CN106542520B - The preparation method of green orange red three fluorescence graphene quantum dot - Google Patents
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Abstract
The present invention relates to a kind of preparation methods of green orange red three fluorescence graphene quantum dot.The present invention selects inexpensive pyrene for predecessor, pyrene is nitrified at low temperature to obtain intermediate product 1, then 3,6-trinitro- pyrenes carry out the surface-functionalized of the solvent heat dehydrogenation of low temperature, growth and original position under the action of the catalyst acetic acid of different solvents and various concentration.The quantum dot that the present invention synthesizes can be stably dispersed in various organic solvents, and luminescent color or wavelength are adjustable within the scope of 510-620 nm, and fluorescence efficiency is high.The quanta point material that the present invention synthesizes shows tempting application prospect in high-technology fields such as environmental protection, bio-nanotechnology, new energy, nano-devices, and synthetic method is simple and environmentally-friendly, low energy consumption, is suitble to industrialized production.
Description
Technical field
The present invention relates to a kind of preparation methods of green orange red three fluorescence graphene quantum dot.
Background technique
A kind of two-dimentional carbon material of the graphene as monoatomic thickness, because of its special calorifics, mechanics and electrical properties,
Domestic and international researcher is attract in past more than ten years widely to pay close attention to.Graphene quantum dot is in addition to having the outstanding property of graphene
Matter, also with the peculiar optical characteristics of quantum dot, with other semiconductor-quantum-points compared with abundant raw materials, it is cheap,
Good chemical stability, anti-light bleaching power is strong, biological safety is high, advantages of environment protection.These characteristics make it too
The fields such as positive energy battery, luminescent device, bio-imaging and target drug-carrying have potential application.
The synthetic method of graphene quantum dot is divided into two major classes from top to bottom and from bottom to top.Method is to pass through object from top to bottom
Reason or chemical cleavage method are by large-sized carbon matrix precursor (such as graphite, carbon fiber, fullerene, carbon nanotube, graphene oxide
Piece, carbon black or coal, even flue dust etc.) the small sized graphene quantum dot of cutting mainly includes hydro-thermal patterning method, electrochemistry
Method, strong acid oxidation stripping method, organic solvent stripping method and microwave patterning method etc..Method refers to from bottom to top is with small organic molecule
Presoma prepares graphene quantum dot, including hydrothermal synthesis method, microwave process for synthesizing, pyrolysismethod by a series of chemical reaction
With organic synthesis method etc., the small molecule predecessor used includes cool polyphenyl imines, six benzos, glucose, citric acid, pyrene etc..It arrives
So far, the synthetic technology for obtaining the graphene quantum dot of efficient long wavelength's fluorescence (green, orange, red) is never broken through, this
Kind synthetic technology status limits application of long wavelength's fluorescence graphene quantum dot in many technical fields.
Summary of the invention
Goal of the invention is to break through the synthetic technology bottleneck of the graphene quantum dot of long wavelength's fluorescence, molten by a kind of low temperature
Agent thermal method, the oil-soluble graphene quantum dot of efficiently green, orange, the red three fluorescence of preparation.
In order to achieve the above objectives, the present invention adopts the following technical scheme:
A kind of preparation method of green orange red three fluorescence graphene quantum dot, it is characterised in that the specific steps of this method
Are as follows:
A. pyrene is stirred down and is slowly added to full nitric acid or is made of sulfuric acid and concentrated nitric acid by the volume ratio of 3:1 ~ 1:1
It is back flow reaction 24~48 hours, cooling in mixed acid；
B. reaction solution obtained by step a is added slowly in deionized water, is filtered using filter membrane, remove acid solution, then
It washes always until the solution of filtering is neutrality, obtained solid carries out；
C. step b obtained solid and dopant is taken to be added according to the mass ratio of 1:0.3 ~ 1:1 in organic solvent and ultrasonic
Dispersion forms uniform suspension, then concentration 1.25mg/ml~7.5mg/ml of suspension reacts 3 at 180 ~ 230 DEG C
~12 h；It is cooling；
D. by the organic membrane filtration of suspension obtained by step c, filtered solution is removed into solvent, finally obtains green orange
Red trichromatism fluorescence graphene quantum dot；
The dopant is glacial acetic acid, hydrobromic acid or acetate；
When the solvent is ethyl alcohol, green fluorescence graphene quantum dot is obtained；The solvent is N, N- dimethyl methyl
When amide, fluorescent orange graphene quantum dot is obtained；The solvent obtains red when being toluene, hexamethylene, dichloro-benzenes or chloroform
Color fluorescence graphene quantum dot.
