enzyme. In addition, it plays an important role in various physiological processes, such as hemoglobin formation, oxygen metabolism, DNA synthesis and repair, muscle and brain functions, and thermoregulation. Fe (Fe) 3+ The concentration disorder of (a) can pose a great threat to the human body such as skin diseases, insomnia, diabetes, anemia, liver injury, breast cancer, parkinson's disease, etc. Therefore, fe in food can be detected with high specificity and sensitivity 3+ Has very important significance. Traditionally, a typical atomic spectrum is mainly usedThe method is used for Fe 3+ Is a quantitative detection of (a). However, these methods require large-scale precise instruments and rely on the manipulation of professionals, and thus are not suitable for Fe in actual samples 3+ Is provided. Therefore, there is a need to develop a simple and rapid method for Fe without instrumentation 3+ Is a quantitative detection of (a).
Ionic liquids have been successfully used as a functional material in various fields such as catalysts, synthesis, electrochemistry and extraction. Is widely used in the fields of gas trapping, solvent, catalyst, extraction and the like, and achieves good effect. More importantly, in recent years, ionic liquids have shown great potential as fluorescent probes for detecting target objects, particularly metal ions, due to their high degree of tunability. The ionic liquid has stable structure, excellent thermal stability and good biocompatibility, and simultaneously has high adjustability and great development potential.
Here, we designed and synthesized a nitro-modified 8-hydroxyquinoline ionic liquid ([ HDQNO) through a simple acid-base proton exchange reaction 2 ][P 66614 ]). Due to Fe 3+ And [ HDQNO ] 2 ][P 66614 ]Complexing the [ HDQNO ] by oxygen atom 2 ][P 66614 ]The color of (C) is changed from pale yellow to dark green. A colorimetric sensor for detecting Fe in an actual sample was developed 3 + Is Fe in a complex system 3+ Provides the possibility of a fast and accurate detection of (c).
Disclosure of Invention
The invention designs and synthesizes a novel ionic liquid type fluorescent probe with high sensitivity and specificity, and in addition, the designed and synthesized fluorescent probe has the advantages of good stability (120 days), short response time (2 s), good specificity and the like. In particular when it is applied to Fe in a real sample 3+ During detection of (2), fe can be realized by simple pretreatment 3+ Is the quantitative detection of Fe in complex matrix 3+ Provides a new idea for convenient detection.
The invention uses fluorescent ionic liquid [ HDQNO ] 2 ][P 66614 ]Is a colorimetric probe and is applied to rapid and accurate determinationQuantity detection of Fe 3+ . When Fe is added 3+ The ultraviolet absorption spectrum of the quinoline-based ionic liquid is obviously changed. When Fe is added at a concentration of 0-10 mu M 3+ Rear [ HDQNO 2 ][P 66614 ]The ultraviolet absorption peaks at 355nm and 458nm gradually decrease and increase, respectively. When Fe with concentration of 20-90 mu M is added 3+ Rear [ HDQNO 2 ][P 66614 ]The ultraviolet absorption peaks at 317nm and 389nm are both gradually increased. Meanwhile, the color of the solution is added with Fe 3+ The increase in concentration gradually changed from pale yellow to dark green. And can be observed by the naked eye in sunlight. [ HDQNO ] 2 ][P 66614 ]For Fe 3+ The linear range of (2) is 0-90. Mu.M and the detection limit is 0.15. Mu.M.
The technical scheme of the invention is as follows:
a fluorescent ionic liquid has a chemical formula of [ HDQNO ] 2 ][P 66614 ]The structural formula is shown as formula (I):
the synthesis method of the fluorescent ionic liquid comprises the following steps:
[P 66614 ][OH]reacting with 5-nitro-8-hydroxyquinoline in absolute ethanol solvent at 40-100 ℃ for 6-24 h, and removing solvent by rotary evaporation to obtain brown viscous ionic liquid [ HDQNO ] 2 ][P 66614 ]；
The [ P ] 66614 ][OH]The molar ratio of the 5-nitro-8-hydroxyquinoline is 1:1, a step of;
the [ P ] 66614 ][OH]From trihexyl (tetradecyl) phosphine bromide ([ P ] 66614 ][Br]) The method is obtained through debromination treatment of the strong-alkaline anion exchange resin, and the specific debromination treatment method comprises the following steps:
will [ P ] 66614 ][Br]Adding the ethanol solution into a chromatographic column filled with strong alkaline anion exchange resin, and collecting effluent liquid 66614 ][OH]Is used directly for the reaction without evaporation to dryness.
