CN105713020A - Fluorescent material [Cu(tidc)2]n and synthesis method - Google Patents
Fluorescent material [Cu(tidc)2]n and synthesis method Download PDFInfo
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- CN105713020A CN105713020A CN201610171268.0A CN201610171268A CN105713020A CN 105713020 A CN105713020 A CN 105713020A CN 201610171268 A CN201610171268 A CN 201610171268A CN 105713020 A CN105713020 A CN 105713020A
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- tidc
- htidc
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- fluorescent material
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- 239000000463 material Substances 0.000 title claims abstract description 11
- 238000001308 synthesis method Methods 0.000 title abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 15
- FABVMBDCVAJXMB-UHFFFAOYSA-N 3,5-dichloro-2-hydroxybenzaldehyde Chemical compound OC1=C(Cl)C=C(Cl)C=C1C=O FABVMBDCVAJXMB-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000002262 Schiff base Substances 0.000 claims abstract description 6
- -1 monohydrate cupric acetate Chemical class 0.000 claims abstract description 6
- 230000003321 amplification Effects 0.000 claims abstract description 5
- 238000003199 nucleic acid amplification method Methods 0.000 claims abstract description 5
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims abstract description 5
- 238000010992 reflux Methods 0.000 claims abstract description 5
- 238000005406 washing Methods 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(II) acetate Substances [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims abstract 2
- 239000010949 copper Substances 0.000 claims description 35
- 239000013078 crystal Substances 0.000 claims description 14
- 238000005286 illumination Methods 0.000 claims description 7
- 238000010189 synthetic method Methods 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- FMCUPJKTGNBGEC-UHFFFAOYSA-N 1,2,4-triazol-4-amine Chemical class NN1C=NN=C1 FMCUPJKTGNBGEC-UHFFFAOYSA-N 0.000 claims description 4
- 238000004020 luminiscence type Methods 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 238000004458 analytical method Methods 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- 239000012153 distilled water Substances 0.000 abstract description 4
- 238000000034 method Methods 0.000 abstract description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 5
- 238000001035 drying Methods 0.000 abstract 2
- 229940076286 cupric acetate Drugs 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000003446 ligand Substances 0.000 abstract 1
- NQFNBCXYXGZSPI-UHFFFAOYSA-L copper;diacetate;dihydrate Chemical compound O.O.[Cu+2].CC([O-])=O.CC([O-])=O NQFNBCXYXGZSPI-UHFFFAOYSA-L 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
Classifications
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- 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
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- 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)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
Abstract
The invention discloses a fluorescent material [Cu(tidc)2]n and a synthesis method. The molecular formula of the fluorescent material [Cu(tidc)2]n is C18H10CuC14N8O2, the molecular weight is 575.69 g/mol, and Htidc is 3, 5-dichloro salicylaldehyde condensation4-amidogen-1, 2, 4 triazole schiff base; 3, 5-dichloro salicylaldehyde of analytical reagent and 4-amidogen-1, 2, 4-triazole of analytical reagent are dissolved in an analytical reagent ethanol solution, heating reflux and filtering are conducted, washing is conducted with analytical reagent alcohol three times, drying is conducted, and a ligand Htidc is obtained; the dried Htidc and analytical reagent monohydrate cupric acetate are dissolved in analytical reagent N' N-dimethylformamide, distilled water is added, and drying is conducted; the [Cu(tidc)2]n generates fluorescence with the strength being 376.5 a.u. and the length being 522 nm under irradiation of incident light with the length being 450 nm; a 800 V photomultiplier is arranged, and the [Cu(tidc)2]n is placed in a potassium peroxodisulfate solution and generates quite stable light with the strength being 2830 a. u. under three times of the amplification coefficient. The fluorescent material is simple in process, low in cost, good in repeatability and high in yield, and chemical components are easy to control.
Description
Technical field
The present invention relates to a kind of fluorescent material [Cu (tidc)2]n, (Htidc is 3,5-dichloro-salicylaldehyde contracting 4-amino-1,2,
4 triazole schiff bases) and synthetic method.
Background technology
The development of many decades gone through by modern fluorescence material, oneself become information show, the field such as lighting source, photoelectric device
Backing material, plays the effect become more and more important for social development and technological progress.Particularly energy scarcity is present, and exploitation turns
Changing the high fluorescent material of efficiency is to solve one of energy scarcity problem method.
Summary of the invention
The purpose of the present invention is exactly the functional material for design synthesis photoluminescent property excellence, utilizes micro-reaction bulb solution methods
Synthesis [Cu (tidc)2]n。
[the Cu (tidc) that the present invention relates to2]nMolecular formula be: C18H10CuCl4N8O2, molecular weight is: 575.69g/mol,
Htidc is 3,5-dichloro-salicylaldehyde contracting 4-amino-1,2,4 triazole schiff bases, and crystal structural data is shown in Table one, bond distance's bond angle number
According to being shown in Table two.
