CN107556305A - One kind is used to detect aluminium ion fluorescence probe, preparation method and application - Google Patents
One kind is used to detect aluminium ion fluorescence probe, preparation method and application Download PDFInfo
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- CN107556305A CN107556305A CN201710816511.4A CN201710816511A CN107556305A CN 107556305 A CN107556305 A CN 107556305A CN 201710816511 A CN201710816511 A CN 201710816511A CN 107556305 A CN107556305 A CN 107556305A
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- 239000000523 sample Substances 0.000 title claims abstract description 70
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 title claims abstract description 54
- 238000002360 preparation method Methods 0.000 title claims description 16
- -1 aluminum ions Chemical class 0.000 claims abstract description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 5
- SOGBOGBTIKMGFS-UHFFFAOYSA-N thiophene-2-carbohydrazide Chemical class NNC(=O)C1=CC=CS1 SOGBOGBTIKMGFS-UHFFFAOYSA-N 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 239000002244 precipitate Substances 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 3
- 239000012043 crude product Substances 0.000 claims description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 238000001291 vacuum drying Methods 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 11
- 238000001514 detection method Methods 0.000 abstract description 7
- 230000035945 sensitivity Effects 0.000 abstract description 5
- 230000008859 change Effects 0.000 description 12
- 239000004411 aluminium Substances 0.000 description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 11
- 238000002189 fluorescence spectrum Methods 0.000 description 7
- 229910021645 metal ion Inorganic materials 0.000 description 7
- 239000007788 liquid Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- 239000007995 HEPES buffer Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 0 *C(C[C@]1C=NNC(c2ccc[s]2)=O)=CC(c2nc3ccccc3[s]2)=C1O Chemical compound *C(C[C@]1C=NNC(c2ccc[s]2)=O)=CC(c2nc3ccccc3[s]2)=C1O 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 208000014644 Brain disease Diseases 0.000 description 1
- 208000032274 Encephalopathy Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000004993 emission spectroscopy Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000009616 inductively coupled plasma Methods 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- RECVMTHOQWMYFX-UHFFFAOYSA-N oxygen(1+) dihydride Chemical compound [OH2+] RECVMTHOQWMYFX-UHFFFAOYSA-N 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000011895 specific detection Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
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- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Abstract
It is used to detect aluminium ion fluorescence probe the invention discloses one kind, the aluminum ions fluorescence probe of the detection has the characteristics of high selectivity, high sensitivity and good water solubility.The present invention is used to detect aluminium ion fluorescence probe, and the probe described in it has structure shown in formula I：Wherein R is H, CH3Or t Bu.
Description
Technical field
The present invention relates to a kind of fluorescence probe, preparation method and application, more specifically to one kind be used to detecting aluminium from
Sub- fluorescence probe, preparation method and application.
Background technology
Aluminium, content comes the element of the 3rd in the earth's crust, oxygen element and element silicon is only second to, which dictates that it is in life
Extensive use.In addition, due to its unique physical and chemical properties, aluminium has been widely used in electronic material, catalysis
The multiple fields such as agent, medicine, sensor.While being widely used in of aluminium brings of all kinds convenient to our life,
The problem of many inevitable is left on its road being also evolving.It is well known that a large amount of activities of the mankind and aluminium
Extensive use aluminium is existed in nature in the form of aluminium ion rather than monomer.However, the horizontal aluminium of high concentration from
Son causes certain harm to environment and human body.According to the World Health Organization (WHO) issue standard, it is aluminum ions per capita
Intake should be controlled in 3-10mg, and in the content no more than 200 μ g/L of daily Aluminium in Drinking Water ion.Result of study table
It is bright, when the aluminium composition in human body is too high, it will cause a variety of diseases, including the gloomy disease of Alzheimer's disease, pa aluminium with
And dialysis encephalopathy.As can be seen here, can effectively aluminum ions content be to closing weight in monitoring of environmental and biological specimen immediately
Want.Being traditionally used for detecting aluminum ions method has ion mass spectrometry, atomic absorption spectrography (AAS), inductively coupled plasma former
Sub- emission spectrometry and electrochemical method etc..But these methods most analysis time length, required instrument price it is expensive and
It is not easy to operate.And compared with these methods, fluorescence probe then possesses the good, high sensitivity of selection specificity, easy to operate, instant inspection
Survey and respond numerous advantages such as rapid.It is relatively broad that these advantages make it that it is suffered from ambits such as chemistry, biomedicines
Application, especially in biomedical sector, fluorescence probe can be used not only for the image that analyzed in vitro can be also used for live body
Learn research.In recent years, the energy aluminum ions small-molecule fluorescent probe of specific detection is largely reported, however, many of which probe
Poorly water-soluble, sensitivity is low, pH change is larger to the influential effect of detection；Separately have that some probe bio-toxicities are big, cell membrane
Penetrating power is poor, and these defects largely have impact on the application of probe.Therefore, the new of these defects can be overcome by developing
Fluorescence probe is very important.
