CN107488135B - Graphene quantum dot is grafted azo derivative composite material and preparation method and application - Google Patents
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- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
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- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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Abstract
The invention discloses a kind of graphene quantum dot grafting azo derivative composite material and preparation method and applications.The preparation process of the composite material includes: to disperse graphene quantum dot GQDs in thionyl chloride and n,N-Dimethylformamide (DMF) to carry out back flow reaction, obtains graphene quantum dot (GQDs-COCl) material of chloride；P-aminobenzene sulfonic acid azophenol (SUL-Ph) is reacted in tetrahydrofuran with GQDs-COCl material, graphene quantum dot is made and is grafted azo derivative composite material.Graphene quantum dot produced by the present invention is grafted azo derivative composite material, have many advantages, such as in molecular fluorescence it is strong to the recognition capability of metal ion, selectivity is high, stability is good, be expected to biological medicine, sensor, optics and electricity device, solar battery, electronic equipment, optics fuel and in terms of be applied.
Description
Technical field
The invention belongs to light, electricity and transductive material technical fields, and in particular to a kind of graphene quantum dot grafting azo spreads out
Biocomposite material and preparation method thereof.
Background technique
Azo derivative has unique photic cis-trans isomerism characteristic, is not only widely used in traditional chemical industry, will also
Applied to photochemistry molecular switch, the identification of Subjective and Objective supramolecular chemistry, self assembly liquid crystal material, biomedical imaging and chemistry point
Many emerging scientific domains such as analysis and CD-ROM drive molecular motor.Especially tool challenge is that exploitation has high chemical stability and heat
The azo chromophore that stability easily detects again.The photochromic characteristic of azo derivative is since intramolecular-N=N- group exists
Caused by carrying out cis- anti-or trans- suitable isomery under the action of light or heat, in recent years by the highest attention of researchers.
Partial size less than 100nm graphene nanometer sheet be referred to as graphene quantum dot (graphenequantumdots,
It GQDs), is a kind of emerging carbon material.Graphene quantum dot not only has that the electric conductivity of graphene is good, intensity is big, specific surface
The advantages that accumulating the excellent characteristics such as big, and combining the quantum confined effect, small-size effect and edge effect of quantum dot, shows
The characteristics such as good biocompatibility, hypotoxicity, strong water-soluble, high fluorescent stability, make it in biological medicine, sensor, light
Before and electricity device, solar battery, electronic equipment, optics fuel and multiple microparticles system etc. have potential application
Scape.
Therefore, carry out graphene quantum dot grafting azo derivative composite material research have it is extremely important value and
Meaning.
Summary of the invention
The purpose of the present invention is to provide a kind of graphene quantum dot grafting azo derivative composite material and its preparation sides
Method, the graphene quantum dot are grafted azo derivative composite material, have in molecular fluorescence to the recognition capability of metal ion
By force, the advantages that selectivity is high, stability is good, preparation method are simple, economical.
In order to achieve the above objectives, the technical solution adopted by the present invention is that:
A kind of graphene quantum dot grafting azo derivative composite material, which is by p-aminobenzene sulfonic acid azophenol
Hydroxyl group on the phenyl ring of one end and the acid chloride groups on the graphene quantum dot of chloride are formed by connecting.
It is specific as follows the present invention also provides the preparation method of graphene quantum dot grafting azo derivative:
1) graphene quantum dot is dispersed in the mixed liquor of chloride and organic solvent composition with chloride effect
In, it is reacted 24-36 hours at 65-75 DEG C, vacuum distillation removes chloride, product vacuum at 50-70 DEG C after reaction stops
It is 12-24 hours dry, obtain the graphene quantum dot of chloride；
The chloride with chloride effect is in thionyl chloride, phosphorus trichloride, phosphorus pentachloride or phosphorus oxychloride
It is a kind of；
The organic solvent is one of anhydrous n,N-Dimethylformamide, tetrahydrofuran, hexamethylene, benzene or toluene；
2) p-aminobenzene sulfonic acid azophenol, the graphene quantum dot of above-mentioned chloride and tetrahydrofuran are pressed into quality
It than 1: 2-3: 200-300 mixing, is reacted 48-72 hours at 40-60 DEG C of temperature after ultrasonic disperse is uniform, reaction terminates to be cooled to
Room temperature, by product filter and with ethanol washing twice, collect filter cake simultaneously be dried in vacuo 60-72 hours, obtain graphene quantum dot
It is grafted azo derivative composite material.
