CN107033111B - A kind of synthesis and application of the near infrared fluorescent probe detecting hydrogen sulfide - Google Patents
A kind of synthesis and application of the near infrared fluorescent probe detecting hydrogen sulfide Download PDFInfo
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Abstract
The invention belongs to the fluorescence probe field of sensing technologies of analytical chemistry, are related to the synthetic method and application of a kind of novel highly selective, highly sensitive, Visual retrieval hydrogen sulfide near infrared fluorescent probe.The method includes ethyl acetoacetate and bigcatkin willow aldehyde reaction are obtained presoma, it is subsequently added into N, in dinethylformamide (DMF) and phosphorus oxychloride, reaction obtains coumarin derivative, then reacts to obtain above-mentioned fluorescence probe at room temperature with malononitrile and catalyst.The probe preparation method is simple, highly selective can respond in high sensitivity with hydrogen sulfide, show as fluorescence enhancement, realize Visual retrieval.
Description
Technical field
The invention belongs to the fluorescence probe field of sensing technologies of analytical chemistry, are related to a kind of highly selective, highly sensitive, close
The synthesis and application of infrared, Visual retrieval hydrogen sulfide fluorescence probe.
Background technique
With the production of industrial or agricultural, hydrogen sulfide is prevalent in nature, pollution pole of the excessive hydrogen sulfide to environment
It is serious, while also very big to the harm of biology, may cause the various diseases of the mankind, such as: Alzheimer's disease, glycosuria
Disease, chronic hepatitis, Down syndrome etc..Thus, developing the method that one kind effectively, accurately, easily detects hydrogen sulfide seems outstanding
It is important.
It is constantly explored by people, is suggested there are many hydrogen sulfide method for measuring and obtains certain success.It passes
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 measurement 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 measurings are complicated for operation, and cost is more expensive, additionally, due to some hydrogen sulfide containing sample liquids
Ingredient becomes increasingly complex, some colorimetric methods can not Accurate Determining hydrogen sulfide content etc..It overcomes difficulties, breaks through limitation, it is continuous deep
Enter research, a kind of method of novel fluorescence probe measurement hydrogen sulfide is presented in people at the moment and constantly develops.Fluorescence probe
The hydrogen sulfide content in solution can not only be measured, while applying also for the measurement of hydrogen sulfide in biological tissue or cell, is had
It is of great significance.Therefore, the fluorescence of a kind of highly selective, highly sensitive, near-infrared, Visual retrieval hydrogen sulfide is developed
Probe not only has the significance of environmental monitoring, but also has a very important significance to the clinical diagnosis of some diseases.
The present invention relates to a kind of fluorescence probes of novel detection hydrogen sulfide.We pass through coumarin derivative and malononitrile
Reaction, design a kind of novel fluorescence probe.The probe presents its highly selective, high sensitivity on detection hydrogen sulfide,
Visual advantage.It will be further appreciated that the probe be it is a kind of can Dual channel detection probe, utilize different wavelength excitations
Probe with after hydrogen sulfide response, has stronger fluorescence, and the fluorescence near infrared region in visible region and near infrared region
It is the fluorescence that probe itself always exists, can be used as fluorescence internal standard.Near-infrared fluorescent is when carrying out biological tissue or cell detection
Living organism is damaged small.Meanwhile biological tissue is minimum to the absorption of near infrared region fluorescence, near infrared light can penetrate biological group
The distance knitted is big, can tissue to deep layer and organ detected and be imaged.Therefore, before which has potential application
Scape.
Summary of the invention
The object of the present invention is to provide a kind of highly selective, highly sensitive, near-infrareds, the fluorescence of Visual retrieval hydrogen sulfide
The synthesis of probe and the application of the probe.
