CN109354592A - A kind of cadmium complex and preparation method thereof based on pyridinecarboxamide - Google Patents
A kind of cadmium complex and preparation method thereof based on pyridinecarboxamide Download PDFInfo
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- CN109354592A CN109354592A CN201811207512.XA CN201811207512A CN109354592A CN 109354592 A CN109354592 A CN 109354592A CN 201811207512 A CN201811207512 A CN 201811207512A CN 109354592 A CN109354592 A CN 109354592A
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- pyridinecarboxamide
- cadmium
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- 229910052793 cadmium Inorganic materials 0.000 title claims abstract description 21
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 title claims abstract description 21
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title abstract description 10
- 238000010668 complexation reaction Methods 0.000 title abstract description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 13
- QRYWJFOBXFDERP-UHFFFAOYSA-N n-[(2-amino-6-methylpyridin-3-yl)methyl]-3,4,5-trimethoxybenzamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)NCC=2C(=NC(C)=CC=2)N)=C1 QRYWJFOBXFDERP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000000463 material Substances 0.000 claims abstract description 10
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims abstract description 5
- 229910001914 chlorine tetroxide Inorganic materials 0.000 claims abstract description 4
- 229910001915 chlorine(VII) oxide peroxide Inorganic materials 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 claims abstract description 4
- 239000013078 crystal Substances 0.000 claims description 11
- AIUIJBDEQKTMHT-UHFFFAOYSA-N perchloric acid;hydrate Chemical compound O.OCl(=O)(=O)=O AIUIJBDEQKTMHT-UHFFFAOYSA-N 0.000 claims description 7
- 235000019441 ethanol Nutrition 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 2
- -1 cadmium perchlorate metal complex Chemical class 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 239000003446 ligand Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- CLWRFNUKIFTVHQ-UHFFFAOYSA-N [N].C1=CC=NC=C1 Chemical group [N].C1=CC=NC=C1 CLWRFNUKIFTVHQ-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PSIBWKDABMPMJN-UHFFFAOYSA-L cadmium(2+);diperchlorate Chemical compound [Cd+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O PSIBWKDABMPMJN-UHFFFAOYSA-L 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000013110 organic ligand Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000005260 alpha ray Effects 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006664 bond formation reaction Methods 0.000 description 1
- 150000001661 cadmium Chemical class 0.000 description 1
- JGOODDPGJGAPCG-UHFFFAOYSA-N cadmium;perchloric acid;hydrate Chemical compound O.[Cd].OCl(=O)(=O)=O JGOODDPGJGAPCG-UHFFFAOYSA-N 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 238000005564 crystal structure determination Methods 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012621 metal-organic framework Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000011232 storage material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
-
- 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
- C09K2211/18—Metal complexes
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Pyridine Compounds (AREA)
Abstract
The present invention relates to a kind of cadmium complex and preparation method thereof based on pyridinecarboxamide.The chemical formula of the complex is [CdII 5(L1)4(OClO3)2(EtOH)4(OH2)2](ClO4)8·2H2O, wherein L1 is N', -1,3,5- benzene trimethamide of N ", N " '-three (2- pyridyl group-methylene).The complex is first and contains N', the cadmium perchlorate metal complex of N ", N " '-three (2- pyridyl group-methylene) -1,3,5- benzene trimethamide.Its raw material is easy to get, preparation method is simple, reproducible, synthetic yield is high.The complex shows strong blue-light-emitting property, and light property result of study shows that it can be used as blue light material and is applied in technical field of material chemistry.
Description
Technical field
The invention belongs to metal-organic coordination compounds technical field, in particular to one kind contains pyridinecarboxamide
Cadmium complex and preparation method thereof.The complex invented has novel metal-organic framework.