Table one: [Cu (tidc)2]nCrystallographic parameter
aR1=Σ | | Fo|–|Fc||/Σ|Fo|.bwR2=[Σ w (| Fo 2|–|Fc 2|)2/Σw(|Fo 2|)2]1/2
Table two: the bond distance of [Cu (tidc) 2] nWith bond angle °
| C1—C2 | 1.414(7) | C7—N4 | 1.265(6) |
| C1—C6 | 1.411(7) | C8—N2 | 1.316(6) |
| C1—C7 | 1.455(7) | C8—N3 | 1.339(6) |
| C2—C3 | 1.436(6) | C9—N1 | 1.290(6) |
| C2—O1 | 1.278(5) | C9—N3 | 1.364(6) |
| C3—C4 | 1.369(7) | N1—N2 | 1.375(6) |
| C3—Cl1 | 1.734(5) | N2—Cu1i | 2.048(4) |
| C4—C5 | 1.383(8) | N3—N4 | 1.421(5) |
| C5—C6 | 1.375(8) | N4—Cu1ii | 2.344(4) |
| C5—Cl2 | 1.738(6) | O1—Cu1 | 1.946(3) |
| C6—C1—C2 | 121.5(5) | N4—N3—C8 | 126.7(4) |
| C7—C1—C2 | 122.7(4) | N4—N3—C9 | 126.7(4) |
| C7—C1—C6 | 115.8(5) | N3—N4—C7 | 112.7(4) |
| C3—C2—C1 | 114.6(4) | Cu1ii—N4—C7 | 119.7(3) |
| O1—C2—C1 | 126.3(4) | Cu1ii—N4—N3 | 122.2(3) |
| O1—C2—C3 | 119.1(4) | Cu1—O1—C2 | 125.6(3) |
| C4—C3—C2 | 123.6(5) | N2iii—Cu1—N2iv | 180.0 |
| Cl1—C3—C2 | 117.3(4) | N4—Cu1—N2iv | 93.85(15) |
| Cl1—C3—C4 | 119.1(4) | N4—Cu1—N2iii | 86.15(15) |
| C5—C4—C3 | 119.3(5) | N4ii—Cu1—N2iv | 86.15(15) |
| C6—C5—C4 | 120.5(5) | N4ii—Cu1—N2iii | 93.85(15) |
| Cl2—C5—C4 | 118.7(4) | N4ii—Cu1—N4 | 180.0 |
| Cl2—C5—C6 | 120.7(5) | O1ii—Cu1—N2iii | 91.08(14) |
| C5—C6—C1 | 120.2(5) | O1—Cu1—N2iv | 91.08(14) |
| N4—C7—C1 | 125.0(5) | O1—Cu1—N2iii | 88.92(14) |
| N3—C8—N2 | 109.1(4) | O1ii—Cu1—N2iv | 88.92(14) |
| N3—C9—N1 | 109.6(5) | O1ii—Cu1—N4ii | 82.06(13) |
| N2—N1—C9 | 107.5(4) | O1—Cu1—N4ii | 97.94(13) |
| N1—N2—C8 | 107.6(4) | O1ii—Cu1—N4 | 97.94(13) |
| Cu1i—N2—C8 | 128.3(4) | O1—Cu1—N4 | 82.06(13) |
| Cu1i—N2—N1 | 124.0(3) | O1ii—Cu1—O1 | 180.0 |
| C9—N3—C8 | 106.2(4) |
Symmetry codes:(i)-x+2,y-1/2,-z+3/2；(ii)-x+2,-y+1,-z+1；(iii)x,-y+1/2,
z-1/2；(iv)-x+2,y+1/2,-z+3/2.
Described [Cu (tidc)2]nSynthetic method concretely comprise the following steps:
(1) by analytically pure for 1.91g 3,5-dichloro-salicylaldehyde and 0.841g analytically pure 4-amino-1,2,4-triazoles,
It is dissolved in 30mL analytical pure ethanol solution, after being heated to reflux and stirring two hours, has solid to separate out, filter, use 10mL analytical pure
Washing with alcohol three times, is dried at placing 50 DEG C, obtains part Htidc.By dried for 0.056-0.112g Htidc and 0.040-
0.080g analytical pure copper acetate dihydrate is dissolved in 5mL analytical pure N, in N '-dimethyl Methanamide, is placed in micro-reaction bulb, then adds
Enter 5mL distilled water, in 90 DEG C of baking ovens, stand five days, have red crystals to generate i.e. [Cu (tidc)2]n.Surveyed by single crystal diffractometer
Fixed [Cu (tidc)2]nStructure, crystal structural data is shown in Table one, and bond distance's bond angle data are shown in Table two.