It is according to the present invention, described that the method for preparing fluorescent probe molecule is reacted with malononitrile by coumarin derivative,
Synthesis step specifically includes: (1) in ethanol, basic catalyst is added dropwise in ethyl acetoacetate and the dissolution of diethylin salicylide,
It is stirred at reflux 7~14 hours.Stop reaction, is cooled to room temperature, bright yellow precipitate is obtained by filtration, wash one with ice dehydrated alcohol
It is secondary.Dehydrated alcohol recrystallization, obtains yellow solid product 7- diethylin benzopyrone.(2) it in three-necked flask, is added
DMF solvent, for cooling and stirring to -5~10 DEG C, POCl is slowly added dropwise in constant pressure funnel3, it is slow added into 7- diethylin benzo
Pyranone stirs at -5~10 DEG C, then stirs at 70-90 DEG C, stops stirring, is cooled to room temperature, reaction solution is added dropwise to
It is cooling that depth is carried out in trash ice, adjusts pH with sodium carbonate liquor, and solid, ice water washing, vacuum drying, column chromatography point is obtained by filtration
The coumarin derivative of yellow is obtained from purification；(3) above-mentioned coumarin derivative and malononitrile are dissolved in dehydrated alcohol, are added dropwise
Basic catalyst is stirred at room temperature, and TLC monitoring, reaction terminates, and extraction is collected, and fluorescence probe can be obtained in column chromatography for separation purification.
The art of this patent has the advantage that compared with prior art
1. selectivity is good, common ion and similar compound does not interfere substantially；
2. high sensitivity, detection limit reaches 13.9nM；
3. synthesis is simple, easy to detect；
4. near-infrared visualizes, small to biological bulk damage, there is potential application foreground.
Detailed description of the invention
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 concentration hydrogen sulfide
Fig. 4 is the selective figure of probe.
Fig. 5 is that the pH of probe optimizes figure.
Fig. 6 is the Visual retrieval figure of probe.
Specific embodiment
Below with reference to embodiment, the present invention will be further described, and the embodiment of the present invention is merely to illustrate of the invention
Technical solution, and the non-limiting present invention.
Embodiment 1
Ethyl acetoacetate (3.17g, 24mmol), diethylin salicylide (3.77g, 19.5mmol) are dissolved in 20ml second
In alcohol, 3 drop piperidines are added dropwise, are stirred at reflux 10 hours.Stop reaction, be cooled to room temperature, bright yellow precipitate be obtained by filtration, with ice without
Water-ethanol (5ml) washed once.Dehydrated alcohol recrystallization, obtaining 7- diethylin benzopyrone, (yellow solid 4.74g is produced
Rate 91.4%).In 25ml three-necked flask, 5 DEG C of 8ml DMF cooling and stirring, POCl is slowly added dropwise in constant pressure funnel3(3.5ml,
It 23.0mmol) (maintains the temperature at 5 DEG C), is slowly added to compound 1 (1g, 3.9mmol), 3h is stirred in reaction at 5 DEG C, is then existed
2h is reacted at room temperature, is transferred to oil bath pan and is heated 80 DEG C of reaction 7h.Stop reaction, is cooled to room temperature, is added dropwise in trash ice and carries out
Depth is cooling, with pH=8 (process maintains the temperature at 10 DEG C or less) in sodium carbonate, solid is obtained by filtration, ice water washing, 50 DEG C true
Sky is dry, and column chromatography for separation purifies to obtain coumarin derivative (523mg, yield 43.9%).Above-mentioned coumarin derivative
(520mg, 1.7mmol) and malononitrile (112.5mg, 1.7mmol) are dissolved in anhydrous 10ml ethyl alcohol, and 4 drop piperidines are added dropwise, and room temperature is stirred
It mixes, TLC monitoring reaction, reaction terminates separating-purifying and obtains fluorescence probe (148mg, yield 24.7%).1H NMR: δ 8.66 (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).13CNM: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), diethylin salicylide (1.93g, 10mmol) are dissolved in 15ml second
In alcohol, 5 drop piperidines are added dropwise, are stirred at reflux 8 hours.Stop reaction, is cooled to room temperature, bright yellow precipitate is obtained by filtration, with 8ml ice
Dehydrated alcohol washed once.Dehydrated alcohol recrystallization, obtains 7- diethylin benzopyrone (yellow solid 2.31g, yield
89.1%).In 25ml three-necked flask, 0 DEG C of 6ml DMF cooling and stirring, POCl is slowly added dropwise in constant pressure funnel3(4.7ml,
It 30.9mmol) (maintains the temperature at 0 DEG C), is slowly added to compound 1 (1.5g, 5,85mmol), reaction stirs 4h at 0 DEG C, connects
React 4h at room temperature, be transferred to oil bath pan heat 75 DEG C of reaction 8h.Stop reaction, is cooled to room temperature, is added dropwise in trash ice
It is cooling to carry out depth, with pH=7 (process maintains the temperature at 10 DEG C or less) in sodium carbonate, solid is obtained by filtration, ice water washs, and 40
DEG C vacuum drying, column chromatography for separation purifies to obtain coumarin derivative (790mg, yield 44.3%).Above-mentioned coumarin derivative
(790mg, 2.58mmol) and malononitrile (250mg, 3.8mmol) are dissolved in anhydrous 15ml ethyl alcohol, and 6 drop piperidines are added dropwise, and room temperature is stirred
It mixes, TLC monitoring reaction, reaction terminates separating-purifying and obtains fluorescence probe (248mg, yield 27.2%).
