CN105693637B - Luminescent material [Cu (tibc)2]nAnd synthetic method - Google Patents
Luminescent material [Cu (tibc)2]nAnd synthetic method Download PDFInfo
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- CN105693637B CN105693637B CN201610171246.4A CN201610171246A CN105693637B CN 105693637 B CN105693637 B CN 105693637B CN 201610171246 A CN201610171246 A CN 201610171246A CN 105693637 B CN105693637 B CN 105693637B
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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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Abstract
The invention discloses a kind of fluorescent material [Cu (tibc)2]nAnd synthetic method.Monomer molecule formula is：C18H10CuBr4N8O2, molecular weight is：797.70g/mol, Htibc are 3,5 dichloro-salicylaldehydes contracting 4 amino, 1,2,4 triazole schiff bases.It will analyze pure 3, and 5 Dibromosalicylaldehydes and analyze pure 4 amino, 1,2,4 triazole, and be dissolved in analysis straight alcohol, be heated to reflux, it is dry, obtain ligand Htibc.Htibc after drying is dissolved in the pure copper acetate of analysis and analyzes pure N, in N ' dimethylformamides, distilled water is added, three days is stood in 80 DEG C of baking ovens.[Cu(tibc)2]nThe fluorescence of the 520nm of 193.7a.u. intensity is generated under the incident light irradiation of 450nm；Under the photomultiplier of 800V, 3 times of amplification coefficient, in 1mol/L potassium persulfate solutions, shining for 2750a.u. intensity and stabilization is produced.Present invention process is simple, of low cost, chemical constituent is easily controllable, reproducible and yield is high.
Description
Technical field
The present invention relates to a kind of luminescent material of stabilization [Cu (tibc)2]n, (Htibc is bis- bromo- 6- (1,2,4)-three of 2,4-
Nitrogen azoles -4- formaminos phenol) and synthetic method.
Background technology
Development of the modern luminescent material after many decades, oneself becomes the fields such as presentation of information, lighting source, photoelectric device
Backing material plays the effect to become more and more important for social development and technological progress.Especially now, there is a energy deficiency exploitation turns
It is to solve one of energy deficiency method to change efficient luminescent material.
Invention content
The purpose of the present invention is exactly to synthesize the excellent functional material of luminosity for design, and micro- bottle of reaction method is utilized to synthesize
[Cu(tibc)2]n。
[Cu (tibc) of the present invention2]nMonomer molecule formula be：C18H10CuBr4N8O2, relative molecular weight is：
Bis- bromo- 6- (1,2,4) of 753.5, Htibc 2,4--triazole -4- formamino phenol, crystal structural data are shown in Table one, bond distance
Bond angle data are shown in Table two.
Table one:[Cu(tibc)2]nCrystallographic parameter
a R1=Σ | | Fo|–|Fc||/Σ|Fo|.b wR2=[Σ w (| Fo 2|–|Fc 2|)2/Σw(|Fo 2|)2]1/2
Table two:[Cu(tibc)2]nBond distanceWith bond angle °
| Br4—C12 | 1.894(9) | N9—C0AA | 1.288(11) |
| Br8—C6 | 1.898(10) | N11—C2 | 1.297(11) |
| Cu9—O3 | 1.939(5) | N19—Cu9iv | 2.385(7) |
| Cu9—O3i | 1.939(5) | N19—C21 | 1.253(12) |
