CN107629786B - 2-methylimidazole quinoline is as pH value and Fe3+The application of difunctional fluorescence probe and its fluorescence probe - Google Patents
2-methylimidazole quinoline is as pH value and Fe3+The application of difunctional fluorescence probe and its fluorescence probe Download PDFInfo
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- CN107629786B CN107629786B CN201710996321.5A CN201710996321A CN107629786B CN 107629786 B CN107629786 B CN 107629786B CN 201710996321 A CN201710996321 A CN 201710996321A CN 107629786 B CN107629786 B CN 107629786B
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Abstract
The present invention relates to pH probe and metal ions to identify application field, and in particular to a kind of 2-methylimidazole quinoline is as pH value and Fe3+The application of difunctional fluorescence probe, and it is manufactured for pH sensing and Fe using 2-methylimidazole quinoline3+The difunctional fluorescence probe of detection.Beneficial effects of the present invention: the fluorescent material 2-methylimidazole quinoline toxic side effect is small, the good, high sensitivity of selectivity, finds it for the first time with good fluorescence characteristic and is applied to fluorescence probe field.The fluorescent chemicals synthesis mechanism is mature, and at low cost and high water solubility is, it can be achieved that aqueous acid medium (2.0~5.0) pH measurement and Fe in physiological environment3+Identification and quantitative detection.
Description
Technical field
The present invention relates to pH probes and metal ion to identify application field, is free of Representative fluorescence in particular to one kind
The small molecule 2-methylimidazole quinoline of group is as pH value and Fe3+Application on difunctional fluorescence probe.
Background technique
It is well known that the photoluminescent property of some organic compounds may be used to indicate pH value in destination media with the variation of pH
Change.Fluorescence probe is mainly used in bioanalytical chemistry and cell biology at present, and abnormal pH variation can be led
Cause cell functional disorders, especially when internal pH under acidic conditions, the effect of cell, which dies down, can cause its metabolism to slow down,
Organ function is had some impact on.And fluorescence probe measurement pH can be using mitigation mode operation real-time monitoring internal pH
DYNAMIC DISTRIBUTION and regional change.Equally, iron is highest one kind of content in micro elements needed by human, health and disease with the mankind
Disease is closely related.Free state Fe in organism3+Overload causes a variety of liver diseases, diabetes, cardiovascular and cerebrovascular disease etc..This
Outer iron is also one of the most abundant metallic element in the earth's crust, is the sensory properties index of Drinking Water detection.Iron can come in water
From in natural environment and industrial wastewater pollution, when content is exceeded, threat is generated to residents ' health.Therefore, accurately quantitative analysis
Iron content has important practical significance to the treatment and prevention of disease in human body and in drinking water.
In recent years, the material with optical property has received widespread attention in information sensing field.Wherein have typical raw
The conventional fluorescent probe of color group is since synthesis process is more complex, easy self aggregation in water, and toxicity is big, makes its answering in water phase
With receiving certain restrictions.Researchers' discovery at present is some monofunctional to be contained containing the letter such as primary amine, secondary amine, tertiary amine and amide
Nitrogen micromolecular also has fluorescence property, but since correlative study is still in infancy, luminous mechanism and structure with it is glimmering
Relationship between optical property also fails to be widely applied also in exploration.Therefore, many researchers are dedicated to designing and open
Hair is simple with synthesis, the reaction time is short, operation is convenient, highly sensitive, low toxin fluorescent material replaces tradition glimmering
Light probe.
Summary of the invention
The purpose of the present invention is to provide 2-methylimidazole quinolines as pH and Fe3+The application of difunctional fluorescence probe, it is described
The 2-methylimidazole quinoline for not having conventional fluorescent aromatic rings can not only measure the pH value in 2.0~5.0 ranges, in physiological environment
And also to Fe in drinking water3+With good selection recognition performance.And raw material mix is simple, fluorescence quantum yield is higher
(8.6%), high water solubility, toxic side effect are small, and whole operation process is simple, using convenient.
It uses made of 2-methylimidazole quinoline the present invention also provides a kind of for pH sensing and Fe3+That detects is difunctional glimmering
Light probe is, it can be achieved that aqueous acid medium (2.0~5.0) pH measurement and Fe in physiological environment3+Identification and quantitative detection.
The present invention is realized by following measures
The invention discloses 2-methylimidazole quinolines as pH value and Fe3+The application of difunctional fluorescence probe.
The application of foregoing invention, it is preferred that the pH value response range is 2.0~5.0.