Embodiment 3
Ethyl acetoacetate (1.5g, 11.25mmol), diethylin salicylide (2.17g, 11.25mmol) are dissolved in
In 10ml ethyl alcohol, 4 drop piperidines are added dropwise, are stirred at reflux 10 hours.Stop reaction, be cooled to room temperature, bright yellow precipitate is obtained by filtration,
It washed once with 10ml ice dehydrated alcohol.Dehydrated alcohol recrystallization, obtains 7- diethylin benzopyrone (yellow solid
1.8g, yield 61.7%).In 25ml three-necked flask, -5 DEG C of cooling and stirring of 10ml DMF, POCl is slowly added dropwise in constant pressure funnel3
(2.3ml, 15mmol) (maintains the temperature at -5 DEG C), is slowly added to compound 1 (1.8g, 7.02mmol), and reaction is stirred at -5 DEG C
6h is mixed, then reacts 3h at room temperature, oil bath pan is transferred to and heats 90 DEG C of reaction 11h.Stop reaction, be cooled to room temperature, is added dropwise
It is cooling to enter to carry out depth in trash ice, with pH=9 (process maintains the temperature at 0 DEG C or less) in sodium carbonate, solid, ice water is obtained by filtration
Washing, 30 DEG C of vacuum drying, column chromatography for separation purify to obtain coumarin derivative (810mg, yield 37.8%).Above-mentioned cumarin
Derivative (800mg, 2.61mmol) and malononitrile (2g, 20.9mmol) are dissolved in anhydrous 20ml ethyl alcohol, and 5 drop piperidines, room is added dropwise
Temperature stirring, TLC monitoring reaction, reaction terminate separating-purifying and obtain fluorescence probe (286mg, yield 31.0%).
Application example 1: such as Fig. 1, fluorescence titration, the fluorescence of probe itself is very weak under the light excitation of wavelength 420nm, such as
Fig. 2, probe has stronger transmitting light near infrared region under the excitation of the light of wavelength 530nm.When probe and hydrogen sulfide respond it
Afterwards, the fluorescence intensity at 500nm greatly enhances, 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 concentration shows good linear relationship, R2=0.997, detection 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 ion (1:Arg, 2:Trp, 3:Pro, 4:Ala, 5:Thr, 6:Gly, the 7:Na seen+,8:K+,9:Mg2+,10:Ca2+,11:
H2PO4 -,12:HPO4 2-,3:NO2 -,14:NO3 -,15:Br-,16:I-,17:Ac-,18:SO4 2-,19:SO3 2-,20:S2O3 2-,1:
Cys,2:Hcy,23:GSH,24:Probe,25:HS-), these chaff interferents have little effect probe as the result is shown, only when
Just there is apparent change in fluorescence in the presence of hydrogen sulfide, has embodied the probe to the highly selective of detection hydrogen sulfide.
Application example 3: it if Fig. 5, pH optimize, keeps testing change pH value in the identical situation of other test conditions
Experiment, it is known that probe can preferably respond hydrogen sulfide between pH=6~10.Finally we select the system of pH=7.4 to carry out
A series of test.
Application example 4: such as Fig. 6, visualization application, under ultraviolet lamp 365nm light, probe itself glows, and with vulcanization
Then there is blue green light after hydrogen response.To realize probe to the Visual retrieval of hydrogen sulfide.