The content of the invention
The technical problems to be solved by the invention are：Overcome the shortcomings of the prior art, there is provided one kind is used to detect aluminium
Ion fluorescence probe, the aluminum ions fluorescence probe of the detection have the characteristics of high selectivity, high sensitivity and good water solubility.
The present invention also provides preparation method, mono-crystalline structures and the probe answering in aluminium ion detection of the fluorescence probe
With.
The technical concept of the present invention is as follows：It has been investigated that 2- (5- alkyl -4- aldehyde radical -2- hydroxy phenyls) benzene should be based on
And the derivative probe alternative of thiazole is reacted with aluminium ion and blue-shifted phenomenon occurs, and in 0-100 μM of aluminium ion concentration model
In enclosing, 476nm at fluorescence intensity and 568nm the ratio (I476nm/I568nm) of fluorescence intensity and aluminium ion concentration have compared with
Good linear relationship.The present inventor prepares 2- (5- alkyl -4- aldehyde radical -2- hydroxy phenyls) benzothiazole derivants and first first
Aluminum ions selective enumeration method is used it for, so as to solve above-mentioned technical problem.
The technical scheme that the present invention solves its technical problem is as follows：
The present invention is used to detect aluminium ion fluorescence probe, and the probe described in it has structure shown in formula I：
Wherein R is H, CH3Or t-Bu.
The above-mentioned preparation method for being used to detect aluminium ion fluorescence probe of the present invention, it comprises the following steps：
2- (5- alkyl -4- aldehyde radical -2- hydroxy phenyls) benzothiazoles and 2- thenoyls hydrazine compound is anti-in a solvent
Should, that is, generate for detecting aluminium ion fluorescence probe.
The present invention is above-mentioned to be used to detecting the preparation method of aluminium ion fluorescence probe, its further technical scheme be include with
Lower step:
First 2- (5- alkyl -4- aldehyde radical -2- hydroxy phenyls) benzothiazole is added in reactor, solubilizer dissolving, so
After add 2- thenoyl hydrazines, reaction is 12h or more under normal temperature, obtains yellow solid precipitate, is used for after purification
Detect aluminium ion fluorescence probe.
The above-mentioned preparation method for being used to detect aluminium ion fluorescence probe of the present invention, its further technical scheme is described
Solvent be methanol, ethanol, acetonitrile, dichloromethane or chloroform.
The present invention is above-mentioned to be used to detecting the preparation method of aluminium ion fluorescence probe, and its further technical scheme can be with
It is that described purification step is as follows：Described yellow solid precipitate is separated out in reaction dissolvent, and reaction solution is filtered to obtain
The solid crude product of yellow, again with methanol and each 3 times of dichloromethane cross washing or more, most it is after drying in vacuum drying chamber
It must be used to detect aluminium ion fluorescence probe.
The present invention is above-mentioned to be used to detecting the preparation method of aluminium ion fluorescence probe, and its further technical scheme can be with
The dosage mass ratio for being described 2- (5- alkyl -4- aldehyde radical -2- hydroxy phenyls) benzothiazoles and 2- thenoyl hydrazines is 1.26-
1.89:1。
The present invention is above-mentioned can be applied for detecting aluminium ion fluorescence probe in aluminium ion is detected.
The invention has the advantages that：
1) fluorescence probe of the present invention is orange in colourless and fluorescence in pH=7.4 cushioning liquid, is reacted with aluminium ion
Light green color is showed afterwards and sends strong blue-fluorescence.
2) using after fluorescence probe of the present invention, detection sensitivity is high, and 10 are can reach to aluminum ions test limit-6mol/L。
3) fluorescence reaction only occurs with aluminium ion for fluorescence probe of the present invention, reactionless to other ions, has good
Selectivity and specificity.In addition, detection performance is resistant to larger pH excursions and with the transmitting of preferable ratio fluorescent
Property.
4) preparation is simple for fluorescence probe of the present invention, is easy to large-scale production.
Brief description of the drawings
Fig. 1 is the fluorescence probe of the embodiment of the present invention 2 and the fluorescence emission spectrum of various ionic reactions.
Fig. 2 is the fluorescence probe of the embodiment of the present invention 2 and the change in fluorescence figure of various ionic reactions.
Fig. 3 is the fluorescence probe of the embodiment of the present invention 3 and the change in fluorescence figure of aluminium ion reaction.
Fig. 4 is the fluorescence probe of the embodiment of the present invention 3 and the I of aluminium ion reaction476nm/I568nmIncrement graph.
Fig. 5 is the fluorescence probe of the embodiment of the present invention 3 to 0-100 μM of aluminium ion concentration I476nm/I568nmLinear relationship chart.
Fig. 6 is change in fluorescence figure of the fluorescence probe of the embodiment of the present invention 4 under different water volume percentages.
Fig. 7 is the fluorescence probe of the embodiment of the present invention 4 fluorescence intensity ratio (I/I under different water volume percentages0) change
Change figure.
Fig. 8 is the fluorescence probe of the embodiment of the present invention 5 and metal ion filter paper experimental fluorescence figure.
Fig. 9 is the mono-crystalline structures phenogram of the fluorescence probe of the embodiment of the present invention 1.
Figure 10 is the nucleus magnetic hydrogen spectrum phenogram of the fluorescence probe of the embodiment of the present invention 1.
Figure 11 is the mass spectral characteristi figure of the fluorescence probe of the embodiment of the present invention 1
Embodiment
The present invention is described in further detail with reference to the accompanying drawings and in conjunction with the embodiments.
Embodiment 1 prepares aluminium ion fluorescence probe
The 2- thenoyl hydrazines of 269mg 2- (5- methyl -4- aldehyde radical -2- hydroxy phenyls) benzothiazoles and 156mg are dissolved in
In 30mL methanol, stirring reaction 12 hours under room temperature condition.The solid for having yellow after question response terminates, in reaction solution is analysed
Going out, the solid that reaction solution is filtered to obtain to yellow precipitates, then each 3 times with methanol and dichloromethane cross washing, Yu Zhen
The solid 320mg of drying to obtain yellow in empty drying box, as aluminium ion fluorescence probe sterling (mono-crystalline structures,1H-NMR figures,
High resolution mass spectrum figure is shown in Fig. 9, Figure 10, Figure 11).Gained fluorescence probe sterling actual measurement molecular weight is 393.
The present embodiment process route：
The spectral quality of aluminium ion fluorescence probe and various ionic reactions is made in embodiment 2
Weigh 3.9mg embodiments 1 and aluminium ion fluorescence probe is made, the 10mL DMF solutions that concentration is 1mM are made into, as mother
Liquid.
Fluorescence spectrum is tested：The 30 above-mentioned mother liquors of μ L are added to a certain amount of 10mM HEPES cushioning liquid (pH 7.4)
In, it is then respectively adding each metal ion species：Al3+,Zn2+,Cu2+,Fe2+,Fe3+,Hg2+,Ag+,Co2+,Ni2+,Cr3+,Ca2+,Cs+,Cd2+,Pb2+,Mn2+,Zr4+,K+,Mg2+,Li+,Na+, the ultimate density that makes metal ion in measurement system is 1mM, fluorescence probe
Final concentration of 10 μM.Test its fluorescence emission spectrum immediately under 380nm excitation wavelengths.Exciting light and the slit for launching light are wide
Spend for 10nm/5nm.Acquired results are as shown in Figure 1.By above-mentioned configured solution 365nm ultra violet lamps, the change of its fluorescence is observed
Change, as a result see Fig. 2.
Result above shows：
(1) it is in itself orange in colourless and fluorescence in cushioning liquid, but add with aluminum ions that fluorescence probe, which is made, in embodiment 1
Enter, probe fluorescent orange at 568nm fades away, and blue-fluorescence gradually strengthens at 476nm.
(2) fluorescence probe, which is made, in embodiment 1 has the selectivity and specificity of height to aluminium ion, and in above-mentioned condition
Under, can be from Zn2+, Ag+,Cd2+,Pb2+,Cu2+,Cr3+,Hg2+,Mn2+Etc. distinguishing aluminium ion in common heavy metal ion.
The spectral quality of aluminium ion fluorescence probe and aluminium ion reaction product is made in embodiment 3
Mother liquor in 30 μ L embodiments 2 is added in a certain amount of 10mM HEPES cushioning liquid (pH 7.4), made glimmering
Ultimate density of the light probe in test system is 10 μM, states the aluminium ion that different equivalents are added in test system then up,
Aluminium ion final concentration be respectively 0mM, 0.2mM, 0.4mM, 0.6mM, 0.8mM, 1mM, 1.2mM, 1.4mM, 1.6mM, 1.8mM,
2mM.After ion adds, its fluorescence emission spectrum is measured immediately.Fluorescence emission spectrum is excited when determining with 380nm；Exciting light with
The slit width for launching light is 10nm/5nm.Gained fluorescence intensity ratio I476nm/I568nmIncrement graph is shown in Fig. 3；With I476nm/I568nm
Data creating working curve, as a result see Fig. 4.
Should test result indicates that, with the progress of reaction, fluorescence intensity ratio I476nm/I568nmWith the increasing of aluminium ion concentration
Add and increase, and fluorescence intensity ratio I476nm/I568nmIt is in preferable linear relationship with the aluminium ion concentration in the range of 0-100 μM,
It can be used for the quantitative analysis detection of aluminium composition, with I476nm/I568nmIt is linear with the aluminium ion concentration in the range of 0-100 μM
Relation curve is shown in Fig. 5.
Fluorescent spectroscopic properties of the aluminium ion fluorescence probe under different water volume percentages are made in embodiment 4
Maintain the cumulative volume of tetrahydrofuran and deionized water certain, change the percentage by volume (0%-95%) of water, detect
The change of the fluorescence spectrum of aluminium ion fluorescence probe under different water volume percentages.As a result show, in the range of 0%-90%, with
The increase of water volume percentage, the fluorescence intensity of aluminium ion fluorescence probe and the ratio (I/I of fluorescence intensity0) all increase therewith；
And after the percentage by volume of water is more than 90%, the fluorescence intensity of aluminium ion fluorescence probe and the ratio (I/I of fluorescence intensity0)
Reduce therewith again, these experimental results illustrate that aluminium ion fluorescence probe has the effect of aggregation-induced emission.Aluminium ion fluorescence is visited
Fluorescence spectrum of the pin under different water volume percentages is shown in Fig. 6 and Fig. 7.
Aluminium ion fluorescence probe and the fluorescent spectroscopic properties of metal ion filter paper experiment is made in embodiment 5
The circular filter paper piece being ready for is put into beaker, states 1.5mL embodiments 2 are separately added into beaker then up
In mother liquor make it that circular filter paper piece is flooded completely.It is all taken out after filter paper impregnates 12h, 12h is dried under normal temperature.
Now, the fluorescence of red is presented in filter paper under 365nm ultraviolet excitation irradiation.It is 10mM's to pipette concentration respectively with liquid-transfering gun
Al3+,Zn2+,Cu2+,Fe2+,Fe3+,Hg2+,Ag+,Co2+,Ni2+,Cr3+,Ca2+,Cs+,Cd2+,Pb2+,Mn2+,Zr4+,K+,Mg2+,Li+,Na+Each 10 μ L, the filter paper center of above-mentioned drying is dropped in, makes its free diffusing.After complete reaction, fluorescence on each filter paper is checked
Change.As a result show, under 365nm ultraviolet excitation irradiation, metal ion Hg has been added dropwise2+,Ni2+,Co2+,Cu2+,Fe3+
And Fe2+The fluorescence of filter paper part be quenched completely；Other metal ions have been added dropwise such as：Zn2+,Ag+,Cr3+,Ca2+,Cs+,Cd2 +,Pb2+,Mn2+,Zr4+,K+,Mg2+,Li+,Na+The fluorescence of filter paper part do not change；And Al is only added dropwise3+Filter paper
Partial fluorescence becomes very strong blue-fluorescence from red.Aluminium ion fluorescence probe is shown in metal ion filter paper experimental fluorescence figure
Fig. 8.
In addition to the implementation, the present invention can also have other embodiment.It is all to use equivalent substitution or equivalent transformation shape
Into technical scheme, all fall within the protection domains of application claims.
Claims (7)
1. one kind is used to detect aluminium ion fluorescence probe, it is characterised in that described probe has structure shown in formula I：
Wherein R is H, CH3Or t-Bu.
2. a kind of preparation method for being used to detect aluminium ion fluorescence probe as claimed in claim 1, it is characterised in that including following
Step：2- (5- alkyl -4- aldehyde radical -2- hydroxy phenyls) benzothiazoles and 2- thenoyls hydrazine compound are reacted in a solvent,
Generate for detecting aluminium ion fluorescence probe.
3. preparation method according to claim 2, it is characterised in that comprise the following steps:
First 2- (5- alkyl -4- aldehyde radical -2- hydroxy phenyls) benzothiazole is added in reactor, solubilizer dissolving, Ran Houzai
2- thenoyl hydrazines are added, reaction is 12h or more under normal temperature, obtains yellow solid precipitate, obtains being used to detect after purification
Aluminium ion fluorescence probe.
4. the preparation method according to Claims 2 or 3, it is characterised in that described solvent is methanol, ethanol, acetonitrile, dichloro
Methane or chloroform.
5. preparation method according to claim 4, it is characterized in that being that described purification step is as follows：Described yellow solid
It is deposited in reaction dissolvent and separates out, reaction solution is filtered to obtain the solid crude product of yellow, again with methanol and dichloromethane are handed over
Fork washing each 3 times or more, most after being drying to obtain in vacuum drying chamber for detecting aluminium ion fluorescence probe.
6. the preparation method according to Claims 2 or 3, it is characterised in that described 2- (5- alkyl -4- aldehyde radical -2- hydroxyls
Phenyl) the dosage mass ratio of benzothiazole and 2- thenoyl hydrazines is 1.26-1.89:1.
It is 7. a kind of as claimed in claim 1 for detecting application of the aluminium ion fluorescence probe in aluminium ion is detected.
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| CN109722241A (en) * | 2019-01-08 | 2019-05-07 | 东北农业大学 | A kind of identification copper ion and the difunctional fluorescence probe of mercury ion and its preparation method and application |
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| CN114907336A (en) * | 2022-07-01 | 2022-08-16 | 廊坊师范学院 | Zinc ion fluorescent probe based on benzothiazole, and preparation method and application thereof |
| CN117447465A (en) * | 2023-10-25 | 2024-01-26 | 东北农业大学 | On-off-on fluorescent probe, reagent, chemical sensor, preparation method and application |
| CN117720106A (en) * | 2023-12-28 | 2024-03-19 | 安徽泽升科技股份有限公司 | Purification method of dichloromethane |
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| CN109438386A (en) * | 2018-11-02 | 2019-03-08 | 东北农业大学 | A kind of identification aluminium ion and the difunctional fluorescence probe of zinc ion and its preparation method and application |
| CN109722241A (en) * | 2019-01-08 | 2019-05-07 | 东北农业大学 | A kind of identification copper ion and the difunctional fluorescence probe of mercury ion and its preparation method and application |
| CN109722241B (en) * | 2019-01-08 | 2021-07-27 | 东北农业大学 | Bifunctional fluorescent probe for identifying copper ions and mercury ions and preparation method and application thereof |
| CN113004220A (en) * | 2021-03-12 | 2021-06-22 | 南京工业大学 | Esterase detection fluorescent probe, preparation method and application |
| CN113004220B (en) * | 2021-03-12 | 2022-03-11 | 南京工业大学 | Esterase detection fluorescent probe, preparation method and application |
| CN114907336A (en) * | 2022-07-01 | 2022-08-16 | 廊坊师范学院 | Zinc ion fluorescent probe based on benzothiazole, and preparation method and application thereof |
| CN114907336B (en) * | 2022-07-01 | 2023-08-29 | 廊坊师范学院 | Zinc ion fluorescent probe based on benzothiazole and preparation method and application thereof |
| CN117447465A (en) * | 2023-10-25 | 2024-01-26 | 东北农业大学 | On-off-on fluorescent probe, reagent, chemical sensor, preparation method and application |
| CN117447465B (en) * | 2023-10-25 | 2024-04-12 | 东北农业大学 | On-off-on fluorescent probe, reagent, chemical sensor, preparation method and application |
| CN117720106A (en) * | 2023-12-28 | 2024-03-19 | 安徽泽升科技股份有限公司 | Purification method of dichloromethane |
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| CN107556305B (en) | 2019-12-06 |
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