| Cu9—N11i | 2.048(7) | C21—C2AAv | 1.469(12) |
| Cu9—N11 | 2.048(7) | C2AA—C21ii | 1.469(12) |
| Cu9—N19ii | 2.385(7) | C2AA—C1AA | 1.396(13) |
| Cu9—N19iii | 2.385(7) | C2AA—C18 | 1.421(13) |
| O3—C18 | 1.284(10) | C6—C1AA | 1.379(14) |
| N7—N19 | 1.415(9) | C6—C20 | 1.369(15) |
| N7—C2 | 1.335(11) | C12—C18 | 1.422(11) |
| N7—C0AA | 1.350(11) | C12—C20 | 1.351(13) |
| N9—N11 | 1.368(10) | ||
| O3—Cu9—O3i | 180.0 | C2—N11—N9 | 108.1(7) |
| O3i—Cu9—N11i | 89.3(3) | N7—N19—Cu9iv | 122.4(5) |
| O3i—Cu9—N11 | 90.7(3) | C21—N19—Cu9iv | 119.3(6) |
| O3—Cu9—N11i | 90.7(3) | C21—N19—N7 | 112.5(7) |
| O3—Cu9—N11 | 89.3(3) | N19—C21—C2AAv | 125.3(8) |
| O3—Cu9—N19iii | 99.3(2) | N11—C2—N7 | 109.5(8) |
| O3i—Cu9—N19ii | 99.3(2) | N9—C0AA—N7 | 110.6(8) |
| O3i—Cu9—N19iii | 80.7(2) | C1AA—C2AA—C21ii | 115.7(8) |
| O3—Cu9—N19ii | 80.7(2) | C1AA—C2AA—C18 | 122.3(8) |
| N11i—Cu9—N11 | 180.0(2) | C18—C2AA—C21ii | 122.1(8) |
| N11—Cu9—N19ii | 85.6(3) | C1AA—C6—Br8 | 119.9(8) |
| N11—Cu9—N19iii | 94.4(3) | C20—C6—Br8 | 119.2(8) |
| N11i—Cu9—N19iii | 85.6(3) | C20—C6—C1AA | 120.6(9) |
| N11i—Cu9—N19ii | 94.4(3) | C6—C1AA—C2AA | 119.2(9) |
| N19iii—Cu9—N19ii | 180.0 | C18—C12—Br4 | 116.9(6) |
| C18—O3—Cu9 | 126.0(5) | C20—C12—Br4 | 119.0(7) |
| C2—N7—N19 | 127.5(7) | C20—C12—C18 | 124.1(8) |
| C2—N7—C0AA | 105.3(7) | O3—C18—C2AA | 125.5(7) |
| C0AA—N7—N19 | 126.8(7) | O3—C18—C12 | 120.7(8) |
| C0AA—N9—N11 | 106.4(7) | C2AA—C18—C12 | 113.8(8) |
| N9—N11—Cu9 | 123.2(5) | C12—C20—C6 | 119.8(9) |
| C2—N11—Cu9 | 128.5(6) |
To this operation:(i)-x,-y+1,-z；(ii)x,-y+1/2,z-1/2；(iii)-x,y+1/2,-z+1/2；(iv)-
x,y-1/2,-z+1/2；(v)x,-y+1/2,z+1/2.
[the Cu (tibc)2]nSynthetic method the specific steps are：
(1) by analytically pure 3, the 5- Dibromosalicylaldehydes of 2.79g and the analytically pure 4- amino -1,2 of 0.841g, 4- triazoles,
It is dissolved in 30mL analysis straight alcohol solution, is heated to reflux and has solid precipitation after stirring two hours, filter, analyzed with 10mL pure
Ethyl alcohol washs three times, places drying at 50 DEG C, obtains ligand Htibc.Htibc after 0.069-0.138g is dried and
0.040-0.080g, which analyzes pure copper acetate and is dissolved in 5mL, analyzes pure N, in N '-dimethyl formamide, is placed in micro- reaction bulb, then add
Enter 5mL distilled water, three days are stood in 80 DEG C of baking ovens, there are red crystals to generate i.e. [Cu (tibc)2]n.It is surveyed by single crystal diffractometer
Fixed [Cu (tibc)2]nStructure, crystal structural data is shown in Table one, and bond distance's bond angle data are shown in Table two.
(2) [Cu (tibc) obtained by step (1) is taken2]nIt is dissolved in the pure N of analysis, concentration is made into N '-dimethyl formamide solvent
It is 5.0 × 10-6The solution of mol/L carries out fluorometric investigation ,-[Cu (tibc)2]nIt is generated under the incident light irradiation of 450nm
The fluorescence of the 520nm of 193.7a.u. intensity；Under the photomultiplier of 800V, 3 times of amplification coefficient, take 100 μ L are above-mentioned to prepare
Solution be placed in 1mol/L potassium persulfate solutions (conducting medium), shining for 2750a.u. intensity is produced, and in this condition
Under, it can continue and stabilized illumination.