Background technique
Metal-organic coordination compounds are a kind of complications formed by organic ligand and metal center by coordination bonding
Close object.There is inorganic and organic component simultaneously in complex composition, deposited in nature with simple inorganic matter or organic matter
In biggish difference.It is obtained by the reasonable selection of metal center and the Reasonable Regulation And Control of organic ligand or screening modification, people
A large amount of metal-organic coordination compounds with novel framework structure, wherein many Coordinative Chemistry object have good light,
The properties such as electricity, magnetic, also system in depth has studied them in such as photoelectric material, gas storage material, separation material, energy to people
The application of source material etc..However due to the presence of many factors in assembling process, the metal-of controlled architecture and property is organic
The synthesis of complex or a very big challenge, need a large amount of Experimental Research.Amide groups is widely present in nature
In, may act as receptor in hydrogen bond formation kind can also be used as donor, therefore be capable of forming hydrogen bond abundant, in life system
Kind has very important status.If this advantage is introduced into complex, hydrogen bond composition abundant will necessarily be given
System brings objective application prospect, has good expection in the Subjective and Objectives research such as Chemical Decomposition, absorption.There are commonly
In machine ligand, pyridine is since its is from a wealth of sources, preparation is simple, while coordination ability is strong, composition is stablized, and is conducive to entire
The structure and properties of metal organic complex are studied, and have very important status always in correlative study.So far, make
For a kind of common nitrogen ligand, flexible tripod amido pyridine complex construct and its property explore it is more rare, especially
It is that -1,3,5- benzene trimethamide cadmium perchlorate complex of N', N ", N " '-three (2- pyridyl group-methylene) has not been reported, the present invention
Result of study shows that the designed complex synthesized has relatively new crystal structure, and preparation method is simple, is easy to repeat, light
Property is learned research shows that it is expected to be applied in fluorescent material field.
Summary of the invention
It is an object of that present invention to provide cadmium complexes of a kind of pyridinecarboxamide and preparation method thereof.The complex
It is first to be prepared by (2- pyridyl group-the methylene) -1,3,5- benzene trimethamide ligand of N', N ", N " '-three and cadmium perchlorate
The complex arrived.Its raw material is easily prepared, preparation method is simple, favorable reproducibility, synthetic yield are high, purity is high.
To achieve the above object, the present invention provides following technology contents:
The present invention is based on the cadmium complex of pyridinecarboxamide, chemical formula is [CdII 5(L1)4(OClO3)2(EtOH)4
(OH2)2](ClO4)8·2H2O, wherein L1 is N', N ", -1,3,5- benzene trimethamide of N " '-three (2- pyridyl group-methylene), root
It is prepared according to document (Y Wang, et al., Chem.Eur.J., 2007,13,7523) method.
The present invention is based on the preparation methods of the cadmium complex of pyridinecarboxamide: six perchloric acid hydrate cadmiums, N' will be contained,
The ethanol solution of -1,3,5- benzene trimethamide of N ", N " '-three (2- pyridyl group-methylene) place in closed reaction kettle, in
After being reacted 72 hours at 80-100 DEG C, it is cooled to room temperature, obtains colourless acicular crystal, the production calculated based on six perchloric acid hydrate cadmiums
Rate is 70%, wherein six perchloric acid hydrate cadmiums, N', N ", -1,3,5- benzene trimethamide of N " '-three (2- pyridyl group-methylene)
Ratio is 1:1.
The monocrystalline of the above-mentioned cadmium complex based on pyridinecarboxamide, structure feature are as follows: it is tiltedly brilliant that crystal belongs to three
System, space group are α=80.381 (9) °, β=
85.630 (12) °, γ=75.234 (11) °,Mr=3734.92, Z=1, F (000)=1882, Dc=
1.652g/cm3, μ=0.972mm-1, R=0827, wR=0.2066.The coordination context diagram of complex is as shown in Figure 1a, it is not
There are three types of the Cd that crystallography environment is different in symmetrical cellIIIn the presence of they are all hexa-coordinates: Cd1 by three amide oxygen atoms,
Two pyridine nitrogen atoms and the oxygen atom ligand of a perchlorate, Cd1-O, Cd1-N bond distance's range are that 2.271 (5) are arrivedO-Cd1-O, O-Cd1-N, N-Cd1-N bond angle change within the scope of 77.9 (3) ° to 176.25 (18) °；Cd2 by
From two pyridine nitrogen atoms, two amide oxygen atoms and two water molecule coordinations of two ligands, Cd2-N, Cd2-O key
Long is respectively 2.274 (7), 2.300 (5) andBond angle range is then 85.6 (2) ° to 180.0 °；Cd3 is also six to match
Position, coordination atom is on two pyridine nitrogen atoms and two amide oxygen atoms and two ethanol molecules of two ligands respectively
Oxygen atom, bond distance's range around Cd3 is that 2.271 (5) are arrivedBond angle is in 83.1 (2) ° to 171.9 (3) ° range
Interior variation.Therefore, three kinds of CdIIIt is all the N of distortion2O4Octahedral coordination configuration.Four Cd in complexII(two Cd1, two
A Cd3) and four ligands constitute 32 yuan of big rings, on the other hand two Cd1 and two ligands constitute one 16 yuan again
Ring, two kinds big ring are arranged successively along the direction b, form the one-dimensional catenary structure (Fig. 1 b, c) in complex.And such chain
Shape structure is further by Cd2-Npyridyl,Cd2-OcarboxylCoordination is connected to become novel two-dimensional network structure (Fig. 1 d).
