CN108037101A - A kind of preparation and application of the water-soluble fluorescent carbon point sensor that can detect formaldehyde - Google Patents
A kind of preparation and application of the water-soluble fluorescent carbon point sensor that can detect formaldehyde Download PDFInfo
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- CN108037101A CN108037101A CN201711201445.6A CN201711201445A CN108037101A CN 108037101 A CN108037101 A CN 108037101A CN 201711201445 A CN201711201445 A CN 201711201445A CN 108037101 A CN108037101 A CN 108037101A
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- 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
Abstract
The invention discloses a kind of preparation and application of the water-soluble fluorescent carbon point sensor that can detect formaldehyde, the fluorescent carbon point sensor is using p-phenylenediamine as raw material, according to a kind of water-soluble fluorescent carbon point sensor with formaldehyde examination work(of improved prior art preparation.The fluorescent carbon point sensor can realize that the high selectivity of PARA FORMALDEHYDE PRILLS(91,95) quickly detects in pure water solution.Compared to existing detection technique, the fluorescent carbon point sensor that the present invention obtains is simple with preparation method, it is easy to operate, cytotoxicity is low, the advantages that water dispersible is excellent, and input cost is relatively low, and synthetic route is simple, suitable for amplification synthesis and production application, there is huge application prospect in technical fields such as analytical chemistry, life sciences.
Description
Technical field
The invention belongs to the water-soluble fluorescent carbon point sensor for formaldehyde examination, and specifically, being related to one kind can detect
The preparation and application of the water-soluble fluorescent carbon point sensor of formaldehyde.
Background technology
Formaldehyde is a kind of colourless gas with specific stimulation smell, is confirmed to be and makees with strong carcinogenic and rush cancer
With, it is easy to the eyes of people, nose, the position that respiratory tract and skin etc. are exposed in environment produces injury.Formaldehyde at the same time
And important endogenous material in human body, first can be gone by semicarbazide-sensitive amine oxidase and lysine specific histone
The grade of base enzyme 1 biological enzyme produces.Research finds that normal levels of formaldehyde is 0.1mM-0.4mM in human body, normal level
Formaldehyde plays an important role the spatial memory of people and the formation of cognitive ability.But when concentration of formaldehyde is exceeded in blood,
It can cause the generation of some diseases, such as cancer, diabetes, senile dementia etc..Therefore, design synthesizes a kind of detectable formaldehyde
Sensor is of great significance.
At present, having grown up, some are directed to the fluorescence probe of formaldehyde examination, but are mainly passed with organic molecule
Based on sensor.It however, being related to organic molecule sensor, just cannot ignore its specific defect, be most of to have first
Machine small molecule sensor works in pure organic solvent or in the mixed solvent, because the bio-toxicity of organic solvent limits its
Applicability；Secondly organic molecule sensor can cause to assemble because of π-π interactions each other in water, into one
Step limits applicability.This also causes this kind of sensor to be reduced in the feasibility of actually detected middle utilization.Water-soluble fluorescent carbon
Point sensor is because of its excellent water solubility, low cytotoxicity, organic solvent-free remains, designability is strong, high sensitivity, high selection
It is the advantages that property, of increased attention, shown in research fields such as chemistry, medicine, analysis, environmental sciences extremely wide
Wealthy application prospect.Therefore, invent a kind of simple, inexpensive, excellent water solubility, bio-toxicity based on formaldehyde examination it is low,
And efficient water-soluble fluorescent carbon point sensor has considerable realistic meaning and application prospect.
In view of this it is special to propose the present invention.
The content of the invention
The technical problem to be solved in the present invention, which is to overcome the deficiencies of the prior art and provide, a kind of can detect the water-soluble of formaldehyde
The preparation and application of property fluorescent carbon point sensor, it is an object of the invention to provide a kind of water-soluble fluorescent carbon that can detect formaldehyde
The preparation and application of point sensor, the fluorescent carbon point sensor with the improved prior art (Angew.Chem.Int.Ed.2015,
54,5360-5363), i.e., red fluorescence carbon quantum dot, compared with prior art, this skill are prepared as raw material using p-phenylenediamine
The advantage of art is that first, crude product needs to expend substantial amounts of dichloromethane and first when being purified with silicagel column in the prior art
Alcohol, but in the present invention, precipitated first using suitable n-hexane, more than 90% accessory substance can be removed, it is then simple again
Can be obtained by product with a silica gel column purification, can significantly reduce the dosage of dichloromethane and methanol, it is more environmentally-friendly
Economy, and cumbersome silicagel column purification time can also be greatly reduced, it is more conducive to practical application.Further application study
Show, which can realize the detection to the high sensitivity, high selectivity of formaldehyde in water.
