CN109370569A - A kind of preparation method of carbon containing quantum dot white light emission ionic liquid at room temperature - Google Patents
A kind of preparation method of carbon containing quantum dot white light emission ionic liquid at room temperature Download PDFInfo
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Abstract
The invention discloses a kind of preparation methods of carbon containing quantum dot white light emission ionic liquid at room temperature.This method is using o-phenylenediamine as presoma, by hydro-thermal method and phosphoric acid thermal method, is prepared for the carbon quantum dot of green emission and red emission respectively.Above two carbon quantum dot is dissolved into ionic liquid at room temperature, carbon containing quantum dot green emission and red emission ionic liquid at room temperature are obtained, and the carbon containing quantum of preparation is combined to fill enamel light emitting ionic liquid at room temperature, by the mixed proportion for deploying three, the carbon containing quantum dot white light emission ionic liquid at room temperature that chromaticity coordinates is (0.3298,0.3284) is obtained.Green emission prepared by the present invention, red emission carbon quantum dot can be directly dissolved in ionic liquid at room temperature；Prepared white light emission ionic liquid at room temperature chromophore is made of carbon quantum dot completely.Preparation method of the invention is easy to operate, is suitble to large-scale industrial production, and is conducive to widen carbon quantum dot in the application in fluorescent ink field.
Description
Technical field
The present invention relates to a kind of preparation methods of carbon containing quantum dot white light emission ionic liquid at room temperature, belong to new material neck
Domain.
Background technique
Ionic liquid is a kind of low temperature molten salt being made of the relatively large cation of volume with anion, wherein room
The ionic liquid being in a liquid state under temperature is known as ionic liquid at room temperature.Ionic liquid at room temperature have good thermal stability, it is low volatilization, no
It is flammable, referred to as molecule can design, property it is adjustable " green solvent ".In recent years, with the room-temperature ion of photoluminescence property
Liquid is by researcher's extensive concern.Common practice is fluorescent chromophore to be grafted on ionic liquid, or utilize coordination
Rare earth element is introduced ionic liquid at room temperature by effect.Diphenylethlene, azobenzene etc. are contained pi-conjugated group by existing document report
Be introduced into ionic liquid (referring to: Chem.Lett., 2010,39,240-241；Chem.Commun.,2011,47,6641-
6643), but the above method is related to more complicated organic synthesis, and luminous efficiency is low.Chinese patent document CN105949225A
Disclose a kind of luminescent material of liquid containing rare-earth europium ion for preparing: bromination 3- (2-1,10- phenanthroline) -1- methylimidazole europium is matched
Object is closed, which prepares glyoxaline ion liquid using quaternization reaction, first pass through season with N- methylimidazole and the bromo- ferrosin of 2-
Ammonium reaction prepares ionic liquid, after europium ion is added in ionic liquid, using complexation reaction preparation rare earth containing europium from
Bromination 3- (2-1,10- phenanthroline) -1- methylimidazole europium complex of son.But material prepared by this method is because containing rare earth
Element and lead at high price and poor biocompatibility.Therefore, using common ionic liquid at room temperature as solvent, in conjunction with new cheap hair
Luminescent material constructs luminous ionic liquid at room temperature, becomes the important R&D direction in one, the field.
Carbon quantum dot is a nova in fluorescent material field, refers to that size is less than 10nm, has torispherical structure, energy steady
Surely luminous a kind of nano-sized carbon.Carbon quantum dot have good water solubility, biocompatibility, stable photoluminescent property, by force
Anti-light bleaching power, easily preparation, it is at low cost the advantages that.Therefore, carbon quantum dot and ionic liquid at room temperature are organically combined,
It is to prepare one good research direction of luminous ionic liquid at room temperature.But carbon quantum dot reported in the literature, periphery are main at present
It is soluble easily in water for hydroxyl, carboxyl, amino isopolarity base group modification；Also there is the oil-soluble carbon of a small amount of document report alkyl chain modification
Quantum dot, such as Chinese patent document CN108441209A are related to a kind of alkyl modified oil-soluble carbon quantum dot, the carbon quantum dot
It is prepared by the following method: single tail chain small organic molecule is dissolved in benzene kind solvent, under argon gas protection, 100-180 DEG C
It is heated to reflux 24-72 hours, obtains appearance in flaxen solution, be then cooled to room temperature this solution, revolve solvent evaporated, mistake
Toluene gel column removes raw material, and outflow mixed liquor revolving is dry, crosses ethyl alcohol silicagel column, revolves solvent evaporated, vacuumize 10-20 hours
To obtain the final product.Solubility of these carbon quantum dots in common ionic liquid at room temperature is extremely limited, thus limits them in illuminated chamber
Application in temperature ionic liquid.
Summary of the invention
In view of the deficiencies of the prior art, especially luminous ionic liquid at room temperature construction method is complex at present, and shine effect
The problems such as rate is low, the present invention provides a kind of preparation method of carbon containing quantum dot white light emission ionic liquid at room temperature, this method is first
It is first prepared for carbon containing quantum dot green emission and red emission ionic liquid at room temperature, and fills enamel photoemissive room in conjunction with carbon containing quantum
Temperature ionic liquid, by deploying the mixed proportion of three, final obtained chromaticity coordinates is the carbon containing quantum dot of (0.3298,0.3284)
White light emission ionic liquid at room temperature.
