CN110172344A - For monitoring the fluorescent carbon quantum dot and its preparation method and application of acidic environment pH - Google Patents
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Abstract
The present invention provides a kind of for monitoring the fluorescent carbon quantum dot and its preparation method and application of acidic environment pH.Preparation method: (1) by o-phenylenediamine and p-aminobenzene sulfonic acid, dehydrated alcohol is added, rear ultrasonic dissolution is sufficiently stirred；(2) it is transferred in hydrothermal reaction kettle, is placed in baking oven by above-mentioned, 180~200 DEG C of 8~10h of reaction；(3) stands and be cooled to room temperature after reacting and stopping, filtering, centrifugation removes insoluble matter and obtains navy blue solution, with obtaining pure carbon dots aqueous solution after membrane filtration；(4) it is dried in vacuo above-mentioned carbon dots aqueous solution to obtain target product.This method is simple, and preparation condition requirement is low, without pretreatment and purification process.The features such as obtained carbon quantum dot has long wavelength emission, and optical property is stablized, good biocompatibility, higher quantum yield；Carbon quantum dot has very sensitive response to pH, and rapidly can enter cell by penetrating cell film, reaches the fluctuation of pH in real-time monitoring living cells, can be used for acidic environment especially pole acidic environment pH monitoring.
Description
Technical field
It is specifically a kind of for monitoring acyclic acidic the present invention relates to Illuminant nanometer material more particularly to fluorescent carbon quantum dot
The fluorescent carbon quantum dot and its preparation method and application of border pH.
Background technique
Hydrogen ion is one of most important intracellular species.Cell survival depends primarily on the pH for maintaining balance, and adjusting is permitted
More metabolic pathways, such as cell growth and apoptosis, signal transduction and defence etc..The minor change of internal pH can indicate abnormal cell
Event and cause cell dysfunction and cardiopulmonary and the nervous system disease, such as cancer and Alzheimer's disease.Maintain pH steady
State is the basis of all organisms.Intracellular pH variation and distribution measuring is for more fully understanding cell function and in early days
Medical diagnosis on disease provides crucial auxiliary and is of great significance.Therefore, physiology and pathologic process in order to better understand, it is also very desirable to right
PH carries out sensitive, accurate real-time in-situ monitoring in living cells.PH or other numerous areas important parameters, such as protected in environment
Shield, blowdown detection, chemical production etc. have application.Especially in the industrial production, a large amount of highly acid industrial wastewaters are often generated,
To environment and ecological protection cause in immense pressure, therefore accurate pH value determination, especially highly acid system pH have it is great
Meaning.
Fluorescent spectrometry has the advantages that high sensitivity, non-invasive, quick response, easily operated and real-time monitoring, in conjunction with
Induced Fluorescence Microscopy, pH fluorescence probe are capable of the DYNAMIC DISTRIBUTION and regional change of real-time in-situ monitoring internal pH, display
Its unique time and the high property of spatial resolution out.Currently, many outstanding pH dependence fluorescence probes have weakly acidic pH
Or faintly acid reflex action is developed in biosystem.Unfortunately, it is used for the research of pole acid pH probe (pH < 4)
Report is seldom.Therefore the probe of exploitation detection strong acidic environment is very necessary
In recent years, carbon quantum dot is caused greatly as a kind of new fluorescent nano material due to its good performance
Research interest.Such as good water solubility, biocompatibility, outstanding fluorescent characteristic, low cost, hypotoxicity and the feature of environmental protection,
These features promote carbon dots in biomedicine, the multifunctional application in many fields such as sensor and photoelectric device.However big
In majority application, the transmitting of various carbon dots all concentrates on green and blue region, and due to the weak penetration capacity of carbon dots and short
Wave radiation has great light injury and side effect to biological tissue, this greatly limits their applications in biology.Therefore,
Simple and carbon dots the effective ways there is an urgent need to develop a kind of synthetic method.Therefore, exploitation is simple and has long wavelength emission
Fluorescent carbon point have very important significance for bio-sensing and biomedicine.