Claims (9)
1. a kind of synthesis for the near infrared fluorescent probe for detecting hydrogen sulfide, which is characterized in that specifically includes the following steps:
A: ethyl acetoacetate and the dissolution of diethylin salicylide in ethanol, are added dropwise basic catalyst, it is small to be stirred at reflux 7~14
When, stop reaction, is cooled to room temperature, bright yellow precipitate is obtained by filtration, washed once with ice dehydrated alcohol, dehydrated alcohol is tied again
Crystalline substance, obtaining yellow solid product is 7- diethylin benzopyrone；
B: in three-necked flask, DMF solvent is added, for cooling and stirring to -5~10 DEG C, POCl is slowly added dropwise in constant pressure funnel3, then
It is slowly added to 7- diethylin benzopyrone, is stirred at -5~10 DEG C, is then stirred at 70-90 DEG C, stirring is stopped, it is cooling
To room temperature, reaction solution is added dropwise in trash ice and carries out depth cooling, adjusted pH with sodium carbonate liquor, solid, ice water is obtained by filtration
Washing, vacuum drying, column chromatography for separation purify to obtain the coumarin derivative of yellow；
C: above-mentioned coumarin derivative and malononitrile are dissolved in dehydrated alcohol, and basic catalyst is added dropwise, is stirred at room temperature, TLC prison
It surveys, reaction terminates, and extraction is collected, and fluorescence probe can be obtained in column chromatography for separation purification；
The probe chemical name is (Z) -2- (3-chloro-3- (7- (diethylamino) -2-oxo-2H-chromen-
3-yl) allylidene) ma lononitrile, molecular structure are as follows:
2. a kind of synthesis of near infrared fluorescent probe for detecting hydrogen sulfide according to claim 1, which is characterized in that step
Basic catalyst described in a is piperidines or triethylamine.
3. a kind of synthesis of near infrared fluorescent probe for detecting hydrogen sulfide according to claim 1, which is characterized in that step
DMF is placed at -5~10 DEG C stirs cooling 3~6h before this by reaction described in b, and phosphorus oxychloride reaction is slowly added dropwise into thick shape liquid
After body, it is slow added into 7- diethylin benzopyrone, 70~90 DEG C of rear oil bath heating are reacted 5~12 hours, reaction condition
For anhydrous state.
4. a kind of synthesis of near infrared fluorescent probe for detecting hydrogen sulfide according to claim 1, which is characterized in that step
PH is adjusted with sodium carbonate liquor described in b, pH value is 7~9.
5. a kind of synthesis of near infrared fluorescent probe for detecting hydrogen sulfide according to claim 1, which is characterized in that step
The molar ratio of coumarin derivative described in c and malononitrile substance is 1:1~10.
6. a kind of synthesis of near infrared fluorescent probe for detecting hydrogen sulfide according to claim 1, which is characterized in that step
Basic catalyst used in reaction process described in c is piperidines or triethylamine, and dosage 2~8 is dripped.
7. a kind of synthesis of near infrared fluorescent probe for detecting hydrogen sulfide according to claim 1, which is characterized in that close red
Outer fluorescence probe is for detecting hydrogen sulfide.
8. a kind of synthesis of near infrared fluorescent probe for detecting hydrogen sulfide according to claim 7, which is characterized in that described
Near infrared fluorescent probe need to detect hydrogen sulfide in the different ratio system of acetonitrile and PBS.
9. a kind of synthesis of near infrared fluorescent probe for detecting hydrogen sulfide according to claim 7, which is characterized in that described
Near infrared fluorescent probe when detecting hydrogen sulfide the excitation wavelength selected in 400nm~450nm and 500nm~550nm.
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| 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 |
| CN110016008B (en) * | 2019-04-19 | 2022-04-15 | 南宁师范大学 | Fluorescent probe for specifically recognizing hydrogen polysulfide and biological thiol |
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| CN112778288B (en) * | 2021-01-22 | 2022-08-09 | 湖南大学 | Near-infrared solid-state light-emitting fluorescent probe and preparation method and application thereof |
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| A real-time colorimetric and ratiometric fluorescent probe for sulfite;Ming-Yu Wu,et al.,;《Analyst》;20130308;第138卷;第3018–3025页 |
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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 |
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