In order to solve the above technical problems, the present invention is using the basic conception of technical solution：
A kind of preparation for the water-soluble fluorescent carbon point sensor that can detect formaldehyde, comprises the following steps：
S1：Prepare solution a：P-phenylenediamine is dissolved in ethanol, 12h is reacted under the conditions of 180-200 DEG C, after question response is completed
Revolving removes 90% ethanol, obtains solution a；
S2：Prepare solution b：N-hexane is added into solution a, solution a is reacted with n-hexane, is produced precipitation, is filtered to remove precipitation,
Take filtrate revolving to remove n-hexane, obtain solution b；
S3：Solution b is purified：Solution b is obtained into solid with silica gel column purification, solid is then configured to aqueous solution, that is, obtains one
Kind can detect the water-soluble fluorescent carbon point sensor of formaldehyde.
In the present invention, the mass ratio of phenylenediamine described in S1 and ethanol is 1:50-1:200.
In the present invention, the volume ratio of solution a and n-hexane is 1 in S2：50-1:150.
In the present invention, the solid obtained in S3 is dark red solid, and a kind of water soluble fluorescence carbon dots that can detect formaldehyde passes
Sensor is a kind of water-soluble fluorescent carbon point sensor enhanced based on red fluorescence.
In the present invention, the mass-volume concentration for the aqueous solution being configured in S3 is 1-5mg/mL.
In the present invention, when preparing fluorescent carbon point sensor by hydro-thermal method using p-phenylenediamine for raw material, in purification process
Main accessory substance is removed by the use of n-hexane as precipitating reagent.
A kind of application for the water-soluble fluorescent carbon point sensor that can detect formaldehyde, it is characterised in that comprise the following steps：
T1：Configure solution x：Water-soluble fluorescent carbon point sensor with formaldehyde detection function is configured to mass-volume concentration is
The aqueous solution of 1-5mg/mL, obtains solution x；
T2：The buffer solution that pH is 7.4 is added in solution x, 3-7min is stirred, obtains solution y；
T3：Formaldehyde is added into solution y, after stirring 5min under room temperature, solution z is obtained, using the light wave of 500nm wavelength as exciting light
Ripple wavelength, the fluorescence emission spectrum of measure solution z, the fluorescence detected at 577nm are shown with the increase of concentration of formaldehyde
Significant enhancing, and can be detected after formaldehyde adds 1min, show the ability that solution y has Rapid Detection of Formaldehyde.
In the present invention, the volume ratio of solution x described in T2 and buffer solution is 1:500-1:1000.
The optium concentration of carbon quantum dot is 0.1 ~ 10 μ g/mL when detecting formaldehyde in the present invention, in T3 in aqueous.
In the present invention, the concentration of formaldehyde is 0 × 10 in T3-2mol/L-3.0×10-2mol/L。
Inventive principle：The present invention prepares required water-soluble fluorescent carbon point sensor using p-phenylenediamine as raw material, should
Fluorescent carbon point sensor pH be 7.4 buffer solution dilution after, in the presence of having formaldehyde, the fluorescence meeting at 577nm
As the increase of concentration of formaldehyde shows significant enhancing.And the detection of the fluorescent carbon point sensor PARA FORMALDEHYDE PRILLS(91,95) has significantly
High selectivity quick response feature.Compared to some existing detection techniques, the fluorescent carbon point sensor in the present invention overcomes
Traditional small molecule sensor poorly water-soluble, the shortcomings that cytotoxicity is big, and cost input is less, synthetic route is simple, rear place
Manage it is more convenient, can directly PARA FORMALDEHYDE PRILLS(91,95) realize rapidly and efficiently identify, especially physiological environment pH be 7 or so organism inner ring
The application in border has extremely important meaning.Also, the improved prior art is based on, making for organic solvent can be greatly reduced
Dosage so that building-up process is more economically environmentally friendly.