Technical scheme is as follows:
A kind of preparation method of carbon containing quantum dot white light emission ionic liquid at room temperature, comprises the following steps that
(1) preparation of carbon containing quantum dot green emission ionic liquid at room temperature
O-phenylenediamine and aminooimidazole bromide are dissolved in deionized water, solution I is obtained, is heated, it is anti-at 140~200 DEG C
Answer, after reaction, cooling, purification obtains green emission carbon quantum dot, by gained green emission carbon quantum dot be added room temperature from
In sub- liquid, ultrasound is completely dissolved to carbon quantum dot obtains phosphorus content sub- point green emission ionic liquid at room temperature；
In the carbon containing quantum dot green emission ionic liquid at room temperature concentration of green emission carbon quantum dot be 0.01~
0.15mg/mL；
(2) preparation of carbon containing quantum dot red emission ionic liquid at room temperature
O-phenylenediamine and aminooimidazole bromide are dissolved in concentrated phosphoric acid, solution II is obtained, is heated, it is anti-at 140~200 DEG C
Answer, after reaction, cooling, purification obtains red emission carbon quantum dot, by gained red emission carbon quantum dot be added room temperature from
In sub- liquid, ultrasound is completely dissolved to carbon quantum dot obtains phosphorus content sub- point red emission ionic liquid at room temperature；
In the carbon containing quantum dot red emission ionic liquid at room temperature concentration of red emission carbon quantum dot be 0.01~
0.15mg/mL；
(3) carbon containing quantum is filled enamel the preparation of light emitting ionic liquid at room temperature
Citric acid and aminooimidazole bromide are dissolved in deionized water, solution III is obtained, heating distillation obtains jelly, will
Jelly is pyrolyzed at 210~270 DEG C, is cooled to room temperature addition deionized water and is obtained dispersion liquid, dispersion liquid dialysis purification, concentration are frozen
It is dry to obtain blue emission carbon quantum dot, blue emission carbon quantum dot aqueous solution is mixed with ionic liquid at room temperature, concussion makes carbon amounts
Son point from water phase is transferred to ionic liquid at room temperature, obtains carbon containing quantum and fills enamel light emitting ionic liquid at room temperature；
The carbon containing quantum fill enamel the concentration of blue emission carbon quantum dot in light emitting ionic liquid at room temperature be 0.05~
1.0mg/mL；
(4) modulation of carbon containing quantum dot white light emission ionic liquid at room temperature
By the carbon containing quantum dot green emission ionic liquid at room temperature of step (1) preparation, the carbon containing quantum dot of step (2) preparation
Red emission ionic liquid at room temperature and step (3) preparation carbon containing quantum fill enamel light emitting ionic liquid at room temperature mixing, adjust three
The ratio of person obtains carbon containing quantum dot white light emission ionic liquid at room temperature；The carbon containing quantum dot white light emission room-temperature ion
The mass ratio of green emission, red emission and blue emission carbon quantum dot is (4~5): (20~27): 50 in liquid.
, according to the invention it is preferred to, in solution I described in step (1) concentration of o-phenylenediamine be 0.045~
0.21mol/L；The molar ratio of the o-phenylenediamine and aminooimidazole bromide is 1:(0~1), further preferred 1:0.5；
Preferably, the aminooimidazole bromide is 1- amine propyl -3- methylimidazole bromide, 1- amine ethyl -3- methyl miaow
Azoles bromide, 1- amine butyl -3- methylimidazole bromide.
, according to the invention it is preferred to, reaction temperature described in step (1) is 160~180 DEG C；Reaction time be 8~
14h, further preferred 10~12h；
Preferably, it is cooled to reaction system cooled to room temperature described in step (1).
, according to the invention it is preferred to, purification described in step (1) is that the reaction solution that will be cooled down utilizes silica gel column layer
Analysis is purified, and eluant, eluent used is ethyl acetate, and solvent revolving is dry up to green emission carbon quantum dot；
Preferably, before being purified, the measurement of fluorescence quantum yield is carried out to carbon quantum dot in obtained reaction solution.
, according to the invention it is preferred to, ionic liquid at room temperature described in step (1) is 1- butyl -3- methylimidazole bis- (three
Fluoromethane sulphonyl) inferior amine salt, bis- (fluoroform sulphonyl) inferior amine salts of 1- hexyl -3- methylimidazole, 1- octyl -3- methylimidazole pair
(fluoroform sulphonyl) inferior amine salt, 1- butyl -3- methylimidazole hexafluorophosphate, 1- hexyl -3- methylimidazole hexafluorophosphate,
1- octyl -3- methylimidazole hexafluorophosphate or bis- (fluoroform sulphonyl) inferior amine salts of N- butyl-N- methyl piperidine；
Preferably, the concentration of green emission carbon quantum dot is in the carbon containing quantum dot green emission ionic liquid at room temperature
0.05~0.10mg/mL.
, according to the invention it is preferred to, in solution II described in step (2) concentration of o-phenylenediamine be 0.045~
0.21mol/L；The molar ratio of the o-phenylenediamine and aminooimidazole bromide is 1:(0~1), further preferred 1:0.5；
Preferably, the aminooimidazole bromide is 1- amine propyl -3- methylimidazole bromide, 1- amine ethyl -3- methyl miaow
Azoles bromide, 1- amine butyl -3- methylimidazole bromide；
Preferably, the mass fraction of the concentrated phosphoric acid is 85%.
, according to the invention it is preferred to, reaction temperature described in step (2) is 160~180 DEG C；Reaction time be 8~
14h, further preferred 10~12h；
Preferably, it is cooled to reaction system cooled to room temperature described in step (2).
, according to the invention it is preferred to, purification described in step (2) is the reaction solution dialysis purification that will be cooled down, and is seeped
The molecular cut off for analysing bag is 100~2000 dalton, and the dialysis time is 4~6 days；When carrying out dialysis purification, replaced every 12h
Deionized water outside dialysis bag, until dialysis terminates when diffusate is substantially colorless.
