CN113248430A - Quinoline derivative-based fluorescence sensor, synthesis thereof and application thereof in aluminum ion detection - Google Patents
Quinoline derivative-based fluorescence sensor, synthesis thereof and application thereof in aluminum ion detection Download PDFInfo
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- 229910052782 aluminium Inorganic materials 0.000 title claims description 11
- 238000001514 detection method Methods 0.000 title abstract description 18
- 238000003786 synthesis reaction Methods 0.000 title description 5
- 230000015572 biosynthetic process Effects 0.000 title description 4
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000000243 solution Substances 0.000 claims abstract description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 27
- 150000003248 quinolines Chemical class 0.000 claims abstract description 20
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 claims abstract description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 12
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 10
- 239000005725 8-Hydroxyquinoline Substances 0.000 claims abstract description 8
- 229960003540 oxyquinoline Drugs 0.000 claims abstract description 8
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000758 substrate Substances 0.000 claims abstract description 7
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims abstract description 6
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 6
- RGHQKFQZGLKBCF-UHFFFAOYSA-N 2-bromoethyl acetate Chemical compound CC(=O)OCCBr RGHQKFQZGLKBCF-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims abstract description 4
- 239000007864 aqueous solution Substances 0.000 claims abstract description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
- -1 aluminum ions Chemical class 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000013078 crystal Substances 0.000 claims description 6
- 239000012043 crude product Substances 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 239000012044 organic layer Substances 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 230000001376 precipitating effect Effects 0.000 claims description 3
- 238000010898 silica gel chromatography Methods 0.000 claims description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 3
- 235000011152 sodium sulphate Nutrition 0.000 claims description 3
- 238000003828 vacuum filtration Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims 5
- 125000001967 indiganyl group Chemical group [H][In]([H])[*] 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 abstract description 7
- 239000002184 metal Substances 0.000 abstract description 7
- 150000001768 cations Chemical class 0.000 abstract description 5
- 230000035945 sensitivity Effects 0.000 abstract description 3
- 230000008569 process Effects 0.000 abstract description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000002795 fluorescence method Methods 0.000 description 1
- 235000010855 food raising agent Nutrition 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000004896 high resolution mass spectrometry Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000012629 purifying agent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- 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
- C07D215/26—Alcohols; Ethers thereof
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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"
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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Abstract
The invention designs and synthesizes a fluorescence sensor based on quinoline derivatives, which is to take 8-hydroxyquinoline and 2-bromoethyl acetate as substrates to react in acetonitrile solvent to prepare 2- (quinoline-8-acyloxy) ethyl acetate; then hydrazine hydrate and 2- (quinoline-8-acyloxy) ethyl acetate are used as substrates to react in methanol to obtain 2- (quinoline-8-acyloxy) acethydrazide; and finally, reacting in absolute methanol by using 2- (quinoline-8-acyloxy) acethydrazide and salicylaldehyde as substrates to obtain the quinoline derivative-based fluorescence sensor QB. DMSO/H in fluorescence sensor QB2Respectively adding Al into the O solution3+,Zn2+,Pb2+,Cd2+,Ni2+,Fe3+,Co2+,Ag+,Ca2+,Cu2+,Mg2+,Cr3+,Ba2+,Tb3+,Eu4+,La3+In the aqueous solution of (1), only Al was found3+Can open the fluorescence of the fluorescence sensor QB, thereby realizing the effect of the fluorescence sensor QB on Al3+The single selective recognition is realized, the sensitivity is high, the recognition process is not interfered by other metal cations, and the recognition rate is higher than that of Al3+Has good application prospect in the detection.
Description
Technical Field
The invention relates to a fluorescence sensor based on quinoline derivatives and a synthesis method thereof; the invention also relates to the application of the fluorescence sensor in Al detection3+Belonging to the fields of chemical synthesis and ion detection.
Background
Aluminum (Al)3+) As a common metal, it is widely used. Aluminum is considered as a non-toxic element for a long time, aluminum cookware, aluminum-containing leavening agent, water purifying agent and the like are commonly used, and direct toxicity of aluminum is not found, but recent researches show that aluminum can disturb metabolism of a human body and cause long-term and slow harm to health of the human body. Thus, for Al3+The detection has important application value.
At present, various ion detection methods have been developed, and the fluorescence method has become a main detection means in the field of ion detection due to its advantages of simple and convenient operation, rapidness, high sensitivity, and the like.