Summary of the invention
The purpose of the present invention is to provide a kind of fluorescent carbon quantum dots that structural property is excellent, and establish a kind of operation letter
Single, device simple and the cheap preparation method of raw material；And the fluorescent carbon quantum dot is used for the monitoring of the pH in acidic environment,
For pH variation and cell imaging in real-time monitoring living cells.
It is provided by the invention a kind of to be walked for monitoring the preparation method of the fluorescent carbon quantum dot of acidic environment pH, including as follows
It is rapid:
1) o-phenylenediamine and p-aminobenzene sulfonic acid are placed in container, dehydrated alcohol is added, rear ultrasonic dissolution is sufficiently stirred
15-20 minutes, the mass ratio of the o-phenylenediamine, p-aminobenzene sulfonic acid and dehydrated alcohol are as follows: 0.03-0.2:0.05-0.3:10-
30；
2) above-mentioned solution is transferred in hydrothermal reaction kettle, is placed in baking oven, 180~200 DEG C of 8~10h of reaction；
3) it stands and is cooled to room temperature after reacting and stopping, filtering, 15min is centrifuged under 8000r/m revolving speed, remove insoluble matter
Navy blue solution is obtained, with obtaining the aqueous solution of pure carbon dots after 0.22 μm of membrane filtration；
4) target product will be obtained after the vacuum drying of above-mentioned solution.
The mass ratio of o-phenylenediamine, p-aminobenzene sulfonic acid and dehydrated alcohol is preferred in the step 1) are as follows: 0.054-
0.108:0.087-0.173:10-20.
The quality of o-phenylenediamine is 0.108 in step 1), and the quality of p-aminobenzene sulfonic acid is 0.173, the matter of dehydrated alcohol
Amount is 15-20.
Hydrothermal temperature is 200 DEG C in step 2), and the reaction time is 8 hours.
Resulting carbon quantum dot is dissolved in PBS buffer solution and is added in the culture solution of liver cancer SMMC7721 cell,
Hatch 5-10min, then passes through the image formation state of confocal laser scanning microscope SMMC7721 cell.The carbon quantum dot is in pH
When being 7.0, cell shows bright yellow fluorescence；For the carbon quantum dot when pH is 1.5, it is glimmering that cell shows bright red
Light, and as the reduction of pH, the yellow fluorescence of the carbon quantum dot gradually weaken, red fluorescence gradually increases, and illustrates the carbon amounts
Son point can be used as detection reagent for monitoring the variation of pH in acid living cells.
Compared with prior art, present invention has the advantage that
(1) carbon dots preparation method of the present invention is easy, can be prepared by using a step hydrothermal synthesis method, without cumbersome sample
Product pretreatment and purification process are not required to handle or modify by surface passivator that fluorescent carbon quantum dot can be obtained.
(2) carbon quantum dot obtained by the present invention has long wavelength emission, and good water-soluble and biocompatibility etc. is special
Point；
(3) the carbon quantum dot yield prepared by the present invention is higher, with quinine sulfate (quantum yield 54%) for object of reference,
The quantum yield of gained carbon dots is 15.97%.
(4) carbon quantum dot obtained by the present invention has very sensitive response, especially in acid condition (pH2.6- to pH
3.8) it, can be used for monitoring the variation of pH in acid living cells.
Detailed description of the invention
Fig. 1 is the transmission electron microscope picture of carbon quantum dot prepared by embodiment 1；
Fig. 2 is the ultra-violet absorption spectrum and fluorescent excitation-emmision spectra of carbon quantum dot prepared by embodiment 1；
Fig. 3 is the spectrogram that carbon quantum dot fluorescence emission curves prepared by embodiment 1 change with excitation wavelength；
Fig. 4 is the infrared spectrogram of carbon quantum dot prepared by embodiment 1, and abscissa is Detection wavelength in figure, and ordinate is
Transmitance；
Fig. 5 is the XPS spectrum figure of carbon quantum dot prepared by embodiment 1；
Fig. 6 be embodiment 1 prepare carbon quantum dot at 563nm fluorescence intensity with pH value change curve (1.0-7.4)；
Fig. 7 is that carbon quantum dot prepared by embodiment 1 enters work under conditions of pH=7.0, pH=3.0, pH=1.5 respectively
Laser co-focusing in cell shows that figure, the cell are human hepatocellular SMMC7721 cell.