, according to the invention it is preferred to, ionic liquid at room temperature described in step (2) is 1- butyl -3- methylimidazole bis- (three
Fluoromethane sulphonyl) inferior amine salt, bis- (fluoroform sulphonyl) inferior amine salts of 1- hexyl -3- methylimidazole, 1- octyl -3- methylimidazole pair
(fluoroform sulphonyl) inferior amine salt, 1- butyl -3- methylimidazole hexafluorophosphate, 1- hexyl -3- methylimidazole hexafluorophosphate,
1- octyl -3- methylimidazole hexafluorophosphate or bis- (fluoroform sulphonyl) inferior amine salts of N- butyl-N- methyl piperidine；
Preferably, the concentration of red emission carbon quantum dot is in the carbon containing quantum dot red emission ionic liquid at room temperature
0.05~0.10mg/mL；
, according to the invention it is preferred to, carbon containing quantum described in step (3) is filled enamel the preparation of light emitting ionic liquid at room temperature
Including one or more in the following conditions:
A1: the molar ratio of the citric acid and aminooimidazole bromide is 1:(1~5)；The aminooimidazole bromide is
1- amine propyl -3- methylimidazole bromide, 1- amine ethyl-3-methylimidazole bromide, 1- amine butyl -3- methylimidazole bromide；It is described
Solution III in citric acid and aminooimidazole bromide gross mass and deionized water volume ratio be 1:(3~7) g/mL；
A2: the pyrolysis temperature is 230~250 DEG C；Pyrolysis time is 1~4h, preferably 2h；Lemon in the dispersion liquid
The volume ratio of the gross mass and deionized water of lemon acid and aminooimidazole bromide is 1:(3~10) g/mL；
A3: the molecular cut off of the dialysis bag of the dialysis is 1000 dalton；The dialysis time is 7 days, every for 24 hours more
Change the deionized water outside dialysis bag；
A4: the concentration of the blue emission carbon quantum dot aqueous solution is 0.1~2.0mg/mL, the blue emission carbon amounts
Son point aqueous solution volume and the volume ratio of ionic liquid at room temperature are (0.5~4): 2；
A5: the ionic liquid at room temperature be bis- (fluoroform sulphonyl) inferior amine salts of 1- butyl -3- methylimidazole, 1- oneself
Bis- (fluoroform sulphonyl) inferior amine salts of base -3- methylimidazole, bis- (fluoroform sulphonyl) inferior amine salts of 1- octyl -3- methylimidazole,
1- butyl -3- methylimidazole hexafluorophosphate, 1- hexyl -3- methylimidazole hexafluorophosphate, 1- octyl -3- methylimidazole hexafluoro
Phosphate or bis- (fluoroform sulphonyl) inferior amine salts of N- butyl-N- methyl piperidine；
A6: the carbon containing quantum concentration of blue emission carbon quantum dot in light emitting ionic liquid at room temperature of filling enamel is 0.25
~0.5mg/mL.
, according to the invention it is preferred to, green light in carbon containing quantum dot white light emission ionic liquid at room temperature described in step (4)
The mass ratio of transmitting, red emission and blue emission carbon quantum dot is (4~5): (24~27): 50.
It technical characteristic of the invention and has the beneficial effect that:
1., by hydro-thermal method and phosphoric acid thermal method, being prepared for green emission respectively using o-phenylenediamine as presoma in the present invention
With the carbon quantum dot of red emission, above two carbon quantum dot is dissolved into ionic liquid at room temperature, has obtained carbon containing quantum dot
Green emission and red emission ionic liquid at room temperature in conjunction with blue emission ionic liquid at room temperature, pass through allotment on this basis
The mixed proportion of three kinds of luminous ionic liquid at room temperature, obtained chromaticity coordinates be (0.3298,0.3284) white light emission room temperature from
Sub- liquid has widened the spectral region of the luminous ionic liquid at room temperature of carbon containing quantum dot.
2. green emission of the invention, is easy to scale at the preparation method simple possible of red emission carbon quantum dot；It is made
Standby green emission, red emission carbon quantum dot can be directly dissolved in ionic liquid at room temperature；Prepared white light emission room
Temperature ionic liquid chromophore is made of carbon quantum dot completely.
3. preparing carbon containing quantum dot green emission, red emission, white light emission room-temperature ion liquid the present invention provides a kind of
The method of body, the preparation method is easy to operate, is suitble to large-scale industrial production, and is conducive to widen carbon quantum dot in fluorescence
The application of ink area.
Detailed description of the invention
Fig. 1 is carbon containing quantum dot green emission ionic liquid at room temperature prepared by embodiment 15 under different excitation wavelengths
Fluorescent emission spectrogram.
Fig. 2 is carbon containing quantum dot red emission ionic liquid at room temperature prepared by embodiment 22 under different excitation wavelengths
Fluorescent emission spectrogram.
Fig. 3 is that carbon containing quantum prepared by embodiment 32 fills enamel light emitting ionic liquid at room temperature under different excitation wavelengths
Fluorescent emission spectrogram.
Fig. 4 is to identify carbon containing quantum dot green emission (A), red emission (B), blue emission (C) and embodiment respectively
The chromaticity coordinates of 42 gained white light emission (D) ionic liquid at room temperature.
Specific embodiment
The present invention is further detailed With reference to embodiment, but not limited to this.
