CN108276383A - A kind of fluorescence probe and preparation method thereof of identification iodide ion and recognition methods - Google Patents
A kind of fluorescence probe and preparation method thereof of identification iodide ion and recognition methods Download PDFInfo
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- CN108276383A CN108276383A CN201810138206.9A CN201810138206A CN108276383A CN 108276383 A CN108276383 A CN 108276383A CN 201810138206 A CN201810138206 A CN 201810138206A CN 108276383 A CN108276383 A CN 108276383A
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Abstract
The invention discloses a kind of fluorescence probe of identification iodide ion and preparation method thereof and recognition methods.Preparation method includes：1）4 bromobenzaldehydes are dissolved in ethyl alcohol, A product are obtained；2）2 acetylpyridines, potassium hydroxide and ammonium hydroxide are dissolved in ethyl alcohol, B product are obtained；3）A product and B product are reacted, is recrystallized after precipitation is filtered, obtains C product；4）Hybrid reaction in triethylamine is added in C product, 4 pyridine ethylene, palladium and triphenylphosphine, product is dissolved in chloroform, is recrystallized after being spin-dried for, D product are obtained；5）1,8 naphthalimide is suspended in N, in the mixture of N dimethylformamides and DMSO, sodium methoxide is added and stir and stands, Isosorbide-5-Nitrae dibromobutane is then added, precipitation filtering and will recrystallize, and obtain E product；6）N is added in D product, in N dimethylformamides, E product are added, ether is added, to precipitation is precipitated, filters and dries, obtain probe.The present invention, which has, identifies at low cost, simple and quick, sensitivity height, the good feature of selectivity.
Description
Technical field
The present invention relates to a kind of fluorescence probe and preparation method thereof and recognition methods, especially a kind of to identify the glimmering of iodide ion
Light probe and preparation method thereof and recognition methods.
Background technology
The identification and detection of anion all play an important roll in fields such as bio-sensing, chemical analysis and environment measurings.
In numerous anion, iodide ion is widely paid close attention to because of its important biomedical meaning.Iodine is that human body is essential
One of trace element, it grows human normal, neurodevelopment and thyroid function play a crucial role.However it is different
Normal iodide ion concentration level is typically related with disease, and iodine deficiency or excessive iodine can all lead to such as Thyroid Gland Swell, first
The diseases such as shape adenasthenia and hyperthyroidism influence the health of people, therefore the detection of iodide ion has very
Important meaning.
Fluorescence detection method receives researcher's favor due to its sensitivity and ease-to-operate.Secondly, for anion
Detection, since the ionic radius of anion is big, with probe occur electrostatic interaction during, selectivity it is poor；
Anion easily interacts with aqueous solution, for example forms hydrogen bond action.Anion has very important in life entity
Basic effect, so synthesis can identify that the fluorescence probe of anion becomes particularly important in aqueous solution.
At present, common iodide ion analysis method has Capillary Electrophoresis, chromatography, electrochemical method and atomic spectroscopy
Deng, but these instruments that method cost is relatively high, time-consuming, sample preparation procedure is complicated, needs are more expensive, these are all limited
The application of these detection methods in practice is made.Therefore, developing low-cost, simple and quick, high sensitivity, highly selective inspection
It is always the important research content that iodide ion quantitatively detects to survey new method.
Invention content
The object of the present invention is to provide a kind of fluorescence probe of identification iodide ion and preparation method thereof and recognition methods.
The present invention, which has, identifies at low cost, simple and quick, sensitivity height, the good feature of selectivity.
Technical scheme of the present invention：
A kind of fluorescence probe of identification iodide ion, the molecular formula of probe is C44H34BrN5O2 +, structural formula is：
Wherein, n=4,6,8,10 or 12.