Specific embodiment
With reference to the accompanying drawing and specific embodiment makes further explanation to the present invention, and embodiment gives detailed reality
Mode and specific operating process are applied, but protection scope of the present invention is not limited to following embodiments.
Embodiment 1
The preparation method of carbon dots:
(1) it takes 0.108g o-phenylenediamine and 0.173g p-aminobenzene sulfonic acid to be placed in container respectively, the anhydrous second of 20mL is added
Alcohol, is sufficiently stirred rear ultrasonic dissolution 20 minutes；
(2) it is transferred in hydrothermal reaction kettle, is placed in baking oven by above-mentioned, 200 DEG C of reaction 8h；
(3) it stands and is cooled to room temperature after reacting and stopping, filtering, 15min is centrifuged under 8000r/m revolving speed, remove insoluble
Object obtains navy blue solution, with obtaining pure carbon dots aqueous solution after 0.22 μm of membrane filtration；
(4) target product will be obtained after the vacuum drying of above-mentioned carbon dots aqueous solution, Relative quantum yields (are with quinine sulfate
Standard) it is 15.97%；
Resulting carbon quantum dot is dissolved in respectively in the PBS buffer solution of pH=7.0, pH=3.0 and pH=1.5, is made into
The solution of 0.4mg/ml is added separately in the culture solution of liver cancer SMMC7721 cell, hatches 5min, is then copolymerized by laser
The image formation state of focusing microscope observation SMMC7721 cell.
The carbon quantum dot of above-mentioned synthesis is characterized, transmission electron microscope figure such as Fig. 1.The carbon quantum dot is in form
Upper presentation monodisperse spherical particle, partial size is about 3.14nm.
Spectrum property research, such as Fig. 2 are carried out to the carbon quantum dot of above-mentioned synthesis.The maximum excitation wavelength of the carbon quantum dot and
Best launch wavelength is respectively 383nm and 563nm.
The infrared spectrogram of the carbon quantum dot of above-mentioned synthesis such as Fig. 4.The carbon quantum dot has benzene ring structure and surface is contained
The functional groups such as amino, carboxyl.
The change in fluorescence that the carbon quantum dot of above-mentioned synthesis is showed at different pH, such as Fig. 6.The carbon quantum dot is in pH=
S type curve is presented in 1.0-5.6, and pKa 3.01, the range of linearity is 2.6-3.8.
Situation after entering cell by the carbon quantum dot of the above-mentioned synthesis of laser co-focusing experimental observation, such as Fig. 7.The carbon amounts
For son point when pH is 7.0, cell shows bright yellow fluorescence；When pH is 1.5, cell shows bright the carbon quantum dot
Red fluorescence, and as the reduction of pH, the yellow fluorescence of the carbon quantum dot gradually weaken, red fluorescence is gradually increased, and says
The bright carbon quantum dot can be used as detection reagent for monitoring the variation of pH in acid living cells.
Embodiment 2
(1) it takes 0.108g o-phenylenediamine and 0.087g p-aminobenzene sulfonic acid to be placed in container respectively, the anhydrous second of 20mL is added
Alcohol, is sufficiently stirred rear ultrasonic dissolution 20 minutes；
(2) it is transferred in hydrothermal reaction kettle, is placed in baking oven by above-mentioned, 200 DEG C of reaction 8h；
(3) it stands and is cooled to room temperature after reacting and stopping, filtering, 15min is centrifuged under 8000r/m revolving speed, remove insoluble
Object obtains navy blue solution, with obtaining pure carbon dots aqueous solution after 0.22 μm of membrane filtration；
(4) target product will be obtained after the vacuum drying of above-mentioned carbon dots aqueous solution, Relative quantum yields (are with quinine sulfate
Standard) it is 9.93%.