The ClO not being coordinated4 -It between the layers with solvent water molecules filling, will be two-dimentional by N-HO and C-HO hydrogen bond
Grid is combined together to form three-dimensional structure and is stabilized.There is the ligand of two kinds of different coordination modes in complex: first
Kind ligand connects two Cd1 and Cd3 ions, and two in three arms of the ligand are using O, the coordination moulds of N chelating
Formula is coordinated with Cd3, Cd1 respectively, and another arm then only has amide oxygen atom to take part in the coordination with another Cd1；It is another
Kind ligand is then separately connected Cd1, Cd2 and Cd3 each one, and three arms are the O used, the coordination mode (Fig. 1 a) of N chelating.
The elemental analysis of the above-mentioned cadmium complex based on pyridinecarboxamide: theoretical value: C116H128Cl10N24O60Cd5:
C, 37.30；H, 3.46；N, 9.00；Experiment value: C, 37.21；H, 3.51；N, 9.18.Instrument is VARIO EL III element
Analyzer (Germany, Elementar).
The above-mentioned cadmium complex based on pyridinecarboxamide shows under the light excitation of 360nm strong at room temperature
Blue-light-emitting property, emission peak are located at 412nm (Fig. 2), are expected to have good application in terms of blue emitting material.It is used
Instrument is F-4500 (Japan, Hitachi)
Cadmium complex the present invention is based on pyridinecarboxamide is first containing N', N ", (the 2- pyridyl group-Asia of N " '-three
Methyl) -1,3,5- benzene trimethamide cadmium perchlorate metal complex.It uses solvent-thermal method to prepare, and raw material is easy to get, is repeated
It is good, with high purity, show strong blue-light-emitting property at room temperature, be expected to be applied on fluorescent material field.
Detailed description of the invention
Fig. 1 is the crystal structure figure of the cadmium complex of pyridinecarboxamide of the present invention；
Fig. 2 is the fluorescence curve figure of the cadmium complex of pyridinecarboxamide of the present invention.
Specific embodiment
It is [Cd the present invention is based on the chemical formula of the cadmium complex of pyridinecarboxamideII 5(L1)4(OClO3)2(EtOH)4
(OH2)2](ClO4)8·2H2O, wherein L1 is N', N ", -1,3,5- benzene trimethamide of N " '-three (2- pyridyl group-methylene).
Below with reference to specific implementation example, the present invention is further explained.
Embodiment 1: by six perchloric acid hydrate cadmiums, N', N ", three formyl of N " '-three (2- pyridyl group-methylene) -1,3,5- benzene
Reaction 30 minutes is sufficiently stirred in each 0.05mmol of amine after mixing in 5mL ethyl alcohol, close after being transferred in 15mL stainless steel cauldron
Colourless acicular crystal is obtained by filtration in envelope, cooled to room temperature after sufficiently reacting under the conditions of 80 DEG C of -100 DEG C of temperature 72 hours,
It is 70% based on six perchloric acid hydrate cadmium yields.