A kind of preparation method of the fluorescence probe of identification iodide ion above-mentioned, includes the following steps：
1）4- bromobenzaldehydes are dissolved in ethyl alcohol, A product are obtained；
2）2- acetylpyridines, potassium hydroxide and ammonium hydroxide are dissolved in ethyl alcohol, B product are obtained；
3）A product and B product are mixed at -5-5 DEG C, stir 0.5-1.5h, are flowed back 0.5-1.5 days, then 0.5- is stirred at room temperature
Precipitation is filtered, is recrystallized with ethyl alcohol, obtain C product by 1.5h；
4）C product, 4- pyridines ethylene, palladium and triphenylphosphine are added in triethylamine and mixed, mixture is sealed in N2Atmosphere
Under reaction under high pressure bottle in, at 110-130 DEG C react 65-75h, product is dissolved in chloroform, is then spin-dried for, is carried out with ethyl alcohol is pure
Recrystallization, obtains D product；
5）1,8-naphthalimide is suspended in the mixture of n,N-Dimethylformamide and DMSO, sodium methoxide is then added
It is stirred at room temperature, is then allowed to stand to solution turned clear, Isosorbide-5-Nitrae-dibromobutane is then added, and stir 4-8 hours and fall back
In, so that solid crude product is slowly precipitated, by filtration of crude product and with ethyl alcohol recrystallization, obtains E product；
6）D product are added in n,N-Dimethylformamide, E product are then added, are heated to 75-85 DEG C, react 20-28h, second is added
Precipitation is precipitated in ether, filters, is washed twice with ether, dries, obtains probe.
The preparation method of the fluorescence probe of identification iodide ion above-mentioned, a concentration of 95% or more of the ethyl alcohol.
The preparation method of the fluorescence probe of identification iodide ion above-mentioned, the step 1）In, it is to add in every 30ml ethyl alcohol
Enter 2g 4- bromobenzaldehydes；The step 2）In, it is that 2.42g 2- acetylpyridines, 1.7g hydroxides are added in every 40ml ethyl alcohol
Potassium and 29ml ammonium hydroxide.
The preparation method of the fluorescence probe of identification iodide ion above-mentioned, the step 3）In, the mass ratio of A product and B product is
1：2, mixing temperature is 0 DEG C, is stirring 1h, flows back 1 day, then 1h is stirred at room temperature.
The preparation method of the fluorescence probe of identification iodide ion above-mentioned, the step 4）In, it is mixed in every 500mg C product
150mg 4- pyridines ethylene, 30mg palladiums, 102mg triphenylphosphines and 10ml triethylamines, reaction temperature is 120 DEG C, when reaction
Between be 72h, before being spin-dried for, be washed with distilled water organic phase 3 times, then with saturated common salt water washing organic phase 3 times.
The preparation method of the fluorescence probe of identification iodide ion above-mentioned, the step 5）In, 1,8-naphthalimide, first
The mass ratio of sodium alkoxide and 1,4- dibromobutanes is 1:1.3-2.6：3, reaction temperature is room temperature, and mixing time is 6 hours.
The preparation method of the fluorescence probe of identification iodide ion above-mentioned, the step 6）In, the mass ratio of D product and E product is
1：1, heating temperature is 80 DEG C, and the reaction time is for 24 hours.
A kind of recognition methods of the fluorescence probe of identification iodide ion above-mentioned, is that probe is dissolved in DMSO, then uses water
Dilution, obtains fluorescent reagent, sample to be identified is then added dropwise into fluorescent reagent, then carry out fluorescence excitation, and tests fluorescence and swash
The wavelength of fluorescence of hair.
The recognition methods of the fluorescence probe of identification iodide ion above-mentioned, a concentration of the 1.00 × 10 of the fluorescent reagent- 5mol·L-1, excitation wavelength 337nm, when recognizing iodide ion, the maximum fluorescence wavelength of reagent excitation is 560nm.
Beneficial effects of the present invention
This patent utilizes AIE for the first time（Such molecule but launches very strong fluorescence, this phenomenon when under state of aggregation or solid-state
It is named as aggregation-induced emission）Effect provides good application prospect to detect iodide ion in aqueous solution.Specific effect
It is：
1, the linear concentration minimum of quantitative analysis of the present invention for iodide ion in aqueous solution, quantitative analysis is 1.0 × 10- 6mol·L-1。
2, other that common anion not interference measurement coexists.
3, the present invention is easy to operate, and test result is visual, and analysis is more direct.