Embodiment 3
(1) it takes 0.108g o-phenylenediamine and 0.087g p-aminobenzene sulfonic acid to be placed in container respectively, the anhydrous second of 10mL is added
Alcohol, is sufficiently stirred rear ultrasonic dissolution 20 minutes；
(2) it is transferred in hydrothermal reaction kettle, is placed in baking oven by above-mentioned, 180 DEG C of reaction 10h；
(3) it stands and is cooled to room temperature after reacting and stopping, filtering, 15min is centrifuged under 8000r/m revolving speed, remove insoluble
Object obtains navy blue solution, with obtaining pure carbon dots aqueous solution after 0.22 μm of membrane filtration；
(4) target product will be obtained after the vacuum drying of above-mentioned carbon dots aqueous solution, Relative quantum yields (are with quinine sulfate
Standard) it is 8.08%.
Embodiment 4
(1) it takes 0.054g o-phenylenediamine and 0.173g p-aminobenzene sulfonic acid to be placed in container respectively, the anhydrous second of 20mL is added
Alcohol, is sufficiently stirred rear ultrasonic dissolution 20 minutes；
(2) it is transferred in hydrothermal reaction kettle, is placed in baking oven by above-mentioned, 200 DEG C of reaction 8h；
(3) it stands and is cooled to room temperature after reacting and stopping, filtering, 15min is centrifuged under 8000r/m revolving speed, remove insoluble
Object obtains navy blue solution, with obtaining pure carbon dots aqueous solution after 0.22 μm of membrane filtration；
(4) target product will be obtained after the vacuum drying of above-mentioned carbon dots aqueous solution, Relative quantum yields (are with quinine sulfate
Standard) it is 9.04%.
Embodiment 5
(1) it takes 0.054g o-phenylenediamine and 0.173g p-aminobenzene sulfonic acid to be placed in container respectively, the anhydrous second of 10mL is added
Alcohol, is sufficiently stirred rear ultrasonic dissolution 20 minutes；
(2) it is transferred in hydrothermal reaction kettle, is placed in baking oven by above-mentioned, 180 DEG C of reaction 8h；
(3) it stands and is cooled to room temperature after reacting and stopping, filtering, 15min is centrifuged under 8000r/m revolving speed, remove insoluble
Object obtains navy blue solution, with obtaining pure carbon dots aqueous solution after 0.22 μm of membrane filtration；
(4) target product will be obtained after the vacuum drying of above-mentioned carbon dots aqueous solution, Relative quantum yields (are with quinine sulfate
Standard) it is 7.15%.
The resulting carbon quantum dot quantum yield of embodiment 1 and yield are all apparently higher than other embodiments.
Claims (9)
1. a kind of for monitoring the preparation method of the fluorescent carbon quantum dot of acidic environment pH, which comprises the steps of:
1) o-phenylenediamine and p-aminobenzene sulfonic acid are placed in container, dehydrated alcohol is added, rear ultrasonic dissolution 15-20 is sufficiently stirred
Minute, the mass ratio of the o-phenylenediamine, p-aminobenzene sulfonic acid and dehydrated alcohol are as follows: 0.03-0.2:0.05-0.3:10-30；
2) above-mentioned solution is transferred in hydrothermal reaction kettle, is placed in baking oven, 180~200 DEG C of 8~10h of reaction；
3) it stands and is cooled to room temperature after reacting and stopping, filtering, 15min is centrifuged under 8000r/m revolving speed, removal insoluble matter obtains
Navy blue solution, with obtaining the aqueous solution of pure carbon dots after 0.22 μm of membrane filtration；
4) target product will be obtained after the vacuum drying of above-mentioned solution.
2. the preparation method of fluorescent carbon quantum dot as described in claim 1, it is characterised in that o-phenylenediamine in step 1), to ammonia
The mass ratio of base benzene sulfonic acid and dehydrated alcohol are as follows: 0.054-0.108:0.087-0.173:10-20.
