CN110423609A - A kind of fluorescence probe identifying thiocyanate radical and its preparation and recognition methods - Google Patents
A kind of fluorescence probe identifying thiocyanate radical and its preparation and recognition methods Download PDFInfo
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
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- 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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- 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
Abstract
The invention discloses a kind of fluorescence probe for identifying thiocyanate radical and its preparation and recognition methods, its molecular formula of the probe is C57H75Br3N4.Preparation method is first to mix 4- Iodoaniline and 4- pyridine boronic acid, is then dissolved in the mixed solution of dioxane and water, obtains A product；A product are placed in the environment of nitrogen protection, Pd (PPh is added3)4And Na2CO3, stir 10-20h at 80-100 DEG C, after be cooled to 20-30 DEG C, be diluted with water, then extract, obtain B product；Use anhydrous Na2SO4Solvent, is then spin-dried for, obtains yellow solid C product with column chromatographic purifying by dry B product；C product are dissolved in n,N-Dimethylformamide, bromooctane is then added, are heated to 75-85 DEG C, react 30-40h, ether is added in reaction solution and is precipitated completely to it, filters, solids is washed with ether, is dried, and the fluorescence probe of identification thiocyanate radical is obtained.Probe of the invention can identify thiocyanate radical, and have and identify feature sensitive, that selectivity is high, easy to operate, pollution-free, at low cost.
Description
Technical field
The present invention relates to a kind of fluorescence probe and its preparation and recognition methods, especially a kind of fluorescence for identifying thiocyanate radical
Probe and its preparation and recognition methods.
Background technique
Rhodanate is a kind of toxic industrial chemicals, and sodium sulfocyanate is used as chemical analysis reagent, for manufacturing thiocarbamide, mustard
Seed oil configures electroplate liquid, the production as refrigerant, steel analysis reagent and dyestuff, drug etc..
Free thiocyanate radical is a kind of electronegative multi-atomic ion, and in environmental monitoring, thiocyanate radical is to aquatic organism
And human body is with potentially hazardous.Thiocyanate radical inhibits the thyroid function of human body, can also inhibit nervous system, lead to metabolic
Many health problems such as acid poisoning and cardiovascular system are unstable.In wastewater environment, thiocyanate radical is easily chlorinated into have and wave
The extremely toxic substance hydrogen chloride of property is sent out, chloride can also be generated under the action of ultraviolet light in the environment.So thiocyanate radical from
The detection of son has great importance.
The measurement to thiocyanate radical may be implemented there are many method at present, common are electrode method, chromatography, luminosity
Method, polarography, voltammetry etc. is cumbersome although some are sensitiveer for these methods, some easy but sensitivity are not high,
Some even need to use noxious material, can cause secondary pollution to environment, some instruments are more expensive, popularize inconvenience.And fluorescence
Probe is a kind of reagent that certain ion is identified by change in fluorescence, has highly selective, highly sensitive, inexpensive and result
Visual feature is a kind of ideal detection method.
Summary of the invention
The object of the present invention is to provide a kind of fluorescence probe for identifying thiocyanate radical and its preparations and recognition methods.This
The probe of invention can identify thiocyanate radical, and have and identify that sensitive, selectivity is high, easy to operate, pollution-free, at low cost
The characteristics of.
Technical solution of the present invention: a kind of fluorescence probe identifying thiocyanate radical, molecular formula C57H75Br3N4, chemistry
Structural formula is as shown in Fig. 1.
A method of the fluorescence probe preparing identification thiocyanate radical described in claim 1 includes the following steps:
(1) first 4- Iodoaniline and 4- pyridine boronic acid are mixed, is then dissolved in the mixed solution of dioxane and water, obtains
A product；
(2) A product are placed in the environment of nitrogen protection, Pd (PPh is added3)4And Na2CO3, 10- is stirred at 80-100 DEG C
20h, after be cooled to 20-30 DEG C, be diluted with water, then extract, obtain B product；
(3) anhydrous Na is used2SO4Solvent, is then spin-dried for, obtains yellow solid C product with column chromatographic purifying by dry B product；
(4) C product are dissolved in n,N-Dimethylformamide, bromooctane is then added, be heated to 75-85 DEG C, react 30-
Ether is added in reaction solution and precipitates completely to it, filters by 40h, and solids is washed with ether, is dried, and identification thiocyanate radical is obtained
Fluorescence probe.
The preparation method of the fluorescence probe of identification thiocyanate radical above-mentioned, step (1) the 4- Iodoaniline and 4- pyridine boron
The mass ratio of acid is 1:0.5-1.5；The volume ratio of the dioxane and water is 4:1-3.
The preparation method of the fluorescence probe of identification thiocyanate radical above-mentioned, step (2) Pd (PPh3)4Additional amount be
The 10-30% of 4- Iodoaniline；Na2CO3Additional amount be 4- Iodoaniline 50-70%.
The preparation method of the fluorescence probe of identification thiocyanate radical above-mentioned, step (2) extraction is first to use methylene chloride
Extraction 2-4 times, then extracted 2-4 times with saturated salt solution.
The preparation method of the fluorescence probe of identification thiocyanate radical above-mentioned, flowing when step (3) the column chromatographic purifying
It is mutually EtOAc/MeOH, ratio 4:1.
The preparation method of the fluorescence probe of identification thiocyanate radical above-mentioned, the molar ratio of step (4) the C product and bromooctane
For 1:3-5.
It is a kind of to identify thiocyanate radical method using fluorescence probe above-mentioned, it is that the fluorescence probe is dissolved in DMSO, uses
Secondary water dilution, obtains fluorescent reagent, sample to be identified is then instilled into reagent, obtains sample solution, carries out to sample solution glimmering
Light excitation and the glimmering light activated wavelength of fluorescence of test analysis.
Fluorescence probe above-mentioned identifies that thiocyanate radical method, the concentration of the fluorescent reagent are 10-5mol·L-1。
Fluorescence probe above-mentioned identifies that thiocyanate radical method, the glimmering light activated excitation wavelength are 438nm, when detecting
When thiocyanate radical, maximum fluorescence emission peak of the fluorescent reagent at 598nm wavelength sharply enhances.
Beneficial effects of the present invention
Fluorescence probe of the invention can identify thiocyanate radical, and when identification has stronger interference free performance, no
It will receive the influence of common counter anion, identify that sensitive, selectivity is high；Meanwhile fluorescence probe of the invention is in identification
It only needing to be made into identification agent, fluorescence excitation observation change in fluorescence after prepare liquid is added, operating process is simple,
More easily promote；In addition, fluorescence probe of the invention not will cause the pollution of environment during identification, it is more environmentally-friendly；Most
Afterwards, fluorescence probe low manufacture cost of the invention, compared with existing complex device and method, identification cost is lower.
To further illustrate beneficial effects of the present invention, inventor has done following experiment:
One, qualitative analysis is tested
It is 10 in concentration range-5-10-4mol·L-1Fluorescence probe aqueous solution in, when excitation wavelength be 438nm when, it is glimmering
The maximum emission wavelength of light probe is 598nm, as addition thiocyanate ion (SCN in fluorescence probe aqueous solution-) after, fluorescence is visited
Maximum fluorescence emission peak of the needle at 598nm wavelength sharply enhances.
Two, detection limit analysis test
1, the preparation method of fluorescence probe solution: weighing the probe of 10.56mg, and being configured to volume with DMSO is 10mL, dense
Degree is 1.0 × 10-3mol·L-1Solution, take 1 100.0mL volumetric flask, take 1mL in capacity configured probe solution
It is interior, it is diluted to graduation mark with secondary water, obtaining concentration is 1.0 × 10-5mol·L-1Probe solution.
2, the thiocyanate radical for weighing excellent pure grade is configured to 10mL aqueous solution, and concentration is 1.0 × 10-2mol·L-1, according to need
It is diluted step by step with secondary water.
3, fluorescent reagent 1.0 × 10 is taken-5mol·L-1Titer, toward cuvette in be added 3mL fluorescent reagent, be added dropwise respectively
Enter 1.0 × 10-3mol·L-1SCN-Solion introduces fluorescence spectrum and is measured, excitation wavelength 438nm.
4, respectively with SCN-Ion concentration is abscissa, and fluorescence intensity is ordinate, obtains working curve.
5, sample measures: taking two 10.0mL volumetric flasks, is separately added into fluorescent reagent 1.0 × 10-3mol·L-1Titer
0.1mL is separately added into thiocyanate ion solution in two capacity, is diluted to scale, is placed at room temperature for 5 minutes, introduces 3.0cm
Quartz colorimetric utensil carry out fluoremetry, sample concentration is found on working curve according to fluorescence intensity.Detection identifies minimum
Concentration value is 6.79 × 10-6mol·L-1。
Three, anti-interference test
It is 1.00 × 10 in concentration and probe concentration-5mol·L-1SCN is added in reagent-Blue shift occurs for fluorescence afterwards, then respectively to fluorescence
Other anion (S is added in reagent2-、SO4 2-、HSO3-、HSO4 -、F-、Cl-、Br-、I-、OH-、ClO4 -、CO3 2-、HCO3 -、Ac-、
NO3 -、P2O7 4-、HPO4 2-、H2PO4 -), other anion will not interfere the measurement of thiocyanate radical.
Detailed description of the invention
Fig. 1 is the chemical structural formula of fluorescent probe molecule of the present invention；
Fig. 2 is the nucleus magnetic hydrogen spectrum figure of fluorescent probe molecule of the present invention；
Fig. 3 is the fluorescence spectra of fluorescent probe molecule of the present invention and different anions effect；
Fig. 4 is that fluorogram of each anion under the ultraviolet light irradiation of 365nm is added in probe solution of the present invention；
Fig. 5 is the fluorescence titration figure that fluorescent probe molecule of the present invention is added after thiocyanate ion；
Fig. 6 is the working curve diagram that fluorescent probe molecule of the present invention is added after thiocyanate ion；
Fig. 7 is the interference figure that fluorescent probe molecule of the present invention identifies thiocyanate ion.
Specific embodiment
Below with reference to embodiment, the present invention is further illustrated, but is not intended as the foundation limited the present invention.
The embodiment of the present invention
Embodiment 1: the preparation method of the fluorescence probe of thiocyanate radical is identified, steps are as follows:
(1) by 4- Iodoaniline and 4- pyridine boronic acid in mass ratio it is first that 1:1 is mixed, it is mixed is then dissolved in 2:1 by volume
In the dioxane of conjunction and the mixed solution of water, A product are obtained；
(2) A product are placed in the environment of nitrogen protection, 20% Pd (PPh of 4- Iodoaniline quality is added3)4With 4- iodobenzene
60% Na of amine quality2CO3, stir 15h at 90 DEG C, after be cooled to 25 DEG C, be diluted with water, then first use dichloromethane
Alkane extracts 3 times, then is extracted 3 times with saturated salt solution, obtains B product；
(3) anhydrous Na is used2SO4Solvent, is then spin-dried for by dry B product, chromatographs (SiO with column2) purifying (EtOAc/MeOH 4:
1) yellow solid C product are obtained；
(4) C product are dissolved in n,N-Dimethylformamide, then press C product: it is pungent that bromine is added in the molar ratio 1:4 of bromooctane
Alkane is heated to 80 DEG C, reacts 35h, and ether is added in reaction solution and precipitates completely to it, filters, solids is washed with ether, is dried
It is dry, obtain the fluorescence probe of identification thiocyanate radical.
Embodiment 2: the preparation method of the fluorescence probe of thiocyanate radical is identified, steps are as follows:
(1) first by 4- Iodoaniline and 4- pyridine boronic acid be in mass ratio 1:0.5 mix, be then dissolved in 4:1 by volume
In the mixed solution of mixed dioxane and water, A product are obtained；
(2) A product are placed in the environment of nitrogen protection, 10% Pd (PPh of 4- Iodoaniline quality is added3)4With 4- iodobenzene
50% Na of amine quality2CO3, stir 10h at 80 DEG C, after be cooled to 20 DEG C, be diluted with water, then first use dichloromethane
Alkane extracts 2 times, then is extracted 2 times with saturated salt solution, obtains B product；
(3) anhydrous Na is used2SO4Solvent, is then spin-dried for by dry B product, chromatographs (SiO with column2) purifying (EtOAc/MeOH 4:
1) yellow solid C product are obtained；
(4) C product are dissolved in n,N-Dimethylformamide, then press C product: it is pungent that bromine is added in the molar ratio 1:3 of bromooctane
Alkane is heated to 75 DEG C, reacts 30h, and ether is added in reaction solution and precipitates completely to it, filters, solids is washed with ether, is dried
It is dry, obtain the fluorescence probe of identification thiocyanate radical.
Embodiment 3: the preparation method of the fluorescence probe of thiocyanate radical is identified, steps are as follows:
(1) first by 4- Iodoaniline and 4- pyridine boronic acid be in mass ratio 1:1.5 mix, be then dissolved in 4:3 by volume
In the mixed solution of mixed dioxane and water, A product are obtained；
(2) A product are placed in the environment of nitrogen protection, 30% Pd (PPh of 4- Iodoaniline quality is added3)4With 4- iodobenzene
70% Na of amine quality2CO3, stir 20h at 100 DEG C, after be cooled to 30 DEG C, be diluted with water, then first use dichloromethane
Alkane extracts 4 times, then is extracted 4 times with saturated salt solution, obtains B product；
(3) anhydrous Na is used2SO4Solvent, is then spin-dried for by dry B product, chromatographs (SiO with column2) purifying (EtOAc/MeOH 4:
1) yellow solid C product are obtained；
(4) C product are dissolved in n,N-Dimethylformamide, then press C product: it is pungent that bromine is added in the molar ratio 1:5 of bromooctane
Alkane is heated to 85 DEG C, reacts 40h, and ether is added in reaction solution and precipitates completely to it, filters, solids is washed with ether, is dried
It is dry, obtain the fluorescence probe of identification thiocyanate radical.
Embodiment 4: the preparation method of the fluorescence probe of thiocyanate radical is identified, steps are as follows:
(1) 4- Iodoaniline (1.01g, 1.62mmol) and 4- pyridine boronic acid are sequentially added in dry Schlenk flask
Dioxane (40ml) and water (20ml) is then added in (717mg, 5.84mmol).
(2) it will be passed through nitrogen protection in solution, adds Pd (PPh3)4(187mg, 0.16mmol) and Na2CO3(650mg,
6.13mmol), 16h is stirred at 91 DEG C, is cooled to 25 DEG C after reaction, is diluted with water, uses CH2Cl2(3 × 200ml) extraction
It takes.
(3) anhydrous Na is used2SO4Dry organic extract liquid, solvent are spin-dried for, and column chromatographs (SiO2) purifying (mobile phase) (EtOAc/
MeOH 4:1) obtain the yellow solid A of 700mg.
(4) solid A is added in n,N-Dimethylformamide and is dissolved, bromooctane is then added, is heated to 75-85 DEG C, instead
30-40h is answered, ether is added in reaction solution and is precipitated completely to it, filters, is washed twice with ether, dried, obtains identification thiocyanic acid
The fluorescence probe of root.
Embodiment 5: fluorescence probe identifies thiocyanate radical method, is that the fluorescence probe is dissolved in DMSO, uses secondary water
Being diluted to concentration is 10-5mol·L-1, fluorescent reagent is obtained, sample to be identified is then instilled into reagent, obtains sample solution, uses wave
The exciting light of a length of 438nm carries out fluorescence excitation to sample solution, and when containing thiocyanate radical, fluorescent reagent is in 598nm wavelength
The maximum fluorescence emission peak at place sharply enhances, and is otherwise free of thiocyanate radical.
Claims (10)
1. a kind of fluorescence probe for identifying thiocyanate radical, it is characterised in that: its molecular formula is C57H75Br3N4, chemical structural formula are as follows:
Wherein, R=C8H17。
2. a kind of method for the fluorescence probe for preparing identification thiocyanate radical described in claim 1, which is characterized in that including as follows
Step:
(1) 4- Iodoaniline and 4- pyridine boronic acid are mixed, is then dissolved in the mixed solution of dioxane and water, obtains A product；
(2) A product are placed in the environment of nitrogen protection, Pd (PPh is added3)4And Na2CO3, 10-20h is stirred at 80-100 DEG C,
After be cooled to 20-30 DEG C, be diluted with water, then extract, obtain B product；
(3) anhydrous Na is used2SO4Solvent, is then spin-dried for, obtains yellow solid C product with column chromatographic purifying by dry B product；
(4) C product are dissolved in n,N-Dimethylformamide, bromooctane are then added, be heated to 75-85 DEG C, react 30-40h,
Ether is added in reaction solution and is precipitated completely to it, filters, solids is washed with ether, is dried, and the glimmering of identification thiocyanate radical is obtained
Light probe.
3. the preparation method of the fluorescence probe of identification thiocyanate radical according to claim 2, it is characterised in that: step (1)
The mass ratio of the 4- Iodoaniline and 4- pyridine boronic acid is 1:0.5-1.5；The volume ratio of the dioxane and water is 4:1-3.
4. the preparation method of the fluorescence probe of identification thiocyanate radical according to claim 2, it is characterised in that: step (2)
Pd (the PPh3)4Additional amount be 4- Iodoaniline 10-30%；Na2CO3Additional amount be 4- Iodoaniline 50-70%.
5. the preparation method of the fluorescence probe of identification thiocyanate radical according to claim 2, it is characterised in that: step (2)
The extraction is first to be extracted with dichloromethane 2-4 times, then extracted 2-4 times with saturated salt solution.
6. the preparation method of the fluorescence probe of identification thiocyanate radical according to claim 2, it is characterised in that: step (3)
Mobile phase when the column chromatographic purifying is EtOAc/MeOH, ratio 4:1.
7. the preparation method of the fluorescence probe of identification thiocyanate radical according to claim 2, it is characterised in that: step (4)
The molar ratio of the C product and bromooctane is 1:3-5.
8. a kind of identify thiocyanate radical method using fluorescence probe described in claim 1, it is characterised in that: be by the fluorescence
Probe is dissolved in DMSO, is diluted with secondary water, and fluorescent reagent is obtained, and sample to be identified is then instilled into reagent, obtains sample solution,
Fluorescence excitation and the glimmering light activated wavelength of fluorescence of test analysis are carried out to sample solution.
9. fluorescence probe according to claim 8 identifies thiocyanate radical method, it is characterised in that: the fluorescent reagent it is dense
Degree is 10-5mol·L-1。
10. fluorescence probe according to claim 8 identifies thiocyanate radical method, it is characterised in that: described glimmering light activated
Excitation wavelength is 438nm, and when detecting thiocyanate radical, maximum fluorescence emission peak of the fluorescent reagent at 598nm wavelength is sharply
Enhancing.
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| CN113105387A (en) * | 2021-04-17 | 2021-07-13 | 贵州医科大学 | Cyanite ion fluorescent probe and preparation method and application thereof |
| CN113582917A (en) * | 2021-08-12 | 2021-11-02 | 广东工业大学 | Triphenylamine-quaternary ammonium salt type polymer and preparation method and application thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113105387A (en) * | 2021-04-17 | 2021-07-13 | 贵州医科大学 | Cyanite ion fluorescent probe and preparation method and application thereof |
| CN113582917A (en) * | 2021-08-12 | 2021-11-02 | 广东工业大学 | Triphenylamine-quaternary ammonium salt type polymer and preparation method and application thereof |
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