For the advantageous effect further illustrated the present invention, inventor has done following experiment：One, qualitative analysis is tested
1, in concentration range 10-6~10-4In the fluorescence probe aqueous solution of mol/L, when excitation wavelength is 337nm, with carbochain
For n=4, the maximum emission wavelength of fluorescence probe is 560nm, launch wavelength that there are two fluorescence probes, and maximum emission wavelength is
The places maximum emission wavelength 560nm fluorescence decline after iodide ion is added in 560nm, and constant at 400nm, fluorescence is eventually exhibited as blue
Fluorescence；The detection of iodide ion limits most down to 1.52 × 10-7 mol·L-1。
Two, test of quantitative analysis
1, the probe for weighing 7.52 milligrams, is dissolved with DMSO, is configured to 10.0 mL, and a concentration of 1.0 × 10-3mol·L-1, 1 100.0 mL volumetric flask is taken, the probe configured is poured into volumetric flask, graduation mark is diluted to aqueous solution, obtains
To a concentration of 1.00 × 10-5mol·L-1Probe, shake up, obtain fluorescent reagent；
2, it weighs top pure grade iodized salt and is configured to 10ml aqueous solutions, a concentration of the 1.00 × 10 of iodide ion-2 mol·L-1, root
According to needing to be diluted step by step with secondary water；
3, fluorescent reagent 1.00 × 10 is taken-5mol·L-1 Titer, toward cuvette in be added 3ml fluorescent reagents, be added dropwise respectively
Enter 1.00 × 10-3mol·L-1, 0-60 microlitres of iodide ion molecular blend solutions, introduce fluorescence spectrum and be measured, swash
Send out wavelength 337nm；
4, using iodide ion concentration as abscissa, fluorescence intensity is ordinate, obtains working curve；
5, sample measures, and takes fluorescent reagent standard solution, is added and is tested iodide ion solution, is diluted to scale, is placed at room temperature for 5 points
Clock, the quartz colorimetric utensil for introducing 3.0 cm carry out fluoremetry, sample concentration are found on working curve according to fluorescence intensity,
The present invention measures the concentration range 0~60 × 10 of iodide ion-6, the range of linearity 0~8 × 10-6（Linear equation y=- 17.746+
283.86）, detection sensitivity is high, and the minimum concentration value for detecting identification is 1.52 × 10-7mol·L-1。
Three, anti-interference test
It is 1.00 × 10 in concentration and probe concentration-5mol·L-1Reagent in, the places 560nm fluorescence decline after iodide ion is added, then distinguishes
It tests and other anion is added into fluorescent reagent（Br-, F-, SO42-, H2PO4-, NO3-, Cl-, HSO4-, BF4-, PF6-,
CH3COO-, ClO4-, S2-）, as a result as attached drawing 6 shows that only iodide ion makes probe molecule fluorescence decline, fluorescence at 560nm
Reagent only detects iodide ion, is not influenced by other above-mentioned anion.
Description of the drawings
Attached drawing 1 is fluorescence probe B sequence of chemical molecular structures；
Attached drawing 2 is fluorescence probe B molecules in organic solvent and aqueous solution（Aggregation）In change in fluorescence figure；
Attached drawing 3 is fluorescence probe B solution with the change in fluorescence figure that iodide ion is added；
Attached drawing 4 is the PH ranges that fluorescence probe B solution detects iodide ion；
5 fluorescence probe B solution of the attached drawing relational graph that fluorescence intensity changes with iodide ion concentration at 560nm and linearly interval work
Make curve；
6 fluorescence probe B solution of attached drawing detects the change in fluorescence figure of other interference anion of iodide ion.