Embodiment 1
The preparation of green emission carbon quantum dot
0.16g o-phenylenediamine is weighed, 0.083g 1- amine propyl -3- methylimidazole bromide, stirring and dissolving is in 10mL deionization
In water；Above-mentioned solution is transferred in autoclave, is heated using baking oven, reacts 12h at 180 DEG C；After reaction, turn off
Baking oven, cooled to room temperature obtain reaction solution, and the fluorescence quantum yield of carbon quantum dot is in measurement gained reaction solution
6.94%；Reaction solution is further utilized into silica gel column chromatography, is purified by eluant, eluent of ethyl acetate, rotation solvent evaporated obtains
Green emission carbon quantum dot.
Embodiment 2
The preparation of green emission carbon quantum dot
As described in Example 1, except that the additional amount of 1- amine propyl -3- methylimidazole bromide is 0g, gained reaction
The fluorescence quantum yield of carbon quantum dot is 7.90% in liquid.
Embodiment 3
The preparation of green emission carbon quantum dot
As described in Example 1, except that the additional amount of 1- amine propyl -3- methylimidazole bromide is 0.17g, gained is anti-
The fluorescence quantum yield for answering carbon quantum dot in liquid is 10.31%, and the fluorescent quantum of gained green emission carbon quantum dot produces after purification
Rate is 11.68%.
Embodiment 4
The preparation of green emission carbon quantum dot
As described in Example 1, except that the additional amount of 1- amine propyl -3- methylimidazole bromide is 0.25g, gained is anti-
The fluorescence quantum yield for answering carbon quantum dot in liquid is 8.29%.
Embodiment 5
The preparation of green emission carbon quantum dot
As described in Example 1, except that the additional amount of 1- amine propyl -3- methylimidazole bromide is 0.33g, gained is anti-
The fluorescence quantum yield for answering carbon quantum dot in liquid is 7.71%.
Embodiment 6
The preparation of green emission carbon quantum dot
As described in Example 1, except that the additional amount of o-phenylenediamine is 0.054g, 1- amine propyl -3- methylimidazole
The additional amount of bromide is 0.055g, and the fluorescence quantum yield of carbon quantum dot is 8.18% in gained reaction solution.
Embodiment 7
The preparation of green emission carbon quantum dot
As described in Example 1, except that the additional amount of o-phenylenediamine is 0.11g, 1- amine propyl -3- methylimidazole bromine
The additional amount of salt is 0.11g, and the fluorescence quantum yield of carbon quantum dot is 8.97% in gained reaction solution.
Embodiment 8
The preparation of green emission carbon quantum dot
As described in Example 1, except that the additional amount of o-phenylenediamine is 0.22g, 1- amine propyl -3- methylimidazole bromine
The additional amount of salt is 0.22g, and the fluorescence quantum yield of carbon quantum dot is 7.84% in gained reaction solution.
Embodiment 9
The preparation of green emission carbon quantum dot
As described in Example 3, except that reaction temperature is 140 DEG C, the fluorescence volume of carbon quantum dot in gained reaction solution
Sub- yield is 7.98%.
Embodiment 10
The preparation of green emission carbon quantum dot
As described in Example 3, except that reaction temperature is 160 DEG C, the fluorescence volume of carbon quantum dot in gained reaction solution
Sub- yield is 8.30%.
Embodiment 11
The preparation of green emission carbon quantum dot
As described in Example 3, except that reaction temperature is 200 DEG C, the fluorescence volume of carbon quantum dot in gained reaction solution
Sub- yield is 7.08%.
Embodiment 12
The preparation of green emission carbon quantum dot
As described in Example 3, except that the reaction time is 8h, the fluorescent quantum of carbon quantum dot is produced in gained reaction solution
Rate is 6.28%.
Embodiment 13
The preparation of green emission carbon quantum dot
As described in Example 3, except that the reaction time is 10h, the fluorescent quantum of carbon quantum dot in gained reaction solution
Yield is 7.56%.
Embodiment 14
The preparation of green emission carbon quantum dot
As described in Example 3, except that the reaction time is 14h, the fluorescent quantum of carbon quantum dot in gained reaction solution
Yield is 7.28%.
Embodiment 1-14 can be summarized as following table 1.
1 embodiment 1-14 experiment condition of table and result
* illustrate: fluorescence quantum yield described in table is the fluorescence quantum yield of carbon quantum dot in reaction solution.
Embodiment 15
The preparation of carbon containing quantum dot green emission ionic liquid at room temperature
Green emission carbon quantum dot prepared by 0.3mg embodiment 3 is weighed, 3mL 1- butyl -3- methylimidazole is added to
In bis- (fluoroform sulphonyl) inferior amine salts, ultrasound obtains the carbon containing quantum dot green emission that concentration is 0.1mg/mL to being completely dissolved
Ionic liquid at room temperature.
Fluorescence hair of the carbon containing quantum dot green emission ionic liquid at room temperature manufactured in the present embodiment under different excitation wavelengths
Spectrogram is penetrated as shown in Figure 1, its maximum excitation wavelength is in 390nm as seen from Figure 1, best launch wavelength is in 549nm.
Embodiment 16
The preparation of carbon containing quantum dot green emission ionic liquid at room temperature
As described in Example 15, except that bis- (fluoroform sulphonyl) inferior amine salts of 1- butyl -3- methylimidazole are replaced
It is changed to bis- (fluoroform sulphonyl) inferior amine salts of 1- hexyl -3- methylimidazole.
Embodiment 17
The preparation of carbon containing quantum dot green emission ionic liquid at room temperature
As described in Example 15, except that bis- (fluoroform sulphonyl) inferior amine salts of 1- butyl -3- methylimidazole are replaced
It is changed to bis- (fluoroform sulphonyl) inferior amine salts of 1- octyl -3- methylimidazole.