The invention relates to a fluorescent ionThe liquid can be used as a fluorescence/colorimetric probe for Fe in an actual sample 3+ Is provided.
The invention also relates to a paper-based sensor, which is obtained by immersing a filter paper strip in [ HDQNO ] 2 ][P 66614 ]The solution (1 mM, 1min of immersion) was then removed from the strip of filter paper and naturally air-dried to give a base [ HDQNO ] 2 ][P 66614 ]Is a paper-based sensor of (2). The obtained paper-based sensor is vertically placed at different concentrations of Fe 3+ After 2s in solution, the color change of the strip was recorded.
The invention adopts a simple impregnation method to prepare the portable paper-based sensor. When loaded with [ HDQNO ] 2 ][P 66614 ]The paper-based sensor of (1) is dripped with Fe with different concentrations 3+ After the solution, it is loaded with [ HDQNO ] 2 ][P 66614 ]The paper-based sensor of (2) is obviously changed from pale yellow to dark green, which is also similar to [ HDQNO 2 ][P 66614 ]The change of the ultraviolet absorption spectrum is consistent, and Fe can be realized 3+ Is convenient and rapid to detect.
Fluorescent ionic liquid [ HDQNO ] prepared by the invention 2 ][P 66614 ]Colorimetric probes may be used for actual samples such as: fe in jelly, salt, tap water, mineral water, etc 3+ Is detected.
The invention uses fluorescent ionic liquid [ HDQNO ] 2 ][P 66614 ]Is colorimetric probe, fe 3+ For the object to be measured by Fe 3+ And [ HDQNO ] 2 ][P 66614 ]Specific binding causes the ultraviolet absorption spectrum of the quinoline-based ionic liquid to be obviously changed, and Fe is utilized by taking the ultraviolet absorption intensity as the ordinate 3+ Quantitative analysis is carried out on a linear curve with concentration being abscissa fitting, so that Fe in an actual sample is realized 3+ Is used for accurate identification and quantitative detection of the test pieces.
Compared with the prior art, the invention has the beneficial effects that:
the invention successfully synthesizes the functional ionic liquid [ HDQNO ] 2 ][P 66614 ]And apply it to quick, accurate and quantitative detection of Fe 3+ . When Fe is added 3+ When the quinoline-based ionic liquid emits ultraviolet absorption spectrumObvious changes occur. Meanwhile, the color of the solution is added with Fe 3+ The increase in concentration gradually changed from pale yellow to dark green. And can be observed by the naked eye in sunlight. [ HDQNO ] 2 ][P 66614 ]For Fe 3+ The linear range of (2) is 0-90. Mu.M and the detection limit is 0.15. Mu.M. In addition, the designed and synthesized fluorescent probe has the advantages of good stability (120 days), short response time (2 s), good specificity and the like. In particular when it is applied to Fe in a real sample 3+ During detection of (2), fe can be realized by simple pretreatment 3+ Is the quantitative detection of Fe in complex matrix 3+ Provides a new idea for convenient detection.
The invention synthesizes the ionic liquid with yellow fluorescence emission by an ion exchange method, and the method has simple synthesis steps and high synthesis yield; synthetic [ HDQNO ] 2 ][P 66614 ]The fluorescent ion liquid has good thermal stability, is not easy to volatilize and has small environmental pollution; ionic liquid [ HDQNO ] 2 ][P 66614 ]For Fe 3+ Has stronger specificity and sensitivity, and can realize Fe in a wider linear range 3+ Is detected; the invention can be used for preparing Fe in actual samples 3+ Performing qualitative analysis and quantitative detection to obtain Fe in complex system 3+ Provides a possibility for detection of (c).
Drawings
FIG. 1 shows the present invention [ HDQNO ] 2 ][P 66614 ]Ultraviolet absorption intensity of (2) is on the ordinate, fe 3+ Ultraviolet absorption spectrum (A) and linear curve (B) with concentration (0-10 mu M) as abscissa; by [ HDQNO ] 2 ][P 66614 ]Fluorescence intensity of (2) is on ordinate, fe 3+ The concentration (20 to 90. Mu.M) is an ultraviolet absorption spectrum (C) and a linear curve (D) on the abscissa.
FIG. 2 shows the present invention in [ HDQNO ] 2 ][P 66614 ]Fe with different concentrations (10 mu M-300 mu M) is added into the ethanol solution of (a) 3+ Visual photographs taken under irradiation of ultraviolet lamp.