Specific implementation mode
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：A kind of preparation method of the fluorescence probe of identification iodide ion, steps are as follows：
1）2g 4- bromobenzaldehydes are dissolved in every 30ml ethyl alcohol, obtain A product；
2）2.42g 2- acetylpyridines, 1.7g potassium hydroxide and 29ml ammonium hydroxide are dissolved in every 40ml ethyl alcohol, obtain B product；
3）By A product and B product at 0 DEG C in mass ratio 1:2 mixing, stir 1h, flow back 1 day, then 1h is stirred at room temperature, will precipitate
Filter, is recrystallized with ethyl alcohol, obtains C product；
4）150mg 4- pyridines ethylene, tri- second of 30mg palladiums, 102mg triphenylphosphines and 10ml are mixed into every 500mgC product
Mixture is sealed in N by amine2In reaction under high pressure bottle under atmosphere, 70h is reacted at 120 DEG C, product is washed with distilled water organic
Phase 3 times, then with after saturated common salt water washing organic phase 3 times, be dissolved in chloroform, be then spin-dried for, recrystallized, obtained with ethyl alcohol is pure
D product；
5）1,8-naphthalimide is suspended in the mixture of n,N-Dimethylformamide and DMSO, sodium methoxide is then added
It is stirred at room temperature, is then allowed to stand to solution turned clear, Isosorbide-5-Nitrae-dibromobutane is then added, and stir 6 hours and fall back,
So that solid crude product is slowly precipitated, by filtration of crude product and with ethyl alcohol recrystallization, obtains E product, wherein 1,8-naphthalimide,
The mass ratio of sodium methoxide and 1,4- dibromobutanes is 1:1.9：3；
6）The D product in mass ratio in n,N-Dimethylformamide：Product=1 E:1 ratio sequentially adds D product and E product, is heated to 80
DEG C, for 24 hours, ether is added in reaction, until precipitation is precipitated, filters, is washed twice with ether, dries, obtain probe.
A concentration of the 95% of the ethyl alcohol.
Embodiment 2：A kind of preparation method of the fluorescence probe of identification iodide ion, steps are as follows：
1）2g 4- bromobenzaldehydes are dissolved in every 30ml ethyl alcohol, obtain A product；
2）2.42g 2- acetylpyridines, 1.7g potassium hydroxide and 29ml ammonium hydroxide are dissolved in every 40ml ethyl alcohol, obtain B product；
3）By A product and B product at -5 DEG C in mass ratio 1:2 mixing, stir 0.5h, flow back 0.5 day, then 0.5h is stirred at room temperature,
Precipitation is filtered, is recrystallized with ethyl alcohol, obtains C product；
4）150mg 4- pyridines ethylene, tri- second of 30mg palladiums, 102mg triphenylphosphines and 10ml are mixed into every 500mgC product
Mixture is sealed in N by amine2In reaction under high pressure bottle under atmosphere, 75h is reacted at 110 DEG C, product is washed with distilled water organic
Phase 3 times, then with after saturated common salt water washing organic phase 3 times, be dissolved in chloroform, be then spin-dried for, recrystallized, obtained with ethyl alcohol is pure
D product；
5）1,8-naphthalimide is suspended in the mixture of n,N-Dimethylformamide and DMSO, sodium methoxide is then added
It is stirred at room temperature, is then allowed to stand to solution turned clear, Isosorbide-5-Nitrae-dibromobutane is then added, and stir 4 hours and fall back,
So that solid crude product is slowly precipitated, by filtration of crude product and with ethyl alcohol recrystallization, obtains E product, wherein 1,8-naphthalimide,
The mass ratio of sodium methoxide and 1,4- dibromobutanes is 1:1.3：3；
6）The D product in mass ratio in n,N-Dimethylformamide：Product=1 E:1 ratio sequentially adds D product and E product, is heated to 75
DEG C, 28h is reacted, ether is added, until precipitation is precipitated, filters, is washed twice with ether, dry, obtain probe.
A concentration of the 97% of the ethyl alcohol.
