CN105838364B - A kind of method for being pyrolyzed ammonium carboxylate salt and preparing fluorescent carbon point - Google Patents
A kind of method for being pyrolyzed ammonium carboxylate salt and preparing fluorescent carbon point Download PDFInfo
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Abstract
The invention discloses a kind of method for being pyrolyzed ammonium carboxylate salt and preparing fluorescent carbon point, comprise the steps of：1）Polybasic carboxylic acid is dissolved in deionized water, ultrasonic vibration, under nitrogen protective condition, adds diamine reaction, petroleum ether is used after reacting completely, separate water-yielding stratum, decompression rotary evaporation removes unreacted diamine, obtains yellow solid；2）Yellow solid is placed in tube furnace, heated under nitrogen protection, grinding obtains black powder after insulation；3）Black powder is dissolved in absolute ethyl alcohol, bag filter dialysis, the solution rotating outside bag filter is evaporated to obtain fluorescent carbon point.The preparation method of the present invention is simple to operate, and raw material is easy to get, and cost is low, and environmental contaminants are not discharged in preparation process, belongs to environmentally friendly preparation technology；The average grain diameter of fluorescent carbon point prepared by the present invention is 11nm, and good water solubility, fluorescent stabilization, fluorescence quantum yield reaches 22.46%, available for Fe3+Detection.
Description
Technical field
The present invention relates to a kind of method for being pyrolyzed ammonium carboxylate salt and preparing fluorescent carbon point, belong to nano-carbon material fabricating technology
Field.
Background technology
Carbon point (CarbonDots), its core are particle diameter for the carbon nano-particle less than 10nm, due to good glimmering
Optical property, excellent biocompatibility, nontoxic and be easy to surface-functionalized, the research heat being increasingly becoming in luminescence generated by light field
Point.But current preparation method fluorescent yield is few higher than 20%, and most processing steps are cumbersome, gained fluorescent carbon point needs
Surface passivator can be only achieved certain fluorescence property after carrying out surface modification process, cause its reaction yield low, it is difficult to scale
Production is promoted, and therefore, it is very necessary to develop effective, simple, cheap, large-scale production fluorescent carbon point.
The content of the invention
In order to solve the above technical problems, the invention provides the pyrolysis carboxylic acid ammonium that a kind of preparation method is simple, raw material is easy to get
The method that salt prepares fluorescent carbon point, the fluorescent carbon point can be used for Fe in detection water3+Concentration.
The purpose of the present invention is achieved by the following technical solution：
A kind of method for being pyrolyzed ammonium carboxylate salt and preparing fluorescent carbon point, is comprised the steps of：
1）Polybasic carboxylic acid is dissolved in deionized water, ultrasonic vibration, under nitrogen protective condition, adds diamine reaction, instead
Petroleum ether should be used afterwards completely, separate water-yielding stratum, decompression rotary evaporation removes unreacted diamine, obtains yellow solid；
The polybasic carboxylic acid is ethylenediamine tetra-acetic acid or citric acid；
The diamine is one kind in ethylenediamine, propane diamine and butanediamine；
2）Yellow solid is placed in tube furnace, heated under nitrogen protection, grinding obtains black powder after insulation；
3）Black powder is dissolved in absolute ethyl alcohol, bag filter dialysis, the solution rotating outside bag filter is evaporated to obtain glimmering
Light carbon point.
Preferably, polybasic carboxylic acid is ethylenediamine tetra-acetic acid；Preferably, diamine is ethylenediamine.
Described, the mass ratio of polybasic carboxylic acid and deionized water is 1：5-15.
Described, the time of ultrasonic vibration is 1-10min.
Described, the mol ratio of polybasic carboxylic acid and diamine is 1：1-3.
Described, reaction temperature is 10-50 DEG C, reaction time 5-10h.
Described, the rate of heat addition is 1-5 DEG C/min, is heated to 300 DEG C -450 DEG C, soaking time 0.5-2h.
Described, milling time 10min.
Described, bag filter specification molecular weight is 3500, dialysis time 48-72h.