FIG. 3 shows an ionic liquid probe [ HDQNO2 ] designed according to the present invention][P66614]pH stability (a); [ HDQNO ] 2 ][P 66614 ]Time stability (B); [ HDQNO ] 2 ][P 66614 ]For Fe 3+ Response time study (C).
FIG. 4 shows the present invention in [ HDQNO ] 2 ][P 66614 ]Adding Fe into ethanol solution of (C) 3+ The ratio of the ultraviolet absorption intensity of the ethanol solution of (c) and other common metal salts.
FIG. 5 the results of the invention in actual samples (jelly solution, table salt solution, tap water and mineral water) were recovered by labelling.
Detailed Description
For a better understanding of the present invention, the following description will further illustrate the present invention in conjunction with the following examples, but is not to be construed as limiting the scope of the present invention.
The chemicals and solvents used in the examples were all analytically pure.
The strongly basic anion exchange resin used was 717 strongly basic type I anion exchange resin available from ala Ding Huaxue limited.
Example 1
The specific synthesis method of the fluorescent ionic liquid comprises the following steps:
(1)[P 66614 ][Br]is added to the (3):
will [ P ] 66614 ][Br]Is slowly added to a chromatographic column ([ P ] containing a strongly basic anion exchange resin 66614 ][Br]The mass ratio of the resin to the strong-alkali anion exchange resin is 1: 6) Collecting effluent liquid to obtain [ P ] 66614 ][OH]Is a solution of (a) in ethanol.
(2) Fluorescent ionic liquid [ HDQNO ] 2 ][P 66614 ]Is synthesized by the following steps:
0.1805g of 5-nitro-8-hydroxyquinoline and [ P ] obtained in the step (1) 66614 ][OH]Ethanol solution of (containing [ P ] 66614 ][OH]5.1847 g) was added to a 250mL round bottom flask, 50mL absolute ethanol was added and the reaction was stirred at 60℃for 12h with an oil bath, wherein [ P ] 66614 ][OH]The molar ratio of the 5-nitro-8-hydroxyquinoline to the water-soluble polymer is 1:1. Removing solvent ethanol from the reacted product by rotary evaporator, heating at 80deg.C in nitrogen atmosphere for 6 hr to remove trace ethanol and water in the product, and obtaining final productBrown viscous liquid. And (5) sealing and preserving at room temperature. The reaction formula is as follows:
example 2
Ionic liquid as colorimetric/fluorescent probe for Fe in actual samples 3+ The specific steps include:
(1) Probe pair Fe 3+ Ultraviolet detection of (c):
the ionic liquid was accurately weighed and configured as a 1mM stock solution in ethanol. Taking 100 mu L of stock solution, adding Fe with different concentrations 3+ And absolute ethanol is used for constant volume to 1mL, and [ HDQNO ] is recorded 2 ][P 66614 ]Ultraviolet absorption spectrum. The results are shown in FIG. 1.
Fe 3+ The concentration showed good linear relationship in the range of 0-10. Mu.M, and the linear correlation coefficient (R2) was 0.990. The quantitative equation is calculated as y= -0.336x +5.161.Fe (Fe) 3+ The concentration showed good linearity in the range of 20-50. Mu.M, and R2 was 0.997. The quantitative equation is calculated as y=0.025 x+0.473.
(2) In [ HDQNO ] 2 ][P 66614 ]Fe with different concentrations (10 mu M-300 mu M) is added into the ethanol solution of (a) 3+ A visual photograph taken under ultraviolet lamp irradiation of the ethanol solution of (c) is shown in fig. 2.
(3)[HDQNO 2 ][P 66614 ]Stability and sensitivity study
[HDQNO 2 ][P 66614 ]Stability study of UV absorbance in solutions with pH values in the range of 4-8, as shown in FIG. 3A, [ HDQNO ] 2 ][P 66614 ]The uv absorbance of (c) remained stable for 120 days as shown in fig. 3B. When Fe is added 3+ After that, [ HDQNO ] 2 ][P 66614 ]The ultraviolet absorption value of (2) can obviously change within 2s, and the Fe is finished 3+ And preserve [ HDQNO ] within 180s 2 ][P 66614 ]And remains stable as shown in figure 3C.