The present invention has many advantages, such as that simple for process, of low cost, chemical constituent is easily controllable, reproducible and yield is high.
Description of the drawings
Fig. 1 is the present invention [Cu (tibc)2]nStructure chart.
Fig. 2 is the present invention [Cu (tibc)2]n2 d plane picture.
Fig. 3 is the present invention [Cu (tibc)2]nTomograph.
Fig. 4 is the present invention [Cu (tibc)2]nFluorescence spectra.
Fig. 5 is the present invention [Cu (tibc)2]nElectrochemical luminescence spectrogram.
Specific implementation mode
Embodiment 1：
[Cu (tibc) of the present invention2]nMolecular formula be：C18H10CuBr4N8O2, relative molecular weight is： 753.5,
Htibc is 2,4-, bis- bromo- 6- (1,2,4)-triazole -4- formamino phenol, and crystal structural data is shown in Table one, bond distance's bond angle
Data are shown in Table two.
[Cu(tibc)2]nSynthetic method the specific steps are：
(1) by analytically pure 3, the 5- Dibromosalicylaldehydes of 2.79g and the analytically pure 4- amino -1,2 of 0.841g, 4- triazoles,
It is dissolved in 30mL analysis straight alcohol solution, is heated to reflux and has solid precipitation after stirring two hours, filter, analyzed with 10mL pure
Ethyl alcohol washs three times, places drying at 50 DEG C, obtains ligand Htibc.Yield：3.214g yield 94%.0.069g is dried
Rear Htibc and 0.040g, which analyzes pure copper acetate and is dissolved in 5mL, analyzes pure N, in N '-dimethyl formamide, is placed in micro- reaction bulb
In, 5mL distilled water is added, three days are stood in 80 DEG C of baking ovens, there are red crystals to generate i.e. [Cu (tibc)2]n.Yield：
0.039g, yield 43%.[Cu (tibc) is measured by single crystal diffractometer2]nStructure, crystal structural data is shown in Table one, Jian Changjian
Angular data is shown in Table two.
(2) [Cu (tibc) obtained by step (1) is taken2]nIt is dissolved in the pure N of analysis, concentration is made into N '-dimethyl formamide solvent
It is 5.0 × 10-5The solution of mol/L carries out fluorometric investigation, [Cu (tibc)2]nIt is generated under the incident light irradiation of 450nm
The fluorescence of the 520nm of 193.7a.u. intensity；Under the photomultiplier of 800V, 3 times of amplification coefficient, take 100 μ L are above-mentioned to prepare
Solution be placed in 1mol/L potassium persulfate solutions (conducting medium), shining for 2750a.u. intensity is produced, and in this condition
Under, it can continue and stabilized illumination.
Embodiment 2：
[Cu (tibc) of the present invention2]nMolecular formula be：C18H10CuBr4N8O2, relative molecular weight is： 753.5,
Htibc is 2,4-, bis- bromo- 6- (1,2,4)-triazole -4- formamino phenol, and crystal structural data is shown in Table one, bond distance's bond angle
Data are shown in Table two.
[Cu(tibc)2]nSynthetic method the specific steps are：
(1) by analytically pure 3, the 5- Dibromosalicylaldehydes of 2.79g and the analytically pure 4- amino -1,2 of 0.841g, 4- triazoles,
It is dissolved in 30mL analysis straight alcohol solution, is heated to reflux and has solid precipitation after stirring two hours, filter, analyzed with 10mL pure
Ethyl alcohol washs three times, places drying at 50 DEG C, obtains ligand Htibc.Yield：3.214g yield 94%.0.138g is dried
Rear Htibc and 0.080g, which analyzes pure copper acetate and is dissolved in 5mL, analyzes pure N, in N '-dimethyl formamide, is placed in micro- reaction bulb
In, 5mL distilled water is added, three days are stood in 80 DEG C of baking ovens, there are red crystals to generate i.e. [Cu (tibc)2]n.Yield：
0.078g, yield 43%.Pass through single crystal diffractometer measurement-[Cu (tibc)2]nStructure, crystal structural data is shown in Table one, bond distance
Bond angle data are shown in Table two.