Further, the step 1), graphene quantum dot, the chloride with chloride effect, the dosage of organic solvent
Than are as follows: 100mg: 20-25ml: 0.5-1ml.
Further, the step 2, p-aminobenzene sulfonic acid azophenol, the graphene quantum dot of chloride and tetrahydro furan
The mass ratio muttered is 1: 2: 200.
Graphene quantum dot the preparation method is as follows: 2.5g citric acid to be placed in 175 DEG C of oil bath pan in the step 1)
Citric acid is taken out after reaction and is dissolved in the sodium hydroxide solution of 250 ml 10mg/ml, then uses water by middle heating 30min
It is 0.22um filtering with microporous membrane, until invisible particulate matter, the bag filter for being then 3000Da with molecule interception are saturating
Analysis, changes a ultrapure water every 1h, until dialysis system stabilization and outer liquid pH=7 of bag filter, obtain quantum dot solution, be centrifuged,
Freeze-drying, obtains solid graphite alkene quantum dot.
The Preparation Method of p-aminobenzene sulfonic acid azophenol is as follows in the step 2: 0.01mol p-aminobenzene sulfonic acid is molten
Solution obtains the hydrochloric acid solution of p-aminobenzene sulfonic acid in 7.7mL hydrochloric acid；
Under agitation, above-mentioned p-aminobenzene sulfonic acid is added in the sodium nitrite in aqueous solution that solutes content is 0.690g
In hydrochloric acid solution, 0.5h is reacted under the conditions of 0-5 DEG C of temperature, generates diazonium salt solution；
It weighs and is dissolved in deionized water with the phenol of p-aminobenzene sulfonic acid corresponding amount, obtain phenol solution, control temperature
It is 0-5 DEG C, phenol solution is added in above-mentioned diazonium salt solution and is adjusted pH=4-7 under agitation, is stood overnight, filters
Crude product is obtained, is recrystallized and is purified with dehydrated alcohol again after crude product is washed, obtain p-aminobenzene sulfonic acid azophenol.
Preparation process of the present invention is simple, and graphene quantum dot obtained is grafted azo derivative composite material, in acetone,
Acetonitrile has good dissolubility in the organic solvents such as methanol, ethyl alcohol, and on molecular fluorescence, the composite material is to metal ion
Selectivity with higher, can by the heavy metal ion in luminescent photochemical sensing detection environment, as the tin in contaminant water from
Son, mercury ion etc..Graphene quantum dot grafting azo derivative composite material of the invention be expected to biological medicine, sensor,
Optics and electricity device, solar battery, electronic equipment, optics fuel and multiple microparticles system etc. are applied.
Detailed description of the invention
Fig. 1 is that the SEM of 1 graphene quantum dot of embodiment schemes；
Fig. 2 is the SEM figure that 3 graphene quantum dot of embodiment is grafted p-aminobenzene sulfonic acid azophenol；
Fig. 3 is that 7 graphene quantum dot of embodiment is grafted dissolubility song of the azo derivative composite material in different solvents
Line chart；
Fig. 4 is that 8 graphene quantum dot of embodiment is grafted azo derivative composite material to the recognition performance of metal ion
Figure.
Specific embodiment
Below in conjunction with the specific embodiment content that the present invention is furture elucidated, but these embodiments are not intended to limit the present invention
Protection scope.
Embodiment 1: the preparation of graphene quantum dot (GQDs)
Weighing 2.5g citric acid, which is put into 175 DEG C of oil bath pan, in weighing bottle heats 30min, takes out after reaction, by it
It is completely dissolved in the sodium hydroxide solution of 250 ml 10mg/ml, then uses water system 0.22um filtering with microporous membrane, until meat
It can not see particulate matter, dialysed with the bag filter that molecule interception is 3000Da, replace a ultrapure water every 1h, until dialysis
Liquid measures pH=7 with pH test paper outside system stabilization and bag filter, and the flaxen quantum dot solution prepared is placed on low temperature
Place is protected from light to save.It takes and is centrifuged in right amount, be freeze-dried 48h, obtain solid graphite alkene quantum dot.
Embodiment 2: the preparation of p-aminobenzene sulfonic acid azophenol
Taking 1.732g(0.01mol) p-aminobenzene sulfonic acid is in 50mL beaker, then 7.7mL hydrochloric acid is added into beaker, it stirs
Mixing dissolves p-aminobenzene sulfonic acid, obtains in the hydrochloric acid solution of p-aminobenzene sulfonic acid；Prepare 0.690g's in another beaker
Sodium nitrite in aqueous solution is poured under stiring in the hydrochloric acid solution of p-aminobenzene sulfonic acid, is reacted in the environment of 0-5 DEG C of low temperature
0.5h generates colourless diazonium salt.
It weighs and is dissolved in deionized water with the phenol of p-aminobenzene sulfonic acid corresponding amount (about 0.941g), controlled at 0-
It 5 DEG C, is added in above-mentioned diazonium salt solution and is adjusted within the scope of pH=4-7 under stiring；Reaction 2h increasingly generates yellowish-brown pasty liquid
Body is stood overnight.Pair suction filtration obtains crude product, is recrystallized and is purified with dehydrated alcohol again after product washing, obtains yellowish-brown product, i.e.,
Aminobenzenesulfonic acid azophenol is labeled as SUL-Ph.
Embodiment 3: graphene quantum dot is grafted the preparation of p-aminobenzene sulfonic acid azophenol (GQDs-g-SUL-Ph)
1) graphene quantum dot of 100mg is dispersed in the thionyl chloride of 20ml and the anhydrous N of 0.5ml, N- dimethyl methyl
It in amide, flows back 24 hours at 70 DEG C, vacuum distillation removes thionyl chloride after reaction stops, and product is dried in vacuo at 60 DEG C
24 hours, obtain the graphene quantum dot of chloride；
2) is by the graphene quantum dot and tetrahydro furan of chloride made from p-aminobenzene sulfonic acid azophenol and step 1)
Mutter in mass ratio 1: 1: 200 mixing, react 55 hours under temperature 45 C after ultrasonic disperse is uniform, reaction end be cooled to room
Temperature, product is filtered and with ethanol washing twice, collect filter cake and be simultaneously dried in vacuo 72 hours, it is even to obtain graphene quantum dot grafting
Azepine derivatives composite material.
Embodiment 4: the preparation of graphene quantum dot grafting p-aminobenzene sulfonic acid azophenol
1) it disperses the graphene quantum dot of 100mg in the phosphorus trichloride of 20ml and the tetrahydrofuran of 0.5ml, 65
It flows back 36 hours at DEG C, vacuum distillation removes phosphorus trichloride after reaction stops, and product is dried in vacuo 24 hours at 50 DEG C, obtains
The graphene quantum dot of chloride；
2) is by the graphene quantum dot and tetrahydro furan of chloride made from p-aminobenzene sulfonic acid azophenol and step 1)
Mutter in mass ratio 1: 2: 250 mixing, react 72 hours at 40 DEG C of temperature after ultrasonic disperse is uniform, reaction end be cooled to room
Temperature, product is filtered and with ethanol washing twice, collect filter cake and be simultaneously dried in vacuo 72 hours, it is even to obtain graphene quantum dot grafting
Azepine derivatives composite material.
Embodiment 5: the preparation of graphene quantum dot grafting p-aminobenzene sulfonic acid azophenol
1) it disperses the graphene quantum dot of 100mg in the phosphorus pentachloride of 25ml and the hexamethylene of 1ml, at 75 DEG C
Reflux 24 hours, vacuum distillation removes phosphorus pentachloride after reaction stops, and product is dried in vacuo 12 hours at 70 DEG C, obtains acyl chlorides
The graphene quantum dot of change；
2) is by the graphene quantum dot and tetrahydro furan of chloride made from p-aminobenzene sulfonic acid azophenol and step 1)
Mutter in mass ratio 1: 3: 300 mixing, react 48 hours under temperature 60 C after ultrasonic disperse is uniform, reaction end be cooled to room
Temperature, product is filtered and with ethanol washing twice, collect filter cake and be simultaneously dried in vacuo 60 hours, it is even to obtain graphene quantum dot grafting
Azepine derivatives composite material.
Embodiment 6: the preparation of graphene quantum dot grafting p-aminobenzene sulfonic acid azophenol
1) it disperses the graphene quantum dot of 100mg in the phosphorus oxychloride of 25ml and the toluene of 1ml, next time at 70 DEG C
Stream 30 hours, vacuum distillation removes phosphorus oxychloride after reaction stops, and product is dried in vacuo 18 hours at 60 DEG C, obtains chloride
Graphene quantum dot；
2) is by the graphene quantum dot and tetrahydro furan of chloride made from p-aminobenzene sulfonic acid azophenol and step 1)
Mutter in mass ratio 1: 2: 200 mixing, react 60 hours under temperature 50 C after ultrasonic disperse is uniform, reaction end be cooled to room
Temperature, product is filtered and with ethanol washing twice, collect filter cake and be simultaneously dried in vacuo 72 hours, it is even to obtain graphene quantum dot grafting
Azepine derivatives composite material.
Fluorescence identifying research of the embodiment 7:GQDs-g-SUL-Ph in different solvents
Take 1mL GQDs-g-SUL-Ph solution that 3 mL ultrapure water wiring solution-formings are added, it is wide in excitation wavelength 370nm, slit
Degree is to use S under 5nmXThe U.S. Z-4-10 Varian sepectrophotofluorometer is detected.GQDs-g- in other solvents
SUL-Ph fluorescence detection operation is same as above.Final result is as shown in figure 3, graphene quantum dot grafting of the invention as shown in Figure 3
Azo derivative composite material, in acetone, acetonitrile has good dissolubility in the organic solvents such as methanol, ethyl alcohol, and
Fluorescence intensity change rule of the GQDs-g-SUL-Ph in different solvents are as follows: original solution > acetone > acetonitrile > ethyl alcohol > methanol > water.
Study of recognition of the embodiment 8:GQDs-g-SUL-Ph aqueous solution to cation
Prepare 1 × 10-4 mol·L-1GQDs-g-SUL-Ph aqueous solution and 1 × 10-3The cationic solution of molL-1,
It takes 2 mL GQDs-g-SUL-Ph solution and adds 2 mL cationic solutions in quartz colorimetric utensil, in 380 nm excitation wavelengths, 10
Its fluorescent absorption light map is measured under nm slit width, as shown in Figure 4, GQDs is grafted on SUL-Ph to testing result as shown in Figure 4
When upper, the fluorescence intensity of GQDs-g-SUL-Ph product is almost quenched, and makes GQDs-g- after metal ion solution is added
The fluorescence property of SUL-Ph is enhanced, wherein Sn2+The fluorescence enhancement of ion pair product it is more apparent, increase 13 times or so.
The position of emission peak is also deviated, it was demonstrated that GQDs-g-SUL-Ph can pass through the weight in luminescent photochemical sensing detection environment
Metal ion.
Claims (7)
1. graphene quantum dot is grafted azo derivative composite material, it is characterised in that: the composite material is by Pyrogentisinic Acid's idol
Hydroxyl group on the phenyl ring of nitrogen -4- benzene sulfonic acid one end and the acid chloride groups on the graphene quantum dot of chloride are formed by connecting.
2. a kind of preparation method of graphene quantum dot grafting azo derivative composite material as described in claim 1, special
Sign is: itself the following steps are included:
1) it disperses graphene quantum dot in the mixed liquor of the chloride with chloride effect and organic solvent composition, In
It is reacted 24-36 hours at 65-75 DEG C, vacuum distillation removes chloride after reaction stops, and product is dried in vacuo at 50-70 DEG C
12-24 hours, obtain the graphene quantum dot of chloride；
The chloride with chloride effect is one of thionyl chloride, phosphorus trichloride, phosphorus pentachloride or phosphorus oxychloride；
The organic solvent is one of anhydrous n,N-Dimethylformamide, tetrahydrofuran, hexamethylene, benzene or toluene；
2) by Pyrogentisinic Acid azo -4- benzene sulfonic acid, the graphene quantum dot and tetrahydrofuran in mass ratio 1: 1- of above-mentioned chloride
3: 200-300 mixing, reacts 48-72 hours at 40-60 DEG C of temperature after ultrasonic disperse is uniform, and reaction terminates to be cooled to room temperature,
Product is filtered to and used ethanol washing, collect filter cake and is dried in vacuo 60-72 hours, graphene quantum dot grafting azo is obtained and spreads out
Biocomposite material.
3. the preparation method of graphene quantum dot grafting azo derivative composite material according to claim 2, feature
It is: the step 1), graphene quantum dot, the chloride with chloride effect, the amount ratio of organic solvent are as follows: 100mg:
20-25ml∶0.5-1ml。
4. the preparation method of graphene quantum dot grafting azo derivative composite material according to claim 2, feature
It is: the step 2, Pyrogentisinic Acid azo -4- benzene sulfonic acid, the graphene quantum dot of chloride and the mass ratio of tetrahydrofuran
It is 1: 1: 200.
5. the preparation method of graphene quantum dot grafting azo derivative composite material according to claim 2, feature
Be: graphene quantum dot heats the preparation method is as follows: 2.5g citric acid is placed in 175 DEG C of oil bath in the step 1)
Citric acid is taken out after reaction and is dissolved in the sodium hydroxide solution of 250 ml 10mg/ml, then uses water system by 30min
0.22um filtering with microporous membrane, until invisible particulate matter, is then dialysed with the bag filter that molecule interception is 3000Da,
A ultrapure water is replaced every 1h, until dialysis system stabilization and outer liquid pH=7 of bag filter, obtain quantum dot solution, be centrifuged,
Freeze-drying, obtains solid graphite alkene quantum dot.
6. the preparation method of graphene quantum dot grafting azo derivative composite material according to claim 2, feature
Be: the Preparation Method of Pyrogentisinic Acid's azo -4- benzene sulfonic acid is as follows in the step 2:
P-aminobenzene sulfonic acid is dissolved in hydrochloric acid, the hydrochloric acid solution of p-aminobenzene sulfonic acid is obtained；
Under agitation, sodium nitrite in aqueous solution is added in the hydrochloric acid solution of above-mentioned p-aminobenzene sulfonic acid, at 0-5 DEG C of temperature
Under the conditions of react 0.5h, generate diazonium salt solution；
Phenol solution is added in above-mentioned diazonium salt solution and is adjusted pH=4-7 under 0-5 DEG C of temperature, stirring condition, was stood
Night, suction filtration obtain crude product, are recrystallized and are purified with dehydrated alcohol again after crude product is washed, obtain Pyrogentisinic Acid's azo -4- benzene sulphur
Acid.
7. the graphene quantum dot grafting azo derivative composite material obtained according to any preparation method of claim 2-6 is in weight
Application in metal ion detection.
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| CN109813690B (en) * | 2018-12-20 | 2021-03-26 | 广东省微生物研究所（广东省微生物分析检测中心） | Graphene quantum dot fluorescent probe and synthetic method and application thereof |
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