The method of the present invention key step includes mixed acid nitrification, washing, solvent heat, washing and drying and other steps.Side of the present invention
Method simple process, meets environmental requirement；Ultraviolet light and visible light catalytic test result show, graphene quantum produced by the present invention
Point sample has preferable fluorescent effect.Oil-soluble graphene quantum dot made from the method for the present invention is applicable to required in oil system
The application requirement of dispersion.
Raw material used in the present invention can directly be bought by commercial sources.The wherein mixed acid nitrification in step a
Ratio nitric acid: sulfuric acid also can change, by adjust organic solvent type and dopant type it is adjustable obtained
The fluorescence emission wavelengths of graphene quantum dot can adjust the red fluorescence to 620nm from the green fluorescence of 520nm.
Heretofore described organic solvent can be the nonpolar solvents such as toluene, hexamethylene, dichloro-benzenes, chloroform, can also
To be ethyl alcohol, ethylene glycol, N,N-dimethylformamide isopolarity solvent.
In the present invention used dopant have glacial acetic acid, hydrobromic acid, containing acetate salt (such as sodium acetate, zinc acetate,
Potassium acetate etc.).
In the present invention in step d reactant reaction density range: 1.25mg/ml-7.5mg/ml.
Compared with the conventional method, features and advantages are as follows for the method for the present invention:
(1) product yield is high (80%-90%), easy to separate and purify.
(2) quantum dot is mono-crystalline structures.
(3) optical property is excellent, and luminescent properties are adjustable: visible absorption range is wide, and ABSORPTION EDGE may extend into 600 Donnas
Rice；Fluorescence quantum yield is high, up to 70% or more；Fluorescence color can be simply by changing solvent and additive in long wavelength range
Interior (520-620 nanometers) are regulated and controled very well, such as molten in n,N-Dimethylformamide, toluene, ethyl alcohol (adding a small amount of glacial acetic acid)
Red, orange and green fluorescence quantum dot is respectively obtained in agent hot system.
(4) graphene quantum dot of nitro functionalization is made in the method for the present invention for the first time, is suitable for all to be dispersion in oil
Application requirement.
(5) preparation process of the present invention is simple, and two steps have prepared oil-soluble graphene quantum dot, easily operated, answers
It is wide with range, it is conducive to industrialization promotion.
Detailed description of the invention
Fig. 1 is the XRD spectrum of 2 graphene quantum dot sample of the embodiment of the present invention；
Fig. 2 is the Raman map of the resulting graphene quantum dot sample of the embodiment of the present invention 2；
Fig. 3 is TEM the and HRTEM photo of 2 graphene quantum dot sample of the embodiment of the present invention；
Fig. 4 is the ultraviolet-visible absorption spectroscopy and fluorescence pattern of the resulting three kinds of graphene quantum dot samples of the present invention.
Specific embodiment
After now specific embodiments of the present invention are described in.
Embodiment 1 has the preparation of the graphene quantum dot of red fluorescence
Specific preparation process is as follows for the present embodiment:
(1) at room temperature, 240 ml concentrated nitric acids are measured and the 80 ml concentrated sulfuric acids is added in the round-bottomed flask of 500ml, stirred
It mixes uniformly；
(2) 4 g of pyrene is weighed, pyrene is added in nitration mixture under stirring, 80 DEG C of oil baths nitrify back flow reaction 24-48 h, cold
But it takes out afterwards；
(3) above-mentioned steps gained reactant is added slowly in 2000 ml deionized waters, is filtered using water system filter membrane,
Acid solution is removed, is then washed always until the solution of filtering is neutrality, 60 DEG C of obtained solid 48 h of vacuum drying remove water；
(4) solid after then taking drying is added in 40 ml n,N-Dimethylformamide and 2 h of ultrasonic disperse, is allowed to shape
At uniform suspension, 40 ml suspension are put into the reaction kettle that 80 ml polytetrafluoroethylene (PTFE) are liner immediately after, 180
DEG C reaction 12 h；
(5) it takes out after naturally cooling to room temperature, with the organic membrane filtration of 220 nm, filtered solution is transferred to
In round-bottomed flask, 80 DEG C of rotary evaporation drying are finally obtained with oil-soluble graphene quantum dot powder.
Embodiment 2 has the preparation of the graphene quantum dot of fluorescent orange
The present embodiment is prepared as follows:
(1) at room temperature, 240 ml concentrated nitric acids are measured and the 80 ml concentrated sulfuric acids is added in the round-bottomed flask of 500ml, stirred
It mixes uniformly；
(2) 4 g of pyrene is weighed, pyrene is added in nitration mixture under stirring, 80 DEG C of oil baths nitrify back flow reaction 24-48 h, cold
But it takes out afterwards；
(3) above-mentioned steps gained reactant is added slowly in 2000 ml deionized waters, is filtered using water system filter membrane,
Acid solution is removed, is then washed always until the solution of filtering is neutrality, 60 DEG C of obtained solid 48 h of vacuum drying remove water；
(4) simultaneously 2 h of ultrasonic disperse is then added in 40 ml toluene in the solid after drying, is allowed to form uniform suspension
40 ml suspension are put into the reaction kettle that 80 ml polytetrafluoroethylene (PTFE) are liner, 180 DEG C of 12 h of reaction by liquid immediately after；
(5) it takes out after naturally cooling to room temperature, with the organic membrane filtration of 220 nm, filtered solution is transferred to
In round-bottomed flask, 50 DEG C of rotary evaporation drying are finally obtained with oil-soluble graphene quantum dot powder.
Embodiment 3 has the preparation of the graphene quantum dot of green fluorescence
The present embodiment is prepared as follows:
(1) at room temperature, 240 ml concentrated nitric acids are measured and the 80 ml concentrated sulfuric acids is added in the round-bottomed flask of 500ml, stirred
It mixes uniformly；
(2) 4 g of pyrene is weighed, pyrene is added in nitration mixture under stirring, 80 DEG C of oil baths nitrify back flow reaction 24-48 h, cold
But it takes out afterwards；
(3) above-mentioned steps gained reactant is added slowly in 2000 ml deionized waters, is filtered using water system filter membrane,
Acid solution is removed, is then washed always until the solution of filtering is neutrality, 60 DEG C of obtained solid 48 h of vacuum drying remove water；
(4) solid after then taking drying is added in 40 ml ethyl alcohol and 2 h of ultrasonic disperse, is allowed to form uniform suspension
40 ml suspension are put into the reaction kettle that 80 ml polytetrafluoroethylene (PTFE) are liner immediately after, and 0.1ml ice vinegar are added by liquid
Acid.180 DEG C of 12 h of reaction；
(5) it takes out after naturally cooling to room temperature, with the organic membrane filtration of 220 nm, filtered solution is transferred to
In round-bottomed flask, 45 DEG C of rotary evaporation drying are finally obtained with oil-soluble graphene quantum dot black powder.
Products therefrom of the present invention can be stably dispersed in conventional organic solvent (toluene, ethyl alcohol etc.), but cannot be soluble in water,
Show good lipophilicity.The concentration range of graphene quantum dot solution reaches 2.0-4.0g/L.Under ultraviolet excitation, show
Show bright green, orange, red fluorescence.
X-ray diffraction analysis (XRD) is referring to Fig. 1: sample crystal face is away from (002) interplanar distance 3.34, with blocky graphite
Unanimously；The Raman spectrum analysis of sample shows the peak D and the peak G of typical graphene quantum dot referring to fig. 2, is located at 1356
cm-1With 1580 cm-1, corresponding unordered sp3Hydridization carbon structure and orderly sp2Graphitic carbon structure；Utilize transmitted electron
Microscope is observed referring to Fig. 3, and graphene quantum dot prepared by embodiment 1 is graininess, average particle size 2.8nm
Left and right.High-resolution photo shows the atomic structure of graphene quantum dot, is mono-crystalline structures.Absorption and fluorescence spectrum (figure
4) it shows, graphene quantum dot has wide absorption spectra and excitation spectrum, narrow and symmetrical fluorescence Spectra, emission wavelength and color one
It causes, respectively in 517 nm, 607nm, 620nm, quantum yield is up to 72%.
Claims (1)
1. a kind of preparation method of green orange red three fluorescence graphene quantum dot, it is characterised in that the specific steps of this method are as follows:
A., pyrene is stirred down to the mixing for being slowly added to full nitric acid or being made of sulfuric acid and concentrated nitric acid by the volume ratio of 3:1~1:1
It is back flow reaction 24~48 hours, cooling in acid；
B. reaction solution obtained by step a is added slowly in deionized water, is filtered using filter membrane, remove acid solution, then always
Until the solution of filtering is neutrality, obtained solid is dried for washing；
C. take step b obtained solid and dopant that simultaneously ultrasonic disperse shape is added in organic solvent according to the mass ratio of 1:0.3~1:1
At uniform suspension, or take step b obtained solid be added organic solvent in and ultrasonic disperse form uniform suspension, hang
Then concentration 1.25mg/ml~7.5mg/ml of supernatant liquid reacts 3~12h at 180~230 DEG C；It is cooling；
D. by the organic membrane filtration of suspension obtained by step c, filtered solution is removed into solvent, finally obtains green orange red three
Color fluorescence graphene quantum dot；
The dopant is glacial acetic acid, hydrobromic acid or acetate；
When the solvent is ethyl alcohol, green fluorescence graphene quantum dot is obtained；When the solvent is N, N- dimethyl formyl
When amine, red fluorescence graphene quantum dot is obtained；When the solvent is toluene, fluorescent orange graphene quantum dot is obtained；
The fluorescence emission wavelengths of obtained graphene quantum dot are adjustable by the type of adjusting organic solvent and the type of dopant,
To obtain to generate the green orange red three fluorescence graphene quantum dot of the red fluorescence from the green fluorescence of 520nm to 620nm.
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| CN108046236B (en) * | 2017-05-24 | 2020-11-06 | 北京师范大学 | Preparation method and application of red carbon quantum dots with high quantum yield |
| CN109704313A (en) * | 2019-03-06 | 2019-05-03 | 泉州师范学院 | A kind of high efficiency preparation method of hyperfluorescence graphene quantum dot |
| CN109705859A (en) * | 2019-03-06 | 2019-05-03 | 泉州师范学院 | A method of by changing solvent adjustment graphene quantum dot fluorescence |
| CN110272359B (en) * | 2019-06-26 | 2021-12-10 | 上海市第六人民医院 | Preparation method and application of yellow fluorescent biological imaging material |
| CN110540192B (en) * | 2019-09-11 | 2023-04-25 | 上海市第六人民医院 | Preparation method of graphene quantum dots |
| CN115074125B (en) * | 2022-08-16 | 2022-11-18 | 广东省科学院微生物研究所(广东省微生物分析检测中心) | GSH-based fluorescent nanoprobe and synthesis method and application thereof |
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