Embodiment 3：A kind of preparation method of the fluorescence probe of identification iodide ion, steps are as follows：
1）2g 4- bromobenzaldehydes are dissolved in every 30ml ethyl alcohol, obtain A product；
2）2.42g 2- acetylpyridines, 1.7g potassium hydroxide and 29ml ammonium hydroxide are dissolved in every 40ml ethyl alcohol, obtain B product；
3）By A product and B product at 5 DEG C in mass ratio 1:2 mixing, stir 1.5h, flow back 1.5 days, then 1.5h is stirred at room temperature, will
Precipitation filtering, is recrystallized with ethyl alcohol, obtains C product；
4）150mg 4- pyridines ethylene, tri- second of 30mg palladiums, 102mg triphenylphosphines and 10ml are mixed into every 500mgC product
Mixture is sealed in N by amine2In reaction under high pressure bottle under atmosphere, 65h is reacted at 130 DEG C, product is washed with distilled water organic
Phase 3 times, then with after saturated common salt water washing organic phase 3 times, be dissolved in chloroform, be then spin-dried for, recrystallized, obtained with ethyl alcohol is pure
D product；
5）1,8-naphthalimide is suspended in the mixture of n,N-Dimethylformamide and DMSO, sodium methoxide is then added
It is stirred at room temperature, is then allowed to stand to solution turned clear, Isosorbide-5-Nitrae-dibromobutane is then added, and stir 8 hours and fall back,
So that solid crude product is slowly precipitated, by filtration of crude product and with ethyl alcohol recrystallization, obtains E product, wherein 1,8-naphthalimide,
The mass ratio of sodium methoxide and 1,4- dibromobutanes is 1: 2.6：3；
6）The D product in mass ratio in n,N-Dimethylformamide：Product=1 E:1 ratio sequentially adds D product and E product, is heated to 85
DEG C, 20h is reacted, ether is added, until precipitation is precipitated, filters, is washed twice with ether, dry, obtain probe.
A concentration of the 96% of the ethyl alcohol.
Embodiment 4：A kind of recognition methods of the fluorescence probe of identification iodide ion, probe is dissolved in DMSO, water is then used
Dilution, is configured to a concentration of 1.00 × 10-5molL-1 fluorescent reagents, sample to be identified is then added dropwise into fluorescent reagent,
Then it is that 337nm laser carries out fluorescence excitation, and tests the wavelength of fluorescence of fluorescence excitation with wavelength, the maximum fluorescence of reagent excitation
Wavelength is 560nm, it was demonstrated that has recognized the iodide ion in solution.
Claims (10)
1. a kind of fluorescence probe of identification iodide ion, it is characterised in that：The molecular formula of probe is C44H34BrN5O2 +, structural formula is：
Wherein, n=4,6,8,10 or 12.
2. a kind of preparation method of the fluorescence probe of identification iodide ion according to claim 1, which is characterized in that including such as
Lower step：
1）4- bromobenzaldehydes are dissolved in ethyl alcohol, A product are obtained；
2）2- acetylpyridines, potassium hydroxide and ammonium hydroxide are dissolved in ethyl alcohol, B product are obtained；
3）A product and B product are mixed at -5-5 DEG C, stir 0.5-1.5h, are flowed back 0.5-1.5 days, then 0.5- is stirred at room temperature
Precipitation is filtered, is recrystallized with ethyl alcohol, obtain C product by 1.5h；
4）C product, 4- pyridines ethylene, palladium and triphenylphosphine are added in triethylamine and mixed, mixture is sealed in N2Under atmosphere
Reaction under high pressure bottle in, at 110-130 DEG C react 65-75h, product is dissolved in chloroform, is then spin-dried for, with ethyl alcohol it is pure carry out weight
Crystallization, obtains D product；
5）1,8-naphthalimide is suspended in the mixture of n,N-Dimethylformamide and DMSO, sodium methoxide is then added
It is stirred at room temperature, is then allowed to stand to solution turned clear, Isosorbide-5-Nitrae-dibromobutane is then added, and stir 4-8 hours and fall back
In, so that solid crude product is slowly precipitated, by filtration of crude product and with ethyl alcohol recrystallization, obtains E product；
6）D product are added in n,N-Dimethylformamide, E product are then added, are heated to 75-85 DEG C, react 20-28h, second is added
Ether is filtered, is washed twice with ether until precipitation is precipitated, and is dried, is obtained probe.
3. the preparation method of the fluorescence probe of identification iodide ion according to claim 2, it is characterised in that：The ethyl alcohol
A concentration of 95% or more.
4. the preparation method of the fluorescence probe of identification iodide ion according to claim 2, it is characterised in that：The step 1）
In, it is the addition 2g 4- bromobenzaldehydes in every 30ml ethyl alcohol；The step 2）In, it is that 2.42g is added in every 40ml ethyl alcohol
2- acetylpyridines, 1.7g potassium hydroxide and 29ml ammonium hydroxide.