Disclosure of Invention
The invention aims to provide a fluorescence sensor based on quinoline derivatives and a synthesis method thereof;
it is also an object of the present invention to provide the use of the fluorescence sensor for detecting aluminum ions.
Quinoline derivative-based fluorescence sensor and synthesis thereof
The invention relates to a quinoline derivative-based fluorescence sensor, which has the molecular formula: c18H15N3O3The structural formula is as follows:
the synthesis method of the fluorescence sensor comprises the following steps:
(1) adding potassium hydroxide into an acetonitrile solution of 8-hydroxyquinoline, then adding 2-bromoethyl acetate, stirring at room temperature for reaction for 1.5-2 h, then adding water, extracting with ethyl acetate, drying an organic layer with sodium sulfate, then filtering under reduced pressure to obtain a crude product, and separating and purifying the crude product through silica gel column chromatography to obtain yellow oily 2- (quinoline-8-acyloxy) ethyl acetate. Wherein the molar ratio of 8-hydroxyquinoline to 2-bromoethyl acetate is 1: 1-1: 1.5; the molar ratio of the 8-hydroxyquinoline to the potassium hydroxide is 1: 1.5-1: 2.
(2) And (2) taking 2- (quinoline-8-acyloxy) ethyl acetate and hydrazine hydrate as substrates, taking methanol as a solvent, stirring and reacting at 65 ℃ for 1.5-2 h, collecting precipitates through vacuum filtration, washing with water, and drying under vacuum to obtain white solid 2- (quinoline-8-acyloxy) acethydrazide. Wherein the molar ratio of the ethyl 2- (quinoline-8-acyloxy) acetate to the hydrazine hydrate is 1: 1-1: 1.5.
(3) The method comprises the steps of taking 2- (quinoline-8-acyloxy) acethydrazide and salicylaldehyde as substrates, taking absolute methanol as a solvent, reacting for 10-12 h at 55-65 ℃, cooling and standing for 10-12 h, precipitating needle-shaped orange transparent crystals in the solution, and recrystallizing with absolute ethanol to obtain orange transparent crystals, namely the quinoline derivative-based fluorescence sensor QB (N' - (2-hydroxybenzylidene) -2- (quinoline-8-acyloxy) acethydrazide). Wherein the molar ratio of the 2- (quinoline-8-acyloxy) acethydrazide to the salicylaldehyde is 1: 1.5.
The hydrogen spectrum and mass spectrum of fluorescence sensor QB are shown in fig. 1 and 2.
Secondly, detecting Al by a fluorescent sensor3+Application of
1. Fluorescence properties of fluorescence sensor QB
Research on the fluorescence property of the fluorescence sensor QB shows that the fluorescence sensor QB has better solubility in DMSO solution. When the excitation wavelength is 365nm, the QB molecules of the sensor have no fluorescence emission performance, and the fluorescence intensity is almost zero.
2. Fluorescence sensor QB fluorescence recognition Al3+
DMSO/H in fluorescence sensor QB2O (1:9, v/v) solution (C)QB=1×10-5M), 5 times the equivalent (relative to the supramolecular sensor QB) of Al are added respectively3+ , Zn2+ , Pb2+, Cd2+, Ni2+, Fe3+, Co2+, Ag+, Ca2+, Cu2+, Mg2+, Cr3+, Ba2+, Tb3+, Eu4+, La3+An aqueous solution of (a). As a result, it was found that only Al3+Can be added to the DMSO/H of the QB fluorescence sensor2Fluorescence of O (1:9, v/v) solution is turned on, while addition of other metal cations does not allow DMSO/H of fluorescence sensor QB2Fluorescence opening of O (1:9, v/v) solution (as shown in FIG. 3), indicating that fluorescence sensor QB can be used for Al3+Single selective fluorescent recognition.
Anti-interference experimental results show that the existence of other metal cations can identify Al to the QB fluorescence sensor3+Without any interference (as shown in fig. 4).
The fluorescence titration experiment shows that the fluorescence sensor QB is opposite to Al3+Has a minimum detection limit of 2.9 × 10-7M (as shown in fig. 5 and 6).
3. Al identification by fluorescence sensor QB3+Analysis of mechanism of (1)
DMSO/H in fluorescence sensor QB2Adding Al into O (1:9, v/v) solution3+Drying the solvent, performing solid infrared spectrum test, and comparing with infrared spectrogram of fluorescence sensor QB (shown in FIG. 7), wherein the fluorescence sensor QB and Al are3+A complex is formed between them, allowing the fluorescence of QB to be turned on. And the fluorescence sensors QB and Al can be known by high-resolution mass spectrometry3+The ratio of complex formation was 1:1 (as shown in fig. 8).