It uses made of 2-methylimidazole quinoline the invention also discloses a kind of for pH sensing and Fe3+That detects is difunctional glimmering
Light probe.
The fluorescence probe of foregoing invention, it is preferred that the pH value response range is 2.0~5.0.
The fluorescence probe of foregoing invention, it is preferred that the 2-methylimidazole quinoline is dissolved in phosphate buffer solution, described
The concentration of 2-methylimidazole quinoline is 10mmol/L, and the pH of phosphate buffer solution is 7.4.
The fluorescence probe of foregoing invention, preferred: the fluorescence intensity liquid of measurement is 427nm.
As fluorescence probe, chemical structural formula is 2-methylimidazole quinoline of the invention
The 2-methylimidazole quinoline with specific structure be according to " Synthetic Communications, 1997,
27, (15): the method that 2701-2707 " this article is recorded is synthesized, and a kind of chemical substance having disclosed, 2- first are belonged to
Base imidazoline is widely applied as important chemical products intermediate although having in fields such as medicine, veterinary drug, dyestuffs,
There are no data proposition 2-methylimidazole quinolines to have excellent fluorescence property, is applied to pH detection and ion identification, this patent
The field that is applied to 2-methylimidazole quinoline of report still belongs to pioneering.
Difunctional fluorescent small molecule probe disclosed by the invention has the following beneficial effects:
1, the fluorescent material 2-methylimidazole quinoline toxic side effect it is small, selectivity good, high sensitivity, find it with good for the first time
Good fluorescent characteristic is simultaneously applied to fluorescence probe field.
2, fluorescent chemicals synthesis mechanism is mature, at low cost and high water solubility, it can be achieved that aqueous acid medium (2.0~
5.0) pH measurement and Fe in physiological environment3+Identification and quantitative detection.
Detailed description of the invention
It in order to more clearly explain the embodiment of the invention or the technical proposal in the existing technology, below will be to needed for embodiment
Attached drawing to be used is briefly described.
Fig. 1 is ultraviolet visible light absorption spectrum, best excitation and the transmitting fluorescence spectrum of 2-methylimidazole quinoline；
Fig. 2 is in different pH solution, and excitation wavelength 333nm, 2-methylimidazole quinoline solution is in fluorescence emission spectrum
Emit peak intensity；
Fig. 3 is the linear relationship chart of acid pH and fluorescence intensity；
Fig. 4 is the fluorescence intensity histogram after fluorescence probe and different metal ions effect；
Fig. 5 fluorescence probe and various concentration Fe3+Fluorescence emission spectrogram of compound after effect；
Fig. 6 is fluorescence probe Fe3+Detect the linear relationship chart of limit.
Specific embodiment
Embodiment 1
Using 2-methylimidazole quinoline as fluorescence probe, chemical structural formula is the embodiment of the present invention
The 2-methylimidazole quinoline with specific structure be according to " Synthetic Communications, 1997,
27, (15): the method that 2701-2707 " this article is recorded is synthesized, and a kind of chemical substance having disclosed, 2- first are belonged to
Base imidazoline is widely applied as important chemical products intermediate although having in fields such as medicine, veterinary drug, dyestuffs,
Its excellent fluorescence property is found there are no data and can detect in pH and apply in ion identification, and 2-methylimidazole quinoline is at this
The application in field still belongs to pioneering.
At room temperature, the relative fluorescence quantum yield measurement of 2-methylimidazole quinoline is with quinine sulfate (φ=0.54) for ginseng
Than object, under identical conditions, by measuring the integrated fluorescence intensities of 2-methylimidazole quinoline and the matched weak solution of reference material and being somebody's turn to do
The absorbance of excitation wavelength incident light, the relative fluorescence quantum yield that 2-methylimidazole quinoline is calculated is 8.6%.
It is configured to 3mL mixed solution (pH 7.4) with 2-methylimidazole quinoline and phosphate buffer solution, it is overall to form reaction
System, the concentration of the fluorescent small molecule probe are 10mmol/L.With the excitation of 333nm fluorescence, 340-650nm fluorescence signal is recorded.
Measurement result is as shown in Figure 1.It can be seen from the figure that the fluorescence intensity at 427nm is most with the excitation of 333nm fluorescence
By force.
The operating process of pH probe detection carries out as follows:
1) aqueous solution for preparing the 2-methylimidazole quinoline of 10mmol/L adjusts pH with hydrochloric acid and sodium hydroxide, is made respectively
PH=1.0~12.0 are divided into 1 each 3mL of solution.
