CN107033111A - A kind of synthesis and application of the near infrared fluorescent probe for detecting hydrogen sulfide - Google Patents
A kind of synthesis and application of the near infrared fluorescent probe for detecting hydrogen sulfide Download PDFInfo
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- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
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Abstract
The invention belongs to the fluorescence probe field of sensing technologies of analytical chemistry, it is related to a kind of new high selectivity, high sensitivity, the synthetic method of the near infrared fluorescent probe of Visual retrieval hydrogen sulfide and application.Methods described includes ethyl acetoacetate and bigcatkin willow aldehyde reaction obtaining presoma, it is subsequently added into N, in N dimethylformamides (DMF) and POCl3, reaction obtains coumarin derivative, then is reacted at room temperature with malononitrile and catalyst and obtain above-mentioned fluorescence probe.The probe preparation method is simple, can high selectivity responded in high sensitivity with hydrogen sulfide, show as Fluorescence Increasing, realize Visual retrieval.
Description
Technical field
The invention belongs to the fluorescence probe field of sensing technologies of analytical chemistry, it is related to a kind of high selectivity, high sensitivity, near
The synthesis and application of infrared, Visual retrieval hydrogen sulfide fluorescence probe.
Background technology
With the production of industrial or agricultural, hydrogen sulfide is prevalent in nature, the pollution pole of excessive hydrogen sulfide to environment
It is serious, at the same it is also very big to biological harm, the various diseases of the mankind may be caused, such as：Alzheimer's disease, glycosuria
Disease, chronic hepatitis, Down syndrome etc..Thus, develop a kind of effective, accurate, easily detection hydrogen sulfide method and seem outstanding
To be important.
Constantly explored by people, there are many hydrogen sulfide methods for measuring to be suggested and obtain certain success.Pass
The Methods For Determining Hydrogen Sulfide of system, such as：Silver sulfide colorimetric method；Methylene-blue colorimetric method；Lead acetate paper method；Coulomb equation；
Chromatography of ions etc., the measure applied to hydrogen sulfide that these methods are extensively sent out also obtains ten-strike very, but they are wherein
There is also some defects, such as：Some Instrument measuring complex operations, cost is more expensive, additionally, due to some hydrogen sulfide containing sample liquids
Composition becomes increasingly complex, and some colorimetric methods can not Accurate Determining hydrogen sulfide content etc..Overcome difficulties, break through limitation, it is constantly deep
Enter research, a kind of method that new fluorescence probe determines hydrogen sulfide is presented in people at the moment and constantly developed.Fluorescence probe
The hydrogen sulfide content in solution can not only be determined, while applying also for the measure of hydrogen sulfide in biological tissue or cell, is had
It is of great significance.Therefore, a kind of high selectivity, high sensitivity, near-infrared, the fluorescence of Visual retrieval hydrogen sulfide are developed
Probe not only has the significance of environmental monitoring, and the clinical diagnosis tool of some diseases is of great significance.
The present invention relates to a kind of fluorescence probe of new detection hydrogen sulfide.We pass through coumarin derivative and malononitrile
Reaction, design a kind of new fluorescence probe.The probe presents its high selectivity on detection hydrogen sulfide, high sensitivity,
Visual advantage.It will be further appreciated that the probe be it is a kind of can Dual channel detection probe, excited using different wavelength
Probe after being responded with hydrogen sulfide, has stronger fluorescence in visible region and near infrared region, and in the fluorescence of near infrared region
It is the fluorescence that probe exists always in itself, fluorescence internal standard can be used as.Near-infrared fluorescent is when carrying out biological tissue or cell detection
Small is damaged to living organism.Meanwhile, absorption of the biological tissue near infrared region fluorescence is minimum, and near infrared light can penetrate biological group
The distance knitted is big, the tissue and organ of deep layer can be detected and is imaged.Therefore, the probe has before potential application
Scape.
The content of the invention
It is an object of the invention to provide a kind of high selectivity, high sensitivity, near-infrared, Visual retrieval hydrogen sulfide fluorescence
The synthesis of probe and the application of the probe.
According to the present invention, the method that fluorescent probe molecule is prepared by coumarin derivative and malononitrile reaction, its
Synthesis step is specifically included：(1) ethyl acetoacetate and salicylide dissolving in ethanol, are added dropwise base catalyst, are stirred at reflux 7
~14 hours.Stop reaction, be cooled to room temperature, be filtrated to get bright yellow precipitate, washed once with ice absolute ethyl alcohol.Absolute ethyl alcohol
Recrystallization, obtains yellow solid product 7- diethylin benzopyrones.(2) in three-necked flask, DMF solvent, cooling are added
Stirring is to -5~10 DEG C, and POCl is slowly added dropwise in constant pressure funnel3, 7- diethylin benzopyrones are slow added into, -5
Stirred at~10 DEG C, then in 70-90 DEG C of stirring, stop stirring, be cooled to room temperature, it is deep that reaction solution is added dropwise into progress in trash ice
Degree cooling, pH is adjusted with sodium carbonate liquor, is filtrated to get solid, and frozen water washing, vacuum drying, column chromatography for separation purification obtains Huang
The coumarin derivative of color；(3) above-mentioned coumarin derivative and malononitrile are dissolved in absolute ethyl alcohol, base catalyst are added dropwise,
It is stirred at room temperature, TLC monitorings, reaction terminates, and extraction is collected, column chromatography for separation purification can obtain fluorescence probe.
The art of this patent has advantages below compared with prior art：
1. selectivity is good, common ion and similar compound are not disturbed substantially；
2. sensitivity is high, test limit reaches 13.9nM；
3. synthesis is simple, easy to detect；
4. near-infrared is visualized, small to biological bulk damage, with potential application foreground.
Brief description of the drawings
Fig. 1 is the fluorescence titration figure at the 500nm of probe in detecting hydrogen sulfide
Fig. 2 is the fluorescence titration figure at the 650nm of probe in detecting hydrogen sulfide
Fig. 3 is the linear relationship chart of fluorescence intensity change after probe response various concentrations hydrogen sulfide
Fig. 4 is the selective figure of probe.
Fig. 5 schemes for the pH optimizations of probe.
Fig. 6 is the Visual retrieval figure of probe.
Embodiment
Below with reference to embodiment, the present invention will be further described, and embodiments of the invention are merely to illustrate the present invention's
Technical scheme, and the non-limiting present invention.
Embodiment 1
Ethyl acetoacetate (3.17g, 24mmol), salicylide (3.77g, 19.5mmol) is dissolved in 20ml ethanol, drop
Plus 3 and drip piperidines, be stirred at reflux 10 hours.Stop reaction, be cooled to room temperature, be filtrated to get bright yellow precipitate, use ice absolute ethyl alcohol
(5ml) washed once.Absolute ethyl alcohol is recrystallized, and obtains 7- diethylin benzopyrone (yellow solid 4.74g, yield
91.4%).In 25ml three-necked flasks, 5 DEG C of 8ml DMF cooling and stirrings, POCl is slowly added dropwise in constant pressure funnel3(3.5ml,
23.0mmol) (maintain the temperature at 5 DEG C), be slowly added to compound 1 (1g, 3.9mmol), reaction is stirred 3h, then existed at 5 DEG C
2h is reacted at room temperature, is transferred to oil bath pan and is heated 80 DEG C of reaction 7h.Stop reaction, be cooled to room temperature, be added dropwise in trash ice and carry out
Depth is cooled down, with pH=8 (process maintains the temperature at less than 10 DEG C) in sodium carbonate, is filtrated to get solid, and frozen water is washed, and 50 DEG C true
Sky is dried, and column chromatography for separation purification obtains coumarin derivative (523mg, yield 43.9%).Above-mentioned coumarin derivative
(520mg, 1.7mmol) and malononitrile (112.5mg, 1.7mmol) are dissolved in anhydrous 10ml ethanol, are added dropwise 4 and are dripped piperidines, room temperature is stirred
Mix, TLC monitoring reactions, reaction terminates separating-purifying and obtains fluorescence probe (148mg, yield 24.7%).1H NMR：δ8.66(s,
1H), 8.41~8.32 (q, 2H), 7.72 (d, J=12.0Hz, 1H), 6.88 (d, J=8.0Hz, 1H), 6.67 (s, 1H), 3.56
~3.51 (q, 4H), 1.16 (t, J=4.0Hz, 6H).13C NMR：158.61,157.19,156.91,153.95,147.44,
145.24,132.80,120.48,114.86,113.24,111.40,111.35,109.29,96.32,81.74,45.12,
12.91。
Embodiment 2
Ethyl acetoacetate (2.0g, 15.1mmol), salicylide (1.93g, 10mmol) is dissolved in 15ml ethanol, is added dropwise
5 drop piperidines, are stirred at reflux 8 hours.Stop reaction, be cooled to room temperature, be filtrated to get bright yellow precipitate, with 8ml ice absolute ethyl alcohols
It washed once.Absolute ethyl alcohol is recrystallized, and obtains 7- diethylin benzopyrone (yellow solid 2.31g, yield 89.1%).
