CN114989820B - 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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- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title claims abstract description 18
- 238000006073 displacement reaction Methods 0.000 title claims abstract description 13
- 238000010276 construction Methods 0.000 title claims abstract description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 title abstract description 27
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 30
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 27
- 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 26
- 238000000502 dialysis Methods 0.000 claims abstract description 22
- 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 13
- 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 13
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229960001553 phloroglucinol Drugs 0.000 claims abstract description 13
- 239000012043 crude product Substances 0.000 claims abstract description 8
- 238000001914 filtration Methods 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- 239000000047 product Substances 0.000 claims abstract description 7
- 238000001035 drying Methods 0.000 claims abstract description 6
- 238000004108 freeze drying Methods 0.000 claims abstract description 5
- 239000012528 membrane Substances 0.000 claims abstract description 5
- 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 7
- 235000019441 ethanol Nutrition 0.000 claims description 5
- 238000010521 absorption reaction Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 238000012544 monitoring process Methods 0.000 claims description 3
- 238000007605 air drying Methods 0.000 claims description 2
- 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
- 238000001816 cooling Methods 0.000 abstract description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 18
- 238000005424 photoluminescence Methods 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000002189 fluorescence spectrum Methods 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 238000000695 excitation spectrum Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000002086 nanomaterial Substances 0.000 description 2
- 238000003825 pressing Methods 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
- 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
- 238000012512 characterization method Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 230000005284 excitation Effects 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 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
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
- C09K11/65—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing carbon
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- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y20/00—Nanooptics, e.g. quantum optics or photonic crystals
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- B82Y40/00—Manufacture or treatment of nanostructures
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- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
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Abstract
The invention provides a construction method of a carbazolyl fluorescent carbon point with large Stokes displacement, which comprises the steps of dissolving 3, 6-dibromocarbazole and phloroglucinol in absolute ethyl alcohol, carrying out ultrasonic treatment, pouring into a reaction kettle, reacting in a blast drying box, and cooling to room temperature to obtain a crude product; filtering the obtained crude product by using an organic filter membrane, and placing filtrate into a dialysis bag for dialysis after the filtration is completed; and (3) freeze-drying the product obtained after the dialysis is finished in a freeze dryer at the temperature of-40 ℃ for 48 hours, and finally taking out to obtain the final product, namely the carbazolyl fluorescent carbon point with large Stokes displacement. The invention expands the application of carbon dots in the PL field, and prepares a novel carbazolyl fluorescent carbon dot by utilizing 3, 6-dibromocarbazole and phloroglucinol through a solvothermal method, wherein the carbon dot shows great Stokes displacement and is expected to have great application prospect in the fields of analytical chemistry, bioscience and the like.
Description
Technical Field
The invention relates to a construction method of a carbazolyl fluorescent carbon dot with large Stokes displacement, belonging to the field of functional polymer materials.
Background
The carbon dots are typically zero-dimensional carbon nanomaterials, typically less than 10nm in size. As a typical member of the carbon family, carbon dots have Photoluminescence (PL) properties with adjustable emission wavelength due to the influence of size effect, surface effect and edge effect, which is rarely observed in carbon materials such as graphene, fullerene and carbon nanotube. As a powerful photoluminescent nanomaterial, carbon dots have attracted considerable attention in the last decade due to their characteristics of low toxicity, excellent stability, good biocompatibility, and the like. Since 2004 findings, researchers have devoted much effort to the study of high quality carbon dots with adjustable PL emission properties from the ultraviolet to the visible band. However, the conventional carbon dots have a small stokes shift, which causes self-quenching in imaging, thereby greatly limiting the application range of the carbon dots. In order to expand the application of 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 displacement 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 prepares a large stokes shift carbazolyl fluorescent carbon dot by utilizing 3, 6-dibromocarbazole and phloroglucinol through a solvothermal method. The carbon dot shows great Stokes shift and is expected to have great application prospect in the fields of analytical chemistry, bioscience and the like.
The purpose of the invention is realized in the following way: a novel carbazolyl fluorescent carbon point with large Stokes displacement is synthesized, and is characterized by using a Fourier infrared spectrum and a transmission electron microscope, so that the structure of the carbazolyl fluorescent carbon point meets the expected target. And its performance was characterized using a fluorescence spectrophotometer.
The specific technical scheme is as follows:
a construction method of a carbazolyl fluorescent carbon dot with large Stokes displacement comprises the following steps:
step one: dissolving 3, 6-dibromocarbazole and phloroglucinol in absolute ethyl alcohol, carrying out ultrasonic treatment to uniformly disperse the 3, 6-dibromocarbazole and the phloroglucinol in the absolute ethyl alcohol, pouring the mixture into a reaction kettle, reacting in a blast 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 completed, placing the filtrate into a dialysis bag for dialysis, removing unreacted reactants and aggregates with too small molecular weight, changing the dialysate every 12 hours when the solvent and the dialysate are ethanol, 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) freeze-drying the product obtained after the dialysis is finished in a freeze dryer at the temperature of-40 ℃ for 48 hours, and finally taking out to obtain the final product, namely the carbazolyl fluorescent carbon point with large Stokes displacement.
The temperature of the reaction in the forced air drying box 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;
1g of 3, 6-dibromocarbazole and 0.25g of phloroglucinol are taken and dissolved in 50mL of absolute ethyl alcohol;
and fourthly, firstly taking a proper amount of solid KBr, grinding the solid KBr into powder, and putting the powder into a vacuum drying oven at 60 ℃ for drying for 12 hours. After removal, KBr was pressed into small flakes by a tablet press (note that the pressure of the tablet press does not exceed 15 MPa) as a test background, then the carbon dots to be tested and the treated potassium bromide were mixed together in a mass ratio of about 1:100, and after grinding uniformly, the flakes were pressed by a tablet press to obtain test samples.
And (3) dissolving the sample in absolute ethyl alcohol, dripping the solution on a carbon support film, and airing the solution to obtain a transmission electron microscope test sample.
Samples were dissolved in absolute ethanol and fluorescence emission and excitation spectra were measured using a fluorescence spectrophotometer.
The 3, 6-dibromocarbazole, phloroglucinol and other raw materials adopted by the invention have wide sources, low cost and easy availability, 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 carbon dots in the PL field, and prepares a novel carbazolyl fluorescent carbon dot by utilizing 3, 6-dibromocarbazole and phloroglucinol through a solvothermal method, wherein the carbon dot shows great Stokes displacement and is expected to have great application prospect in the fields of analytical chemistry, bioscience and the like.
The invention takes 3, 6-dibromocarbazole and phloroglucinol as raw materials, synthesizes carbazolyl fluorescent carbon points through one-step solvothermal reaction, and obtains target products through purification means such as dialysis, freeze drying and the like. And finally, characterizing the structure of the fluorescent lamp by using Fourier infrared spectrum, and performing detailed characterization on the luminous performance of the fluorescent lamp by using a fluorescence spectrophotometer.
The synthesis route is clear and feasible, the process is mature and easy to realize, and the method can be used for large-scale mass production.
Drawings
FIG. 1 is a synthetic route to carbon dots;
FIG. 2 is a Fourier infrared spectrum of carbon dots;
FIG. 3 is a photograph of carbon dots under a transmission electron microscope;
FIG. 4 is an ultraviolet absorption spectrum of carbon dots;
fig. 5 shows the excitation spectrum and fluorescence emission spectrum of carbon dots.
Detailed Description
The invention is described in further detail below with reference to the drawings and the detailed description.
1. 1g of 3, 6-dibromocarbazole (0.003 mol) and 0.25g of phloroglucinol (0.002 mol) were taken and dissolved in 50mL of absolute ethyl alcohol, and subjected to ultrasonic treatment for 20min to uniformly disperse the materials in the absolute ethyl alcohol, the treated solution was poured into a 100mL reaction kettle, then reacted in a blast drying oven at 180 ℃ for 12 hours, and after the reaction was completed, the system was cooled to room temperature to obtain a crude product.
2. Filtering the crude product obtained in the first step by using a filter membrane with the diameter of 0.2 mu m, transferring filtrate to a dialysis bag with the molecular weight of 1000 for dialysis after the filtration is completed, changing the dialysis liquid once every 12 hours when the solvent and the dialysis liquid are ethanol, monitoring the impurity residual quantity in real time by using an ultraviolet-visible light spectrophotometer in the dialysis process, and ending the dialysis process when the impurity absorption peak in the dialysis liquid completely disappears.
3. The product obtained after the dialysis was transferred to a freeze dryer for freeze drying at-40℃for 48 hours. Finally, the mixture is taken out to obtain the final product with the yield of 73 percent
4. Firstly, taking a proper amount of solid KBr, grinding the KBr into powder, putting the powder into a vacuum drying oven at 60 ℃ for drying for 12 hours, taking out the powder, pressing the KBr into small sheets by a tablet press (note that the pressure of the tablet press does not exceed 15 Mpa), taking the small sheets as a test background, mixing carbon points to be tested and treated potassium bromide together according to the proportion of about 1:100, grinding the carbon points to be tested uniformly, and pressing the carbon points into sheets by the tablet press to obtain a test sample.
1mg of the product was taken and dissolved in 10mL of absolute ethanol, and the solution was dropped on a carbon support film, and the solution was air-dried to obtain a transmission electron microscope test sample.
Dissolving 1mg of the product in 2mL of absolute ethyl alcohol; the concentration is 1.5X10 -3 mol/L, as a sample, fluorescence spectrum was measured.