After adopting the above technical scheme, the present invention has the advantages that compared with prior art.
The present invention provides a kind of preparation and its application of the water-soluble fluorescent carbon point sensor that can detect formaldehyde, locate thereafter
Manage more convenient, economic and environment-friendly, and the fluorescent carbon point transducer sensitivity is high, strong interference immunity, the response time is fast, is expected to
It is used widely in the fields such as analytical chemistry, medicine and chemistry.
The embodiment of the present invention is described in further detail below in conjunction with the accompanying drawings.
Brief description of the drawings
A part of the attached drawing as the application, for providing further understanding of the invention, of the invention is schematic
Embodiment and its explanation are used to explain the present invention, but do not form inappropriate limitation of the present invention.Obviously, drawings in the following description
Only some embodiments, to those skilled in the art, without creative efforts, can be with
Other accompanying drawings are obtained according to these attached drawings.In the accompanying drawings：
Fig. 1 is the infrared spectrum of the fluorescent carbon point sensor prepared；
Fig. 2 is the identification schematic diagram of the fluorescent carbon point sensor PARA FORMALDEHYDE PRILLS(91,95) prepared；
When Fig. 3 is different concentration of formaldehyde, the fluorescence emission spectrum variation diagram of fluorescent carbon point sensor；
Wherein：Excitation wavelength is 500nm, [formaldehyde]=0mol/L (a), 1.0 × 10-3Mol/L (b), 3.0 × 10-3Mol/L (c),
5.0×10-3Mol/L (d), 7.0 × 10-3Mol/L (e), 1.0 × 10-2Mol/L (f), 1.3 × 10-2Mol/L (g), 1.6 × 10-2Mol/L (h), 2.0 × 10-2Mol/L (i), 2.5 × 10-2Mol/L (j), 3.0 × 10-2mol/L(k)；
Fig. 4 changes with the corresponding matched curve of concentration of formaldehyde change and the curve institute for fluorescent carbon point sensor fluorescence intensity level
Corresponding functional arrangement；
Fig. 5 for various chaff interferents to the selective correction data figure of the fluorescent carbon point sensor fluorescence intensity, the analysis after addition
The concentration of thing is 1.0 × 10-2Mol/L, concentration of formaldehyde are 1.0 × 10-2mol/L；
Fig. 6 for fluorescent carbon point sensor after formaldehyde is added with the change of the change of time fluorescence intensity at 577nm.
It should be noted that these attached drawings and word description are not intended as the design model limiting the invention in any way
Enclose, but idea of the invention is illustrated for those skilled in the art by reference to specific embodiment.
Embodiment
To make the purpose, technical scheme and advantage of the embodiment of the present invention clearer, below in conjunction with the embodiment of the present invention,
Technical solution in embodiment is clearly and completely described, following embodiments are used to illustrate the present invention, but are not limited to
The scope of the present invention.
Embodiment 1
A kind of preparation for the water-soluble fluorescent carbon point sensor that can detect formaldehyde, comprises the following steps that：
（1）2g p-phenylenediamine is dissolved in the ethanol of 200mL, 180 DEG C of reaction 12h, concentrated by rotary evaporation arrives after reaction is completed
20mL, is then precipitated with 200mL n-hexanes, is filtered to remove insoluble matter, takes filtrate revolving to use silica gel column purification after removing solvent
Dark red solid is obtained, that is, obtains a kind of water-soluble fluorescent carbon point sensor that can detect formaldehyde, finally passes the fluorescent carbon point
Sensor is configured to the aqueous solution of 2mg/mL.
Embodiment 2
A kind of preparation for the water-soluble fluorescent carbon point sensor that can detect formaldehyde, comprises the following steps that：
1g p-phenylenediamine is dissolved in the ethanol of 200mL, 190 DEG C of reaction 12h, after reaction is completed concentrated by rotary evaporation to 20mL,
Then precipitated with 200mL n-hexanes, be filtered to remove insoluble matter, take filtrate revolving to be obtained secretly with silica gel column purification after removing solvent
Red solid.