The present invention is based on the cadmium complex of pyridinecarboxamide further characterization, process is as follows:
(1) crystal structure determination of the cadmium complex of pyridinecarboxamide
The monocrystalline for choosing suitable size uses Mo-K alpha ray under 200K on CCD Smart Apex diffractometer It collects.The structure that complex is solved with SHELXL-97 direct method, by SHELXL-97 software with complete matrix most
Small square law is modified the anisotropy of non-hydrogen atom.Calculate the individual that Siemens SHELXTL software is housed at one
It is carried out on computer, all non-hydrogen atoms carry out anisotropy refine, H atom situation theory mode meter with complete matrix least square method
It calculates and determines.The partial parameters of crystal diffraction data collection and structure refinement are listed in table 1, and the bond distance of selection and bond angle data are shown in Table 2.
Crystal structure is as shown in Figure 1.
(2) the fluorogram research of the cadmium complex of pyridinecarboxamide:
Complex crystal sample carries out the test of solid luminescence through being fully ground at room temperature after washed, drying process.?
Strong blue-light-emitting property is showed under the light excitation of 360nm, emission peak is located at 412nm (Fig. 2), which sends out in blue
There is potential application in terms of luminescent material.
The predominant crystal data and refined parameters of the cadmium complex of 1 pyridinecarboxamide of table
R1=Σ | | Fo|–|Fc||/Σ|Fo|.wR2=| Σ w (| Fo|2–|Fc|2)|/Σ|w(Fo)2|1/2, w=1/ [s2
(Fo 2)] .P=(Fo 2+2Fc 2)/3.
The selection bond distance of the cadmium complex of 2 pyridinecarboxamide of tableWith bond angle (°)
Symmetric code: (#1)-x+1 ,-y+1 ,-z+1；(#2)-x+1,-y+1,-z；(#3)x,y+1,z.
Claims (4)
1. a kind of cadmium complex based on pyridinecarboxamide, it is characterised in that: the coordination chemistry formula is [CdII 5
(L1)4(OClO3)2(EtOH)4(OH2)2](ClO4)8·2H2O, wherein wherein L1 is N', N ", N " '-three (2- pyridyl group-methylene
Base) -1,3,5- benzene trimethamide.
2. the cadmium complex of pyridinecarboxamide described in claim 1, it is characterised in that the crystal category of the complex
In anorthic system, space group is P ī,α=80.381
γ=75.234 (11) °, β=85.630 (12) °, (9) °Mr=3734.92, Z=1, F (000)=
1882,Dc=1.652g/cm3, μ=0.972mm-1, R=0827, wR=0.2066.
3. the cadmium complex of pyridinecarboxamide described in claim 1, it is characterised in that: by six perchloric acid hydrate cadmiums, N',
- 1,3,5- benzene trimethamide of N ", N " '-three (2- pyridyl group-methylene), ethyl alcohol 8mL are placed in closed reaction kettle, in 80-
It after being reacted 72 hours at 100 DEG C, is cooled to room temperature, colourless acicular crystal is obtained by filtration, calculated and produced based on six perchloric acid hydrate cadmiums
Rate is 70%, wherein six perchloric acid hydrate cadmiums, N', -1,3,5- benzene trimethamide of N ", N " '-three (2- pyridyl group-methylene)
Ratio is 1:1.
4. the application of the cadmium complex of pyridinecarboxamide described in claim 1, it is characterised in that the complex can
To be applied as blue light material.
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| KR20220009690A (en) * | 2020-07-16 | 2022-01-25 | 부경대학교 산학협력단 | New diacetylene compounds, polymers thereof and sensor for detection of cadmium |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105936668A (en) * | 2016-01-26 | 2016-09-14 | 安庆师范大学 | Cd coordination compound based on flexible amido pyridine ligand and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105936668A (en) * | 2016-01-26 | 2016-09-14 | 安庆师范大学 | Cd coordination compound based on flexible amido pyridine ligand and preparation method thereof |
Non-Patent Citations (1)
| Title |
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| WANG, YAN ET AL.: "New metal-organic frameworks with large cavities: selective sorption and desorption of solvent molecules", 《 CHEMISTRY - A EUROPEAN JOURNAL》 * |
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| KR20220009690A (en) * | 2020-07-16 | 2022-01-25 | 부경대학교 산학협력단 | New diacetylene compounds, polymers thereof and sensor for detection of cadmium |
| KR102419725B1 (en) | 2020-07-16 | 2022-07-13 | 부경대학교 산학협력단 | New diacetylene compounds, polymers thereof and sensor for detection of cadmium |
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Application publication date: 20190219 |