CN109369688A - A kind of application of material - Google Patents
A kind of application of material Download PDFInfo
- Publication number
- CN109369688A CN109369688A CN201811495068.6A CN201811495068A CN109369688A CN 109369688 A CN109369688 A CN 109369688A CN 201811495068 A CN201811495068 A CN 201811495068A CN 109369688 A CN109369688 A CN 109369688A
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- Prior art keywords
- picolyl
- temperature
- solvent
- reaction
- piperazine
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- 239000000463 material Substances 0.000 title claims abstract description 20
- 239000013078 crystal Substances 0.000 claims abstract description 28
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 239000002904 solvent Substances 0.000 claims abstract description 14
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims abstract description 12
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims abstract description 12
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- PVAQSGXNQUFOMY-UHFFFAOYSA-N 1,4-bis(pyridin-4-ylmethyl)piperazine Chemical compound C=1C=NC=CC=1CN(CC1)CCN1CC1=CC=NC=C1 PVAQSGXNQUFOMY-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000005406 washing Methods 0.000 claims abstract description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 23
- XZYLSJPLCLKCMR-UHFFFAOYSA-N 1-(pyridin-4-ylmethyl)piperazine Chemical compound C=1C=NC=CC=1CN1CCNCC1 XZYLSJPLCLKCMR-UHFFFAOYSA-N 0.000 claims description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000009210 therapy by ultrasound Methods 0.000 claims description 6
- 235000019441 ethanol Nutrition 0.000 claims description 4
- 238000000034 method Methods 0.000 abstract description 6
- 239000000376 reactant Substances 0.000 abstract description 4
- 238000009825 accumulation Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000004088 simulation Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000000634 powder X-ray diffraction Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- 229910017489 Cu I Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013257 coordination network Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/008—Supramolecular polymers
-
- 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
- G01K—MEASURING TEMPERATURE; MEASURING QUANTITY OF HEAT; THERMALLY-SENSITIVE ELEMENTS NOT OTHERWISE PROVIDED FOR
- G01K11/00—Measuring temperature based upon physical or chemical changes not covered by groups G01K3/00, G01K5/00, G01K7/00 or G01K9/00
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01K—MEASURING TEMPERATURE; MEASURING QUANTITY OF HEAT; THERMALLY-SENSITIVE ELEMENTS NOT OTHERWISE PROVIDED FOR
- G01K11/00—Measuring temperature based upon physical or chemical changes not covered by groups G01K3/00, G01K5/00, G01K7/00 or G01K9/00
- G01K11/32—Measuring temperature based upon physical or chemical changes not covered by groups G01K3/00, G01K5/00, G01K7/00 or G01K9/00 using changes in transmittance, scattering or luminescence in optical fibres
-
- 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)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
The invention discloses a kind of applications of material, belong to Material Field.This method is by cuprous iodide and 1,4- bis- (4- picolyl) piperazine dissolved in a solvent, is transferred in reaction kettle after reactant is ultrasonically treated, and carries out 50~200h of reaction at 100~200 DEG C of temperature, cooled to room temperature after reaction obtains colourless bulk crystals after washing.Preparation method of the invention is simple, and product yield is high, and in 70-200K temperature range, the product being prepared, which varies with temperature, presents fine linear changing relation.
Description
The application is the applying date are as follows: 2018-03-23, application No. is a kind of 2018102452711, titles are as follows: fluorescence temperature
Spend the divisional application of measuring appliance hybrid material and the patent of invention of preparation method and application.
Technical field
The invention belongs to Material Fields, and in particular to a kind of application of material.
Background technique
Temperature is all a kind of essential and basic basic parameter in industrial production and scientific research, and this requires to environment temperature
The thermometer of the precise measurement of degree has higher performance.Using can be quick for the temperature meter of materials synthesis based on fluorescence
Precisely, temperature is intuitively obtained, at high cost when avoiding the measurement of conventional temperature meter, accuracy is low and the time is longer etc. asks
Topic.And go deep into research, it is applied more in scientific experiment and industrial production using fluorescence as the temperature meter of materials synthesis
Come more extensive.
Summary of the invention
The present invention be directed to above-mentioned technical problems to provide a kind of hybrid material preparation side of fluorescence temperature measuring appliance
Method.
The purpose of the present invention can be achieved through the following technical solutions:
Fluorescence temperature measuring appliance hybrid material of the present invention can be achieved through the following technical solutions:
A kind of fluorescence temperature measuring appliance hybrid material, the material are to be prepared via a method which to obtain:
Cuprous iodide and Isosorbide-5-Nitrae-two (4- picolyl) piperazine dissolved in a solvent, are shifted after reactant is ultrasonically treated
Into reaction kettle, 50~200h of reaction is carried out at 100~200 DEG C of temperature, after reaction cooled to room temperature, after washing
Obtain colourless bulk crystals.
In some technical solutions: the molar ratio of cuprous iodide and 1,4- bis- (4- picolyl) piperazine is 1~5:1.
It is preferred that: the molar ratio of cuprous iodide and 1,4- bis- (4- picolyl) piperazine is 2~3:1.
In some technical solutions: the organic solvent is at least one of N,N-dimethylformamide and methanol；
More preferable: the organic solvent is N,N-dimethylformamide.
In some technical solutions: the reaction temperature is 100~140 DEG C.
In some technical solutions: the reaction time is 70~140h.
In some technical solutions: the mass volume ratio of (4- picolyl) piperazine of 1,4- bis- and solvent be 0.03g:2~
12mL；It is preferred that the mass volume ratio of (4- picolyl) piperazine of 1,4- bis- and solvent is 0.03g:2~8mL.
In some technical solutions: the time of ultrasonic treatment is 1~60min.
In some technical solutions: the washing is washed respectively 1~5 time with DMF and ethyl alcohol.
The preparation method of fluorescence temperature measuring appliance hybrid material of the present invention can be achieved through the following technical solutions:
A kind of preparation method of fluorescence temperature measuring appliance hybrid material, this method are by cuprous iodide and (the 4- pyrrole of Isosorbide-5-Nitrae-two
Pyridine methyl) piperazine dissolved in a solvent, be transferred in reaction kettle after reactant is ultrasonically treated, at 100~200 DEG C of temperature into
Row 50~200h of reaction, cooled to room temperature, obtains colourless bulk crystals after reaction after washing.
In above-mentioned preparation method: the molar ratio of cuprous iodide and 1,4- bis- (4- picolyl) piperazine is 1~5:1；It is preferred that:
The molar ratio of cuprous iodide and 1,4- bis- (4- picolyl) piperazine is 2~3:1；
The organic solvent is at least one of N,N-dimethylformamide and methanol；More preferable: described is organic
Solvent is N,N-dimethylformamide；
The reaction temperature is 100~140 DEG C；The reaction time is 70~140h.
The mass volume ratio of (4- picolyl) piperazine of 1,4- bis- and solvent is 0.03g:2~12mL；It is preferred that 1,
The mass volume ratio of (4- picolyl) piperazine of 4- bis- and solvent is 0.03g:2~8mL.
Above-mentioned hybrid material is preparing the application in fluorescence temperature measuring appliance.
Beneficial effects of the present invention:
Preparation method of the invention is simple, and product yield is high, and in 70-200K temperature range, the product being prepared with
Temperature change presents fine linear changing relation.
Detailed description of the invention
Fig. 1 is the minimum asymmetric cell figure for the crystal that embodiment 16 is prepared；
The coordination context diagram of four core Cu clusters in the crystal that Fig. 2 is prepared for embodiment 16；
Fig. 3 is the accumulation graph for the crystal that embodiment 16 is prepared；
Fig. 4 is the X-ray powder diffraction figure for the crystal that embodiment 16 is prepared and the comparison diagram of single crystal data simulation drawing
(upper figure: single crystal data simulation drawing, the following figure: experimental diffraction figure)；
Fig. 5 is the alternating temperature fluorescence spectra for the crystal that embodiment 16 is prepared；
Fig. 6 is the relational graph of the 600nm of crystal that embodiment 16 is prepared or so place's fluorescence intensity and temperature.
Specific embodiment
Below with reference to embodiment, the present invention will be further described, and but the scope of the present invention is not limited thereto:
Isosorbide-5-Nitrae-two (4- picolyl) piperazine is according to document CrystEngcom, 2005,7,624-628, Molecular
tectonics:on the role of counter-ions in the dimensionality of silver
The method synthesis of coordination networks report.