Embodiment 18
The preparation of carbon containing quantum dot green emission ionic liquid at room temperature
As described in Example 15, except that bis- (fluoroform sulphonyl) inferior amine salts of 1- butyl -3- methylimidazole are replaced
It is changed to 1- butyl -3- methylimidazole hexafluorophosphate.
Embodiment 19
The preparation of carbon containing quantum dot green emission ionic liquid at room temperature
As described in Example 15, except that bis- (fluoroform sulphonyl) inferior amine salts of 1- butyl -3- methylimidazole are replaced
It is changed to 1- hexyl -3- methylimidazole hexafluorophosphate.
Embodiment 20
The preparation of carbon containing quantum dot green emission ionic liquid at room temperature
As described in Example 15, except that bis- (fluoroform sulphonyl) inferior amine salts of 1- butyl -3- methylimidazole are replaced
It is changed to 1- octyl -3- methylimidazole hexafluorophosphate.
Embodiment 21
The preparation of carbon containing quantum dot green emission ionic liquid at room temperature
As described in Example 15, except that bis- (fluoroform sulphonyl) inferior amine salts of 1- butyl -3- methylimidazole are replaced
It is changed to bis- (fluoroform sulphonyl) inferior amine salts of N- butyl-N- methyl piperidine.
Embodiment 22
The preparation of carbon containing quantum dot red emission ionic liquid at room temperature
By 0.16g o-phenylenediamine and 0.17g 1- amine propyl -3- methylimidazole bromide, being added to 10mL mass fraction is
In 85% concentrated phosphoric acid, stirring is to being completely dissolved；Above-mentioned solution is transferred to autoclave, is heated using baking oven, at 180 DEG C
12h is reacted, after reaction, turns off baking oven, cooled to room temperature, it is 500 dongles that reaction solution, which is transferred to molecular cut off,
Dialysis purification is carried out in the dialysis bag to pause, the deionized water outside 12h replacement dialysis bag, until diffusate is substantially colorless.It seeps
After analysis, solution in bag is taken out, it is concentrated freeze-dried to obtain red emission carbon quantum dot；
Red emission carbon quantum dot prepared by 0.3mg is weighed in bis- (the fluoroform sulphurs of 3mL 1- butyl -3- methylimidazole
Acyl) in inferior amine salt, ultrasound is completely dissolved to carbon quantum dot, and obtaining concentration is the carbon containing quantum dot red emission room-temperature ion of 0.1mg/mL
Liquid.
Fluorescence hair of the carbon containing quantum dot red emission ionic liquid at room temperature manufactured in the present embodiment under different excitation wavelengths
Spectrogram is penetrated as shown in Fig. 2, its maximum excitation wavelength two hairs occurs in 549nm and 655nm in 480nm as seen from Figure 2
Penetrate peak.
Embodiment 23
The preparation of carbon containing quantum dot red emission ionic liquid at room temperature
As described in Example 22, except that the molecular cut off of dialysis bag is 100 dalton.
Embodiment 24
The preparation of carbon containing quantum dot red emission ionic liquid at room temperature
As described in Example 22, except that the molecular cut off of dialysis bag is 1000 dalton.
Embodiment 25
The preparation of carbon containing quantum dot red emission ionic liquid at room temperature
As described in Example 22, except that the molecular cut off of dialysis bag is 2000 dalton.
Embodiment 26
The preparation of carbon containing quantum dot red emission ionic liquid at room temperature
As described in Example 22, except that by ionic liquid at room temperature by the bis- (fluoroforms of 1- butyl -3- methylimidazole
Sulphonyl) inferior amine salt replaces with bis- (fluoroform sulphonyl) inferior amine salts of 1- hexyl -3- methylimidazole.
Embodiment 27
The preparation of carbon containing quantum dot red emission ionic liquid at room temperature
As described in Example 22, except that by ionic liquid at room temperature by the bis- (fluoroforms of 1- butyl -3- methylimidazole
Sulphonyl) inferior amine salt replaces with bis- (fluoroform sulphonyl) inferior amine salts of 1- octyl -3- methylimidazole.
Embodiment 28
The preparation of carbon containing quantum dot red emission ionic liquid at room temperature
As described in Example 22, except that by ionic liquid at room temperature by the bis- (fluoroforms of 1- butyl -3- methylimidazole
Sulphonyl) inferior amine salt replaces with 1- butyl -3- methylimidazole hexafluorophosphate.
Embodiment 29
The preparation of carbon containing quantum dot red emission ionic liquid at room temperature
As described in embodiment 22, except that by ionic liquid at room temperature by the bis- (fluoroforms of 1- butyl -3- methylimidazole
Alkane sulphonyl) inferior amine salt replaces with 1- hexyl -3- methylimidazole hexafluorophosphate.
Embodiment 30
The preparation of carbon containing quantum dot red emission ionic liquid at room temperature
As described in Example 22, except that by ionic liquid at room temperature by the bis- (fluoroforms of 1- butyl -3- methylimidazole
Sulphonyl) inferior amine salt replaces with 1- octyl -3- methylimidazole hexafluorophosphate.
Embodiment 31
The preparation of carbon containing quantum dot red emission ionic liquid at room temperature
As described in Example 22, except that by ionic liquid at room temperature by the bis- (fluoroforms of 1- butyl -3- methylimidazole
Sulphonyl) inferior amine salt replaces with bis- (fluoroform sulphonyl) inferior amine salts of N- butyl-N- methyl piperidine.