2) the 2-methylimidazole quinoline aqueous solution for accurately drawing 2mL difference pH, is respectively placed in the 1cm fluorescence quartz of four sides light transmission
Cuvette is put into fluorescence spectrophotometer spectrometer, and the 333nm that excitation wavelength selects Fig. 1 to determine measures the fluorescent emission of different pH solution
Spectrum.
Solution ph is measured by pH-3C type precision acidity meter, and fluorescence spectrometry carries out on sepectrophotofluorometer, pH
Value is as shown in Figure 2 equal to the fluorescent emission intensity of 1.0~12.0 2-methylimidazole quinoline aqueous solution.From Figure 2 it can be seen that pH is equal to
2.0~5.0 solution at 427nm fluorescence intensity straight line enhancing, and pH be equal to 6.0~12.0 when solution stability compared with
By force, it is substantially unaffected.
Embodiment 2
The determination of fluorescence probe linear relationship in pH=2.0~5.0 ranges:
The acquirement of the preparation of solution, the set-up procedure of pH value and fluorescence spectrum is referring to embodiment 1.Take respectively pH=2.0,
2.5,3.0,3.5,4.0,4.5,5.0 2-methylimidazole quinoline aqueous solution and its fluorescence emission spectrum is measured.As seen from Figure 3, pH
It is in a linear relationship equal to fluorescence intensity of 2.0~5.0 solution at 427nm, linearly dependent coefficient R2=0.99036, pH inspection
Surveying wider range keeps its application more extensive.
Embodiment 3
Fluorescence probe 2-methylimidazole quinoline solution is to Fe3+Selectivity test following steps carry out:
1) it is simulation normal physiological context, prepares the phosphate buffer solution 100mL that pH is 7.4,0.08g2- methyl is added
Imidazoline makes its concentration reach 10mmol/L, and stirs evenly.
2) it takes 2mL solution to be measured to be placed in fluorescence quartz cuvette respectively, sequentially adds the metal ion (Al of 20 μ L3+,
Br2+, Co2+, Cu2+, Fe3+, Hg2+, K+, Ni2+, Zn2+), detect the fluorescence emission spectrum variation of solution, knot immediately after mixing
Fruit is as shown in Figure 4.As shown in Figure 4, it is compared with blank sample, as addition Fe3+After ion, fluorescence probe solution emits at 427nm
Peak is substantially reduced；However other metal ions, such as Al3+, Br2+, Co2+, Cu2+, Hg2+, K+, Ni2+, Zn2+Afterwards, fluorescence probe solution
Emission peak is without significant change at 427nm；The experimental results showed that Fe is only added3+, can just cause the significant of fluorescence probe solution
Fluorescence reduces, and the fluorescence probe 2-methylimidazole quinoline is in phosphate buffer solution to Fe3+It has good selectivity.
Embodiment 4
Fluorescence probe 2-methylimidazole quinoline solution is to Fe3+Fluorescence titration experiment:
In the phosphate buffer solution (pH 7.4) of 10mmol/L 2-methylimidazole quinoline, Fe is gradually increased3+Concentration,
The fluorescence spectrum of each sample is tested after mixing, as shown in Figure 5.As seen from Figure 5, with Fe3+Concentration is gradually increased,
Fluorescence intensity of the probe solution at 427nm gradually decreases, and works as Fe3+Concentration increases to 1.6 × 10-3When M, titration reaches saturation,
Emissive porwer no longer reduces；As seen from Figure 6, Fe is added dropwise3+Concentration less than 0.5 × 10-3 Fluorescence of the solution of M at 427nm is strong
Spend in a linear relationship, linearly dependent coefficient R2=0.99853, this also illustrates the fluorescence probe to Fe3+With preferable sensitivities
Matter is, it can be achieved that Fe3+Quantitative detection.
Claims (4)
1.2- methylimidazole quinoline is as pH value and Fe3+The application of difunctional fluorescence probe.
2. application according to claim 1, it is characterised in that: the pH value response range is 2.0~5.0.
3. application according to claim 1, it is characterised in that: the 2-methylimidazole quinoline is dissolved in phosphate buffer solution
In, the concentration of the 2-methylimidazole quinoline is 10mmol/L, and the pH of phosphate buffer solution is 7.4.
4. application according to claim 1, it is characterised in that: the wavelength of fluorescence of measurement is 427nm.
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