CN109097027A - Application of the dione pyrrolo-pyrrole compound/tetraphenyl ethylene class compound composite nanoparticle in hypochlorite ion detects - Google Patents

Application of the dione pyrrolo-pyrrole compound/tetraphenyl ethylene class compound composite nanoparticle in hypochlorite ion detects Download PDF

Info

Publication number
CN109097027A
CN109097027A CN201811027838.4A CN201811027838A CN109097027A CN 109097027 A CN109097027 A CN 109097027A CN 201811027838 A CN201811027838 A CN 201811027838A CN 109097027 A CN109097027 A CN 109097027A
Authority
CN
China
Prior art keywords
tetraphenyl ethylene
compound
ethylene class
pyrrole
dione pyrrolo
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
Application number
CN201811027838.4A
Other languages
Chinese (zh)
Other versions
CN109097027B (en
Inventor
刘正春
聂凯旋
梁波
石环环
董波
朝乐蒙
龙孟秋
徐慧
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Central South University
Changsha University of Science and Technology
Original Assignee
Central South University
Changsha University of Science and Technology
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Central South University, Changsha University of Science and Technology filed Critical Central South University
Priority to CN201811027838.4A priority Critical patent/CN109097027B/en
Publication of CN109097027A publication Critical patent/CN109097027A/en
Application granted granted Critical
Publication of CN109097027B publication Critical patent/CN109097027B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • 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
    • 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
    • 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
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1408—Carbocyclic compounds
    • C09K2211/1425—Non-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Nanotechnology (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Immunology (AREA)
  • Biochemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pathology (AREA)
  • Molecular Biology (AREA)
  • General Health & Medical Sciences (AREA)
  • Manufacturing & Machinery (AREA)
  • Analytical Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Composite Materials (AREA)
  • Optics & Photonics (AREA)
  • Organic Chemistry (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)

Abstract

The invention discloses a kind of application of the dione pyrrolo-pyrrole compound/tetraphenyl ethylene class compound composite nanoparticle in hypochlorite ion's detection, the compound particle has fluorescence resonance energy transfer effect (FRET) and good aqueous solubility, it can be achieved that ClO in aqueous systems‑High sensitivity and optional ratio's type detection or intracellular ClO‑Fluorescence imaging, can be widely applied to the fields such as biological detection, imaging.