Embodiment 32
Carbon containing quantum is filled enamel the preparation of light emitting ionic liquid at room temperature
Weigh 1g citric acid and 3.15g 1- amine propyl -3- methylimidazole bromide, ultrasonic dissolution in 25mL deionized water,
By the above mixture, agitating and heating is distilled in oil bath pan, is removed deionized water and is obtained jelly.By obtained jelly 240
Reaction solution is cooled to room temperature by DEG C high temperature pyrolysis 2h naturally, and 25mL deionized water is added and obtains dispersion liquid and is placed in the dispersion liquid
Molecular cut off is dialysis in the dialysis bag of 1000 dalton, per changing deionized water for 24 hours outside dialysis bag, until diffusate substantially without
Color.After dialysis, solution in bag is taken out, it is concentrated freeze-dried to obtain blue emission carbon quantum dot.
It is that the bis- (fluoroforms of 2mL 1- butyl -3- methylimidazole are added in 0.5mg/mL carbon quantum dot aqueous solution to 2mL concentration
Alkane sulphonyl) inferior amine salt, shaking makes carbon quantum dot be transferred to ionic liquid mutually to get the phosphorus content of concentration 0.5mg/mL from water phase
Son point blue emission ionic liquid at room temperature.
Carbon containing quantum obtained by the present embodiment is filled enamel fluorescent emission of the light emitting ionic liquid at room temperature under different excitation wavelengths
Spectrogram is as shown in figure 3, its maximum excitation wavelength is in 390nm as can be seen from Figure 3, and best launch wavelength is in 450nm.
Embodiment 33
Carbon containing quantum is filled enamel the preparation of light emitting ionic liquid at room temperature
As described in embodiment 32, except that by ionic liquid at room temperature by the bis- (fluoroforms of 1- butyl -3- methylimidazole
Sulphonyl) inferior amine salt replaces with bis- (fluoroform sulphonyl) inferior amine salts of 1- hexyl -3- methylimidazole.
Embodiment 34
Carbon containing quantum is filled enamel the preparation of light emitting ionic liquid at room temperature
As described in embodiment 32, except that by ionic liquid at room temperature by the bis- (fluoroforms of 1- butyl -3- methylimidazole
Sulphonyl) inferior amine salt replaces with bis- (fluoroform sulphonyl) inferior amine salts of 1- octyl -3- methylimidazole.
Embodiment 35
Carbon containing quantum is filled enamel the preparation of light emitting ionic liquid at room temperature
As described in embodiment 32, except that by ionic liquid at room temperature by the bis- (fluoroforms of 1- butyl -3- methylimidazole
Sulphonyl) inferior amine salt replaces with 1- butyl -3- methylimidazole hexafluorophosphate.
Embodiment 36
Carbon containing quantum is filled enamel the preparation of light emitting ionic liquid at room temperature
As described in embodiment 32, except that by ionic liquid at room temperature by the bis- (fluoroforms of 1- butyl -3- methylimidazole
Sulphonyl) inferior amine salt replaces with 1- hexyl -3- methylimidazole hexafluorophosphate.
Embodiment 37
Carbon containing quantum is filled enamel the preparation of light emitting ionic liquid at room temperature
As described in embodiment 32, except that by ionic liquid at room temperature by the bis- (fluoroforms of 1- butyl -3- methylimidazole
Sulphonyl) inferior amine salt replaces with 1- octyl -3- methylimidazole hexafluorophosphate.
Embodiment 38
Carbon containing quantum is filled enamel the preparation of light emitting ionic liquid at room temperature
As described in embodiment 32, except that by ionic liquid at room temperature by the bis- (fluoroforms of 1- butyl -3- methylimidazole
Sulphonyl) inferior amine salt replaces with bis- (fluoroform sulphonyl) inferior amine salts of N- butyl-N- methyl piperidine.
Embodiment 39
The preparation of carbon containing quantum dot white light emission ionic liquid at room temperature
Carbon containing quantum dot green emission ionic liquid at room temperature, the 200 μ L embodiments of the preparation of 40 μ L embodiments 15 are measured respectively
The carbon containing quantum dot red emission ionic liquid at room temperature of 22 preparations and the carbon containing quantum of 100 μ L embodiments 32 preparation are filled enamel light emitting
Ionic liquid at room temperature stirs evenly, and obtains carbon containing quantum dot white light emission ionic liquid at room temperature.
Spectrum analysis shows that carbon containing quantum dot white light emission ionic liquid at room temperature manufactured in the present embodiment is in excitation wavelength
The chromaticity coordinates of gained fluorescence emission spectrum is (0.3100,0.3280) under 365nm.
Embodiment 40
The preparation of carbon containing quantum dot white light emission ionic liquid at room temperature
As described in embodiment 39, except that carbon containing volume of the quantum dot red emission containing ionic liquid at room temperature is 240 μ
L。
Spectrum analysis shows that carbon containing quantum dot white light emission ionic liquid at room temperature manufactured in the present embodiment is in excitation wavelength
The chromaticity coordinates of gained fluorescence emission spectrum is (0.3200,0.3282) under 365nm.
Embodiment 41
The preparation of carbon containing quantum dot white light emission ionic liquid at room temperature
As described in embodiment 39, except that the volume of carbon containing quantum dot red emission ionic liquid at room temperature is 250 μ L.
Spectrum analysis shows that carbon containing quantum dot white light emission ionic liquid at room temperature manufactured in the present embodiment is in excitation wavelength
The chromaticity coordinates of gained fluorescence emission spectrum is (0.3223,0.3304) under 365nm.
Embodiment 42
The preparation of carbon containing quantum dot white light emission ionic liquid at room temperature
As described in embodiment 39, except that the volume of carbon containing quantum dot red emission ionic liquid at room temperature is 270 μ L.