Beneficial effects of the present invention：
1. the preparation method of the present invention is simple to operate, raw material is easy to get, and cost is low；
2. the average grain diameter of fluorescent carbon point prepared by the present invention is 11nm, good water solubility, fluorescent stabilization, fluorescence quantum yield
Reach 22.46%；
3. not discharging environmental contaminants in the fluorescent carbon point preparation process of the present invention, belong to environmentally friendly preparation technology；
4. fluorescent carbon point prepared by the present invention can be used for Fe3+Detection.
Brief description of the drawings
Fig. 1 is the transmission electron microscope of the fluorescent carbon point prepared in embodiment 1（TEM）Photo；
Fig. 2 is uv absorption spectra, the fluorescent exciting spectrogram of the fluorescent carbon point prepared in embodiment 1（350nm）With
Fluorescence emission spectrogram of compound（416nm）；
Fig. 3 is the fluorescent carbon point prepared in embodiment 1 in natural light（It is left）With uviol lamp（365nm）（It is right）Reality under irradiation
Thing figure；
Fig. 4 is the infrared spectrogram of the fluorescent carbon point prepared in embodiment 1；
Fig. 5 is influence of the different metal ions to fluorescent carbon point fluorescence intensity in embodiment 1；
Fig. 6 is the fluorescent carbon point prepared in embodiment 1 in various concentrations Fe3+Under fluorescence emission spectrogram of compound；
Fig. 7 is the fluorescent carbon point relative intensity of fluorescence prepared in embodiment 1 to Fe3+The linear relationship chart of concentration.
Embodiment
In order that person skilled in the art more fully understands technical scheme, it is right with reference to the accompanying drawings and examples
The present invention is described in further detail.
Embodiment 1
A kind of method for being pyrolyzed ammonium carboxylate salt and preparing fluorescent carbon point, is comprised the steps of：
1）1g ethylenediamine tetra-acetic acids are dissolved in 10ml deionized waters（Ethylenediamine tetra-acetic acid and the mass ratio of deionized water are
1：10）, ultrasonic vibration 5min, pour into the vacuum capability bottle full of nitrogen and stir, add 0.419g ethylenediamines（Ethylenediamine tetrem
The mol ratio of acid and ethylenediamine is 1：2）, 8h is reacted under the conditions of 20 DEG C, after reaction completely with petroleum ether three times, separates water outlet
Layer, decompression rotary evaporation remove unreacted ethylenediamine, obtain yellow solid；
2）Yellow solid is placed in tube furnace, is heated to 350 DEG C under nitrogen protection, the rate of heat addition is 5 DEG C/min, is protected
10min is ground after warm 1.5h, obtains black powder；
3）Black powder is dissolved in absolute ethyl alcohol, the use of molecular weight is 3500 bag filters dialysis 48h, by outside bag filter
Solution rotating evaporates to obtain fluorescent carbon point.
Fluorescent carbon point manufactured in the present embodiment is detected.Fig. 1 is the transmission electron microscope of sample（TEM）Photograph
Piece, as shown in Figure 1, the present embodiment fluorescent carbon point average grain diameter are 11nm.Fig. 2 is that uv absorption spectra, the fluorescence of sample swash
Hair and emission wavelength spectra figure, it is 350nm and 416nm respectively that fluorescence, which is most preferably excited with launch wavelength, using quinine sulfate as reference
Thing, its fluorescence quantum yield is obtained as 22.46%.Water white transparency is presented and in ultraviolet in sample under natural light in Fig. 3
（365nm）Blue-fluorescence is sent under irradiation.Fig. 4 is the infrared spectrogram of sample, 3500cm be present-1O-H stretching vibrations absorb
Peak, 3400cm-1N-H stretching vibration absworption peaks.2900cm-1And 2840cm-1Saturation methylene stretching vibration absworption peak,
1640cm-1C=O stretching vibration absworption peak, 1425cm-1And 1367cm-1Methyl flexural vibrations absworption peak, 1230cm-1
C-N flexural vibrations absworption peak.This has illustrated in carbon point surface enrichment substantial amounts of carboxyl, methyl and amido functional group.Fig. 5
Pass through carbon point and each metal ion species（Al3+、Ca2+、Co2+、Mg2+、Na+、Ni+、Zn2+、Hg2+）Reaction, it can be seen that Fe3+Ion pair
The quenching effects of carbon point are the most obvious.Fig. 6 is fluorescent carbon point various concentrations Fe3+Under fluorescence emission spectrogram of compound.It can be seen that in Fig. 7
The relative intensity of fluorescence and Fe of carbon point3+Ion concentration is linear, and its slope is approximately 1, and this characteristic can be used for detecting
Fe3+Ion.