Examples 1 to 23
Reaction step: in a solvent by the dissolution of (4- picolyl) piperazine of Isosorbide-5-Nitrae-two (ligand) of cuprous iodide and 0.03g,
Reactant ultrasonic treatment is transferred in reaction kettle after twenty minutes and is reacted, after reaction cooled to room temperature, product
It is washed respectively 3 times with DMF and ethyl alcohol, obtains colourless bulk crystals.The actual conditions of reaction are referring to following table:
The reaction condition of 1 Examples 1 to 21 of table
The crystal that embodiment 16 is prepared carries out X-ray single crystal diffraction, and specific data are as follows:
The structure refinement parameter for the crystal that 2 embodiment 16 of table obtains
The part bond distance for the crystal that 3 embodiment 16 of table obtains
The crystal structure that embodiment 16 is prepared is in monoclinic system, C2/c space group.Fig. 1 show the minimum of the crystal
Asymmetric cell, it is recognised that its minimum asymmetric cell includes two Cu from figure+, two I-And two half of 1,4- bis-
(4- picolyl) piperazine moieties.
Fig. 2 is the coordination environment for the crystal Cu cluster that embodiment 16 is prepared, and what which took is four
The model of core is connected by way of covalent bond between four Cu atoms, the tetrahedron of a distortion is formed, as in Cu cluster
Core, Cu-Cu bond distance existBetween.Four I atoms are connected by way of coordinate bond with Cu atom, equally
A biggish tetrahedron is formed, Cu cluster kernel tetrahedron is comprised among the big tetrahedron of Cu-I.
Fig. 3 is the accumulation graph of crystal that embodiment 16 is prepared, the direction of observation of the accumulation graph along structure cell c- axis, from
It is recognised that the coordination by Cu atom and N atom is keyed in figure, space structure shows three-dimensional netted interspersed model.
Ligand molecular is looped around around Cu cluster, by the orderly accumulation in space, forms the molecular structure of more airways.
Fig. 4 is the comparison of the X-ray powder diffraction collection and monocrystalline analogue data for the crystal that the embodiment 16 is prepared
Figure, by scheming we can see that the position of simulation drawing and lab diagram main diffraction peak is almost the same, it is known that products therefrom is pure phase.
The alternating temperature fluorescence spectrum of the crystal that embodiment 16 is prepared is as shown in figure 5, in 70-200K temperature range, the change
It closes object and presents three transmitting bands, wherein launch wavelength center is located at the transmitting band of 600nm or so, with the reduction of temperature, hair
It hits the heart and red shift has occurred.
Fig. 6 is the relationship of the crystal 600nm that embodiment 16 is prepared or so place's fluorescence intensity and temperature.The compound exists
Transmitting band strength at 600nm varies with temperature in 70-200K temperature range and presents fine linear changing relation (such as Fig. 6
It is shown), therefore, which is a kind of potential fluorescence temperature measuring appliance, very rare in hybrid inorganic-organic crystal.
Claims (2)
1. a kind of material is preparing the application in fluorescence temperature measuring appliance, it is characterised in that: the preparation method of the material include with
Lower step:
Cuprous iodide and Isosorbide-5-Nitrae-two (4- picolyl) piperazine dissolved in a solvent, are transferred in reaction kettle after ultrasonic treatment,
70~200h of reaction is carried out at 100~120 DEG C of temperature, after reaction cooled to room temperature, no color lump is obtained after washing
Shape crystal；
Wherein: the molar ratio of cuprous iodide and 1,4- bis- (4- picolyl) piperazine is 2:1；The solvent is methanol；1,4-
The mass volume ratio of two (4- picolyl) piperazines and solvent is 0.03g:4~8mL；
The molecular formula of the colourless bulk crystals is C32H40Cu4I4N8, space group C2/c, cell parameterα=90 °, β=114.600 (4) °, γ=90 °,
The washing is washed respectively 1~5 time with DMF and ethyl alcohol.
The time of ultrasonic treatment is 1~60min.
2. a kind of material is preparing the application in fluorescence temperature measuring appliance, it is characterised in that: the preparation method of the material include with
Lower step:
Cuprous iodide and Isosorbide-5-Nitrae-two (4- picolyl) piperazine dissolved in a solvent, are transferred in reaction kettle after ultrasonic treatment,
120~200h of reaction is carried out at 100~140 DEG C of temperature, after reaction cooled to room temperature, no color lump is obtained after washing
Shape crystal；
Wherein: the molar ratio of cuprous iodide and 1,4- bis- (4- picolyl) piperazine is 2:1；The solvent is N, N- dimethyl
Formamide；The mass volume ratio of (4- picolyl) piperazine of 1,4- bis- and solvent is 0.03g:4~8mL；
The molecular formula of the colourless bulk crystals is C32H40Cu4I4N8, space group C2/c, cell parameterα=90 °, β=114.600 (4) °, γ=90 °,
The washing is washed respectively 1~5 time with DMF and ethyl alcohol.
The time of ultrasonic treatment is 1~60min.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811495068.6A CN109369688A (en) | 2018-03-23 | 2018-03-23 | A kind of application of material |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811495068.6A CN109369688A (en) | 2018-03-23 | 2018-03-23 | A kind of application of material |
| CN201810245271.1A CN108456217B (en) | 2018-03-23 | 2018-03-23 | A kind of fluorescence temperature measuring appliance hybrid material and preparation method and application |
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| CN201810245271.1A Division CN108456217B (en) | 2018-03-23 | 2018-03-23 | A kind of fluorescence temperature measuring appliance hybrid material and preparation method and application |
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| CN109369688A true CN109369688A (en) | 2019-02-22 |
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| CN201811495068.6A Pending CN109369688A (en) | 2018-03-23 | 2018-03-23 | A kind of application of material |
| CN201810245271.1A Active CN108456217B (en) | 2018-03-23 | 2018-03-23 | A kind of fluorescence temperature measuring appliance hybrid material and preparation method and application |
| CN201811495083.0A Pending CN109438483A (en) | 2018-03-23 | 2018-03-23 | A kind of hybrid material preparation method of fluorescence temperature measuring appliance |
| CN201811500681.2A Pending CN109438484A (en) | 2018-03-23 | 2018-03-23 | A kind of hybrid material for temperature meter |
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| CN201810245271.1A Active CN108456217B (en) | 2018-03-23 | 2018-03-23 | A kind of fluorescence temperature measuring appliance hybrid material and preparation method and application |
| CN201811495083.0A Pending CN109438483A (en) | 2018-03-23 | 2018-03-23 | A kind of hybrid material preparation method of fluorescence temperature measuring appliance |
| CN201811500681.2A Pending CN109438484A (en) | 2018-03-23 | 2018-03-23 | A kind of hybrid material for temperature meter |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109705025B (en) * | 2019-01-26 | 2021-04-20 | 济宁学院 | Organic-inorganic hybrid copper iodide compound and preparation method and application thereof |
| CN109651408B (en) * | 2019-01-26 | 2021-04-13 | 济宁学院 | Novel CuI complex and preparation method and application thereof |
| CN110926649B (en) * | 2019-11-27 | 2020-09-15 | 燕山大学 | High-sensitivity temperature measurement method based on different rare earth ion near-infrared fluorescence |
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| CN107793438A (en) * | 2017-08-29 | 2018-03-13 | 中山大学 | A kind of copper（I）Phosphine benzene heterocycle complex and its preparation method and application |
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| CN104232075B (en) * | 2014-09-30 | 2016-04-13 | 郑州大学 | A kind of thermochromism fluorescence thermometer material and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107793438A (en) * | 2017-08-29 | 2018-03-13 | 中山大学 | A kind of copper（I）Phosphine benzene heterocycle complex and its preparation method and application |
Non-Patent Citations (2)
| Title |
|---|
| ARASH BANISAFAR，等: "Layered copper bromide coordination polymers from bis(pyridyl)piperazine-type precursors: Ligand dependent valence tuning and in situ hydrothermal reaction chemistry", 《INORGANICA CHIMICA ACTA》 * |
| SHUAI YUAN，等: "Two isomeric [Cu4I4] luminophores: solvothermal/mechanochemical syntheses, structures and thermochromic luminescence properties", 《CRYSTENGCOMM》 * |
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| Publication number | Publication date |
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| CN108456217B (en) | 2019-01-25 |
| CN109438484A (en) | 2019-03-08 |
| CN108456217A (en) | 2018-08-28 |
| CN109438483A (en) | 2019-03-08 |
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Application publication date: 20190222 |