Spectrum analysis shows that carbon containing quantum dot white light emission ionic liquid at room temperature manufactured in the present embodiment is in excitation wavelength
The chromaticity coordinates of gained fluorescence emission spectrum is (0.3298,0.3284) under 365nm.Carbon containing quantum dot green light used in the present embodiment
The chromaticity coordinates of white light emission ionic liquid at room temperature such as Fig. 4 institute prepared by transmitting, red emission, blue emission and the present embodiment
Show, excitation wavelength used is 365nm.
Embodiment 43
The preparation of carbon containing quantum dot white light emission ionic liquid at room temperature
As described in embodiment 39, except that the volume of carbon containing quantum dot green emission ionic liquid at room temperature is 50 μ L.
Spectrum analysis shows that carbon containing quantum dot white light emission ionic liquid at room temperature manufactured in the present embodiment is in excitation wavelength
The chromaticity coordinates of gained fluorescence emission spectrum is (0.3089,0.3376) under 365nm.
Above-mentioned, although the foregoing specific embodiments of the present invention is described with reference to the accompanying drawings, not to invention protection scope
Limitation, those skilled in the art should understand that, based on the technical solutions of the present invention, those skilled in the art are not required to
It is still within the scope of the present invention to make the creative labor the various modifications or changes that can be made.
The foregoing is only a preferred embodiment of the present invention, but scope of protection of the present invention is not limited thereto,
Within the technical scope of the present disclosure, any changes or substitutions that can be easily thought of by anyone skilled in the art,
It should all be included within the scope of the present invention.Therefore, protection scope of the present invention should be with the protection of claims
Subject to range.
Claims (10)
1. a kind of preparation method of carbon containing quantum dot white light emission ionic liquid at room temperature, comprises the following steps that
(1) preparation of carbon containing quantum dot green emission ionic liquid at room temperature
O-phenylenediamine and aminooimidazole bromide are dissolved in deionized water, solution I is obtained, heats, is reacted at 140~200 DEG C, instead
After answering, cooling, purification obtains green emission carbon quantum dot, and room-temperature ion liquid is added in gained green emission carbon quantum dot
In body, ultrasound is completely dissolved to carbon quantum dot obtains phosphorus content sub- point green emission ionic liquid at room temperature；
The concentration of green emission carbon quantum dot is 0.01~0.15mg/ in the carbon containing quantum dot green emission ionic liquid at room temperature
mL；
(2) preparation of carbon containing quantum dot red emission ionic liquid at room temperature
O-phenylenediamine and aminooimidazole bromide are dissolved in concentrated phosphoric acid, solution II is obtained, heats, is reacted at 140~200 DEG C, instead
After answering, cooling, purification obtains red emission carbon quantum dot, and room-temperature ion liquid is added in gained red emission carbon quantum dot
In body, ultrasound is completely dissolved to carbon quantum dot obtains phosphorus content sub- point red emission ionic liquid at room temperature；
The concentration of red emission carbon quantum dot is 0.01~0.15mg/ in the carbon containing quantum dot red emission ionic liquid at room temperature
mL；
(3) carbon containing quantum is filled enamel the preparation of light emitting ionic liquid at room temperature
Citric acid and aminooimidazole bromide are dissolved in deionized water, solution III is obtained, heating distillation obtains jelly, will be gluey
Object is pyrolyzed at 210~270 DEG C, is cooled to room temperature and deionized water is added is obtained dispersion liquid, by dispersion liquid dialysis purification, concentrated freeze-dried
To blue emission carbon quantum dot, blue emission carbon quantum dot aqueous solution is mixed with ionic liquid at room temperature, concussion makes carbon quantum dot
It is transferred to ionic liquid at room temperature from water phase, carbon containing quantum is obtained and fills enamel light emitting ionic liquid at room temperature；
The carbon containing quantum concentration of blue emission carbon quantum dot in light emitting ionic liquid at room temperature of filling enamel is 0.05~1.0mg/
mL；
(4) modulation of carbon containing quantum dot white light emission ionic liquid at room temperature
By the carbon containing quantum dot green emission ionic liquid at room temperature of step (1) preparation, the carbon containing quantum dot feux rouges of step (2) preparation
Transmitting ionic liquid at room temperature and step (3) preparation carbon containing quantum fill enamel light emitting ionic liquid at room temperature mixing, adjust three's
Ratio obtains carbon containing quantum dot white light emission ionic liquid at room temperature；The carbon containing quantum dot white light emission ionic liquid at room temperature
The mass ratio of middle green emission, red emission and blue emission carbon quantum dot is (4~5): (20~27): 50.
2. the preparation method of white light emission ionic liquid at room temperature according to claim 1, which is characterized in that in step (1)
The concentration of o-phenylenediamine is 0.045~0.21mol/L in the solution I；The o-phenylenediamine and aminooimidazole bromide
Molar ratio is 1:(0~1), preferably 1:0.5；
Preferably, the aminooimidazole bromide is 1- amine propyl -3- methylimidazole bromide, 1- amine ethyl-3-methylimidazole bromine
Salt, 1- amine butyl -3- methylimidazole bromide.
3. the preparation method of white light emission ionic liquid at room temperature according to claim 1, which is characterized in that in step (1)
The reaction temperature is 160~180 DEG C；Reaction time is 8~14h, preferably 10~12h；Described is cooled to reactant
It is cooled to room temperature.
4. the preparation method of white light emission ionic liquid at room temperature according to claim 1, which is characterized in that in step (1)
The purification is to purify the reaction solution cooled down using silica gel column chromatography, and eluant, eluent used is ethyl acetate,
Solvent revolving is dry up to green emission carbon quantum dot；Preferably, before being purified, to carbon quantum in obtained reaction solution
Point carries out the measurement of fluorescence quantum yield.