(2) [Cu (tibc) obtained by step (1) is taken2]nIt is dissolved in the pure N of analysis, concentration is made into N '-dimethyl formamide solvent
It is 5.0 × 10-5The solution of mol/L carries out fluorometric investigation, [Cu (tibc)2]nIt is generated under the incident light irradiation of 450nm
The fluorescence of the 520nm of 193.7a.u. intensity；Under the photomultiplier of 800V, 3 times of amplification coefficient, take 100 μ L are above-mentioned to prepare
Solution be placed in 1mol/L potassium persulfate solutions (conducting medium), shining for 2750a.u. intensity is produced, and in this condition
Under, it can continue and stabilized illumination.
Claims (1)
1. a kind of luminescent material [Cu (tibc)2]n, it is characterised in that [Cu (tibc)2]nMonomer molecule formula be：
C18H10CuBr4N8O2, relative molecular weight is：753.5, Htibc be bis- bromo- 6- (1,2,4) of 2,4--triazole -4- formaminos
Phenol, crystal structural data are shown in Table one, and bond distance's bond angle data are shown in Table two；193.7a.u. is generated under the incident light irradiation of 450nm
The fluorescence of the 520nm of intensity；Under the photomultiplier of 800V, 3 times of amplification coefficient, in conducting medium 1mol/L potassium peroxydisulfates
In solution, shining for 2750a.u. intensity and stabilization is generated；
Table one:[Cu(tibc)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 (tibc) 2] nWith bond angle °
Symmetry operation:(i)-x,-y+1,-z；(ii)x,-y+1/2,z-1/2；(iii)-x,y+1/2,-z+1/2；(iv)-x,y-
1/2,-z+1/2；(v)x,-y+1/2,z+1/2；
[the Cu (tibc)2]nSynthetic method the specific steps are：
By analytically pure 3, the 5- Dibromosalicylaldehydes of 2.79g and the analytically pure 4- amino -1,2 of 0.841g, 4- triazoles are dissolved in 30mL
It analyzes in straight alcohol solution, is heated to reflux and has solid precipitation after stirring two hours, filter, washed with 10mL analysis straight alcohols
Three times, drying at 50 DEG C is placed, ligand Htibc is obtained；Htibc and 0.040-0.080g points after 0.069-0.138g is dried
It analyses pure copper acetate and is dissolved in 5mL and analyze pure N, in N '-dimethyl formamide, be placed in micro- reaction bulb, add 5mL distilled water,
Three days are stood in 80 DEG C of baking ovens, there are red crystals to generate i.e. [Cu (tibc)2]n。
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106496251A (en) * | 2016-09-13 | 2017-03-15 | 桂林理工大学 | 3 ethoxy salicylaldehydes contracting 3 amino, 2 hydroxy acetophenone schiff bases mononuclear copper complex and synthetic method |
| CN106854216A (en) * | 2016-09-13 | 2017-06-16 | 桂林理工大学 | 3,5 Dibromosalicylaldehydes contracting the hydroxy acetophenone schiff bases copper complex of 3 amino 2 and synthetic method |
| CN106432285A (en) * | 2016-09-13 | 2017-02-22 | 桂林理工大学 | Mononuclear copper complex of 3,5-dichloro salicylaldehyde-3-amino-2-hydroxyacetophenone Schiff base and synthetic method |
| CN106397265A (en) * | 2016-09-13 | 2017-02-15 | 桂林理工大学 | Schiff base tetranuclear Co complex Co4(brah)4 as 2-hydroxyacetophenone derivative and synthetic method |
| CN111992185B (en) * | 2020-09-21 | 2022-04-29 | 桂林理工大学 | Cu-MOF, modified adsorption material thereof and preparation method |
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Effective date of registration: 20191107 Address after: 531105 floor 1-2, building 1, No.146, Wuhua Avenue, Guangxi ASEAN Economic and Technological Development Zone, Nanning City, Guangxi Zhuang Autonomous Region (excluding the top floor) Patentee after: Guangxi baolixing Lighting Technology Co., Ltd Address before: 541004 the Guangxi Zhuang Autonomous Region Guilin Construction Road No. 12 Patentee before: Guilin University of Technology |
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