In 25ml three-necked flasks, 0 DEG C of 6ml DMF cooling and stirrings, POCl is slowly added dropwise in constant pressure funnel3(4.7ml, 30.9mmol) (is kept
Temperature is at 0 DEG C), compound 1 (1.5g, 5,85mmol) is slowly added to, reaction is stirred 4h at 0 DEG C, then reacted at room temperature
4h, is transferred to oil bath pan and heats 75 DEG C of reaction 8h.Stop reaction, be cooled to room temperature, be added dropwise to progress depth cooling, carbon in trash ice
With pH=7 (process maintains the temperature at less than 10 DEG C) in sour sodium, solid, frozen water washing, 40 DEG C of vacuum drying, post layer are filtrated to get
Analysis separating-purifying obtains coumarin derivative (790mg, yield 44.3%).Above-mentioned coumarin derivative (790mg, 2.58mmol)
It is dissolved in malononitrile (250mg, 3.8mmol) in anhydrous 15ml ethanol, is added dropwise 6 and drips piperidines, be stirred at room temperature, TLC monitoring reactions, instead
Separating-purifying should be terminated and obtain fluorescence probe (248mg, yield 27.2%).
Embodiment 3
Ethyl acetoacetate (1.5g, 11.25mmol), salicylide (2.17g, 11.25mmol) is dissolved in 10ml ethanol,
It is added dropwise 4 and drips piperidines, is stirred at reflux 10 hours.Stop reaction, be cooled to room temperature, be filtrated to get bright yellow precipitate, with 10ml ice without
Water-ethanol washed once.Absolute ethyl alcohol is recrystallized, and obtains 7- diethylin benzopyrone (yellow solid 1.8g, yield
61.7%).In 25ml three-necked flasks, -5 DEG C of 10ml DMF cooling and stirrings, constant pressure funnel be slowly added dropwise POCl3 (2.3ml,
15mmol) (maintain the temperature at -5 DEG C), be slowly added to compound 1 (1.8g, 7.02mmol), reaction is stirred 6h at -5 DEG C, connect
And react 3h at room temperature, be transferred to oil bath pan and heat 90 DEG C of reaction 11h.Stop reaction, be cooled to room temperature, be added dropwise in trash ice
Carry out in depth cooling, sodium carbonate and pH=9 (process maintains the temperature at less than 0 DEG C), be filtrated to get solid, frozen water washing, 30
DEG C vacuum drying, column chromatography for separation purification obtain coumarin derivative (810mg, yield 37.8%).Above-mentioned coumarin derivative
(800mg, 2.61mmol) and malononitrile (2g, 20.9mmol) are dissolved in anhydrous 20ml ethanol, are added dropwise 5 and are dripped piperidines, are stirred at room temperature,
TLC monitoring reactions, reaction terminates separating-purifying and obtains fluorescence probe (286mg, yield 31.0%).
Application example 1：Such as Fig. 1, fluorescence titration excites the fluorescence of lower probe in itself very weak, such as in wavelength 420nm light
Fig. 2, probe has stronger transmitting light near infrared region under the exciting of wavelength 530nm light.When probe and hydrogen sulfide respond it
Afterwards, the fluorescence intensity at 500nm greatly strengthens, and the light intensity of near infrared region is constant, therefore the light of near-infrared can be used as internal standard fluorescence.
Such as Fig. 3, the hydrogen sulfide of probe and various concentrations shows good linear relationship, R2=0.997, test limit reaches 75nM, body
Reveal the high sensitivity of the probe.