5. the preparation method of white light emission ionic liquid at room temperature according to claim 1, which is characterized in that in step (1)
The ionic liquid at room temperature is bis- (fluoroform sulphonyl) inferior amine salts of 1- butyl -3- methylimidazole, 1- hexyl -3- methylimidazole
Bis- (fluoroform sulphonyl) inferior amine salts of bis- (fluoroform sulphonyl) inferior amine salts, 1- octyl -3- methylimidazole, 1- butyl -3- methyl
Limidazolium hexafluorophosphate, 1- hexyl -3- methylimidazole hexafluorophosphate, 1- octyl -3- methylimidazole hexafluorophosphate or N- fourth
Bis- (fluoroform sulphonyl) inferior amine salts of base-N- methyl piperidine；
Preferably, in the carbon containing quantum dot green emission ionic liquid at room temperature green emission carbon quantum dot concentration be 0.05~
0.10mg/mL。
6. the preparation method of white light emission ionic liquid at room temperature according to claim 1, which is characterized in that in step (2)
The concentration of o-phenylenediamine is 0.045~0.21mol/L in the solution II；The o-phenylenediamine and aminooimidazole bromide
Molar ratio is 1:(0~1), preferably 1:0.5；The aminooimidazole bromide is 1- amine propyl -3- methylimidazole bromide, 1- amine second
Base -3- methylimidazole bromide, 1- amine butyl -3- methylimidazole bromide；The mass fraction of the concentrated phosphoric acid is 85%.
7. the preparation method of white light emission ionic liquid at room temperature according to claim 1, which is characterized in that in step (2)
The reaction temperature is 160~180 DEG C；Reaction time is 8~14h, preferably 10~12h；Described is cooled to reactant
It is cooled to room temperature；
The purification is the reaction solution dialysis purification that will be cooled down, and the molecular cut off of dialysis bag is 100-2000 dongle
, the dialysis time is 4~6 days；Carry out dialysis when, every 12h replacement dialysis bag outside deionized water, until diffusate substantially without
When color, dialysis terminates.
8. the preparation method of white light emission ionic liquid at room temperature according to claim 1, which is characterized in that in step (2)
The ionic liquid at room temperature is bis- (fluoroform sulphonyl) inferior amine salts of 1- butyl -3- methylimidazole, 1- hexyl -3- methylimidazole
Bis- (fluoroform sulphonyl) inferior amine salts of bis- (fluoroform sulphonyl) inferior amine salts, 1- octyl -3- methylimidazole, 1- butyl -3- methyl
Limidazolium hexafluorophosphate, 1- hexyl -3- methylimidazole hexafluorophosphate, 1- octyl -3- methylimidazole hexafluorophosphate or N- fourth
Bis- (fluoroform sulphonyl) inferior amine salts of base-N- methyl piperidine；
Preferably, in the carbon containing quantum dot red emission ionic liquid at room temperature red emission carbon quantum dot concentration be 0.05~
0.10mg/mL。
9. the preparation method of white light emission ionic liquid at room temperature according to claim 1, which is characterized in that in step (3)
The carbon containing quantum fill enamel light emitting ionic liquid at room temperature preparation include the following conditions in it is one or more:
A1: the molar ratio of the citric acid and aminooimidazole bromide is 1:(1~5)；The aminooimidazole bromide is 1- amine
Propyl -3- methylimidazole bromide, 1- amine ethyl-3-methylimidazole bromide, 1- amine butyl -3- methylimidazole bromide；Described is molten
The volume ratio of the gross mass and deionized water of citric acid and aminooimidazole bromide is 1:(3~7 in liquid III) g/mL；
A2: the pyrolysis temperature is 230~250 DEG C；Pyrolysis time is 1~4h, preferably 2h；Citric acid in the dispersion liquid
It is 1:(3~10 with the gross mass of aminooimidazole bromide and the volume ratio of deionized water) g/mL；
A3: the molecular cut off of the dialysis bag of the dialysis is 1000 dalton；The dialysis time is 7 days, is seeped every replacement for 24 hours
Analyse the deionized water outside bag；
A4: the concentration of the blue emission carbon quantum dot aqueous solution is 0.1~2.0mg/mL, the blue emission carbon quantum dot
Aqueous solution volume and the volume ratio of ionic liquid at room temperature are (0.5~4): 2；
A5: the ionic liquid at room temperature is bis- (fluoroform sulphonyl) inferior amine salts of 1- butyl -3- methylimidazole, 1- hexyl -3-
Bis- (fluoroform sulphonyl) inferior amine salts of methylimidazole, bis- (fluoroform sulphonyl) inferior amine salts of 1- octyl -3- methylimidazole, 1- fourth
Base -3- methylimidazole hexafluorophosphate, 1- hexyl -3- methylimidazole hexafluorophosphate, 1- octyl -3- methylimidazole hexafluorophosphoric acid
Salt or bis- (fluoroform sulphonyl) inferior amine salts of N- butyl-N- methyl piperidine；
A6: the carbon containing quantum fill enamel the concentration of blue emission carbon quantum dot in light emitting ionic liquid at room temperature be 0.25~
0.5mg/mL。
10. the preparation method of white light emission ionic liquid at room temperature according to claim 1, which is characterized in that in step (4)
Green emission, the matter of red emission and blue emission carbon quantum dot in the carbon containing quantum dot white light emission ionic liquid at room temperature
Amount is than being (4~5): (24~27): 50.
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