CN105924642A - Preparation method and application of polymer dots containing perylene bisimide - Google Patents
Preparation method and application of polymer dots containing perylene bisimide Download PDFInfo
- Publication number
- CN105924642A CN105924642A CN201610302832.8A CN201610302832A CN105924642A CN 105924642 A CN105924642 A CN 105924642A CN 201610302832 A CN201610302832 A CN 201610302832A CN 105924642 A CN105924642 A CN 105924642A
- Authority
- CN
- China
- Prior art keywords
- preparation
- imide
- polymer dots
- reaction
- asymmetric
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0206—Polyalkylene(poly)amines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/028—Polyamidoamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G85/00—General processes for preparing compounds provided for in this subclass
- C08G85/004—Modification of polymers by chemical after-treatment
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- 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
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- 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
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N2021/6432—Quenching
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Immunology (AREA)
- Physics & Mathematics (AREA)
- General Chemical & Material Sciences (AREA)
- Optics & Photonics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
The invention relates to a preparation method and application of polymer dots containing perylene bisimide. The method includes the steps that 3,4,9,10-perylene tetracarboxylic acid diacidamide serves as an initial raw material, asymmetric N-substituent perylene tetracarboxylic acid monoimide monoanhydride is generated through a monoamidation reaction of 3,4,9,10-perylene tetracarboxylic acid diacidamide and ethanol amine; then, perylene bisimide monoanhydride and a polyamine polymer like polyethyleneimine or polyamide-amine dendrimer are put into an N,N-dimethylacetamide or N,N-dimethylformamide solvent, the mixture is heated to 90-165 DEG C, stirred and reacted for 8-24 h, the mixture is cooled to the room temperature after the reaction is finished, centrifugation, filtration, dialysis and freeze-drying are carried out, and the perylene bisimide derivate functionalized polymer dots are obtained. By carrying out TEM characterization, infrared characterization, ultraviolet characterization, fluorescence fluorescence and the like on the product, the fluorescence quantum yield of the polymer dots is 2.2%-4.2%. A method for easily and rapidly detecting different metal ions is established based on the synthetic polymer dots.
Description
Technical field
The invention belongs to fluorescent polymer point technical field, it is provided that the preparation method and applications of a kind of novel polymeric object point.
Background technology
Polymerization object point is the one being different from conventional fluorescent dye molecule and the semiconductor-quantum-point emerging high-performance fluorescent nano material grown up in recent years, and polymerization object point can be divided into two classes: conjugated polymers object point and non-conjugated polymeric object point.Conjugated polymers object point is the macromolecular material that a class main chain has conjugated structure, and the overlap of electron cloud makes pi-electron can move along main polymer chain.In general, these pi-conjugated polymer are the quasiconductor of broad-band gap under eigenstate, therefore are semi-conductive polymeric object point also known as it.The preparation of conjugated polymers object point has direct method (directly synthesizing) and indirect method (being converted to from the polymer of high molecular) from the monomer of low-molecular-weight, currently mainly takes indirect method to prepare conjugated polymers object point, including microemulsion method and reprecipitation method.Non-conjugated polymeric object point is with unconjugated polymer or little molecule as raw material, utilize hydro-thermal method or microwave method by being polymerized, cross-link, being dehydrated, the mode such as carbonization has synthesized a class and has been different from the material of conjugated polymers object point, the polymerization object point of this synthesis not only comprises the carbonization center with fluorescence, and one layer of polymeric chain structure is also wrapped up in outside.Polymerization object point has the series of advantages such as fluorescent stability good, good biocompatibility, hypotoxicity so that it is all have broad application prospects in energy development, bio-imaging, environmental monitoring.
Along with the development of modernization, problem of environmental pollution is on the rise, industrial activity some metal ions given off, human body is entered by big gas and water, food etc., accumulate in some organ of human body, cause chronic poisoning, serious harm health.
Summary of the invention
In order to solve upper problem, it is an object of the invention to provide a kind of quenching effect based on different metal ion pair fluorescent polymer point, the feature utilizing spectrum realizes the qualitative analysis to different metal ion and detection by quantitative, establishes a kind of novel polymeric object point simple, quickly detection different metal ion and its preparation method and application.
The technical scheme is that the preparation method of a kind of imide containing polymers point, it is with 3,4,9,10-tetracarboxylic dianhydride is that the monoamidesization reaction that initial feed first passes through with ethanolamine generates asymmetric N-substituent group tetrabasic carboxylic acid list acid imide list acid anhydride, then, the preparation one novel polymeric object point that this acid imide list acid anhydride and polyamine type macromolecule are reacted in organic solvent, and a kind of method that polymerization object point based on this synthesis establishes detection different metal ion simple, quick.
The present invention realizes based on following technical scheme:
The method specifically includes following steps:
Step 1: by 3,4,9,10-tetracarboxylic dianhydrides are by being condensed to yield asymmetric N-substituent group tetrabasic carboxylic acid list acid imide list acid anhydride with the reaction of the N-monoamideization of primary amine；
Step 2: asymmetric N-substituent group tetrabasic carboxylic acid list acid imide list acid anhydride step prepared and polyamine type macromolecule are placed in organic solvent, heating, continuously stirred reaction certain time, reaction is cooled to room temperature after terminating, it is centrifuged, filters, dialyses, lyophilization, i.e. obtains imide containing polymers point.
Further, described polyamine type macromolecule includes polymine and polyamide-amide dendrimer.
Further, the asymmetric N-substituent group tetrabasic carboxylic acid list acid imide list acid anhydride in described step 2 and the high molecular mol ratio of polyamine type are 1:1-20.
Further, described solvent is dimethyl acetylamide or DMF.
Further, the heating-up temperature in described step 2 is 90-165 DEG C, and heat time heating time is 8-24 h.
A kind of imide containing polymers point using said method to prepare is applied in metal ion detection, and method is as follows:
Being selected by imide containing polymers and dilute with the buffer of pH=7.4 and add different types of metal ion, after under specific excitation wavelength, (λ=360 nm) observes and add different metal ion, the cancellation of fluorescence spectrum changes.
The invention has the beneficial effects as follows: owing to using technique scheme, the method quenching effect based on different metal ion pair fluorescent polymer point, the feature utilizing spectrum realizes the qualitative analysis to different metal ion and detection by quantitative, establishes a kind of method simple, quickly detection different metal ion.
Accompanying drawing explanation
Fig. 1 is the transmission electron microscope shape appearance figure of the prepared fluorescent polymer point of the embodiment of the present invention 1.
Fig. 2 is the fluorescent polymer point prepared by the embodiment of the present invention 1 and synthesizes this infrared spectrum being polymerized object point raw material.
Fig. 3 is the fluorescent polymer point uv absorption prepared by the embodiment of the present invention 1-excitation wavelength dependency fluorescent emission spectrogram (corresponding embodiment 1 product)；Fluorescence exciting wavelength is from 300 ~ 440 nm and polymerization object point optical photograph under daylight and 365 nm ultraviolet lightings.
Fig. 4 is that the fluorescence intensity after different metal ion of the fluorescent polymer point prepared by the embodiment of the present invention 1 is according to figure (corresponding embodiment 1 product).
Detailed description of the invention
With specific embodiment, technical scheme is described further below in conjunction with the accompanying drawings.
Embodiment 1
Adding the 3 of 0.8 g in round-bottomed flask, 4,9,10-tetracarboxylic dianhydrides and the potassium hydroxide solution of 80 ml 5% are also heated to 90 DEG C, after all dissolving, dropwise drip the phosphoric acid solution of 10% in solution, until pH=5.0 stop dropping.Then stirring 1 h at 90 DEG C, be cooled to room temperature, filter, be washed with deionized, 110 DEG C are dried, obtain 0.896 g purplish red powder solid, i.e. intermediate tetracarboxylic anhydride monopotassium salt.
Take above-mentioned tetracarboxylic anhydride monopotassium salt 0.3 g, be at room temperature suspended in 10 ml water.Being dissolved in by the ethanolamine of 0.2 g in 1.8 ml water, be added dropwise in above-mentioned suspension, mixed solution is stirred at room temperature 3 h, it was observed that solution gradually becomes red.Then in the red solution that reaction generates, the acetone of 33 ml is added to produce precipitation.Being filtrated to get red precipitate and use acetone rinse, filter cake is resuspended in the hydrochloric acid of 10%, is heated to 90 DEG C and keeps 1 h.By isolated by vacuum filtration out, through washing, at 60 DEG C, dried in vacuum overnight obtains the N-ethoxy tetrabasic carboxylic acid list acid imide list acid anhydride red solid of the Asymmetrical substitute that yield is 0.3 g to product.