Embodiment 2
A kind of method for being pyrolyzed ammonium carboxylate salt and preparing fluorescent carbon point, is comprised the steps of：
1）1g ethylenediamine tetra-acetic acids are dissolved in 10ml deionized waters（Ethylenediamine tetra-acetic acid and the mass ratio of deionized water are
1：10）, ultrasonic vibration 5min, pour into the vacuum capability bottle full of nitrogen and stir, add 0.206g ethylenediamines（Ethylenediamine tetrem
The mol ratio of acid and ethylenediamine is 1：1）, 8h is reacted under the conditions of 20 DEG C, after reaction completely with petroleum ether three times, separates water outlet
Layer, decompression rotary evaporation remove unreacted ethylenediamine, obtain yellow solid；
2）Yellow solid is placed in tube furnace, is heated to 350 DEG C under nitrogen protection, the rate of heat addition is 5 DEG C/min, is protected
10min is ground after warm 1.5h, obtains black powder；
3）Black powder is dissolved in absolute ethyl alcohol, the use of molecular weight is 3500 bag filters dialysis 48h, by outside bag filter
Solution rotating evaporates to obtain fluorescent carbon point.
The present embodiment products therefrom sign is same as Example 1, and its fluorescence quantum yield is 20.10%.
Embodiment 3
A kind of method for being pyrolyzed ammonium carboxylate salt and preparing fluorescent carbon point, is comprised the steps of：
1）1g ethylenediamine tetra-acetic acids are dissolved in 10ml deionized waters（Ethylenediamine tetra-acetic acid and the mass ratio of deionized water are
1：10）, ultrasonic vibration 5min, pour into the vacuum capability bottle full of nitrogen and stir, add 0.617g ethylenediamines（Ethylenediamine tetrem
The mol ratio of acid and ethylenediamine is 1：3）, 8h is reacted under the conditions of 20 DEG C, after reaction completely with petroleum ether three times, separates water outlet
Layer, decompression rotary evaporation remove unreacted ethylenediamine, obtain yellow solid；
2）Yellow solid is placed in tube furnace, is heated to 350 DEG C under nitrogen protection, the rate of heat addition is 5 DEG C/min, is protected
10min is ground after warm 1.5h, obtains black powder；
3）Black powder is dissolved in absolute ethyl alcohol, the use of molecular weight is 3500 bag filters dialysis 48h, by outside bag filter
Solution rotating evaporates to obtain fluorescent carbon point.
The present embodiment products therefrom sign is same as Example 1, and its fluorescence quantum yield is 17.50%.
Embodiment 4
A kind of method for being pyrolyzed ammonium carboxylate salt and preparing fluorescent carbon point, is comprised the steps of：
1）1g ethylenediamine tetra-acetic acids are dissolved in 5ml deionized waters（Ethylenediamine tetra-acetic acid and the mass ratio of deionized water are
1：5）, ultrasonic vibration 1min, pour into the vacuum capability bottle full of nitrogen and stir, add 0.419g ethylenediamines（Ethylenediamine tetrem
The mol ratio of acid and ethylenediamine is 1：2）, 5h is reacted under the conditions of 50 DEG C, after reaction completely with petroleum ether three times, separates water outlet
Layer, decompression rotary evaporation remove unreacted ethylenediamine, obtain yellow solid；
2）Yellow solid is placed in tube furnace, is heated to 350 DEG C under nitrogen protection, the rate of heat addition is 5 DEG C/min, is protected
10min is ground after warm 1.5h, obtains black powder；
3）Black powder is dissolved in absolute ethyl alcohol, the use of molecular weight is 3500 bag filters dialysis 72h, by outside bag filter
Solution rotating evaporates to obtain fluorescent carbon point.
The present embodiment products therefrom sign is same as Example 1, and its fluorescence quantum yield is 21.78%.
Embodiment 5
A kind of method for being pyrolyzed ammonium carboxylate salt and preparing fluorescent carbon point, is comprised the steps of：
1）1g ethylenediamine tetra-acetic acids are dissolved in 10ml deionized waters（Ethylenediamine tetra-acetic acid and the mass ratio of deionized water are
1：10）, ultrasonic vibration 5min, pour into the vacuum capability bottle full of nitrogen and stir, add 0.419g ethylenediamines（Ethylenediamine tetrem
The mol ratio of acid and ethylenediamine is 1：2）, 10h is reacted under the conditions of 10 DEG C, after reaction completely with petroleum ether three times, is isolated
Water layer, decompression rotary evaporation remove unreacted ethylenediamine, obtain yellow solid；
2）Yellow solid is placed in tube furnace, is heated to 300 DEG C under nitrogen protection, the rate of heat addition is 1 DEG C/min, is protected
10min is ground after warm 0.5h, obtains black powder；
3）Black powder is dissolved in absolute ethyl alcohol, the use of molecular weight is 3500 bag filters dialysis 72h, by outside bag filter
Solution rotating evaporates to obtain fluorescent carbon point.
The present embodiment products therefrom sign is same as Example 1, and its fluorescence quantum yield is 15.00%.
Embodiment 6
A kind of method for being pyrolyzed ammonium carboxylate salt and preparing fluorescent carbon point, is comprised the steps of：
1）1g ethylenediamine tetra-acetic acids are dissolved in 15ml deionized waters（Ethylenediamine tetra-acetic acid and the mass ratio of deionized water are
1：15）, ultrasonic vibration 10min, pour into the vacuum capability bottle full of nitrogen and stir, add 0.419g ethylenediamines（Ethylenediamine tetraacetic
The mol ratio of acetic acid and ethylenediamine is 1：2）, 8h is reacted under the conditions of 20 DEG C, after reaction completely with petroleum ether three times, is isolated
Water layer, decompression rotary evaporation remove unreacted ethylenediamine, obtain yellow solid；
2）Yellow solid is placed in tube furnace, is heated to 450 DEG C under nitrogen protection, the rate of heat addition is 1 DEG C/min, is protected
10min is ground after warm 2h, obtains black powder；
3）Black powder is dissolved in absolute ethyl alcohol, the use of molecular weight is 3500 bag filters dialysis 72h, by outside bag filter
Solution rotating evaporates to obtain fluorescent carbon point.
The present embodiment products therefrom sign is same as Example 1, and its fluorescence quantum yield is 5.00%.
Embodiment 7
A kind of method for being pyrolyzed ammonium carboxylate salt and preparing fluorescent carbon point, is comprised the steps of：
1）1g ethylenediamine tetra-acetic acids are dissolved in 10ml deionized waters（Ethylenediamine tetra-acetic acid and the mass ratio of deionized water are
1：10）, ultrasonic vibration 5min, pour into the vacuum capability bottle full of nitrogen and stir, add 0.507g propane diamine（Ethylenediamine tetrem
The mol ratio of acid and propane diamine is 1：2）, 8h is reacted under the conditions of 20 DEG C, after reaction completely with petroleum ether three times, separates water outlet
Layer, decompression rotary evaporation remove unreacted propane diamine, obtain yellow solid；
2）Yellow solid is placed in tube furnace, is heated to 350 DEG C under nitrogen protection, the rate of heat addition is 5 DEG C/min, is protected
10min is ground after warm 1.5h, obtains black powder；
3）Black powder is dissolved in absolute ethyl alcohol, the use of molecular weight is 3500 bag filters dialysis 48h, by outside bag filter
Solution rotating evaporates to obtain fluorescent carbon point.
The present embodiment products therefrom sign is same as Example 1, and its fluorescence quantum yield is 8.30%.
Embodiment 8
A kind of method for being pyrolyzed ammonium carboxylate salt and preparing fluorescent carbon point, is comprised the steps of：
1）1g ethylenediamine tetra-acetic acids are dissolved in 10ml deionized waters（Ethylenediamine tetra-acetic acid and the mass ratio of deionized water are
1：10）, ultrasonic vibration 5min, pour into the vacuum capability bottle full of nitrogen and stir, add 0.603g butanediamine（Ethylenediamine tetrem
The mol ratio of acid and butanediamine is 1：2）, 8h is reacted under the conditions of 20 DEG C, after reaction completely with petroleum ether three times, separates water outlet
Layer, decompression rotary evaporation remove unreacted butanediamine, obtain yellow solid；
2）Yellow solid is placed in tube furnace, is heated to 350 DEG C under nitrogen protection, the rate of heat addition is 5 DEG C/min, is protected
10min is ground after warm 1.5h, obtains black powder；
3）Black powder is dissolved in absolute ethyl alcohol, the use of molecular weight is 3500 bag filters dialysis 48h, by outside bag filter
Solution rotating evaporates to obtain fluorescent carbon point.
The present embodiment products therefrom sign is same as Example 1, and its fluorescence quantum yield is 5.40%.
Embodiment 9
A kind of method for being pyrolyzed ammonium carboxylate salt and preparing fluorescent carbon point, is comprised the steps of：
1）1g citric acids are dissolved in 10ml deionized waters（Citric acid and the mass ratio of deionized water are 1：10）, ultrasound shake
5min is swung, pours into the vacuum capability bottle full of nitrogen and stirs, adds 0.469g ethylenediamines（The mol ratio of citric acid and ethylenediamine
For 1：1.5）, 8h is reacted under the conditions of 20 DEG C, after reaction completely with petroleum ether three times, water-yielding stratum is separated, depressurizes rotary evaporation
Unreacted ethylenediamine is removed, obtains yellow solid；
2）Yellow solid is placed in tube furnace, is heated to 350 DEG C under nitrogen protection, the rate of heat addition is 5 DEG C/min, is protected
10min is ground after warm 1.5h, obtains black powder；
3）Black powder is dissolved in absolute ethyl alcohol, the use of molecular weight is 3500 bag filters dialysis 48h, by outside bag filter
Solution rotating evaporates to obtain fluorescent carbon point.
The present embodiment products therefrom sign is same as Example 1, and its fluorescence quantum yield is 30.70%.
Claims (8)
1. one kind pyrolysis ammonium carboxylate salt prepares fluorescent carbon point Fe in water3+Application in Concentration Testing；
The pyrolysis ammonium carboxylate salt prepares fluorescent carbon point, is as made from following steps：
1）Polybasic carboxylic acid is dissolved in deionized water, ultrasonic vibration, under nitrogen protective condition, adds diamine reaction, reacted
Petroleum ether is used after complete, separates water-yielding stratum, decompression rotary evaporation removes unreacted diamine, obtains yellow solid；
The polybasic carboxylic acid is ethylenediamine tetra-acetic acid；The diamine is ethylenediamine；
2）Yellow solid is placed in tube furnace, heated under nitrogen protection, grinding obtains black powder after insulation；
3）Black powder is dissolved in absolute ethyl alcohol, bag filter dialysis, the solution rotating outside bag filter is evaporated to obtain fluorescent carbon
Point.
2. pyrolysis ammonium carboxylate salt according to claim 1 prepares fluorescent carbon point Fe in water3+Application in Concentration Testing, its
It is characterised by, the mass ratio of the polybasic carboxylic acid and deionized water is 1：5-15.
3. pyrolysis ammonium carboxylate salt according to claim 1 prepares fluorescent carbon point Fe in water3+Application in Concentration Testing, its
It is characterised by, the time of the ultrasonic vibration is 1-10min.
4. pyrolysis ammonium carboxylate salt according to claim 1 prepares fluorescent carbon point Fe in water3+Application in Concentration Testing, its
It is characterised by, the mol ratio of the polybasic carboxylic acid and diamine is 1：1-3.
5. pyrolysis ammonium carboxylate salt according to claim 1 prepares fluorescent carbon point Fe in water3+Application in Concentration Testing, its
It is characterised by, the reaction temperature is 10-50 DEG C, reaction time 5-10h.
6. pyrolysis ammonium carboxylate salt according to claim 1 prepares fluorescent carbon point Fe in water3+Application in Concentration Testing, its
It is characterised by, the rate of heat addition is 1-5 DEG C/min, is heated to 300 DEG C -450 DEG C, soaking time 0.5-2h.
7. pyrolysis ammonium carboxylate salt according to claim 1 prepares fluorescent carbon point Fe in water3+Application in Concentration Testing, its
It is characterised by, the milling time is 10min.
8. pyrolysis ammonium carboxylate salt according to claim 1 prepares fluorescent carbon point Fe in water3+Application in Concentration Testing, its
It is characterised by, the bag filter specification molecular weight is 3500, dialysis time 48-72h.
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