4. Al detection by fluorescence sensor QB3+Practical application of
DMSO/H by dipping silica gel plates into QB2O (1:9, v/v) solution (C)QB=1×10-5M), then dried in air to prepare a film. When mixing Al3+When dropping onto the film, inA clear color change was observed under 365nm illumination using a UV lamp (as shown in FIG. 9), and thus, the film was useful for detecting Al3+The convenient detection reagent detection kit.
In conclusion, the quinoline derivative-based fluorescence sensor QB is synthesized by the method, and only Al is used3+DMSO/H to enable QB2The O solution is opened by fluorescence, so that Al can be identified with high sensitivity and high selectivity3+The recognition process is not interfered by other metal cations, in Al3+Has good application prospect in the detection.
Drawings
FIG. 1 is a hydrogen spectrum of the fluorescence sensor QB of the present invention.
FIG. 2 is a mass spectrum of the fluorescence sensor QB of the present invention.
FIG. 3 shows DMSO/H in QB of fluorescence sensor of the present invention2O solution with different metal cationsλ ex=380 nm)。
FIG. 4 shows DMSO/H in QB of fluorescence sensor of the present invention2Adding Al into O solution3+On the basis, fluorescent anti-interference patterns of different metal cations are added respectively.
FIG. 5 shows DMSO/H in QB of fluorescence sensor of the present invention2Adding Al into O solution3+Fluorescence titration graph of (a).
FIG. 6 shows the fluorescence sensor QB versus Al of the present invention3+Fit curve for fluorescence titration.
FIG. 7 shows fluorescence sensors QB and QB + Al of the present invention3+An infrared spectrum of (1).
FIG. 8 shows QB + Al of the fluorescence sensor of the present invention3+Mass spectrum of (2).
FIG. 9 shows the thin film Al detection of the fluorescence sensor QB of the present invention3+。
Detailed Description
The following preparation of the sensor molecule QB of the invention and the fluorescent recognition of Al by means of the specific examples3+The application of (a) is further illustrated.
Example 1 Synthesis of quinoline derivative-based fluorescence sensor
(1) To a solution of 8-hydroxyquinoline (2 g, 13.78 mmol) in acetonitrile (50 ml) was added potassium hydroxide (1.5 g, 27.56 mmol). The mixture was stirred for about 30 minutes. Ethyl 2-bromoacetate (2.5 g, 15.15 mmol) was then added to the stirred solution in one portion. The reaction mixture was stirred at rt for 2 h. Then, water was added, and the whole solution was extracted with ethyl acetate (30 ml. times.3). The organic layers were combined, dried over sodium sulfate and filtered under reduced pressure to give the crude product, which was further purified by silica gel column chromatography using petroleum ether ethyl acetate (3: 1) as eluent to give ethyl 2- (quinoline-8-acyloxy) acetate E as a yellow oil.
(2) Ethyl 2- (quinoline-8-acyloxy) acetate (500 mg, 2.16 mmol) was dissolved in 5ml of methanol, and 1ml of hydrazine hydrate was added. The resulting solution was stirred at 65 ℃ for 2 hours. The precipitate was then collected by vacuum filtration, washed with water and dried under vacuum to give 2- (quinoline-8-acyloxy) acethydrazide N as a white solid.
(3) 2- (Quinolin-8-acyloxy) acethydrazide (652 mg, 3 mmol) was completely dissolved in 30mL of anhydrous methanol at ordinary temperature, and the solution was placed in a 100mL three-necked flask. Salicylaldehyde (550 mg, 4.5 mmol) was also dissolved in 30mL of anhydrous methanol and added dropwise to a solution of 2- (quinoline-8-acyloxy) acethydrazide in methanol using a constant pressure funnel, and the temperature was set at 60 ℃ and stirred vigorously for 12 h. And cooling and standing for 12 hours, and precipitating needle-shaped orange transparent crystals in the solution. And recrystallizing with absolute ethyl alcohol to obtain an orange transparent crystal, namely a quinoline derivative-based fluorescence sensor QB (N' - (2-hydroxybenzylidene) -2- (quinoline-8-acyloxy) acethydrazide).