Description

Dione pyrrolo-pyrrole compound/tetraphenyl ethylene class compound composite nanoparticle Application in hypochlorite ion's detection
Technical field
The present invention relates to one kind to have fluorescence energy transfer nanoparticle, in particular to one kind is by dione pyrrolo-pyrrole The composite nano-granule for having fluorescence resonance energy transfer effect (FRET) that compound and tetraphenyl ethylene class compound assemble Son, for ClO in water body-Detection or intracellular environment imaging, realize ClO-The method of efficient detection, belongs to field of biological detection.
Background technique
Bioactive oxidation object small molecule plays a significant role in terms of physiology and pathology, and concentration level reflects cell Physio-pathological condition, wherein hypochlorite participates in the intracorporal many of biology as important activating oxide a kind of in organism Physiology course plays a very important role to health tool, but excessive hypochlorous acid can cause various tissue damages and disease packet Include cardiovascular disease and injury of lungs etc..Since the intracorporal hypochlorous acid of biology is at faintly acid (pKa=7.63), active in physiological environment It is high and short there are the time.Therefore the fluorescence probe for designing a kind of highly selective identification hypochlorite has critically important meaning Justice.The fluorescence probe of detection hypochlorite is based primarily upon hypochlorous strong oxidizing property and is designed at present, including hypochlorous acid induction Sulphur/selenolite, oxime oxidation, the oxidation of electron rich radical oxidation, double bond and spirolactams oxidation etc., but most of probes have Quantum efficiency is low, it is anti-light it is Bleachability it is poor, autofluorescence is strong, poorly water-soluble and the deficiencies of poor selectivity, therefore there is an urgent need to design The good hypochlorous acid fluorescence probe of fast response time, selectivity out.
Different from single molecular fluorescence probe, it is anti-light Bleachability good that fluorescent nano probe has, and fluorescence quantum efficiency is high, water-soluble Property it is good and the advantages that be easy to functionalization gradually by the favor of researcher.Wherein, there is fluorescence resonance energy transfer (FRET) fluorescent nano probe of effect can realize the Ratio-type detection to analyte, can be effectively compared with atom environmental background The interference of fluorescence is a kind of probe building form with applications well prospect.Currently, the preparation of FRET nano-probe is mostly used Inorganic heavy metal material, potential security threat are an inevitable problems.The preparation of pure organic FRET nano-probe The then yoke by aggregation fluorescent quenching (ACQ) effect of organic fluorescence materials.
Summary of the invention
In view of the defects existing in the prior art, the purpose of the invention is to provide a kind of dione pyrrolo-pyrrole chemical combination Object/tetraphenyl ethylene class compound composite nanoparticle is as ClO-The application of the FRET Ratio-type probe of detection.Pyrrolopyrrole Cyclohexadione compounds/tetraphenyl ethylene class compound composite nanoparticle has using dione pyrrolo-pyrrole molecule to ClO-'s Specific recognition ability, while having the characteristics that strong fluorescent emission and two-photoninduced fluorescence transmitting, and tetraphenyl ethylene class Molecule can be used as the characteristics of energy donor of FRET nanoparticle, realize ClO-High sensitivity and optional ratio's type detection Or Ratio-type binary channels cell imaging.
In order to achieve the above technical purposes, the present invention provides a kind of dione pyrrolo-pyrrole compound/tetraphenyl ethylenes The application of class compound composite nanoparticle is applied to the detection or imaging of hypochlorite ion as fluorescence probe.
Preferred scheme, the dione pyrrolo-pyrrole compound/tetraphenyl ethylene class compound composite nanoparticle by Dione pyrrolo-pyrrole compound and tetraphenyl ethylene class compound are formed by molecular self-assembling；
The tetraphenyl ethylene class compound has 1 structure of formula:
The dione pyrrolo-pyrrole compound has 2 structure of formula:
Wherein,
R and R1It is independently selected from hydrophilic radical；
R2And R3It is independently selected from thienyl, thiophene derivant group, furyl, furan derivatives group, phenyl, benzenesulfonamide derivative Object group, pyridyl group and pyridine derivate group.
Preferred scheme, R and R1It is independently selected from alkoxy chain, carbohydrate group or other water soluble groups, R2And R3For thiophene Base, furyl, phenyl or pyridyl group.R and R1 main function is to increase dione pyrrolo-pyrrole compound and tetraphenyl ethylene class The hydrophily of compound, theoretically for, all hydrophilic radicals are all satisfied requirement, and enumerated is the common parent in this field Water base group.
R in dione pyrrolo-pyrrole compound of the invention2And R3Mainly increase the conjugated system of molecule, therefore one As aryl or aromatic heterocyclic be all satisfied requirement, it is above-mentioned to illustrate several frequently seen, to be easily obtained substituent group.
Dione pyrrolo-pyrrole compound and tetraphenyl ethylene class compound of the invention is according to existing literature report Conventional method synthesis is commercially available.
Pyrroledione in dione pyrrolo-pyrrole compound of the invention/tetraphenyl ethylene class compound composite nanoparticle Class compound is as energy donor, and tetraphenyl ethylene class compound is as energy acceptor.Pyrrolo-pyrrole-dione of the invention is derivative Object is easy to by hypochlorite oxygenolysis, and tetraphenyl ethylene class compound fluorescent molecule (FRET energy donor) does not change.
Preferred scheme, the dione pyrrolo-pyrrole compound/tetraphenyl ethylene class compound composite nanoparticle by Dione pyrrolo-pyrrole compound and tetraphenyl ethylene class compound are formed 1:3~5 in molar ratio by molecular self-assembling.
Preferred scheme, dione pyrrolo-pyrrole compound/tetraphenyl ethylene class compound composite nanoparticle are applied to In aqueous systems hypochlorite ion Ratio-type detection or intracellular environment in hypochlorite ion Ratio-type imaging analysis.