Embodiment 3
A kind of preparation for the water-soluble fluorescent carbon point sensor that can detect formaldehyde, comprises the following steps that：
（1）1.5g p-phenylenediamine is dissolved in the ethanol of 200mL, 200 DEG C of reaction 12h, concentrated by rotary evaporation arrives after reaction is completed
20mL, is then precipitated with 200mL n-hexanes, is filtered to remove insoluble matter, takes filtrate revolving to use silica gel column purification after removing solvent
Obtain dark red solid.
Embodiment 4
The test experience of formaldehyde in buffer solution：11 5mL sample bottles are taken, are separately added into the fluorescent carbon point of gained in embodiment 1
10 μ L of sensor solution, the concentration of the fluorescent carbon point sensor original solution is 2mg/mL, and the pH for sequentially adding 2.99mL is 7.4
Buffer solution, is separately added into the formaldehyde of various concentrations after stirring 5min, and ultimate density is [formaldehyde]=0mol/L (a), 1.0 ×
10-3Mol/L (b), 3.0 × 10-3Mol/L (c), 5.0 × 10-3Mol/L (d), 7.0 × 10-3Mol/L (e), 1.0 × 10-2mol/
L (f), 1.3 × 10-2Mol/L (g), 1.6 × 10-2Mol/L (h), 2.0 × 10-2Mol/L (i), 2.5 × 10-2Mol/L (j), 3.0
×10-2Mol/L (k), after stirring 5min under room temperature, using 500nm as excitation wavelength, measures the fluorescence emission of each sample respectively
Spectrum, obtains the fluorescence emission spectrum variation diagram of 11 samples, sees Fig. 3.Measurement result shows：The fluorescent carbon point sensor is in 577nm
The fluorescence intensity at place substantially rises, and detection is limited to 45 μM.According in Fig. 3 at 577nm fluorescence intensity change value and concentration change
Relation can make the functional arrangement corresponding to function curve diagram and the curve more satisfactory after corresponding fitting：Y=a+b × x, a=
42.5118, b=5.5705, R2=0.9951, see Fig. 4.
Embodiment 5
The contrasting detection experiment that other analytes influence：9 5mL sample bottles are taken, are separately added into the fluorescent carbon of gained in embodiment 1
10 μ L of point sensor solution, the fluorescent carbon point sensor concentration are 2mg/mL, the pH for then sequentially adding 2.99mL be 7.4 it is slow
Solution is rushed, stirs 5min, headpin will add Cl respectively as blank control group in 2-8 bottles-, S2-, SO3 2-, Na+, K+, half Guang
Propylhomoserin Cys, glutathione GSH, the ultimate density of chaff interferent is 1 × 10-2Mol/mL, No. 9 sample bottles add formaldehyde, ultimate density
Also it is 1.0 × 10-2mol/mL.Fluorescence data of 9 samples under the excitation of 500nm wavelength is measured after stirring 5min respectively,
The fluorescence change at 577nm wavelength transmittings is obtained, the result is shown in Fig. 5.Measurement result shows：It is other above-mentioned in addition to formaldehyde
Various chaff interferents have not significant impact the fluorescence intensity of prepared fluorescent carbon point sensor.
Embodiment 6
The formaldehyde response time tests：1 cuvette is taken, the 10 μ L of fluorescent carbon point sensor solution for adding gained in embodiment 1 should
Fluorescent carbon point sensor concentration is 2mg/mL, and the pH for then adding 2.99mL is 7.4 buffer solution, will be dense after stirring 5min
The formalin spent for 10mol/L takes 9 μ L to add in cuvette, and determination sample is different under the excitation of 500nm wavelength immediately after
The fluorescence data of time, obtains the fluorescence change at 577nm wavelength transmittings, the result is shown in Fig. 6.Measurement result shows：
Just the reaction was complete within 1min, this shows the ability that the sensor has Rapid Detection of Formaldehyde.