Take polymine (PEI) and the N of 50 mL that 0.6 g molecular weight is 600, N-dimethyl acetylamide joins in 100 ml there-necked flasks, stirring makes it dissolve, weigh above-mentioned N-ethoxy tetrabasic carboxylic acid list acid imide list acid anhydride 0.044 g again and join in flask, reaction system is reacted at 120 DEG C 8 h.After question response terminates, continuing stirring 1 h and be cooled to room temperature, being removed by filtration unreacted red solid, the bag filter that solution molecular weight is 500 dialysis after filtering purifies, gained dialysis solution lyophilization i.e. obtains this polymer nano nanodot, and the fluorescence quantum yield recording this polymerization object point is 4.2%.
Being dissolved in the Tris buffer of pH=7.4 by obtained polymerization object point, being placed in some cuvettes and keeping concentration is 0.1 mg/ml, is added thereto to the Na of 1 mmol/l successively+、K+、Cu+、Mg2+、Ca2+、Cr2+、Mn2+、Co2+、Ag+、Zn2+、Al3+、Ni2+、Fe2+、Fe3+Ion, and do one group of blank experiment as comparison, the fluorescence intensity of different metal ionic system is measured under excitation wavelength lambda=360nm, the transmission electron microscope shape appearance figure of prepared fluorescent polymer point is as shown in Fig. 1 a, Fig. 1 b, Fig. 1 c, tetra-kinds of different sizes of Fig. 1 d, as can be seen from the figure, prepared polymerization object point particle diameter wider distribution, from 50 nm ~ 300 nm.
Embodiment 2
Adding the 3 of 0.5 g in round-bottomed flask, 4,9,10-tetracarboxylic dianhydrides and the potassium hydroxide solution of 50 ml 5% are also heated to 90 DEG C, after all dissolving, dropwise drip the phosphoric acid solution of 10% in solution, until pH=5.0 stop dropping.Then stirring 1 h at 90 DEG C, be cooled to room temperature, filter, be washed with deionized, 110 DEG C are dried, obtain 0.56 g purplish red powder solid, i.e. intermediate tetracarboxylic anhydride monopotassium salt.
Take above-mentioned tetracarboxylic anhydride monopotassium salt 0.15 g, be at room temperature suspended in 5 ml water.Being dissolved in by the ethanolamine of 0.1 g in 0.9 ml water, be added dropwise in above-mentioned suspension, mixed solution is stirred at room temperature 3 h, it was observed that solution gradually becomes red.Then in the red solution that reaction generates, the acetone of 30 ml is added to produce precipitation.Being filtrated to get red precipitate and use acetone rinse, filter cake is resuspended in the hydrochloric acid of 10%, is heated to 90 DEG C and keeps 1 h.By isolated by vacuum filtration out, through washing, at 60 DEG C, dried in vacuum overnight obtains the N-ethoxy tetrabasic carboxylic acid list acid imide list acid anhydride red solid of the Asymmetrical substitute that yield is 0.147 g to product.
Take 1 g polyamide-amide dendrimer (three generations) and the N of 100 mL, dinethylformamide joins in 200 ml there-necked flasks, stirring makes it dissolve, then weighs above-mentioned N-ethoxy tetrabasic carboxylic acid list acid imide list acid anhydride 0.1 g and join in flask, and reaction system is reacted at 140 DEG C 24 h.After question response terminates, continue stirring 1 h and be cooled to room temperature, it is removed by filtration unreacted red solid, the bag filter that solution molecular weight is 1000 dialysis after filtering purifies, gained dialysis solution lyophilization i.e. obtains this polymer nano nanodot, and the fluorescence quantum yield recording this polymerization object point is 2.2%.
Being dissolved in the Tris buffer of pH=7.4 by obtained polymerization object point, being placed in some cuvettes and keeping concentration is 0.1 mg/ml, is added thereto to the Na of 1 mmol/L successively+、K+、Cu+、Mg2+、Ca2+、Cr2+、Mn2+、Co2+、Ag+、Zn2+、Al3+、Ni2+、Fe2+、Fe3+Ion, and do one group of blank experiment as comparison, under the nm of excitation wavelength lambda=360, measure the fluorescence intensity of different metal ionic system.