5. the preparation method of the fluorescence probe of identification iodide ion according to claim 2, it is characterised in that：The step 3）
In, the mass ratio of A product and B product is 1：2, mixing temperature is 0 DEG C, is stirring 1h, flows back 1 day, then 1h is stirred at room temperature.
6. the preparation method of the fluorescence probe of identification iodide ion according to claim 2, it is characterised in that：The step 4）
In, mixing 150mg 4- pyridines ethylene, 30mg palladiums, 102mg triphenylphosphines and 10ml triethylamines in every 500mg C product, instead
It is 120 DEG C, reaction time 72h to answer temperature, before being spin-dried for, is washed with distilled water organic phase 3 times, then have with saturated common salt water washing
Machine phase 3 times.
7. the preparation method of the fluorescence probe of identification iodide ion according to claim 2, it is characterised in that：The step 5）
In, the mass ratio of 1,8-naphthalimide, sodium methoxide and Isosorbide-5-Nitrae-dibromobutane is 1:1.3-2.6：3, reaction temperature is room temperature,
Mixing time is 6 hours.
8. the preparation method of the fluorescence probe of identification iodide ion according to claim 2, it is characterised in that：The step 6）
In, the mass ratio of D product and E product is 1：1, heating temperature is 80 DEG C, and the reaction time is for 24 hours.
9. a kind of recognition methods for the fluorescence probe identifying iodide ion according to claim 1-8 any one of them, feature exist
In：It is that probe is dissolved in DMSO, is then diluted with water, obtain fluorescent reagent, sample to be identified is then added dropwise into fluorescent reagent,
Then fluorescence excitation is carried out, and tests the wavelength of fluorescence of fluorescence excitation.
10. the recognition methods of the fluorescence probe of identification iodide ion according to claim 9, it is characterised in that：The fluorescence
A concentration of the 1.00 × 10 of reagent-5mol·L-1, excitation wavelength 337nm, when recognizing iodide ion, the maximum of reagent excitation
Wavelength of fluorescence is 560nm.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109928912A (en) * | 2019-01-29 | 2019-06-25 | 贵州大学 | A kind of fluorescence probe identifying mercury ion and its preparation and recognition methods |
| CN110028952A (en) * | 2019-04-16 | 2019-07-19 | 哈尔滨工程大学 | A kind of iodide ion identification probe and preparation method thereof |
| CN110172339A (en) * | 2019-06-21 | 2019-08-27 | 贵州医科大学 | A kind of fluorescence probe and the preparation method and application thereof |
| CN110204566A (en) * | 2019-06-13 | 2019-09-06 | 贵州大学 | A kind of fluorescence probe and its preparation method and application for identifying and separating mercury ion |
| CN115010675A (en) * | 2022-01-30 | 2022-09-06 | 渤海大学 | Rapid detection I - Preparation method and application of ion covalent organic framework fluorescent probe |
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| US4075211A (en) * | 1973-06-20 | 1978-02-21 | Basf Aktiengesellschaft | Naphthalimide compounds and optical brighteners |
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| CN109928912A (en) * | 2019-01-29 | 2019-06-25 | 贵州大学 | A kind of fluorescence probe identifying mercury ion and its preparation and recognition methods |
| CN110028952A (en) * | 2019-04-16 | 2019-07-19 | 哈尔滨工程大学 | A kind of iodide ion identification probe and preparation method thereof |
| CN110028952B (en) * | 2019-04-16 | 2022-01-14 | 哈尔滨工程大学 | Iodide ion recognition probe and preparation method thereof |
| CN110204566A (en) * | 2019-06-13 | 2019-09-06 | 贵州大学 | A kind of fluorescence probe and its preparation method and application for identifying and separating mercury ion |
| CN110172339A (en) * | 2019-06-21 | 2019-08-27 | 贵州医科大学 | A kind of fluorescence probe and the preparation method and application thereof |
| CN115010675A (en) * | 2022-01-30 | 2022-09-06 | 渤海大学 | Rapid detection I - Preparation method and application of ion covalent organic framework fluorescent probe |
| CN115010675B (en) * | 2022-01-30 | 2023-08-01 | 渤海大学 | Quick detection I - Preparation method and application of ionic covalent organic framework fluorescent probe |
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