FIG. 2 is a Fourier infrared spectrum of carbon dots (potassium bromide as background); as can be seen from FIG. 2, at 1250cm -1 A strong ether bond stretching vibration peak is arranged at the position, which shows that the synthesized carbon point accords with the expected target; FIG. 3 is a photograph of carbon dots under a transmission electron microscope; as can be seen from fig. 3, the carbon dots have regular structure and size of about 20nm, and meet the expected targets; FIG. 4 is an ultraviolet absorption spectrum of carbon dots (ethanol as solvent); as can be seen from fig. 4, the maximum absorption wavelength of the carbon dots is 303nm; fig. 5 is an excitation spectrum (left) and a fluorescence emission spectrum (right) of a carbon dot; the illustration shows an ethanol solution of carbon dots under 365nm ultraviolet lamp irradiation, and it can be seen from FIG. 5 that the excitation wavelength of the carbon dots is 303nm, the emission wavelength is 424nm, and Stokes is carried outThe shift was 121nm, indicating that the carbon dot had a large Stokes shift.
Claims (3)
1. The construction method of the carbazolyl fluorescent carbon point with large Stokes displacement is characterized by comprising the following steps:
step one: 1g of 3, 6-dibromocarbazole and 0.25g of phloroglucinol are taken and dissolved in 50mL absolute ethyl alcohol, ultrasonic treatment is carried out to ensure that the 3, 6-dibromocarbazole and the phloroglucinol are evenly dispersed in the absolute ethyl alcohol, then the mixture is poured into a reaction kettle, reacted in a blast drying oven and cooled to room temperature, thus obtaining a crude product; the temperature of the reaction in the forced air drying box is 180 ℃, and the reaction time is 12 hours;
step two: filtering the obtained crude product by using an organic filter membrane, after the filtration is completed, placing the filtrate into a dialysis bag for dialysis, removing unreacted reactants and aggregates with too small molecular weight, changing the dialysate every 12 hours when the solvent and the dialysate are ethanol, 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) freeze-drying the product obtained after the dialysis is finished in a freeze dryer at the temperature of-40 ℃ for 48 hours, and finally taking out to obtain the final product, namely the carbazolyl fluorescent carbon point with large Stokes displacement.
2. The method for constructing a carbazolyl fluorescent carbon dot having a large stokes shift according to claim 1, wherein the molecular weight of the dialysis bag is 1000.
3. The method for constructing a carbazolyl fluorescent carbon dot having a large stokes shift according to claim 1, wherein the organic filter is 0.2 μm.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104722322A (en) * | 2013-12-20 | 2015-06-24 | 中国科学院理化技术研究所 | Applications of heteroatom-doped water-soluble carbon quantum dot in organic photoxidation |
| WO2016053411A1 (en) * | 2014-06-19 | 2016-04-07 | William Marsh Rice University | Bandgap engineering of carbon quantum dots |
| CN110317606A (en) * | 2019-07-31 | 2019-10-11 | 西南大学 | Utilize the method and product of bromoacetonitrile and glyoxaline compound preparation carbon dots |
| CN110337482A (en) * | 2018-01-02 | 2019-10-15 | 北京师范大学 | Triangle carbon quantum dot and its composition and purposes |
| CN113563878A (en) * | 2021-07-26 | 2021-10-29 | 曲阜师范大学 | Multi-emission carbon spot fluorescent probe with large Stokes displacement and preparation method and application thereof |
| JP2021195434A (en) * | 2020-06-12 | 2021-12-27 | 凸版印刷株式会社 | Manufacturing method of carbon-based nanoparticle luminescent material and fluorescent labeling method of cell and animal and plant using the same |
-
2022
- 2022-05-31 CN CN202210613669.2A patent/CN114989820B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104722322A (en) * | 2013-12-20 | 2015-06-24 | 中国科学院理化技术研究所 | Applications of heteroatom-doped water-soluble carbon quantum dot in organic photoxidation |
| WO2016053411A1 (en) * | 2014-06-19 | 2016-04-07 | William Marsh Rice University | Bandgap engineering of carbon quantum dots |
| CN110337482A (en) * | 2018-01-02 | 2019-10-15 | 北京师范大学 | Triangle carbon quantum dot and its composition and purposes |
| CN110317606A (en) * | 2019-07-31 | 2019-10-11 | 西南大学 | Utilize the method and product of bromoacetonitrile and glyoxaline compound preparation carbon dots |
| JP2021195434A (en) * | 2020-06-12 | 2021-12-27 | 凸版印刷株式会社 | Manufacturing method of carbon-based nanoparticle luminescent material and fluorescent labeling method of cell and animal and plant using the same |
| CN113563878A (en) * | 2021-07-26 | 2021-10-29 | 曲阜师范大学 | Multi-emission carbon spot fluorescent probe with large Stokes displacement and preparation method and application thereof |
Non-Patent Citations (3)
| Title |
|---|
| Structural Engineering toward High Monochromaticity of carbon Dots-Based Light-Emitting Diodes;Zhiyong Zheng et al.,;《J.Phys.Chem.Lett.》;第12卷;第12107-12113页 * |
| Synthesis of graphene quantum dots for their supramolecular polymorphic architectures;Weifeng Chen et al.,;《Nano Res.》;第14卷(第4期);第1228-1231页 * |
| 红色荧光碳点的制备与发光性能研究;汪亦凡等;安徽化工(第01期);第46-49页 * |
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