Application example 2：Such as Fig. 4, Choice tests are separately added into different amino acid and often in identical test system
Some ions (1 seen:Arg,2:Trp,3:Pro,4:Ala,5:Thr,6:Gly,7:Na+,8:K+,9:Mg2+,10:Ca2+,11:
H2PO4 -,12:HPO4 2-,13:NO2 -,14:NO3 -,15:Br-,16:I-,17:Ac-,18:SO4 2-,19:SO3 2-,20:S2O3 2-,21:
Cys,22:Hcy,23:GSH,24:Probe,25:HS-), as a result show that these chaff interferences have little to no effect to probe, only
Just there is obvious change in fluorescence in the presence of hydrogen sulfide, embodied high selectivity of the probe to detection hydrogen sulfide.
Application example 3：Such as Fig. 5, pH optimizations keep testing changing pH value in the case of other test condition identicals
Experiment, it is known that probe can preferably respond hydrogen sulfide between pH=6~10.Finally we select pH=7.4 system to carry out
A series of test.
Application example 4：Such as Fig. 6, visualization application, under uviol lamp 365nm light, probe glows in itself, and with vulcanization
Then there is blue green light after hydrogen response.It is achieved thereby that Visual retrieval of the probe to hydrogen sulfide.
Claims (9)
1. a kind of synthesis and application of the near infrared fluorescent probe for detecting hydrogen sulfide, it is characterised in that specifically include following steps：
a：Ethyl acetoacetate and salicylide dissolving in ethanol, are added dropwise base catalyst, are stirred at reflux 7~14 hours, stop
Reaction, is cooled to room temperature, is filtrated to get bright yellow precipitate, washed once with ice absolute ethyl alcohol, absolute ethyl alcohol recrystallization, obtains Huang
Color solid product is 7- diethylin benzopyrones；
b：In three-necked flask, DMF solvent is added, cooling and stirring is to -5~10 DEG C, and POCl is slowly added dropwise in constant pressure funnel3, then
7- diethylin benzopyrones are slowly added to, are stirred at -5~10 DEG C, then in 70-90 DEG C of stirring, stop stirring, cooling
To room temperature, reaction solution is added dropwise to progress depth cooling in trash ice, pH is adjusted with sodium carbonate liquor, is filtrated to get solid, frozen water
Washing, vacuum drying, column chromatography for separation purifies the coumarin derivative for obtaining yellow；
c：Above-mentioned coumarin derivative and malononitrile are dissolved in absolute ethyl alcohol, base catalyst is added dropwise, is stirred at room temperature, TLC prisons
Survey, reaction terminates, extraction is collected, column chromatography for separation purification can obtain fluorescence probe.
2. the synthesis and application of a kind of near infrared fluorescent probe for detecting hydrogen sulfide according to claim 1, its feature exist
In described probe chemical name is (Z) -2- (3-chloro-3- (7- (diethylamino) -2-oxo-2H-chromen-
3-yl) allylidene) ma lononitrile, molecular structure is：
3. the synthesis and application of a kind of near infrared fluorescent probe for detecting hydrogen sulfide according to claim 1, its feature exist
In the base catalyst described in step a is piperidines or triethylamine.
4. the synthesis and application of a kind of near infrared fluorescent probe for detecting hydrogen sulfide according to claim 1, its feature exist
In, DMF was placed in 3~6h of stirring cooling at -5~10 DEG C by reaction described in step b before this, be slowly added dropwise phosphorus oxychloride reaction into
After thick liquid, 7- diethylin benzopyrones are slow added into, rear 70~90 DEG C of oil bath heating reacts 5~12 hours, instead
It is anhydrous state to answer condition.
5. the synthesis and application of a kind of near infrared fluorescent probe for detecting hydrogen sulfide according to claim 1, its feature exist
In, described in step b with sodium carbonate liquor adjust pH, its pH value be 7~9.
6. the synthesis and application of a kind of near infrared fluorescent probe for detecting hydrogen sulfide according to claim 1, its feature exist
In the mol ratio of coumarin derivative and malononitrile material described in step c is 1:1~10.
7. the synthesis and application of a kind of near infrared fluorescent probe for detecting hydrogen sulfide according to claim 1, its feature exist
In catalyst used is piperidines or triethylamine in the course of reaction described in step c, and consumption 2~8 drips.
8. the synthesis and application of a kind of near infrared fluorescent probe for detecting hydrogen sulfide according to claim 1, its feature exist
In the fluorescence probe described in step c need to detect hydrogen sulfide in acetonitrile and PBS different ratio system.