Claims (6)
1. the preparation method of an imide containing polymers point, it is characterised in that the method specifically includes following steps:
Step 1: by 3,4,9,10-tetracarboxylic dianhydrides are condensed to yield asymmetric N-substituent group tetrabasic carboxylic acid list acid imide list acid anhydride by the reaction of N-monoamideization；
Step 2: asymmetric N-substituent group tetrabasic carboxylic acid list acid imide list acid anhydride step prepared and polyamine type macromolecule are placed in organic solvent, heating, continuously stirred reaction certain time, reaction is cooled to room temperature after terminating, it is centrifuged, filters, dialyses, lyophilization, i.e. obtains imide containing polymers point.
Method the most according to claim 1, it is characterised in that described polyamine type macromolecule includes polymine and polyamide-amide dendrimer.
Method the most according to claim 1, it is characterised in that the asymmetric N-substituent group tetrabasic carboxylic acid list acid imide list acid anhydride in described step 2 and the high molecular mol ratio of polyamine type are 1:1-20.
Preparation method the most according to claim 1, it is characterised in that described solvent is dimethyl acetylamide or DMF.
Preparation method the most according to claim 1, it is characterised in that the heating-up temperature in described step 2 is 90-165 DEG C, heat time heating time is 8-24 h.
6. the imide containing polymers point that one kind such as claim 1-6 any one prepares is applied in metal ion detection.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610302832.8A CN105924642B (en) | 2016-05-09 | 2016-05-09 | A kind of preparation method and applications of imide containing polymers point |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610302832.8A CN105924642B (en) | 2016-05-09 | 2016-05-09 | A kind of preparation method and applications of imide containing polymers point |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105924642A true CN105924642A (en) | 2016-09-07 |
| CN105924642B CN105924642B (en) | 2018-05-18 |
Family
ID=56835423
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610302832.8A Expired - Fee Related CN105924642B (en) | 2016-05-09 | 2016-05-09 | A kind of preparation method and applications of imide containing polymers point |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105924642B (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109054443A (en) * | 2018-06-27 | 2018-12-21 | 西南大学 | A kind of based dye fluorescent carbon point and its preparation method and application |
| CN111057174A (en) * | 2019-12-30 | 2020-04-24 | 常熟涤纶有限公司 | Polystyrene high-fluorescence microsphere and preparation method thereof |
| CN111521593A (en) * | 2020-05-12 | 2020-08-11 | 中国农业大学 | Rapid visual detection method based on water-soluble perylene bisimide derivative |
| CN115611915A (en) * | 2022-10-13 | 2023-01-17 | 上海理工大学 | Preparation method and application of perylene metal compound and composite material thereof |
| CN116285221A (en) * | 2023-03-31 | 2023-06-23 | 米库玻璃纤维增强塑料泰州有限责任公司 | Glass fiber reinforced modified epoxy resin and preparation method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010234746A (en) * | 2009-03-31 | 2010-10-21 | Fujifilm Corp | Relief printing original plate for laser engraving, relief printing plate and method of manufacturing relief printing plate |
-
2016
- 2016-05-09 CN CN201610302832.8A patent/CN105924642B/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010234746A (en) * | 2009-03-31 | 2010-10-21 | Fujifilm Corp | Relief printing original plate for laser engraving, relief printing plate and method of manufacturing relief printing plate |
Non-Patent Citations (2)
| Title |
|---|
| DIANJUN YAO ET AL.: ""Pigment-Mediated Nanoweb Morphology of Poly(dimethylsiloxane)-Substituted Perylene Bisimides"", 《MACROMOLECULES》 * |
| DIANJUN YAO ET AL.: "Self-Assembled Vesicular Nanostructures of Perylene End-Capped Poly(dimethylsiloxane)", 《MACROMOLECULES》 * |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109054443A (en) * | 2018-06-27 | 2018-12-21 | 西南大学 | A kind of based dye fluorescent carbon point and its preparation method and application |
| CN109054443B (en) * | 2018-06-27 | 2020-07-28 | 西南大学 | Perylene dye fluorescent carbon dot and preparation method and application thereof |
| CN111057174A (en) * | 2019-12-30 | 2020-04-24 | 常熟涤纶有限公司 | Polystyrene high-fluorescence microsphere and preparation method thereof |
| CN111057174B (en) * | 2019-12-30 | 2022-03-25 | 常熟涤纶有限公司 | Polystyrene high-fluorescence microsphere and preparation method thereof |