Dione pyrrolo-pyrrole compound of the invention/tetraphenyl ethylene class compound composite nanoparticle has double fluorescence Emission function.
Dione pyrrolo-pyrrole compound of the invention/tetraphenyl ethylene class compound composite nanoparticle preparation side Method, this method are to be added to the water dione pyrrolo-pyrrole compound and tetraphenyl ethylene class compound, ultrasonic treatment to get.
Preferred scheme, dione pyrrolo-pyrrole compound and tetraphenyl ethylene class compound 1:3~5 in molar ratio.
Preferred scheme, the total concentration of dione pyrrolo-pyrrole compound and tetraphenyl ethylene class compound in water are 30 ~60 μM/L.
Technical solution of the present invention is by the pyrrolo-pyrrole-dione of the tetraphenyl ethylene class molecule of hydrophilic modification and hydrophilic modification Class molecule obtains stable FRET fluorescent nano particle by self assembly.Tetraphenyl ethylene class molecule itself is a kind of typical poly- Collect induced luminescence (AIE) molecule, by its FRET energy donor, while introducing a kind of dione pyrrolo-pyrrole fluorescent molecule conduct ClO-Recognition unit can be used for ClO to construct a kind of nano-sensor of Ratio-type-Ratio-type detection.
Compared with the prior art, technical solution of the present invention bring advantageous effects:
Pyrrolo- in dione pyrrolo-pyrrole compound of the invention/tetraphenyl ethylene class compound composite nanoparticle Pyrrole-dione molecule has to ClO-Specific recognition ability, be easy to by ClO-Selective oxidation decomposes, while having strong Fluorescent emission and two-photoninduced fluorescence transmitting, and energy donor of the tetraphenyl ethylene class molecule as FRET nanoparticle, from And ClO may be implemented-The detection of highly selective and sensitivity Ratio-type and Ratio-type binary channels cell imaging.
Tetraphenyl ethylene class molecule and dione pyrrolo-pyrrole molecule assemble to be formed altogether in FRET nanoparticle of the invention Micella, tetraphenyl ethylene class molecule play the role of maintaining the rock-steady structure of nano-micelle, are able to maintain the steady of multifunctional nanoparticle It is qualitative.
Dione pyrrolo-pyrrole compound of the invention/tetraphenyl ethylene class compound composite nanoparticle preparation method letter Single, low cost, is conducive to large-scale production and application.
Detailed description of the invention
[Fig. 1] is that dione pyrrolo-pyrrole compound and tetraphenyl ethylene class compound are self-assembled into FRET nanoparticle Schematic diagram；
[Fig. 2] is the partial size and fluorescence pattern of FRET nanoparticle；
[Fig. 3] is with various concentration ClO-Addition, the fluorescence emission spectrogram of compound of FRET nanoparticle；
[Fig. 4] is fluorescence response histogram of the FRET nanoparticle to different activities oxygen；
[Fig. 5] is FRET nanoparticle for the ClO in HeLa cell-Fluorescence imaging.
Specific embodiment
The content of patent for a better understanding of the present invention further illustrates this below by specific example and legend The technical solution of invention.But these embodiments are not intended to limit the present invention.
Embodiment 1
The preparation of FRET nanoparticle based on thienyl Diketopyrrolopyrrolederivative derivative.As shown in Figure 1, this embodiment Fluorescent molecule (NDPP and TPE1, the two molecular formula are as shown in Figure 1) with two kinds of alkoxies (oligomeric polyethylene glycol) modification is original Material is to prepare FRET nanoparticle.In water, two kinds of fluorescent chemicals are added in the ratio that NDPP:TPE1 is 1:4, keep it total dense Degree is 50 μM/L.Ultrasound was prepared into required composite nanometer particle after 1 minute.As shown in Fig. 2, left figure show transmission electron microscope (TEM) the FRET nano particle diameter pattern measured illustrates that NDPP and TPE1 assemble the regular particle that can get spherical shape altogether.Fig. 2 Middle right figure is the fluorescent emission figure of nano particle.After comparing it is found that mixing with NDPP, the fluorescence intensity of TPE1 particle is compared In less before about 87%, this illustrates that there are strong FRET effects between two molecules.
Embodiment 2
FRET nanoparticle is to ClO-The fluorescence emission spectrum of response is as shown in Figure 3.In aqueous solution, FRET nanoparticle FRET nanoparticle has emission peak in 490nm and 554nm, corresponds respectively to the characteristic fluorescence transmitting of TPE1 and NDPP.With ClO-Addition, the fluorescence of TPE1 gradually increases, and the fluorescence intensity of NDPP gradually weakens.It is fitted as obtained by right figure in Fig. 3 Slope of a curve can calculate, the FRET nanoparticle in water FRET nanoparticle to ClO-Detection limit can reach 92nM, It can be used for ClO in water environment-Real time monitoring.
Embodiment 3
FRET nanoparticle is to ClO-The specificity of response is investigated as shown in Figure 4.8 parts of FRET are prepared with PBS buffer solution to receive The aqueous solution of rice corpuscles, number 1-8.Then water, H are separately added into 1-8 sample2O2,·OH,1O2,NO·,ONOO-,t-BuOOH And ClO-.Map shows: removing ClO-Outside, other active oxygens have little effect the fluorescent emission of solution.The comparative test explanation FRET nanoparticle in the present invention is in ClO-It is had good selectivity in detection.
Embodiment 4
FRET nanoparticle is to ClO in cell-The application of fluorescence imaging is as shown in Figure 5.Cultured with suitable thin In the culture dish of born of the same parents' concentration, the FRET nanoparticle DPBS solution that 50 μM/L is added is incubated for 0.5 hour.Training is washed away with DPBS solution After supporting the FRET nanoparticle in ware, cell is imaged using confocal fluorescent microscopic.As shown in figure 5, FRET nanometers Particle can enter HeLa cell well, and fluorescence picture obtained by two kinds of channels can clearly show cytoplasm and nucleus.With The increase of liquor natrii hypochloritis's concentration, the fluorescence signal of intracellular blue channel (420-520nm) gradually increase, and green is logical The fluorescence signal in road (530-650nm) gradually weakens.This can realize intracellular ClO substantially-Ratio-type fluorescence imaging.