3. the preparation method of fluorescent carbon quantum dot as claimed in claim 2, it is characterised in that the matter of o-phenylenediamine in step 1)
Amount is 0.108, and the quality of p-aminobenzene sulfonic acid is 0.173, and the quality of dehydrated alcohol is 15-20.
4. the preparation method of fluorescent carbon quantum dot as described in claim 1, it is characterised in that hydrothermal temperature in step 2)
It is 200 DEG C, the reaction time is 8 hours.
5. as claim 1,2,3 or 4 the methods prepare fluorescent carbon quantum dot.
6. fluorescent carbon quantum dot as claimed in claim 5 monitors the application in acid living cells pH reagent in preparation.
7. fluorescent carbon quantum dot as claimed in claim 5 is used to monitor the pH in acidic environment.
8. fluorescent carbon quantum dot as claimed in claim 7 is used to monitor the pH in acidic environment, the pH of the acidic environment is
2.6-3.8。
9. fluorescent carbon quantum dot as claimed in claim 5 is preparing the application in live cell fluorescent imaging agents.
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Cited By (11)
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| CN110885680A (en) * | 2019-11-12 | 2020-03-17 | 中国矿业大学 | Method for preparing multicolor fluorescent carbon dots by solvent-free method and multicolor fluorescent carbon dots prepared by method |
| CN111115620A (en) * | 2020-01-16 | 2020-05-08 | 宁波石墨烯创新中心有限公司 | Preparation method of graphene quantum dots |
| CN111286325A (en) * | 2020-04-07 | 2020-06-16 | 四川大学 | Carbon quantum dot emitting yellow fluorescence and preparation method and application thereof |
| CN111573654A (en) * | 2020-06-10 | 2020-08-25 | 山西大学 | Green fluorescent carbon quantum dot for detecting pH value in acidic environment and preparation method thereof |
| CN111849474A (en) * | 2020-08-03 | 2020-10-30 | 山西大学 | Nitrogen-doped carbon dots based on carnation flowers and preparation method and application thereof |
| CN111908450A (en) * | 2020-08-31 | 2020-11-10 | 中国矿业大学 | Preparation method of red fluorescent carbon dots and application of red fluorescent carbon dots in shale gas desulfurization |
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| CN111286325B (en) * | 2020-04-07 | 2021-09-28 | 四川大学 | Carbon quantum dot emitting yellow fluorescence and preparation method and application thereof |
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| CN111849474B (en) * | 2020-08-03 | 2022-05-31 | 山西大学 | Nitrogen-doped carbon dots based on carnation flowers and preparation method and application thereof |
| CN111908450B (en) * | 2020-08-31 | 2022-02-15 | 中国矿业大学 | Preparation method of red fluorescent carbon dots and application of red fluorescent carbon dots in shale gas desulfurization |
| CN111908450A (en) * | 2020-08-31 | 2020-11-10 | 中国矿业大学 | Preparation method of red fluorescent carbon dots and application of red fluorescent carbon dots in shale gas desulfurization |
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| CN112608744A (en) * | 2020-12-29 | 2021-04-06 | 山西大学 | Green fluorescent carbon dot, preparation method thereof and application thereof in rutin detection |
| CN113046074A (en) * | 2021-03-25 | 2021-06-29 | 中国科学技术大学 | Method for synthesizing high-brightness fluorescent carbon quantum dots and application |
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| CN113583525A (en) * | 2021-07-07 | 2021-11-02 | 长春工业大学 | Preparation method and application of fluorescent paint of carbon dot composite acrylic emulsion |
| CN114852993A (en) * | 2022-04-25 | 2022-08-05 | 陕西煤业化工集团神木天元化工有限公司 | Carbon quantum dot and preparation method and application thereof |
| CN114852993B (en) * | 2022-04-25 | 2024-04-30 | 陕西煤业化工集团神木天元化工有限公司 | Carbon quantum dot and preparation method and application thereof |
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