CN107033173A - The structure and its photoluminescent property for the cadmium complex constructed with terephthalic acid (TPA) and pyrazine - Google Patents
The structure and its photoluminescent property for the cadmium complex constructed with terephthalic acid (TPA) and pyrazine Download PDFInfo
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- CN107033173A CN107033173A CN201710272886.9A CN201710272886A CN107033173A CN 107033173 A CN107033173 A CN 107033173A CN 201710272886 A CN201710272886 A CN 201710272886A CN 107033173 A CN107033173 A CN 107033173A
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- Prior art keywords
- tpa
- terephthalic acid
- complex
- pyrazine
- cadmium
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 title claims abstract description 128
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 title claims abstract description 30
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 229910052793 cadmium Inorganic materials 0.000 title description 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 title description 2
- VXIPUXDNYJBFFY-UHFFFAOYSA-N cadmium pyrazine Chemical compound N1=CC=NC=C1.[Cd] VXIPUXDNYJBFFY-UHFFFAOYSA-N 0.000 claims abstract description 13
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 8
- 229910021645 metal ion Inorganic materials 0.000 claims abstract description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- 230000005284 excitation Effects 0.000 claims abstract description 3
- 238000010791 quenching Methods 0.000 claims abstract description 3
- 230000000171 quenching effect Effects 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 239000012153 distilled water Substances 0.000 claims description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 238000013019 agitation Methods 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- 150000001455 metallic ions Chemical class 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 3
- 229910001220 stainless steel Inorganic materials 0.000 claims description 3
- 239000010935 stainless steel Substances 0.000 claims description 3
- -1 Formic acid pyrazine cadmium Chemical compound 0.000 claims description 2
- AJVCUHHHRPBRHU-UHFFFAOYSA-N cadmium nitric acid Chemical compound [Cd].[N+](=O)(O)[O-] AJVCUHHHRPBRHU-UHFFFAOYSA-N 0.000 claims description 2
- HUKFCVYEXPZJJZ-UHFFFAOYSA-N cadmium;hydrate Chemical compound O.[Cd] HUKFCVYEXPZJJZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 150000003216 pyrazines Chemical class 0.000 claims description 2
- XIEPJMXMMWZAAV-UHFFFAOYSA-N cadmium nitrate Inorganic materials [Cd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XIEPJMXMMWZAAV-UHFFFAOYSA-N 0.000 abstract description 4
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003446 ligand Substances 0.000 abstract description 3
- 238000001027 hydrothermal synthesis Methods 0.000 abstract description 2
- 238000000034 method Methods 0.000 abstract description 2
- 239000007787 solid Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 229910052723 transition metal Inorganic materials 0.000 abstract description 2
- 150000003624 transition metals Chemical class 0.000 abstract description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 241000040710 Chela Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- ZSDJVGXBJDDOCD-UHFFFAOYSA-N benzene dioctyl benzene-1,2-dicarboxylate Chemical compound C(C=1C(C(=O)OCCCCCCCC)=CC=CC1)(=O)OCCCCCCCC.C1=CC=CC=C1 ZSDJVGXBJDDOCD-UHFFFAOYSA-N 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 229920001795 coordination polymer Polymers 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- C09K2211/18—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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses the preparation of terephthalic acid (TPA) pyrazine cadmium complex, structure and its photoluminescent property.The complex belongs to anorthic system, and space group is
Description
Technical field
The invention belongs to complex preparing technical field, more particularly to a kind of system of terephthalic acid (TPA) pyrazine cadmium complex
Standby, structure and its photoluminescent property.
Background technology
Carboxylic acids organic coordination compound is developed rapidly in recent years, and as carboxylic acids part, because it is special
A large amount of presence of the weak interaction such as coordination ability and hydrogen bond, receive the extensive concern of domestic and international chemist.To benzene two
Formic acid had been widely used in the construction unit of conformation function type coordination polymer in recent years, and not only its carboxyl has monodentate ligand,
Double coordination, bridging, a variety of coordination modes such as chelating, and its phenyl ring can also form π complexs.In addition, for pyrazine, it
Big pi bond is conjugated with intramolecular, product can be determined as highly effective chromophore, and with good intramolecular electricity
Son transmission and energy transmission property, are a kind of good assistant ligands.
The content of the invention
It is an object of the invention to provide a kind of preparation, structure and its photoluminescent property of terephthalic acid (TPA) pyrazine cadmium complex.
The thinking of the present invention：It is that part and cadmium nitrate obtain terephthaldehyde by hydro-thermal method using terephthalic acid (TPA), pyrazine
Sour pyrazine cadmium complex.
The structure of terephthalic acid (TPA) pyrazine cadmium complex is shown in accompanying drawing 1.The complex belongs to anorthic system, and space group is P ī,
In the complex, the carboxyl on terephthalic acid (TPA) is coordinated in the form of chelating with Metal Ions Cd (II), and pyrazine is with bridge
The oxygen that the form of connection is participated in coordination, water provides lone pair electrons and is coordinated with Metal Ions Cd (II) formation coordinate bond, and
Hydrone and another hydrone formation hydrogen bond, more strengthen the stability of complex.Central metallic ions Cd (II) is respectively with coming
From four oxygen atoms (O3, O4, O6, O5) on two different terephthalic acid (TPA) parts, each nitrogen-atoms of two pyrazines
Oxygen atom (O9) coordination in (N1, N2A), hydrone.Cd-O bond distance existsBetween, Cd-N bond distance is
The preparation method of the terephthalic acid (TPA) pyrazine cadmium complex is：
(1) weigh 0.3~0.6 mM of six nitric hydrate cadmium to be dissolved in 2~4 milliliters of distilled water, cadmium nitrate is made molten
Liquid；
(2) weigh 0.3~0.6 mM of terephthalic acid (TPA) to be dissolved in 5~10 milliliters of distilled water, terephthalic acid (TPA) is made
Solution；
(3) weigh 0.3~0.6 mM of pyrazine to be dissolved in 2~4 milliliters of distilled water, pyrazine solution is made；
(4) above-mentioned solution is mixed and added into 0.6~1.2 mM of triethylamine；
(5) solution obtained above is added in ptfe autoclave inner bag, at room temperature magnetic agitation 0.5~
1 hour, put stainless steel cauldron overcoat be put into 130 degrees Celsius react 48~72 hours, taken the photograph after the completion of reaction with per hour 10
Family name's degree gradient is down to room temperature, and driving kettle after standing 12~24 hours obtains colourless solution, filters to obtain water white transparency bulk crystals, is pair
Phthalic acid pyrazine cadmium complex.
The present invention has the advantages that technique is simple, with low cost, reproducible, has successfully synthesized terephthalic acid (TPA) pyrazine
Cadmium complex, the complex for synthesis transition metal provides certain foundation.
The test of fluorescence property is carried out to part terephthalic acid (TPA) and complex at room temperature, as shown in Figure 2.To benzene
Dioctyl phthalate is in the case where 280nm wavelength is excited, and maximum emission wavelength is at 385nm.Complex under 290nm excitation wavelengths,
Fluorescent quenching.
Brief description of the drawings
Fig. 1 is the molecular structure of the terephthalic acid (TPA) pyrazine cadmium complex of the present invention.
Fig. 2 is the terephthalic acid (TPA) of the present invention and the room temperature solid fluorescence emission spectrum of complex.
Embodiment
Embodiment：
(1) weigh 0.3 mM of (0.0709 gram) cadmium nitrate to be dissolved in 3 milliliters of distilled water, nitric acid cadmium solution is made；
(2) weigh 0.3 mM of (0.0498 gram) terephthalic acid (TPA) to be dissolved in 5 milliliters of distilled water, terephthaldehyde is made
Acid solution；
(3) weigh 0.3 mM of (0.0240 gram) pyrazine to be dissolved in 2 milliliters of distilled water, pyrazine solution is made；
(4) above-mentioned solution is mixed and added into 0.6 mM of (0.0607 gram) triethylamine；
(5) solution made from step (1), (2), (3) and (4) is added in ptfe autoclave inner bag, in room
The lower magnetic agitation of temperature 0.5 hour, puts stainless steel cauldron overcoat and is put into 130 degrees Celsius and react 72 hours, after the completion of reaction with
10 degrees Celsius of gradients are down to room temperature per hour, and driving kettle after standing 12 hours obtains colourless solution, filters to obtain water white transparency bulk crystals,
As terephthalic acid (TPA) pyrazine cadmium complex.
The complex belongs to anorthic system, and space group is P ī, and in the complex, the carboxyl on terephthalic acid (TPA) is with chela
The form of conjunction is coordinated with Metal Ions Cd (II), and the oxygen that pyrazine is participated in the form of bridging in coordination, water provides lone pair electrons
It is coordinated with Metal Ions Cd (II) formation coordinate bond, and hydrone and another hydrone formation hydrogen bond, more strengthen and match somebody with somebody
The stability of compound.Central metallic ions Cd (II) respectively from four oxygen originals on two different terephthalic acid (TPA) parts
Oxygen atom (O9) coordination in sub (O3, O4, O6, O5), each nitrogen-atoms (N1, N2A) of two pyrazines, hydrone.Cd-O keys
Length exists Between, Cd-N bond distance is
Claims (3)
1. a kind of structure of terephthalic acid (TPA) pyrazine cadmium complex.The complex belongs to anorthic system, and space group is P ī, is matched somebody with somebody at this
In compound, the carboxyl on terephthalic acid (TPA) is coordinated in the form of chelating with Metal Ions Cd (II), and pyrazine is with the shape of bridging
The oxygen that formula is participated in coordination, water provides lone pair electrons and is coordinated with Metal Ions Cd (II) formation coordinate bond, and hydrone
With another hydrone formation hydrogen bond, the stability of complex is more strengthened.Central metallic ions Cd (II) respectively with from two
Four oxygen atoms (O3, O4, O6, O5) on different terephthalic acid (TPA) parts, each nitrogen-atoms (N1, N2A) of two pyrazines,
Oxygen atom (O9) coordination in hydrone.Cd-O bond distance existsBetween, Cd-N bond distance is
2. the preparation method of terephthalic acid (TPA) pyrazine cadmium complex according to claim 1, it is characterised in that specific steps
For：
(1) weigh 0.3~0.6 mM of six nitric hydrate cadmium to be dissolved in 2~4 milliliters of distilled water, nitric acid cadmium solution is made；
(2) weigh 0.3~0.6 mM of terephthalic acid (TPA) to be dissolved in 5~10 milliliters of distilled water, terephthalic acid (TPA) is made molten
Liquid；
(3) weigh 0.3~0.6 mM of pyrazine to be dissolved in 2~4 milliliters of distilled water, pyrazine solution is made；
(4) above-mentioned solution is mixed and added into 0.6~1.2 mM of triethylamine；
(5) solution obtained above is added in ptfe autoclave inner bag, magnetic agitation 0.5~1 is small at room temperature
When, put stainless steel cauldron overcoat be put into 130 degrees Celsius react 48~72 hours, with 10 degrees Celsius per hour after the completion of reaction
Gradient is down to room temperature, and driving kettle after standing 12~24 hours obtains colourless solution, filters to obtain water white transparency bulk crystals, is to benzene two
Formic acid pyrazine cadmium complex.
3. the photoluminescent property of complex
The test of fluorescence property has been carried out to part terephthalic acid (TPA) and complex at room temperature.Terephthalic acid (TPA) is 280nm's
Wavelength is excited down, and maximum emission wavelength is at 385nm.Complex is under 290nm excitation wavelengths, fluorescent quenching.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710272886.9A CN107033173A (en) | 2017-04-24 | 2017-04-24 | The structure and its photoluminescent property for the cadmium complex constructed with terephthalic acid (TPA) and pyrazine |
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| CN201710272886.9A CN107033173A (en) | 2017-04-24 | 2017-04-24 | The structure and its photoluminescent property for the cadmium complex constructed with terephthalic acid (TPA) and pyrazine |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112142765A (en) * | 2020-09-29 | 2020-12-29 | 桂林理工大学 | Crystal structure of isophthalic acid cadmium complex and fluorescence property thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106366101A (en) * | 2016-09-12 | 2017-02-01 | 桂林理工大学 | Phthalic acid cadmium complex and preparation method thereof |
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- 2017-04-24 CN CN201710272886.9A patent/CN107033173A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106366101A (en) * | 2016-09-12 | 2017-02-01 | 桂林理工大学 | Phthalic acid cadmium complex and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| LEE, CHIN-FEN ET AL.: "Self-adaptation of a conformationally flexible yet restricted "piperazine-pyrazine" building block toward the design of coordination polymers", 《CRYSTENGCOMM》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112142765A (en) * | 2020-09-29 | 2020-12-29 | 桂林理工大学 | Crystal structure of isophthalic acid cadmium complex and fluorescence property thereof |
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