Claims (5)

1. a kind of application of dione pyrrolo-pyrrole compound/tetraphenyl ethylene class compound composite nanoparticle, feature exist In: it is applied to the detection or imaging of hypochlorite ion as fluorescence probe.
2. a kind of dione pyrrolo-pyrrole compound according to claim 1/tetraphenyl ethylene class compound composite Nano The application of particle, it is characterised in that: the dione pyrrolo-pyrrole compound/tetraphenyl ethylene class compound composite nanoparticle It is formed by dione pyrrolo-pyrrole compound and tetraphenyl ethylene class compound by molecular self-assembling；
The tetraphenyl ethylene class compound has 1 structure of formula:
The dione pyrrolo-pyrrole compound has 2 structure of formula:
Wherein,
R and R1It is independently selected from hydrophilic radical；
R2And R3It is independently selected from thienyl, thiophene derivant group, furyl, furan derivatives group, phenyl, benzene derivative base Group, pyridyl group and pyridine derivate group.
3. a kind of dione pyrrolo-pyrrole compound according to claim 1/tetraphenyl ethylene class compound composite Nano The application of particle, it is characterised in that:
R and R1It is independently selected from alkoxy chain, carbohydrate group or other water soluble groups；
R2And R3For thienyl, furyl, phenyl or pyridyl group.
4. a kind of dione pyrrolo-pyrrole compound according to claim 2/tetraphenyl ethylene class compound composite Nano The application of particle, it is characterised in that: the dione pyrrolo-pyrrole compound/tetraphenyl ethylene class compound composite nanoparticle By dione pyrrolo-pyrrole compound and tetraphenyl ethylene class compound, 1:3~5 are formed by molecular self-assembling in molar ratio.
5. a kind of dione pyrrolo-pyrrole compound/tetraphenyl ethylene class compound according to any one of claims 1 to 4 The application of composite nanoparticle, it is characterised in that: applied to the Ratio-type detection of hypochlorite ion in aqueous systems or intracellular The Ratio-type imaging analysis of hypochlorite ion in environment.
CN201811027838.4A 2018-09-04 2018-09-04 Application of pyrrolo-pyrrole-dione compound/tetra-styrene compound composite nanoparticles in hypochlorite ion detection Active CN109097027B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201811027838.4A CN109097027B (en) 2018-09-04 2018-09-04 Application of pyrrolo-pyrrole-dione compound/tetra-styrene compound composite nanoparticles in hypochlorite ion detection

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201811027838.4A CN109097027B (en) 2018-09-04 2018-09-04 Application of pyrrolo-pyrrole-dione compound/tetra-styrene compound composite nanoparticles in hypochlorite ion detection

Publications (2)

Publication Number Publication Date
CN109097027A true CN109097027A (en) 2018-12-28
CN109097027B CN109097027B (en) 2019-12-10

Family

ID=64865090

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201811027838.4A Active CN109097027B (en) 2018-09-04 2018-09-04 Application of pyrrolo-pyrrole-dione compound/tetra-styrene compound composite nanoparticles in hypochlorite ion detection

Country Status (1)

Country Link
CN (1) CN109097027B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114213338A (en) * 2021-12-30 2022-03-22 深圳市质量安全检验检测研究院 Method for preparing pH sensing compound and method for preparing metal coating piece
WO2022114573A1 (en) * 2020-11-25 2022-06-02 경희대학교 산학협력단 Fluorescent probe for detecting adenosine triphosphate and use thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104818013A (en) * 2015-03-20 2015-08-05 中南大学 Application of diketopyrrolopyrrole derivative in detection of Hg<2+>
CN106478458A (en) * 2015-08-31 2017-03-08 香港科技大学深圳研究院 Schiff base compound based on tetraphenylethylene and Maleic nitrile and its preparation method and application
CN107502344A (en) * 2017-09-12 2017-12-22 中南大学 Based on dione pyrrolo-pyrrole compound and the multi-functional organic fluorescence nano particle of tetraphenyl ethylene class compound and preparation and application
CN107677659A (en) * 2017-09-27 2018-02-09 中南大学 Application of the dione pyrrolo-pyrrole dyestuff in the detection of trace bivalent cupric ion

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104818013A (en) * 2015-03-20 2015-08-05 中南大学 Application of diketopyrrolopyrrole derivative in detection of Hg<2+>
CN106478458A (en) * 2015-08-31 2017-03-08 香港科技大学深圳研究院 Schiff base compound based on tetraphenylethylene and Maleic nitrile and its preparation method and application
CN107502344A (en) * 2017-09-12 2017-12-22 中南大学 Based on dione pyrrolo-pyrrole compound and the multi-functional organic fluorescence nano particle of tetraphenyl ethylene class compound and preparation and application
CN107677659A (en) * 2017-09-27 2018-02-09 中南大学 Application of the dione pyrrolo-pyrrole dyestuff in the detection of trace bivalent cupric ion

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022114573A1 (en) * 2020-11-25 2022-06-02 경희대학교 산학협력단 Fluorescent probe for detecting adenosine triphosphate and use thereof
CN114213338A (en) * 2021-12-30 2022-03-22 深圳市质量安全检验检测研究院 Method for preparing pH sensing compound and method for preparing metal coating piece
CN114213338B (en) * 2021-12-30 2023-12-22 深圳市质量安全检验检测研究院 preparation method of pH sensing compound and preparation method of metal coating piece

Also Published As

Publication number Publication date
CN109097027B (en) 2019-12-10

Similar Documents

Publication Publication Date Title
Cui et al. Carbon dots: Current advances in pathogenic bacteria monitoring and prospect applications
Liu et al. Construction of biomass carbon dots based fluorescence sensors and their applications in chemical and biological analysis
Li et al. Upconversion nanoprobes for biodetections
Xie et al. Graphene quantum dots as smart probes for biosensing
Mehta et al. Recent developments on fluorescent hybrid nanomaterials for metal ions sensing and bioimaging applications: A review
Kundu et al. Facile and green approach to prepare fluorescent carbon dots: emergent nanomaterial for cell imaging and detection of vitamin B2
Wan et al. Facile fabrication of amphiphilic AIE active glucan via formation of dynamic bonds: self assembly, stimuli responsiveness and biological imaging
Wang et al. Recent advances in fluorescent nucleic acid probes for living cell studies
Du et al. Quantum dot: Lightning invisible foodborne pathogens
Chang et al. Lysosome-targeted red-fluorescent carbon dots for turn-on detection of permanganate and pH in vivo and in vitro
CN110982513B (en) Preparation method of fluorescent carbon dots and application of fluorescent carbon dots in cell imaging
Ling et al. Diverse states and properties of polymer nanoparticles and gel formed by polyethyleneimine and aldehydes and analytical applications
Chen et al. Near-infrared to near-infrared upconverting NaYF4: Yb 3+, Tm 3+ nanoparticles-aptamer-Au nanorods light resonance energy transfer system for the detection of mercuric (II) ions in solution
Zhang et al. Rapid microwave synthesis of N-doped carbon nanodots with high fluorescence brightness for cell imaging and sensitive detection of iron (III)
Xu et al. Fluorescent detection of emerging virus based on nanoparticles: From synthesis to application
Omer et al. Carbon nanodots as sensitive and selective nanomaterials in pharmaceutical analysis
WO2022179183A1 (en) Nucleic acid functionalized metal nanoprobe and preparation method therefor
CN109097027A (en) Application of the dione pyrrolo-pyrrole compound/tetraphenyl ethylene class compound composite nanoparticle in hypochlorite ion detects
CN102127586A (en) Magnetic fluorescent bifunctional nano biological probe and preparation method thereof
Wang et al. Fluorophores-modified nanomaterials for trace detection of polychlorobiphenyls and heavy metal ions
Bairi et al. Sensing of Hg+ 2 and Ag+ through a pH dependent FRET system: Fabrication of molecular logic gates
Qie et al. High photoluminescence nitrogen, phosphorus co-doped carbon nanodots for assessment of microbial viability
Zhang et al. Bright red-emitting polymer dots for specific cellular imaging
Yan et al. Carbon dots modified/prepared by supramolecular host molecules and their potential applications: A review
CN107502344B (en) Multi-functional organic fluorescence nano particle and preparation and application based on dione pyrrolo-pyrrole compound and tetraphenyl ethylene class compound

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant