CN107118766A - A kind of carbon point for the functionalization for being applied to detection catechol - Google Patents
A kind of carbon point for the functionalization for being applied to detection catechol Download PDFInfo
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- CN107118766A CN107118766A CN201710387220.8A CN201710387220A CN107118766A CN 107118766 A CN107118766 A CN 107118766A CN 201710387220 A CN201710387220 A CN 201710387220A CN 107118766 A CN107118766 A CN 107118766A
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- catechol
- carbon point
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- fluorescence
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- 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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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y40/00—Manufacture or treatment of nanostructures
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
Abstract
The invention provides a kind of fluorescence chemical sensor for detecting pyrocatechol and preparation method thereof, belong to nano material and prepare and chemical analysis technology field.The present invention, by the method for a step hydro-thermal, is prepared for surface and contains amino-carbon point, then with the 4 Carboxybenzeneboronic acid functionalization carbon point with citric acid, diethylenetriamine.The fluorescent carbon point average diameter of prepared functionalization is 7.5nm, carbon point fluorescence after functionalization is without significant change, because static quenching effect causes its fluorescent quenching after catechol is added, so as to which specific recognition and the detection to catechol can be realized, and sensitivity is high, has broad application prospects.
Description
Technical field：
The invention belongs to carry out the detection of catechol in chemical field using fluorescent carbon nano dot.
Background technology：
Catechol is a kind of typical phenol derivatives, be widely used in hair dye, photographic developer, agricultural chemicals, spices,
The production of antioxidant, secondary coloring and Chemicals for Photograph.Catechol is present in ecological environment and high toxicity, difficulty in environment
In degradability pollutant, it has toxicity to human body and very strong to skin irritation.At present, various analysis sides have been developed
Method detects catechol phenol, including gas chromatography, high performance liquid chromatography, chemoluminescence method, ultraviolet spectrophotometry, electrification
Method and fluorescence method etc..
The method for determining catechol at present is very costly and time consuming.Compared with these methods, fluorescence method, which has, rings
Should it is fast, cost is low, sensitivity is high, selectivity good, need not costliness instrument the advantages of.Because boric acid causes four sides with glycol reaction
The formation of body borate.Therefore, pH value is in 6.5-8.5, and boric acid has triangular form, but because of the presence of vicinal diamines, then becomes
Tetrahedral anion form.It is boric acid base group in addition, boric acid is connected with fluorophor, thus it is possible to vary the transmitting of fluorophor
The development of vicinal diols molecular probe provides a preferable instrument.Utilize aminophenyl boronic acid function CuInS2Quantum dot is made
Dicyandiamide and dopamine can be determined near infrared fluorescent probe.CdTe, the ZnTe and ZnS quantum dot for synthesizing phenyl boric acid modification can
Detection for glucose inside cells.The graphene quantum dot of the 3- amino phenyl boric acid functionalization of synthesis is good as a kind of selectivity
The glucose sensing system high with sensitivity.But the shortcomings of there is potential high toxicity and poor biocompatibility in quantum dot.However,
Carbon point (CDs) has attracted the concern of more and more researchers, due to its excellent physicochemical property, such as good water solubility, compared with
Strong fluorescence, there are higher biocompatibility and good photostability compared with traditional semiconductor-quantum-point.
Premium properties based on CDs, the CDs that we synthesize and anhydrous citric acid amido functional group (CA) and diethylenetriamine
(DETA) 4- Carboxybenzeneboronic acid (CPBA) feature CDs (CPBA-CDs) are prepared by hydrothermal method and can be actually covalently attached to
CDs.Boracic acid functional group can with containing vicinal diols CDs formation macromolecular reaction, formed assembling catechol borate and
The abduction mechanism that CPBA-CDs fluorescent quenchings pass through surface hardening state.This is really reactive functional groups, to vicinal diamines, can be with
The catechol and vicinal diamines structure of covalent bond bridge can cause quenching to pass through surface hardening state fluorescence induction mechanism.With adjacent benzene two
The increase of phenol concentration, fluorescence signal is gradually reduced.The fluorescence response of catechol detection is in 0 μm -56 μm of the range of linearity, inspection
Rising limit is 115nm.Therefore, the CDs that we synthesize can react with catechol, be detected using a kind of high sensitivity, high selectivity
Fluorescence probe to catechol.There is CDs of the present invention good biocompatibility be easy to and rapidly by human umbilical vein
Chrotoplast, is particularly suitable for use in the imaging of polychrome real-time cell.
The content of the invention：
Lack present invention improves over existing detection method toxicity height, poor biocompatibility, water-soluble bad, poor selectivity etc.
Point, realizes the detection to catechol using the fluorescent carbon point of functionalization.