The above is only presently preferred embodiments of the present invention, not makees limitation in any form to the present invention, though
So the present invention is disclosed above with preferred embodiment, but is not limited to the present invention, any technology people for being familiar with this patent
Member without departing from the scope of the present invention, when the technology contents using above-mentioned prompting make it is a little change or be modified to
The equivalent embodiment of equivalent variations, as long as being the content without departing from technical solution of the present invention, the technical spirit pair according to the present invention
Any simple modification, equivalent change and modification that above example is made, in the range of still falling within the present invention program.
Claims (10)
1. a kind of preparation for the water-soluble fluorescent carbon point sensor that can detect formaldehyde, it is characterised in that comprise the following steps：
S1：Prepare solution a：P-phenylenediamine is dissolved in ethanol, 12h is reacted under the conditions of 180-200 DEG C, after question response is completed
Revolving removes 90% ethanol, obtains solution a；
S2：Prepare solution b：N-hexane is added into solution a, solution a is reacted with n-hexane, is produced precipitation, is filtered to remove precipitation,
Take filtrate revolving to remove n-hexane, obtain solution b；
S3：Solution b is purified：Solution b is obtained into solid with silica gel column purification, solid is then configured to aqueous solution, that is, obtains one
Kind can detect the water-soluble fluorescent carbon point sensor of formaldehyde.
2. a kind of preparation of water-soluble fluorescent carbon point sensor that can detect formaldehyde according to claim 1, its feature exist
In the mass ratio of phenylenediamine described in S1 and ethanol is 1:50-1:200.
3. a kind of preparation of water-soluble fluorescent carbon point sensor that can detect formaldehyde according to claim 1, its feature exist
In the volume ratio of solution a and n-hexane is 1 in S2：50-1:150.
4. a kind of preparation of water-soluble fluorescent carbon point sensor that can detect formaldehyde according to claim 1, its feature exist
In the solid obtained in S3 is dark red solid, and a kind of water-soluble fluorescent carbon point sensor that can detect formaldehyde is that one kind is based on
The enhanced water-soluble fluorescent carbon point sensor of red fluorescence.
5. a kind of preparation of water-soluble fluorescent carbon point sensor that can detect formaldehyde according to claim 1, its feature exist
In the mass-volume concentration for the aqueous solution being configured in S3 is 1-5mg/mL.
6. a kind of preparation of water-soluble fluorescent carbon point sensor that can detect formaldehyde according to claim 1, its feature exist
In, when preparing fluorescent carbon point sensor by hydro-thermal method using p-phenylenediamine for raw material, in purification process by the use of n-hexane as
Precipitating reagent removes main accessory substance.
7. a kind of application for the water-soluble fluorescent carbon point sensor that can detect formaldehyde, it is characterised in that comprise the following steps：
T1：Configure solution x：Water-soluble fluorescent carbon point sensor with formaldehyde detection function is configured to mass-volume concentration is
The aqueous solution of 1-5mg/mL, obtains solution x；
T2：The buffer solution that pH is 7.4 is added in solution x, 3-7min is stirred, obtains solution y；
T3：Formaldehyde is added into solution y, after stirring 5min under room temperature, solution z is obtained, using the light wave of 500nm wavelength as exciting light
Ripple wavelength, the fluorescence emission spectrum of measure solution z, the fluorescence detected at 577nm are shown with the increase of concentration of formaldehyde
Significant enhancing, and can be detected after formaldehyde adds 1min, show the ability that solution y has Rapid Detection of Formaldehyde.
8. a kind of application of water-soluble fluorescent carbon point sensor that can detect formaldehyde according to claim 7, its feature exist
In the volume ratio of solution x described in T2 and buffer solution is 1:500-1:1000.
9. a kind of application of water-soluble fluorescent carbon point sensor that can detect formaldehyde according to claim 7, its feature exist
In the optium concentration of carbon quantum dot is 0.1 ~ 10 μ g/mL when detecting formaldehyde in T3 in aqueous.
10. a kind of application of water-soluble fluorescent carbon point sensor that can detect formaldehyde according to claim 7, its feature exist
In the concentration of formaldehyde is 0 × 10 in T3-2mol/L-3.0×10-2mol/L。
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