(2) step (1) gained-[Cu (tidc) is taken2]n-it is dissolved in analytical pure N, N '-dimethyl formamide solvent is made into dense
Degree is 5.0 × 10-6The solution of mol/L, carries out fluorometric investigation ,-[Cu (tidc)2]n-produce under the incident illumination of 450nm irradiates
The fluorescence of the 522nm of 376.5a.u. intensity；Under the photomultiplier tube of 800V, the amplification coefficient of 3 times, take that 100 μ L are above-mentioned to be prepared
Solution be placed in 1mol/L potassium persulfate solution (conducting medium), create the luminescence of 2830a.u. intensity, and in this condition
Under, can continue and stabilized illumination.
The present invention has that technique is simple, with low cost, chemical constituent is easily controllable, reproducible and yield advantages of higher.
Accompanying drawing explanation
Fig. 1 is the present invention [Cu (tidc)2]nStructure chart.
Fig. 2 is the present invention [Cu (tidc)2]n2 d plane picture.
Fig. 3 is the present invention [Cu (tidc)2]nTomograph.
Fig. 4 is the present invention [Cu (tidc)2]nFluorescence spectrum figure.
Fig. 5 is the present invention [Cu (tidc)2]nElectrochemiluminescence spectrogram.
Detailed description of the invention
Embodiment 1:
[the Cu (tidc) that the present invention relates to2]nMolecular formula be: C18H10CuCl4N8O2, molecular weight is: 575.69g/mol,
Htidc is 3,5-dichloro-salicylaldehyde contracting 4-amino-1,2,4 triazole schiff bases, and crystal structural data is shown in Table one, bond distance's bond angle number
According to being shown in Table two.
[Cu(tidc)2]nSynthetic method concretely comprise the following steps:
(1) by analytically pure for 1.91g 3,5-dichloro-salicylaldehyde and 0.841g analytically pure 4-amino-1,2,4-triazoles,
It is dissolved in 30mL analytical pure ethanol solution, after being heated to reflux and stirring two hours, has solid to separate out, filter, use 10mL analytical pure
Washing with alcohol three times, is dried at placing 50 DEG C, obtains part Htidc.Yield: 2.641g, productivity 96%.0.056g is dried
Htidc and 0.040g analytical pure copper acetate dihydrate be dissolved in 5mL analytical pure N, in N '-dimethyl Methanamide, be placed in 25mL micro-
In reaction bulb, add 5mL distilled water, in 90 DEG C of baking ovens, stand five days, have red crystals to generate i.e.-[Cu (tidc)2]n-。
Yield: 0.047g, productivity 52.4%.By single crystal diffractometer mensuration-[Cu (tidc)2]n-structure, crystal structural data is shown in Table
One, bond distance's bond angle data are shown in Table two.
(2) step (1) gained [Cu (tidc) is taken2]nIt is dissolved in analytical pure N, in N '-dimethyl Methanamide (analytical pure) solvent
Being made into concentration is 5.0 × 10-5The solution of mol/L, carries out fluorometric investigation, [Cu (tidc)2]nUnder the incident illumination of 450nm irradiates
Produce the fluorescence of the 522nm of 376.5a.u. intensity；Under the photomultiplier tube of 800V, the amplification coefficient of 3 times, take 100 μ L above-mentioned
The solution prepared is placed in 1mol/L potassium persulfate solution (conducting medium), creates the luminescence of 2830a.u. intensity, and at this
Under the conditions of, can continue and stabilized illumination.
Embodiment 2:
[the Cu (tidc) that the present invention relates to2]nMolecular formula be: C18H10CuCl4N8O2, molecular weight is: 575.69g/mol,
Htidc is 3,5-dichloro-salicylaldehyde contracting 4-amino-1,2,4 triazole schiff bases, and crystal structural data is shown in Table one, bond distance's bond angle number
According to being shown in Table two.
[Cu(tidc)2]nSynthetic method concretely comprise the following steps:
(1) by analytically pure for 1.91g 3,5-dichloro-salicylaldehyde and 0.841g analytically pure 4-amino-1,2,4-triazoles,
It is dissolved in 30mL analytical pure ethanol solution, after being heated to reflux and stirring two hours, has solid to separate out, filter, use 10mL analytical pure
Washing with alcohol three times, is dried at placing 50 DEG C, obtains part Htidc.Yield: 2.641g, productivity 96%.0.112g is dried
Htidc and 0.080g analytical pure copper acetate dihydrate be dissolved in 10mL analytical pure N, in N '-dimethyl Methanamide, be placed in 25mL micro-
In reaction bulb, add 10mL distilled water, in 90 DEG C of baking ovens, stand five days, have red crystals to generate i.e. [Cu (tidc)2]n.Produce
Amount: 0.094g, productivity 52.4%.[Cu (tidc) is measured by single crystal diffractometer2]nStructure, crystal structural data is shown in Table one,
Bond distance's bond angle data are shown in Table two.
(2) step (1) gained [Cu (tidc) is taken2]nIt is dissolved in analytical pure N, in N '-dimethyl Methanamide (analytical pure) solvent
Being made into concentration is 5.0 × 10-5The solution of mol/L, carries out fluorometric investigation, [Cu (tidc)2]nUnder the incident illumination of 450nm irradiates
Produce the fluorescence of the 522nm of 376.5a.u. intensity；Under the photomultiplier tube of 800V, the amplification coefficient of 3 times, take 100 μ L above-mentioned
The solution prepared is placed in 1mol/L potassium persulfate solution (conducting medium), creates the luminescence of 2830a.u. intensity, and at this
Under the conditions of, can continue and stabilized illumination.
Claims (1)
1. a fluorescent material [Cu (tidc)2]n, it is characterised in that [Cu (tidc)2]nMonomer molecule formula be:
C18H10CuCl4N8O2, molecular weight is: 575.69g/mol, Htidc are 3,5-dichloro-salicylaldehyde contracting 4-amino-1,2,4 triazoles
Schiff bases, crystal structural data is shown in Table one, and bond distance's bond angle data are shown in Table two；[Cu(tidc)2]nUnder the incident illumination of 450nm irradiates
Produce the fluorescence of the 522nm of 376.5a.u. intensity, under the photomultiplier tube of 800V, the amplification coefficient of 3 times, at conducting medium
In potassium persulfate solution, produce 2830a.u. intensity and stable luminescence；
Table one: [Cu (tidc)2]nCrystallographic parameter
aR1=Σ | | Fo|–|Fc||/Σ|Fo|.b wR2=[Σ w (| Fo 2|–|Fc 2|)2/Σw(|Fo 2|)2]1/2
Table two: the bond distance of [Cu (tidc) 2] nWith bond angle °
Symmetry codes:(i)-x+2,y-1/2,-z+3/2；(ii)-x+2,-y+1,-z+1；(iii)x,-y+1/2,z-1/
2；(iv)-x+2,y+1/2,-z+3/2.
Described [Cu (tidc)2]nSynthetic method concretely comprise the following steps:
By analytically pure for 1.91g 3,5-dichloro-salicylaldehyde and 0.841g analytically pure 4-amino-1,2,4-triazoles, it is dissolved in 30mL
In analytical pure ethanol solution, after being heated to reflux and stirring two hours, there is solid to separate out, filter, by 10mL analytical pure washing with alcohol
Three times, it is dried at placing 50 DEG C, obtains part Htidc；Dried for 0.056-0.112g Htidc and 0.040-0.080g is divided
Analyse single hydrated copper acetate and be dissolved in 5mL analytical pure N, in N '-dimethyl Methanamide, be placed in micro-reaction bulb, add 5mL distillation
Water, stands five days in 90 DEG C of baking ovens, has red crystals to generate i.e. [Cu (tidc)2]n。
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| Application Number | Priority Date | Filing Date | Title |
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| CN201610171268.0A CN105713020A (en) | 2016-03-23 | 2016-03-23 | Fluorescent material [Cu(tidc)2]n and synthesis method |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610171268.0A CN105713020A (en) | 2016-03-23 | 2016-03-23 | Fluorescent material [Cu(tidc)2]n and synthesis method |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201610171268.0A Pending CN105713020A (en) | 2016-03-23 | 2016-03-23 | Fluorescent material [Cu(tidc)2]n and synthesis method |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103265565A (en) * | 2013-05-31 | 2013-08-28 | 桂林理工大学 | In-situ synthesis method of 3,5-dibromo-salicylic acid azine bis-Schiff base copper complexes |
-
2016
- 2016-03-23 CN CN201610171268.0A patent/CN105713020A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103265565A (en) * | 2013-05-31 | 2013-08-28 | 桂林理工大学 | In-situ synthesis method of 3,5-dibromo-salicylic acid azine bis-Schiff base copper complexes |
Non-Patent Citations (3)
| Title |
|---|
| REDDY, VIDYAVATI ET AL: "Synthesis and characterization of Cu(II), Co(II),Ni(II) complexes with Schiff bases derived from 3-(4-chlorophenoxymethyl)-4-amino-5-mercapto-1,2,4-triazole", 《ORIENTAL JOURNAL OF CHEMISTRY》 * |
| 王长凤: "4-氨基-3,5-二甲基-1,2,4-三唑水杨亚胺铜（II）配合物合成及其单晶结构", 《结构化学》 * |
| 马玲: "三唑席夫碱、"有机爪"四羧酸铜配合物抑制PTPs研究", 《中国博士学位论文全文数据库工程科技I辑》 * |
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Application publication date: 20160629 |