9. the synthesis and application of a kind of near infrared fluorescent probe for detecting hydrogen sulfide according to claim 1, its feature exist
In, the excitation wavelength selected during near infrared fluorescent probe described in step c detection hydrogen sulfide 400nm~450nm and 500nm~
550nm。
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108840818A (en) * | 2018-06-25 | 2018-11-20 | 山西大学 | It is a kind of for detecting the synthesis and application of the ratio colour pattern carbazoles fluorescence probe of hydrogen sulfide |
| CN109467551A (en) * | 2018-10-12 | 2019-03-15 | 曲靖师范学院 | The preparation process of the Coumarins fluorescent probe molecule of selective enumeration method GSH |
| CN110016008A (en) * | 2019-04-19 | 2019-07-16 | 南宁师范大学 | The fluorescence probe of specific recognition hydrogen polysulfide and biological thiol |
| CN111233804A (en) * | 2020-03-03 | 2020-06-05 | 山西大学 | Benzopyranoylium ion-coumarin derivative and synthetic method and application thereof |
| CN112778288A (en) * | 2021-01-22 | 2021-05-11 | 湖南大学 | Near-infrared solid-state light-emitting fluorescent probe and preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD141673A1 (en) * | 1979-02-21 | 1980-05-14 | Peter Czerney | PROCESS FOR THE PREPARATION OF 3 (1'-CHLORO-4'-CYAN-BUTADIENYL-1 ', 3') CUMARINES |
| CN103529009A (en) * | 2013-11-01 | 2014-01-22 | 厦门大学 | Method for detecting hydrogen sulfide in serum through near-infrared fluorescent probe Cy-Cl |
-
2017
- 2017-04-21 CN CN201710263822.2A patent/CN107033111B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD141673A1 (en) * | 1979-02-21 | 1980-05-14 | Peter Czerney | PROCESS FOR THE PREPARATION OF 3 (1'-CHLORO-4'-CYAN-BUTADIENYL-1 ', 3') CUMARINES |
| CN103529009A (en) * | 2013-11-01 | 2014-01-22 | 厦门大学 | Method for detecting hydrogen sulfide in serum through near-infrared fluorescent probe Cy-Cl |
Non-Patent Citations (1)
| Title |
|---|
| MING-YU WU,ET AL.,: "A real-time colorimetric and ratiometric fluorescent probe for sulfite", 《ANALYST》 * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108840818A (en) * | 2018-06-25 | 2018-11-20 | 山西大学 | It is a kind of for detecting the synthesis and application of the ratio colour pattern carbazoles fluorescence probe of hydrogen sulfide |
| CN108840818B (en) * | 2018-06-25 | 2021-09-28 | 山西大学 | Synthesis and application of colorimetric carbazole fluorescent probe for detecting hydrogen sulfide |
| CN109467551A (en) * | 2018-10-12 | 2019-03-15 | 曲靖师范学院 | The preparation process of the Coumarins fluorescent probe molecule of selective enumeration method GSH |
| CN109467551B (en) * | 2018-10-12 | 2021-12-14 | 曲靖师范学院 | Preparation process of coumarin fluorescent probe molecule for selectively detecting GSH |
| CN110016008A (en) * | 2019-04-19 | 2019-07-16 | 南宁师范大学 | The fluorescence probe of specific recognition hydrogen polysulfide and biological thiol |
| CN110016008B (en) * | 2019-04-19 | 2022-04-15 | 南宁师范大学 | Fluorescent probe for specifically recognizing hydrogen polysulfide and biological thiol |
| CN111233804A (en) * | 2020-03-03 | 2020-06-05 | 山西大学 | Benzopyranoylium ion-coumarin derivative and synthetic method and application thereof |
| CN112778288A (en) * | 2021-01-22 | 2021-05-11 | 湖南大学 | Near-infrared solid-state light-emitting fluorescent probe and preparation method and application thereof |
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Application publication date: 20170811 Assignee: Taizhou Xuefu Ecological Environment Research Center Co.,Ltd. Assignor: TAIZHOU University Contract record no.: X2023990000628 Denomination of invention: Synthesis and Application of a Near Infrared Fluorescence Probe for Detecting Hydrogen Sulfide Granted publication date: 20190806 License type: Common License Record date: 20230620 |