The fluorescent sensor QB was synthesized as follows:
example 2 identification of Al by fluorescence sensor QB3+
Respectively transferring 2mL of DMSO/H of fluorescence sensor molecules QB2O (1:9, v/v) solution (C)QB=1×10-5M) in a series of colorimetric tubes, respectivelyAdding Al3+ , Zn2+ , Pb2+, Cd2+, Ni2+, Fe3+, Co2+, Ag+, Ca2+, Cu2+, Mg2+, Cr3+, Ba2+, Tb3+, Eu4+, La3+(iii) an aqueous solution of (C = 0.1M), DMSO/H in the case of fluorescence sensor QB2The fluorescence of the O solution is turned on, which indicates that Al is added3+DMSO/H in the case of fluorescence sensor QB2The fluorescence of the O solution is not changed, which indicates that the added Al is not Al3+。
Example 3 detection of Al by fluorescence sensor QB3+Practical application of
DMSO/H by dipping silica gel plates into QB2O (1:9, v/v) solution (C)QB=1×10-5M), then dried in air to prepare a film. When mixing Al3+Upon dropping onto the film, a clear color change was observed under 365nm irradiation using a UV lamp. Therefore, the film can be used for detecting Al3+The convenient detection reagent detection kit.
Claims (8)
1. A fluorescence sensor based on quinoline derivatives with molecular formula of C18H15N3O3The structural formula is as follows:
2. the method for synthesizing a quinoline derivative-based fluorescence sensor as claimed in claim 1, comprising the steps of:
(1) adding potassium hydroxide into an acetonitrile solution of 8-hydroxyquinoline, then adding 2-bromoethyl acetate, stirring at room temperature to react for 1.5-2 h, then adding water, extracting with ethyl acetate, drying an organic layer with sodium sulfate, then filtering under reduced pressure to obtain a crude product, and separating and purifying the crude product through silica gel column chromatography to obtain yellow oily 2- (quinoline-8-acyloxy) ethyl acetate;
(2) taking 2- (quinoline-8-acyloxy) ethyl acetate and hydrazine hydrate as substrates, taking methanol as a solvent, stirring and reacting at 65 ℃ for 1.5-2 h, collecting precipitates through vacuum filtration, washing with water and drying in vacuum to obtain white solid 2- (quinoline-8-acyloxy) acethydrazide;
(3) the method comprises the steps of taking 2- (quinoline-8-acyloxy) acethydrazide and salicylaldehyde as substrates, taking absolute methanol as a solvent, reacting for 10-12 hours at 55-65 ℃, cooling and standing for 10-12 hours, precipitating needle-shaped orange transparent crystals in the solution, and recrystallizing with absolute ethanol to obtain orange transparent crystals, namely the quinoline derivative-based fluorescence sensor QB.
3. The method for synthesizing a quinoline derivative-based fluorescence sensor according to claim 2, wherein: in the step (1), the molar ratio of 8-hydroxyquinoline to 2-bromoethyl acetate is 1: 1-1: 1.5.
4. The method for synthesizing a quinoline derivative-based fluorescence sensor according to claim 2, wherein: in the step (1), the molar ratio of 8-hydroxyquinoline to potassium hydroxide is 1: 1.5-1: 2.
5. The method for synthesizing a quinoline derivative-based fluorescence sensor according to claim 2, wherein: in the step (2), the molar ratio of the ethyl 2- (quinoline-8-acyloxy) acetate to the hydrazine hydrate is 1: 1-1: 1.5.
6. The method for synthesizing a quinoline derivative-based fluorescence sensor according to claim 2, wherein: in the step (3), the molar ratio of the 2- (quinoline-8-acyloxy) acethydrazide to the salicylaldehyde is 1: 1.5.
7. Use of the quinoline derivative-based fluorescence sensor according to claim 1 for detecting aluminum ions.
8. The use of a quinoline derivative-based fluorescence sensor according to claim 7 for detecting aluminum ions, wherein: in the presence of fluorescenceDMSO/H of sensor QB2Respectively adding Al into the O solution3+, Zn2+ , Pb2+, Cd2+, Ni2+, Fe3+, Co2 +, Ag+, Ca2+, Cu2+, Mg2+, Cr3+, Ba2+, Tb3+, Eu4+, La3+Aqueous solution of (2), only Al3+DMSO/H addition to enable QB fluorescence sensor2Opening fluorescence of the O solution; DMSO/H2In O solution, DMSO and H2The volume ratio of O is 1: 9.
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| CN114426534A (en) * | 2021-12-15 | 2022-05-03 | 南京师范大学 | Reversible fluorescent probe for detecting copper ions and preparation method thereof |
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| CN114426534B (en) * | 2021-12-15 | 2023-01-31 | 南京师范大学 | Reversible fluorescent probe for detecting copper ions and preparation method thereof |
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