(4) Common metal ion and anion pair [ HDQNO 2 ][P 66614 ]Detection of Fe 3+ Interference of (a)
mu.L of stock solution was mixed with 70. Mu.L of 10. Mu.M Fe 3+ Or 100. Mu.L of 10. Mu.M other metal salts (NaCl, KCl, agNO) 3 ，CaCl 2 ，Mn(Ac) 4 ，FeCl 2 ，Co(NO 3 ) 3 ，Ni(NO 3 ) 2 ，Cu(NO 3 ) 2 ，CuSO 4 ，Zn(Ac) 2 ，MgCl 2 ，BaCl 2 ，ZnCl 2 ，Pb(NO 3 ) 2 ，CdCl 2 ，Zn(NO 3 ) 2 ，ZnSO 4 ，MnCl 2 ，Al(NO 3 ) 3 ，CuCl 2 ，FeSO 4 ，Hg 2 SO 4 ) The ultraviolet absorption intensity was measured by constant volume to 1mL using absolute ethanol, and a histogram was drawn with the ratio of ultraviolet absorption peaks (I355/I458) as the ordinate and the kind of metal salt as the abscissa, as shown in fig. 4.
(5) Fe in actual sample 3+ Is detected by (a)
The jelly is crushed by a juicer, and 5mL of absolute ethyl alcohol is added to obtain a jelly solution. 3g of common salt was weighed and dissolved in 10mL of water to obtain an aqueous solution of common salt. After centrifugation of the jelly solution, salt solution, tap water and mineral water at 4800rpm for 10min, the solution was filtered through a 0.22 μm filter membrane and the filtrate was collected for further detection. Determination of Fe added at 0nM, 5nM and 40nM, respectively 3+ Standard solution of [ HDQNO ] 2 ][P 66614 ]Ultraviolet absorption peaks at 355nm, 458nm, 317nm and 389nm were recorded. As a result, as shown in FIG. 5, the recovery rate was between 97.4 and 102.9%, and the Relative Standard Deviation (RSD) was less than 2.73.

Claims (5)

1. A fluorescent ionic liquid has a chemical formula of [ HDQNO ] 2 ][P 66614 ]The structural formula is shown as formula (I):
2. the method for synthesizing the fluorescent ionic liquid according to claim 1, wherein the method for synthesizing the fluorescent ionic liquid comprises the following steps:
[P 66614 ][OH]reacting with 5-nitro-8-hydroxyquinoline in absolute ethanol solvent at 40-100 ℃ for 6-24 h, and removing solvent by rotary evaporation to obtain brown viscous ionic liquid [ HDQNO ] 2 ][P 66614 ]；
The [ P ] 66614 ][OH]The molar ratio of the 5-nitro-8-hydroxyquinoline is 1:1.
3. the synthesis method according to claim 2, wherein [ P ] 66614 ][OH]From [ P ] 66614 ][Br]The catalyst is obtained through debromination treatment of a strong-alkaline anion exchange resin, and the debromination treatment method comprises the following steps:
will [ P ] 66614 ][Br]Adding the ethanol solution into a chromatographic column filled with strong alkaline anion exchange resin, and collecting effluent liquid 66614 ][OH]Is a solution of (a) in ethanol.
4. A paper-based sensor is characterized in that a filter paper strip is immersed in [ HDQNO ] 2 ][P 66614 ]Taking out the filter paper strip, naturally air-drying to obtain the final product based on [ HDQNO ] 2 ][P 66614 ]Is a paper-based sensor of (2).
5. The fluorescent ionic liquid according to claim 1 or the paper-based sensor according to claim 4, wherein Fe in an actual sample 3+ Is used in the detection of (1).
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011091973A1 (en) * 2010-01-28 2011-08-04 University Of Ljubljana 5-nitro-8-hydroxyquinolines as inhibitors of cathepsin b
CN113788788A (en) * 2021-07-23 2021-12-14 浙江工业大学 Fluorescent ionic liquid and synthesis method and application thereof
WO2022253159A1 (en) * 2021-05-31 2022-12-08 江苏亚虹医药科技股份有限公司 Use of 5-nitro-8-hydroxyquinoline

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Publication number Priority date Publication date Assignee Title
FR2845084B1 (en) * 2002-09-26 2009-07-17 Centre Nat Rech Scient COMPOSITIONS CONTAINING IONIC LIQUIDS AND THEIR USES, IN PARTICULAR IN ORGANIC SYNTHESIS

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011091973A1 (en) * 2010-01-28 2011-08-04 University Of Ljubljana 5-nitro-8-hydroxyquinolines as inhibitors of cathepsin b
WO2022253159A1 (en) * 2021-05-31 2022-12-08 江苏亚虹医药科技股份有限公司 Use of 5-nitro-8-hydroxyquinoline
CN113788788A (en) * 2021-07-23 2021-12-14 浙江工业大学 Fluorescent ionic liquid and synthesis method and application thereof

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