| CN111521593A (en) * | 2020-05-12 | 2020-08-11 | 中国农业大学 | Rapid visual detection method based on water-soluble perylene bisimide derivative |
| CN111521593B (en) * | 2020-05-12 | 2021-05-11 | 中国农业大学 | Rapid visual detection method based on water-soluble perylene bisimide derivative |
| CN115611915A (en) * | 2022-10-13 | 2023-01-17 | 上海理工大学 | Preparation method and application of perylene metal compound and composite material thereof |
| CN116285221A (en) * | 2023-03-31 | 2023-06-23 | 米库玻璃纤维增强塑料泰州有限责任公司 | Glass fiber reinforced modified epoxy resin and preparation method thereof |
| CN116285221B (en) * | 2023-03-31 | 2024-03-22 | 米库玻璃纤维增强塑料泰州有限责任公司 | Glass fiber reinforced modified epoxy resin and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105924642B (en) | 2018-05-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105924642A (en) | Preparation method and application of polymer dots containing perylene bisimide | |
| Liu et al. | Carbon dots: synthesis, formation mechanism, fluorescence origin and sensing applications | |
| Wang et al. | Polyethyleneimine‐functionalized fluorescent carbon dots: water stability, pH sensing, and cellular imaging | |
| Hou et al. | Rapid microwave-assisted synthesis of molecularly imprinted polymers on carbon quantum dots for fluorescent sensing of tetracycline in milk | |
| Jiang et al. | Facile fabrication of organic dyed polymer nanoparticles with aggregation-induced emission using an ultrasound-assisted multicomponent reaction and their biological imaging | |
| Edison et al. | Microwave assisted green synthesis of fluorescent N-doped carbon dots: cytotoxicity and bio-imaging applications | |
| Qian et al. | DNA nanosensor based on biocompatible graphene quantum dots and carbon nanotubes | |
| Zhang et al. | Rapid detection of tryptamine by optosensor with molecularly imprinted polymers based on carbon dots-embedded covalent-organic frameworks | |
| Tong et al. | Amorphous carbon dots with high two-photon fluorescence for cellular imaging passivated by hyperbranched poly (amino amine) | |
| Guo et al. | Bottom-up preparation of nitrogen doped carbon quantum dots with green emission under microwave-assisted hydrothermal treatment and their biological imaging | |
| Liu et al. | Constructing carbon dots and CdTe quantum dots multi-functional composites for ultrasensitive sensing and rapid degrading ciprofloxacin | |
| Ngu et al. | Synthesis of carbon nanoparticles from waste rice husk used for the optical sensing of metal ions | |
| Das et al. | One‐step synthesis of fluorescent carbon dots for bio‐labeling assay | |
| Rahmani et al. | One-step hydrothermal-assisted synthesis of highly fluorescent N-doped carbon dots from gum tragacanth: Luminescent stability and sensitive probe for Au3+ ions | |
| Akhgari et al. | Fluorescent carbon dot as nanosensor for sensitive and selective detection of cefixime based on inner filter effect | |
| Liu et al. | Synthesis and biological imaging of fluorescent polymeric nanoparticles with AIE feature via the combination of RAFT polymerization and post-polymerization modification | |
| CN103361047A (en) | Functional fluorescence carbon nanoparticles based on natural saccharide materials and preparation method and application thereof | |
| Wu et al. | Pentosan-derived water-soluble carbon nano dots with substantial fluorescence: properties and application as a photosensitizer | |
| Shi et al. | Concentration-dependent multicolor fluorescent carbon dots for colorimetric and fluorescent bimodal detections of Fe 3+ and l-ascorbic acid | |
| Mao et al. | Surface grafting of zwitterionic polymers onto dye doped AIE-active luminescent silica nanoparticles through surface-initiated ATRP for biological imaging applications | |
| Craciun et al. | Surface passivation of carbon nanoparticles with p-phenylenediamine towards photoluminescent carbon dots | |
| Zhang et al. | Carbon quantum dots: synthesis, characterization, and assessment of cytocompatibility | |
| Lv et al. | Synthesis of Amphiphilic Hyperbranched AIE‐active Fluorescent Organic Nanoparticles and Their Application in Biological Application | |
| Song et al. | Novel single excitation dual-emission carbon dots for colorimetric and ratiometric fluorescent dual mode detection of Cu 2+ and Al 3+ ions | |
| Long et al. | One-step synthesis, self-assembly and bioimaging applications of adenosine triphosphate containing amphiphilies with aggregation-induced emission feature |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20180518 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |