CN106278920B - Nitrilotriacetic acid Holmium complex as cadmium ion fluorescent probe and preparation method thereof - Google Patents
Nitrilotriacetic acid Holmium complex as cadmium ion fluorescent probe and preparation method thereof Download PDFInfo
- Publication number
- CN106278920B CN106278920B CN201610628212.3A CN201610628212A CN106278920B CN 106278920 B CN106278920 B CN 106278920B CN 201610628212 A CN201610628212 A CN 201610628212A CN 106278920 B CN106278920 B CN 106278920B
- Authority
- CN
- China
- Prior art keywords
- nitrilotriacetic acid
- ion
- complex
- atoms
- nta
- 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.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/76—Metal complexes of amino carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
-
- 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
-
- 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
- G01N21/6486—Measuring fluorescence of biological material, e.g. DNA, RNA, cells
-
- 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
- C09K2211/18—Metal complexes
- C09K2211/182—Metal complexes of the rare earth metals, i.e. Sc, Y or lanthanide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Physics & Mathematics (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pathology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Optics & Photonics (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
Abstract
The present invention relates to a kind of nitrilotriacetic acid Holmium complex and preparation method thereof as cadmium ion fluorescent probe.The chemical formula of the complex are as follows: [Ho (NTA) (H2O)]n, wherein NTA=nitrilotriacetic acid；It has two-dimension plane structure, and adjacent flat distance between the surface is aboutAnd it is constructed by hydrogen bond as tridimensional network.When being used as cadmium ion fluorescent probe, the fluorescent emission peak intensity of Holmium complex is with Cd2+The concentration of ion is positively correlated (maximum enhancing amplitude can be of about 5 times, launch wavelength 496nm, excitation wavelength 326nm), Cd2+The presence of ion will not influence the position of the nitrilotriacetic acid Holmium complex fluorescence emission peak；And Cu is added respectively2+、Hg2+、Pb2+、Ca2+And Zn2+After ion, the fluorescence intensity of Holmium complex compared with blank sample fluorescence intensity, emission peak positions there is no displacement and Strength Changes it is little.The complex can be used as Cd2+The fluorescence probe of ion has potential application prospect in environmental monitoring and life science.
Description
Technical field
The present invention relates to one kind to be used as cadmium ion (Cd2+) fluorescence probe nitrilotriacetic acid Holmium complex and preparation method thereof,
The fluorescence probe has potential application prospect in environmental monitoring and life science.
Technical background
Metal-carboxylic acid's class coordination polymer is by having height by what is be self-assembly of between organic ligand and metal ion
There is the complex of the whole infinite networks of metric biggish specific surface area and very high porosity, structure and function to become
In diversification, in gas absorption and separation, magnetic material, bioactivity, selective catalysis, molecular recognition, ion exchange, photoelectricity
The fields such as material, which have, is widely applied [Zhou H C etc., Chem.Rev., 2 (2012) 673].Such complex usually has can
The microcellular structure of control is one of the main reason for it shows excellent functionality, selects the organic ligand and metal with fluorescence
Ions binding, by rationally designing, regulation microcellular structure, bulk and electronic effect preparation have the glimmering of preferable identification function
Light probe be when previous research hotspot [Nagarkar S S etc., Angew.Chem., 10 (2013) 2953；Allendorf M
D etc., Chem.Soc.Rev., 5 (2009) 1330].Such is usually had highly sensitive based on the identification sensor on the basis of fluorescence
Property, it is easy to operate, the response time is short the advantages that.The metal ion or guest molecule of different physicochemical properties can be to the glimmering of complex
Luminous effect has an impact, and accordingly, carries out small organic molecule, escaping gas and the Pb to cause damages to environment and human health2+、
Cd2+、Hg2+Etc. the fluorescence detection of heavy metal ion research, life science, environmental science, medicine and industrial and agricultural production etc. lead
Domain has potential theory significance and application prospect.
Cd2+Ion is one of most common heavy metal contaminants, with organism accumulation, is difficult to the characteristic degraded, easily
It is impaired in causing biologic-organ, it can trigger cancer and even result in death, therefore, how efficiently, delicately detect Cd2+Ion by
To extensive concern.Lippolis etc. has synthesized three kinds in acetonitrile solution to Cd2+Ion has containing for preferable recognition reaction adjacent
The macrocyclic fluorescent probe [Aragoni M C etc., Inorg.Chem., 25 (2002) 6623] of phenanthroline；The synthesis such as Yoon J Y
Two kinds of anthracene derivants containing imino group first acetoacetyl substituent group, to Cd2+Ion has preferable fluorescence identifying effect
[Choi M etc., Org.Lett., 22 (2001) 3455；Kim S K etc., Bull.Korean Chem.Soc., 7 (2003)
1032]；Youn N J etc. has been synthesized to Cd2+Ion generates two substitution Isosorbide-5-Nitraes of identification signal, and 8,11- tetraazacyclododecane tetradecanes spread out
Bioluminescence sensor [Youn N J etc., Tetrahedron Lett., 1 (2005) 125]；The three of the synthesis such as Zhang X B
Pyridylporphyrin, in EtOH/H2To Cd in O solution2+Ion have the higher recognition reaction of sensitivity [Luo H Y etc., Talanta,
2(2007)575]；Peng X etc. has synthesized Cd in active somatic cell for identification2+Ion contains two based on internal electron transfer
The highly selective cadmium fluorescence probe [Peng X etc., J.Am.Chem.Soc., 6 (2007) 1500] of (2- picolyl) amine.It is above-mentioned
Fluorescence probe is the fluorescence probe based on small molecule synthesis, and micropore Holmium complex cadmium ion fluorescent probe of the present invention is then
It is lanthanide complexes made of being constructed as nitrilotriacetic acid, is a kind of novel fluorescence probe system.The present invention relates to be used as
The nitrilotriacetic acid Holmium complex of cadmium ion fluorescent probe, as a certain amount of Cd of addition2+The fluorescence of ion, complex significantly increases, tool
There are higher sensitivity and selectivity, has feature simple and efficient to handle, nontoxic, environmentally friendly and that selectivity is high, it should
Kind nitrilotriacetic acid Holmium complex is as Cd2+The fluorescence probe of ion is there is not yet document report.
Summary of the invention
The present invention is intended to provide a kind of nitrilotriacetic acid Holmium complex and preparation method thereof as cadmium ion fluorescent probe.This
The purpose of invention is realized by following technical solution:
A kind of nitrilotriacetic acid Holmium complex as cadmium ion fluorescent probe, it is characterised in that: its chemical formula is [Ho
(NTA)(H2O)]n, NTA=nitrilotriacetic acid；Elemental analysis data is C6H8NO7Ho (%), theoretical value: C, 19.42；H, 2.17；N,
3.77；Experiment value, C, 19.11；H, 2.21；N, 3.55；The main infrared absorption peak of the complex are as follows: 3421 (br), 1656
(s), 1612 (s), 1458 (w), 1434 (s), 1389 (m), 1357 (m), 1311 (w), 1292 (w), 1241 (w), 1133 (w)
1011 (w), 987 (w), 975 (w), 953 (w), 948 (m), 907 (w), 765 (w), 732 (w), 692 (m), 623 (w), 619
(w), 578 (w), 526 (w), 478 (w).
The elementary structure parameter of the Holmium complex are as follows: the crystal of the Holmium complex belongs to monoclinic system, and space group is
P21/c, cell parameter are as follows:α=γ=
90.00 °, β=106.015 (2) °；Central ion Ho1 and seven coordinating oxygen atoms and a coordination nitrogen-atoms form dodecahedron
Geometric configuration；In eight atoms of Ho1 ion coordination, three oxygen atoms (O (2), O (4) and O (6)) and a nitrogen-atoms (N
(1)) the same nitrilotriacetic acid molecule is come from, four additional oxygen atom is respectively from three nitrilotriacetic acid molecules and a water of coordination
Molecule.
Further, the application provides a kind of cadmium ion fluorescent probe, which is characterized in that the cadmium ion fluorescent probe tool
Have and tridimensional network be formed by by above-mentioned nitrilotriacetic acid Holmium complex, wherein the tridimensional network by nitrilotriacetic acid and
Ho3+ ion self assembly forms, and forms two-dimension plane structure, and constructs to be formed by hydrogen bond.
Further, the present invention relates to the preparation methods of nitrilotriacetic acid Holmium complex, which is characterized in that the preparation method
Include the following steps:
1) by nitrilotriacetic acid (H3NTA) with holmium nitrate (Ho (NO3)3·6H2O it) is stirred at room temperature with the mixed liquor of distilled water
It mixes 30 minutes；The parts by weight of the nitrilotriacetic acid, holmium nitrate and distilled water are as follows: 35~40: 260~280: 10000~
10020；
2) above-mentioned mixed liquor is transferred in the polytetrafluoroethylliner liner of 25mL hydrothermal reaction kettle, at 160 DEG C and pH=5
Reaction 96 hours；
3) products therefrom is filtered and washes twice (1mL/ times) with anhydrous ether, obtains light powder by cooled to room temperature
The target product of color, the target product of the pale pink are bulk crystals；
Preferably, the parts by weight of step 1) nitrilotriacetic acid, holmium nitrate and distilled water are as follows: 35~40: 260~280: 10000
~10020；It is highly preferred that the parts by weight of step 1) nitrilotriacetic acid, holmium nitrate and distilled water are as follows: 38: 262: 10000.
Further, the application the present invention also provides the nitrilotriacetic acid Holmium complex as cadmium ion fluorescent probe,
To monitor the cadmium ion in environmental and biological materials.
Principle explanation: the present invention selects nitrilotriacetic acid as major ligand, and having constructed with holmium nitrate has two-dimensional surface knot
The Holmium complex of structure.When being used as cadmium ion fluorescent probe, cadmium ion will not influence the nitrilotriacetic acid Holmium complex fluorescence hair
The position at peak is penetrated, (maximum enhancing amplitude can be of about 5 as the addition of cadmium ion significantly increases for the intensity of the emission peak of complex
Times), show that the complex can be used as the fluorescence probe of cadmium ion, has in environmental monitoring and life science potential
Application prospect.
It has been reported that and shows to Ca2+、Mg2+、Zn2+、Cu2+、Cd2+、K+、Ag+、H+、Cl-、CO2、F-Ion and small organic molecule
Deng fluorescence probe cause complex fluorescent intensity that a degree of enhancing occurs with the increase for trying concentration of metal ions
Or be quenched, it accordingly, can be with the presence and ion concentration of such ion in qualitative determination and quantitatively calibrating system.It is of the present invention
Nitrilotriacetic acid Holmium complex has good selectivity recognition reaction for cadmium ion, in the presence of cadmium ion, the Holmium complex
Fluorescent emission peak position it is constant, emission peak intensity significantly increases that (maximum enhancing amplitude can as the concentration of cadmium ion increases
Of about 5 times).Cadmium ion is the serious environmental contaminants of harm, and murder by poisoning can be generated by, which being entered after organism by water body, food, makees
With.The present invention is expected to be applied to the qualitative and quantitative detection of cadmium ion in environment and organism.
Detailed description of the invention:
The crystal structure figure of Fig. 1 nitrilotriacetic acid Holmium complex of the present invention.
The two-dimension plane structure figure of Fig. 2 nitrilotriacetic acid Holmium complex of the present invention.
Fig. 3 nitrilotriacetic acid Holmium complex of the present invention connects into tomograph by hydrogen bond.
Fig. 4 nitrilotriacetic acid Holmium complex of the present invention is in Cu2+、Hg2+、Pb2+、Ca2+、Zn2+And Cd2+In the presence of ion
496nm(λex=326nm) at fluorescence intensity.
Specific embodiment
In order to better understand the present invention, below with reference to the embodiment content that the present invention is further explained, but the present invention
Content be not limited solely to the following examples.
The synthesis of 1 complex of embodiment:
By the H of 0.2mmol3NTA and 0.6mmol Ho (NO3)3.6H2O is dissolved in 10mL water, is to adjust by the pH value of mixed liquor
Section is 5, stirs 30 minutes, is transferred in the polytetrafluoroethyllining lining of 25mL, and be loaded into reaction kettle afterwards at room temperature,
It being reacted 96 hours under the conditions of 160 DEG C of temperature, cooled to room temperature, products therefrom washes twice (1mL/ times) with anhydrous ether,
Obtain the crystal of pale pink, yield 66.1%.
The structural characterization of 2 complex of embodiment:
Crystal structure use Bruker Smart CCD X-ray single crystal diffractometer, at 296 (2) K, select having a size of
0.49×0.41×0.32mm3Crystal, use pass through graphite monochromatised MoK alpha rayFor incident radiation
Light source collects point diffraction with the θ scanning mode of ω/2, and cell parameter is through least square method refine, with SADABS program to being collected into
Data carry out absorption correction.The structure that complex is solved with direct method sits non-hydrogen atom with complete matrix least square method
Mark and anisotropic temperature factor carry out refine, complete all to calculate with SHELXTL program.Detailed crystallographic parameter is listed in table
1.Nitrilotriacetic acid Holmium complex [Ho (NTA) (H2O)]nCrystal structure figure, two-dimension plane structure and three-dimensional hole configurations such as Fig. 1,
Shown in Fig. 2 and Fig. 3.
The crystallographic data of 1 nitrilotriacetic acid Holmium complex of table
The photoluminescent property of 3 complex of embodiment:
Using F-7000FL type Fluorescence Spectrometer, the photoluminescent property of complex is determined at room temperature, and complex is distilling
Fluorescence spectra in aqueous solution is as shown in figure 4, a length of 326nm of excitation light wave, emission peak are located at 496nm.Work as Cd2+Ion adds
When adding concentration identical as complex concentration, (Cd is not added with complex blank sample2+Ion) it compares, the transmitting peak position of complex
Set that there is no displacement (launch wavelength 496nm, excitation wavelength 326nm), but the intensity of its emission peak is with Cd2+The addition of ion
And significantly increase (fluorescence intensity enhances amplitude can be of about 5 times)；It is identical as above-mentioned test, add Cu2+、Hg2+、Pb2+、Ca2+With
Zn2+Fluorescence intensity after ion compared with complex blank sample fluorescence intensity, emission peak positions there is no being obviously displaced,
Middle Cu2+、Hg2+And Pb2+Ion weakens its fluorescence intensity, Ca2+And Zn2+Ion enhances its fluorescence intensity slightly, weaken and
Enhancing amplitude is little.Show complex to Cd2+Ion has stronger fluorescence selectivity, and the Holmium complex is expected to become Cd2+
The fluorescence probe of ion.
The rare earth compounding of 4 seven kinds of isomorphous isomorphisms of embodiment is to Cd2+The comparison of ion fluorescence selectivity:
Using nitrilotriacetic acid as ligand, metal uses samaric nitrate, gadolinium nitrate, dysprosium nitrate, neodymium nitrate, praseodymium nitrate and nitre respectively
[Sm (NTA) (H is made using preparation method identical with above-described embodiment 1 in sour erbium2O)]n、[Gd(NTA)(H2O)]n、[Dy
(NTA)(H2O)]n、[Nd(NTA)(H2O)]n、[Pr(NTA)(H2O)]n[Er (NTA) (H2O)]nSix kinds of homologous series rare earth cooperations
Object compares five kinds of rare earth compoundings to Cd using experiment condition identical with embodiment 32+The fluorescence selectivity of ion, table
Bright Cd2+Ion can result in 5 times of nitrilotriacetic acid Holmium complex fluorescence peak enhanced strength involved in the application, other six kinds of rare earths
The fluorescence intensity of complex and position not will receive Cd2+The influence of ion；Experiment shows that the nitrilotriacetic acid Holmium complex can
As Cd2+Ion fluorescence probe, related data are as shown in the table:
Note: 1. "-" expression does not have an impact complex fluorescent intensity.
Nitrilotriacetic acid Holmium complex and preparation method thereof as cadmium ion fluorescent probe of the invention has passed through specifically
Example be described, those skilled in the art can use for reference the content of present invention, and the links such as appropriate feed change, process conditions are come
Realize corresponding other purposes, correlation changes all without departing from the contents of the present invention, all similar substitutions and modifications for
It is it will be apparent that being considered as being included within the scope of the present invention for those skilled in the art.
Claims (4)
1. a kind of nitrilotriacetic acid Holmium complex be used as cadmium ion fluorescent probe application, with monitor the cadmium in environmental and biological materials from
Son, the chemical formula of the nitrilotriacetic acid Holmium complex are [Ho (NTA) (H2O)]n, NTA=nitrilotriacetic acid；Elemental analysis data is
C6H8NO7Ho (%), theoretical value: C, 19.42；H, 2.17；N, 3.77；Experiment value, C, 19.11；H, 2.21；N, 3.55；It is described to match
Close the main infrared absorption peak of object are as follows: 3421 (br), 1656 (s), 1612 (s), 1458 (w), 1434 (s), 1389 (m), 1357
(m), 1311 (w), 1292 (w), 1241 (w), 1133 (w), 1011 (w), 987 (w), 975 (w), 953 (w), 948 (m), 907
(w), 765 (w), 732 (w), 692 (m), 623 (w), 619 (w), 578 (w), 526 (w), 478 (w).
2. application according to claim 1, the elementary structure parameter of the nitrilotriacetic acid Holmium complex are as follows: three second of ammonia
The crystal of sour Holmium complex belongs to monoclinic system, space group P21/c, cell parameter are as follows: α=γ=90.00 °, β=106.015 (2) °；Central ion Ho1 with
Seven coordinating oxygen atoms and a coordination nitrogen-atoms form dodecahedron geometric configuration；In eight atoms of Ho1 ion coordination,
Three oxygen atom O (2), O (4) and O (6) and a nitrogen-atoms N (1) come from the same nitrilotriacetic acid molecule, and four additional oxygen is former
For son respectively from three nitrilotriacetic acid molecules and a water of coordination molecule, three oxygen atoms are O2, O4 and O6；N is N1.
3. a kind of cadmium ion fluorescent probe, which is characterized in that the cadmium ion fluorescent probe has by nitrilotriacetic acid Holmium complex
It is formed by tridimensional network, wherein the tridimensional network is formed by nitrilotriacetic acid and Ho3+ ion self assembly, is formed
Two-dimension plane structure, and construct by hydrogen bond to be formed；The chemical formula of the nitrilotriacetic acid Holmium complex is [Ho (NTA)
(H2O)]n, NTA=nitrilotriacetic acid；Elemental analysis data is C6H8NO7Ho (%), theoretical value: C, 19.42；H, 2.17；N, 3.77；
Experiment value, C, 19.11；H, 2.21；N, 3.55；The main infrared absorption peak of the complex are as follows: 3421 (br), 1656 (s),
1612 (s), 1458 (w), 1434 (s), 1389 (m), 1357 (m), 1311 (w), 1292 (w), 1241 (w), 1133 (w), 1011
(w), 987 (w), 975 (w), 953 (w), 948 (m), 907 (w), 765 (w), 732 (w), 692 (m), 623 (w), 619 (w), 578
(w), 526 (w), 478 (w).
4. probe according to claim 3, which is characterized in that the nitrilotriacetic acid Holmium complex crystal belongs to monoclinic crystal
System, space group P21/c, cell parameter are as follows:
α=γ=90.00 °, β=106.015 (2) °；Central ion Ho1 is formed with seven coordinating oxygen atoms and a coordination nitrogen-atoms
Dodecahedron geometric configuration；In eight atoms of Ho1 ion coordination, three oxygen atom O (2), O (4) and O (6) and a nitrogen
Atom N (1) comes from the same nitrilotriacetic acid molecule, and four additional oxygen atom is matched respectively from three nitrilotriacetic acid molecules and one
Position hydrone, three oxygen atoms are O2, O4 and O6；N is N1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610628212.3A CN106278920B (en) | 2016-08-03 | 2016-08-03 | Nitrilotriacetic acid Holmium complex as cadmium ion fluorescent probe and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610628212.3A CN106278920B (en) | 2016-08-03 | 2016-08-03 | Nitrilotriacetic acid Holmium complex as cadmium ion fluorescent probe and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106278920A CN106278920A (en) | 2017-01-04 |
| CN106278920B true CN106278920B (en) | 2018-12-11 |
Family
ID=57664508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610628212.3A Active CN106278920B (en) | 2016-08-03 | 2016-08-03 | Nitrilotriacetic acid Holmium complex as cadmium ion fluorescent probe and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106278920B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110763822A (en) * | 2019-10-31 | 2020-02-07 | 江苏科技大学 | Experimental method and experimental device for recycling solidified dredged soil of river channel |
| CN112174827B (en) * | 2020-09-29 | 2022-12-30 | 太原工业学院 | Polyoxometalate compound containing tetranuclear cadmium cluster and preparation method and application thereof |
| CN113402728B (en) * | 2021-07-17 | 2022-07-12 | 安庆师范大学 | Rare earth metal material and preparation method and application thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI20095302A0 (en) * | 2009-03-24 | 2009-03-24 | Arctic Partners Oy Ab | Luminesenssimääritysmenetelmä |
| CN103421030B (en) * | 2013-06-25 | 2015-10-07 | 河南大学 | As the binary aromatic acid cerium complexes and preparation method thereof of cadmium ion fluorescent probe |
| CN103965230B (en) * | 2014-05-16 | 2016-07-06 | 北京化工大学 | A kind of functional metal-organic backbone based on rare earth metal bunch and preparation method thereof |
| WO2016019090A1 (en) * | 2014-07-31 | 2016-02-04 | University Of Georgia Research Foundation, Inc. | Metal-encapsulated carbonaceous dots |
| CN105086997A (en) * | 2015-09-08 | 2015-11-25 | 上海海事大学 | Fluorescent probe and preparation method thereof |
-
2016
- 2016-08-03 CN CN201610628212.3A patent/CN106278920B/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN106278920A (en) | 2017-01-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Yi et al. | Highly selective acetone fluorescent sensors based on microporous Cd (II) metal–organic frameworks | |
| Das et al. | Ratiometric fluorescence sensing and intracellular imaging of Al 3+ ions driven by an intramolecular excimer formation of a pyrimidine–pyrene scaffold | |
| CN106278920B (en) | Nitrilotriacetic acid Holmium complex as cadmium ion fluorescent probe and preparation method thereof | |
| CN102070659B (en) | Zinc organic complex as well as preparation method and application thereof | |
| CN109233815B (en) | Ag-MOFs metal-organic framework material, synthesis method and application thereof in ion recognition | |
| Taha et al. | Lanthanide complexes of the tridentate Schiff base ligand salicylaldehyde-2-picolinoylhydrazone: Synthesis, characterization, photophysical properties, biological activities and catalytic oxidation of aniline | |
| CN107722288B (en) | Synthesis of Eu-MOFs material and application thereof in antibiotic identification | |
| CN103421029B (en) | Binuclear zinc complex serving as mercury ion fluorescent probe and preparation method of same | |
| Li et al. | Sensitive detection of the antibiotic pollutants by a solvent-stable luminescent sensor based on a europium (III) metal-organic framework | |
| CN108218900A (en) | A kind of preparation and its application of zinc metal complex fluorescent probe | |
| Piccinelli et al. | New chiral pyridine-based Eu (III) complexes: Study of the relationship between the nature of the ligands and the 5D0 luminescence spectra | |
| Wang et al. | Two metal-organic frameworks based on phenylenediacetate and N, N′-Bis-pyridin-3-ylmethylene-hydrazine used as multi-responsive luminescent sensors for Fe3+, CrO42− and Cr2O72− in aqueous solution | |
| KR101431320B1 (en) | Squarylium dye and method for detecting anion | |
| You et al. | Synthesis, structure and luminescence of lanthanide coordination polymers based on the 1, 3-Bis (carboxymethyl) imidazolium salt | |
| CN110240707B (en) | Post-modified metal-organic framework material for detecting iron ions and preparation method and application thereof | |
| KR101539821B1 (en) | Agent For Selecting Aluminium Ion Comprising ο-phenolsalicylimine And Its Derivative, Detecting Method Using The Same And Detecting Device Thereof | |
| Zhao et al. | Cadmium (II) carboxyphosphonates based on mixed ligands: syntheses, crystal structures and recognition properties toward amino acids | |
| Gusev et al. | Ln (III) complexes of a bis (5-(pyridine-2-yl)-1, 2, 4-triazol-3-yl) methane ligand: synthesis, structure and fluorescent properties | |
| Gomez et al. | Flexible Ligand‐Based Lanthanide Three‐Dimensional Metal–Organic Frameworks with Tunable Solid‐State Photoluminescence and OH‐Solvent‐Sensing Properties | |
| CN106279219A (en) | Dinuclear cadmium complex as Nitrobenzol fluorescence identifying sensor and preparation method thereof | |
| CN108864159A (en) | A kind of pyrroles can be used for detecting Fe3+ under acidic environment-benzene boron fluorine fluorescent chemicals and preparation method thereof | |
| CN110283330B (en) | Zinc-based luminescent metal organic framework material and preparation method and application thereof | |
| Guo et al. | A dual-responsive luminescent TbIII-organic framework with high water stability for selective sensing of Fe3+ and Cr2O72− in water systems | |
| Smith et al. | In situ surface-etched bacterial spore detection using dipicolinic acid–europium–silica nanoparticle bioreporters | |
| Liu et al. | A luminescent Cd (ii) coordination polymer as a multi-responsive fluorescent sensor for Zn 2+, Fe 3+ and Cr 2 O 7 2− in water with fluorescence enhancement or quenching |
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 |