CN114989820A - Construction method of carbazolyl fluorescent carbon dots with large Stokes displacement - Google Patents
Construction method of carbazolyl fluorescent carbon dots with large Stokes displacement Download PDFInfo
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title claims abstract description 20
- 238000010276 construction Methods 0.000 title claims abstract description 6
- 238000006073 displacement reaction Methods 0.000 title abstract description 5
- FIHILUSWISKVSR-UHFFFAOYSA-N 3,6-dibromo-9h-carbazole Chemical compound C1=C(Br)C=C2C3=CC(Br)=CC=C3NC2=C1 FIHILUSWISKVSR-UHFFFAOYSA-N 0.000 claims abstract description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 28
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 26
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 24
- 238000000502 dialysis Methods 0.000 claims abstract description 19
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 claims abstract description 16
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229960001553 phloroglucinol Drugs 0.000 claims abstract description 16
- QPTWWBLGJZWRAV-UHFFFAOYSA-N 2,7-dibromo-9-H-carbazole Natural products BrC1=CC=C2C3=CC=C(Br)C=C3NC2=C1 QPTWWBLGJZWRAV-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000000047 product Substances 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- 239000012043 crude product Substances 0.000 claims abstract description 8
- 238000001914 filtration Methods 0.000 claims abstract description 8
- 238000007605 air drying Methods 0.000 claims abstract description 6
- 239000012528 membrane Substances 0.000 claims abstract description 6
- 238000004108 freeze drying Methods 0.000 claims abstract description 5
- 238000001816 cooling Methods 0.000 claims abstract description 4
- 239000000706 filtrate Substances 0.000 claims abstract description 4
- 239000012467 final product Substances 0.000 claims abstract description 4
- 238000009210 therapy by ultrasound Methods 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 12
- 235000019441 ethanol Nutrition 0.000 claims description 5
- 238000010521 absorption reaction Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 238000012544 monitoring process Methods 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000004729 solvothermal method Methods 0.000 abstract description 5
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 16
- 238000005424 photoluminescence Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 5
- 238000000227 grinding Methods 0.000 description 4
- 238000003825 pressing Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000002189 fluorescence spectrum Methods 0.000 description 3
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 238000000695 excitation spectrum Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000002086 nanomaterial Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000002041 carbon nanotube Substances 0.000 description 1
- 229910021393 carbon nanotube Inorganic materials 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000001506 fluorescence spectroscopy Methods 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 229910021389 graphene Inorganic materials 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000005476 size effect Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
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Abstract
The invention provides a construction method of a carbazolyl fluorescent carbon dot with large Stokes displacement, which comprises the steps of dissolving 3, 6-dibromocarbazole and phloroglucinol in absolute ethyl alcohol, carrying out ultrasonic treatment, then pouring into a reaction kettle, carrying out reaction in a forced air drying oven, cooling to room temperature, and obtaining a crude product; filtering the obtained crude product with an organic filter membrane, and after the filtration is finished, putting the filtrate into a dialysis bag for dialysis; and (3) putting the product obtained after dialysis in a freeze dryer for freeze drying at the temperature of-40 ℃ for 48 hours, and finally taking out the product to obtain the final product, namely the carbazolyl fluorescent carbon dots with the large Stokes shift. The invention expands the application of the carbon dots in the PL field, prepares a novel carbazolyl fluorescent carbon dot by using 3, 6-dibromocarbazole and phloroglucinol through a solvothermal method, shows a large Stokes shift, and is expected to have great application prospects in the fields of analytical chemistry, bioscience and the like.
Description
Technical Field
The invention relates to a construction method of carbazolyl fluorescent carbon dots with large Stokes displacement, belonging to the field of functional polymer materials.
Background
Carbon dots are typical zero-dimensional carbon nanomaterials, which are typically less than 10nm in size. As a typical member of the carbon family, carbon dots have Photoluminescence (PL) properties that can adjust emission wavelengths due to the influence of size effects, surface effects, and edge effects, which are rarely observed in carbon materials such as graphene, fullerene, and carbon nanotubes. As a powerful photoluminescent nanomaterial, carbon dots have attracted much attention in the past decade due to their characteristics of low toxicity, excellent stability, and good biocompatibility. Since the discovery in 2004, researchers have invested much effort in studying high-quality carbon dots with tunable PL emission properties from the ultraviolet region to the visible light band. However, the conventional carbon dot causes self-quenching in imaging due to its small stokes shift, thereby greatly limiting the application range of the carbon dot. In order to expand the application of the carbon dots in the PL field, 3, 6-dibromocarbazole and phloroglucinol are utilized to prepare the carbazolyl fluorescent carbon dots by a solvothermal method, and the carbon dots show large Stokes shift and have wide application prospects in the fields of analytical chemistry, bioscience and the like.
Disclosure of Invention
The invention aims to expand the application of carbon dots in the PL field, and the carbazolyl fluorescent carbon dots with large Stokes shift are prepared by using 3, 6-dibromocarbazole and phloroglucinol through a solvothermal method. The carbon point shows a large Stokes shift and is expected to have a wide application prospect in the fields of analytical chemistry, biological science and the like.
The purpose of the invention is realized as follows: a carbazolyl novel fluorescent carbon dot with large Stokes displacement is synthesized, and a Fourier infrared spectrum and a transmission electron microscope are used for characterization to confirm that the structure of the carbazolyl novel fluorescent carbon dot meets an expected target. And the performance of the sample is characterized by using a fluorescence spectrophotometer.
The specific technical scheme is as follows:
a construction method of carbazolyl fluorescent carbon dots with large Stokes shift comprises the following steps:
the method comprises the following steps: dissolving 3, 6-dibromocarbazole and phloroglucinol in absolute ethyl alcohol, performing ultrasonic treatment to uniformly disperse the 3, 6-dibromocarbazole and the phloroglucinol in the absolute ethyl alcohol, then pouring the mixture into a reaction kettle, reacting in a forced air drying oven, and cooling to room temperature to obtain a crude product;
step two: filtering the obtained crude product by using an organic filter membrane, after the filtration is finished, putting the filtrate into a dialysis bag for dialysis, removing unreacted reactants and aggregates with undersize molecular weight, wherein the solvent and the dialysate are both ethanol, replacing the dialysate every 12 hours, monitoring the dialysate by using an ultraviolet visible light spectrophotometer, and ending the dialysis when no obvious absorption peak exists in the dialysate;
step three: and (3) putting the product obtained after dialysis in a freeze dryer for freeze drying at-40 ℃ for 48 hours, and finally taking out the product to obtain the final product, namely the carbazolyl fluorescent carbon dots with large Stokes shift.
The reaction temperature in the forced air drying oven is 180 ℃, and the reaction time is 12 hours;
the molecular weight of the dialysis bag is 1000;
the organic filter membrane is 0.2 mu m;
dissolving 1g of 3, 6-dibromocarbazole and 0.25g of phloroglucinol in 50mL of absolute ethyl alcohol;
and step four, firstly, taking a proper amount of solid KBr, grinding the solid KBr into powder, and drying the powder in a vacuum drying oven at the temperature of 60 ℃ for 12 hours. Taking out, pressing KBr into small slices (taking care that the pressure of the tablet press is not more than 15Mpa) by using a tablet press as a test background, mixing carbon points to be tested with the treated potassium bromide according to the mass ratio of about 1:100, grinding uniformly, and pressing into slices by using the tablet press as a test sample.
And dissolving the sample in absolute ethyl alcohol, dripping the solution on a carbon support film, and airing the carbon support film to be used as a transmission electron microscope test sample.
The sample was dissolved in absolute ethanol, and fluorescence emission spectroscopy and excitation spectroscopy were performed using a fluorescence spectrophotometer.
The 3, 6-dibromo carbazole, phloroglucinol and other raw materials adopted by the invention have wide sources, are cheap and easily obtained, and the whole synthesis process is simple, mature and easy to control.
Compared with the prior art, the invention has the beneficial effects that:
the invention expands the application of the carbon dots in the PL field, prepares a novel carbazolyl fluorescent carbon dot by using 3, 6-dibromocarbazole and phloroglucinol through a solvothermal method, shows a large Stokes shift, and is expected to have great application prospects in the fields of analytical chemistry, bioscience and the like.
The method takes 3, 6-dibromocarbazole and phloroglucinol as raw materials, synthesizes carbazolyl fluorescent carbon dots through one-step solvothermal reaction, and obtains a target product through purification means such as dialysis and freeze drying. And finally, characterizing the structure of the fluorescent material by a Fourier infrared spectrum, and performing detailed characterization on the luminous performance of the fluorescent material by using a fluorescence spectrophotometer.
The synthesis route is clear and feasible, the process is mature, the implementation is easy, and the method can be used for large-scale batch production.
Drawings
FIG. 1 is a synthetic route to carbon dots;
FIG. 2 is a Fourier transform infrared spectrum of carbon dots;
FIG. 3 is a photograph of a carbon dot under a transmission electron microscope;
FIG. 4 is a UV absorption spectrum of a carbon dot;
fig. 5 shows an excitation spectrum and a fluorescence emission spectrum of a carbon dot.
Detailed Description
The present invention will be described in further detail with reference to the accompanying drawings and specific embodiments.
1. Taking 1g of 3, 6-dibromocarbazole (0.003mol) and 0.25g of phloroglucinol (0.002mol), dissolving the 3, 6-dibromocarbazole and the phloroglucinol in 50mL of absolute ethyl alcohol, carrying out ultrasonic treatment for 20min to uniformly disperse the phloroglucinol in the absolute ethyl alcohol, pouring the treated solution into a 100mL reaction kettle, then reacting for 12 hours in a forced air drying oven at 180 ℃, and cooling the system to room temperature after the reaction is finished to obtain a crude product.
2. And (2) filtering the crude product obtained in the first step by using a 0.2-micron filter membrane, transferring the filtrate to a dialysis bag with the molecular weight of 1000 for dialysis after the filtration is finished, wherein the solvent and the dialysate are both ethanol, replacing the dialysate every 12 hours, monitoring the residual quantity of impurities in real time by using an ultraviolet-visible spectrophotometer during the dialysis process, and ending the dialysis process after the absorption peak of the impurities in the dialysate completely disappears.
3. Transferring the product obtained after dialysis to a freeze dryer for freeze drying at-40 deg.C for 48 hr. Finally, the final product is obtained by taking out, and the yield is 73 percent
4. Taking a proper amount of solid KBr, grinding the solid KBr into powder, putting the powder into a vacuum drying oven at 60 ℃ for drying for 12 hours, taking the powder out, pressing the powder into small slices by using a tablet press (the pressure of the tablet press is not more than 15MPa) to be used as a test background, mixing carbon points to be tested with treated potassium bromide according to a ratio of about 1:100, grinding the mixture uniformly, and pressing the mixture into slices by using the tablet press to be used as a test sample.
1mg of the product is dissolved in 10mL of absolute ethyl alcohol, dropped on a carbon support film and dried to be used as a transmission electron microscope test sample.
Dissolving 1mg of the product in 2mL of absolute ethyl alcohol; the concentration is 1.5X 10 -3 And mol/L, and taking the sample to test the fluorescence spectrum.
FIG. 2 is a Fourier transform infrared spectrum of carbon dots (potassium bromide as background); as can be seen from FIG. 2, at 1250cm -1 A stretching vibration peak with strong ether bonds shows that the carbon points are consistent with the expected targets; FIG. 3 is a photograph of a carbon dot under a transmission electron microscope;as can be seen from FIG. 3, the carbon dots have regular structures, the size is about 20nm, and the expected target is met; FIG. 4 is a UV absorption spectrum of carbon dots (ethanol as solvent); as can be seen from fig. 4, the maximum absorption wavelength of the carbon dots is 303 nm; FIG. 5 is an excitation spectrum (left) and a fluorescence emission spectrum (right) of a carbon dot; the inset is a solution of carbon dots in ethanol under 365nm uv light, and from figure 5 it can be seen that the excitation wavelength of the carbon dots is 303nm, the emission wavelength is 424nm, and the stokes shift is 121nm, indicating that the carbon dots have a large stokes shift.
Claims (5)
1. A construction method of carbazolyl fluorescent carbon dots with large Stokes shift is characterized by comprising the following steps:
the method comprises the following steps: dissolving 3, 6-dibromocarbazole and phloroglucinol in absolute ethyl alcohol, performing ultrasonic treatment to uniformly disperse the 3, 6-dibromocarbazole and the phloroglucinol in the absolute ethyl alcohol, then pouring the mixture into a reaction kettle, reacting in a forced air drying oven, and cooling to room temperature to obtain a crude product;
step two: filtering the obtained crude product by using an organic filter membrane, after the filtration is finished, putting the filtrate into a dialysis bag for dialysis, removing unreacted reactants and aggregates with undersize molecular weight, wherein the solvent and the dialysate are both ethanol, replacing the dialysate every 12 hours, monitoring the dialysate by using an ultraviolet visible light spectrophotometer, and ending the dialysis when no obvious absorption peak exists in the dialysate;
step three: and (3) putting the product obtained after dialysis in a freeze dryer for freeze drying at-40 ℃ for 48 hours, and finally taking out the product to obtain the final product, namely the carbazolyl fluorescent carbon dots with large Stokes shift.
2. The method for constructing a carbazolyl fluorescent carbon dot with a large stokes shift according to claim 1, wherein the temperature of the reaction in the forced air drying oven is 180 ℃ and the reaction time is 12 hours.
3. The method for constructing a carbazolyl fluorescent carbon dot with a large stokes shift according to claim 1, wherein the molecular weight of the dialysis bag is 1000.
4. The method for constructing carbazolyl fluorescent carbon dots with large stokes shift according to claim 1, wherein the organic filter membrane is 0.2 μm.
5. The method for constructing a carbazolyl fluorescent carbon dot with a large Stokes shift according to claim 1, wherein 1g of 3, 6-dibromocarbazole and 0.25g of phloroglucinol are dissolved in 50mL of anhydrous ethanol.
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