After the present invention utilizes this fluorescent carbon point (CDs) by 4- Carboxybenzeneboronic acid functionalization, when catechol is present
When its Quenching of fluorescence is caused due to the influence of static quenching.Different fluorescence intensities are measured with the catechol of various concentrations
Data can obtain equation 1-F0/ F=0.2323+0.3913c, wherein F0To be added without the fluorescence intensity of catechol, F is neighbour
Fluorescence intensity when benzenediol concentration is c, coefficient correlation is 0.9956.Catechol concentration range is at 0 μM to 56 μM.So as to push away
Calculate the detection for catechol and be limited to 115nM.
The present invention has made intensive studies to the disturbing factor in above-mentioned detection process, including temperature, pH value, Yi Jili
Influence of the sub- intensity to carbon point fluorescence intensity.Interference test is carried out in phosphate buffer solution.Test result shows temperature
Degree fluorescence intensity is had little to no effect, in the test of pH value it was found that pH value be 7.0-8.0 when have best detection
Environment in effect, this pH value and organism is much like, can be in field of biology application this demonstrate this carbon point.Ion
Strength test is shown：Influences of the NaCl to result also very little, this illustrates that this carbon point can be applied well in practice.
Embodiment
Embodiment 1
The CDs of present invention synthesis：CDs is generally manufactured by one pot of following hydro-thermal process, will contain citric acid
The clear solution of (1.26g) and diethylenetriamine (1.5mL) is dissolved in 30mL distilled water.Then transfer the solution into poly-
Heated 5 hours in (tetrafluoroethene) autoclave (50mL) and at 200 DEG C.Removed by rotary evaporation after solvent, obtain solid molten
In ethanol, insoluble precipitate (4000rpm, 15 minutes) is removed by centrifugation in solution.Dialysed (MW=to final product
3500Da)。
The CPBA-CDs of present invention synthesis：By 0.5gCPBA be dispersed in 30mL thionyl chlorides and stir the mixture and
Kept for 12 hours at 85 DEG C.It is cooled to after room temperature, the SOCl of residual is distilled under reduced pressure2Obtain (4- chlorocarbonyls phenyl) boric acid
Acid anhydride.Then, (4- chlorocarbonyls phenyl) boric anhydride is added in 30mL DMF solution, continuously added
0.2mgCDs is simultaneously stirred at room temperature 24 hours.After the completion of reaction, reactant mixture continues that concentration is evaporated in vacuo.Residue second
Alcohol washs 5 centrifugations.By the nano particle drying to obtain CPBA-CDs of acquisition.
Embodiment 2
Detections of the functionalization CDs used in the present invention to catechol sensitiveness and concentration.
Catechol according to concentration from 0 μM is added gradually to carbon dots solution to 56 μM, the change of fluorescence intensity
And different catechol concentration (0 μM to 56 μM) and fluorescent quenching efficiency 1-F0Linear relationship between/F.As a result show with
The addition of catechol, fluorescence intensity is gradually decreased, illustrate this carbon point for dopamine sensitiveness very well and have
Very low test limit 115nM.
Claims (1)
1. using citric acid and diethylenetriamine as raw material, carbon point CDs is obtained by one step hydro thermal method, and it is used into 4- carboxyl benzene
CPBA-CDs is obtained after boric acid functionalization, uses it for detecting catechol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710387220.8A CN107118766A (en) | 2017-05-23 | 2017-05-23 | A kind of carbon point for the functionalization for being applied to detection catechol |
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| CN201710387220.8A CN107118766A (en) | 2017-05-23 | 2017-05-23 | A kind of carbon point for the functionalization for being applied to detection catechol |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112251218A (en) * | 2020-10-26 | 2021-01-22 | 南开大学 | Preparation method of ethylenediamine functionalized carbon quantum dots and application of ethylenediamine functionalized carbon quantum dots in catechol detection |
| CN113916845A (en) * | 2020-07-10 | 2022-01-11 | Tcl科技集团股份有限公司 | Method for detecting polyhydroxy compound |
-
2017
- 2017-05-23 CN CN201710387220.8A patent/CN107118766A/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| YE QINGHUA: "Constructing a fluorescent probe for specific detection of catechol based on 4-carboxyphenylboronic acid-functionalized carbon dots", 《SENSORS AND ACTUATORS B: CHEMICAL》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113916845A (en) * | 2020-07-10 | 2022-01-11 | Tcl科技集团股份有限公司 | Method for detecting polyhydroxy compound |
| CN112251218A (en) * | 2020-10-26 | 2021-01-22 | 南开大学 | Preparation method of ethylenediamine functionalized carbon quantum dots and application of ethylenediamine functionalized carbon quantum dots in catechol detection |
| CN112251218B (en) * | 2020-10-26 | 2023-02-17 | 南开大学 | Preparation method of ethylenediamine functionalized carbon quantum dots and application of ethylenediamine functionalized carbon quantum dots in catechol detection |
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