CN105693637A - Luminescent material [Cu(tibc)2]n and synthetic method - Google Patents
Luminescent material [Cu(tibc)2]n and synthetic method Download PDFInfo
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- CN105693637A CN105693637A CN201610171246.4A CN201610171246A CN105693637A CN 105693637 A CN105693637 A CN 105693637A CN 201610171246 A CN201610171246 A CN 201610171246A CN 105693637 A CN105693637 A CN 105693637A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
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- 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 fluorescent material [Cu(tibc)2]n and a synthetic method. The molecular formula of a monomer is C18H10CuBr4N8O2; a molecular weight is 797.70g/mol; Htibc is 3,5-dichlorosalicylidene-4-amino-1,2,4-triazole schiff base. Analytically pure 3,5-dibromosalicylaldehyde and analytically pure 4-amino-1,2,4-triazole are dissolved in analytically pure ethanol; an obtained first mixture is heated, refluxed and dried to obtain the ligand Htibc. The dried Htibc and analytically pure copper acetate are dissolved in analytically pure N,N'-dimethyl formamide; afterwards, distilled water is added into an obtained second mixture; an obtained third mixture is stood for three days in a drying oven at 80 DEG C. The [Cu(tibc)2]n generates 520nm fluorescent light with intensity of 193.7a.u. (astronomical unit) when being irradiated by 450nm incident light, and under an 800V photomultiplier and a 3 times of amplification coefficient, generates emergent light which has intensity of 2750a.u. and is further stable in a 1mol/L of potassium peroxodisulfate solution. The fluorescent material [Cu(tibc)2]n and the synthetic method are simple in process, low in cost, easy in the control of chemical components, good in repeatability and further high in yield.
Description
Technical field
The present invention relates to a kind of stable luminescent material [Cu (tibc)2]n, (Htibc is 3,5-Dibromosalicylaldehyde contracting 4-amino-1,2,4 triazole schiff bases) and synthetic method。
Background technology
The development of many decades gone through by modern luminescent material, oneself become information show, the backing material in the field such as lighting source, photoelectric device, play the effect become more and more important for social development and technological progress。Particularly energy scarcity is present, and the luminescent material that exploitation transformation efficiency is high 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 luminosity excellence, utilizes micro-bottle of reaction method synthesis [Cu (tibc)2]n。
[the Cu (tibc) that the present invention relates to2]nMonomer molecule formula be: C18H10CuBr4N8O2, molecular weight is: 797.70g/mol, Htibc are 3,5-Dibromosalicylaldehyde contracting 4-amino-1, and 2,4 triazole schiff bases, crystal structural data is in Table one, and bond distance's bond angle data are in Table two。
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: [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) |
Symmetrycodes:(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.
Described [Cu (tibc)2]nSynthetic method concretely comprise the following steps:
(1) by analytically pure for 2.79g 3,5-Dibromosalicylaldehyde and the analytically pure 4-amino-1 of 0.841g, 2,4-triazole, is dissolved in 30mL analytical pure alcoholic solution, is heated to reflux and has solid to precipitate out after stirring two hours, filter, by 10mL analytical pure washing with alcohol three times, dry at placing 50 DEG C, obtain part Htibc。Dried for 0.069-0.138g Htibc and 0.040-0.080g analytical pure copper acetate is dissolved in 5mL analytical pure N, in N '-dimethyl Methanamide, it is placed in micro-reaction bulb, adds 5mL distilled water, 80 DEG C of baking ovens stand three days, has red crystals to generate i.e. [Cu (tibc)2]n。[Cu (tibc) is measured by single crystal diffractometer2]nStructure, crystal structural data is in Table one, and bond distance's bond angle data are in Table two。
(2) step (1) gained [Cu (tibc) is taken2]nBeing dissolved in analytical pure N, being made into concentration in N '-dimethyl formamide solvent is 5.0 × 10-6The solution of mol/L, carries out fluorometric investigation ,-[Cu (tibc)2]n-under the incident illumination of 450nm irradiates, produce the fluorescence of 520nm of 193.7a.u. intensity；Under the photomultiplier tube of 800V, the amplification coefficient of 3 times, take the 100 above-mentioned solution prepared of μ L and be placed in 1mol/L potassium persulfate solution (conducting medium), create the luminescence of 2750a.u. intensity, and with this understanding, 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 (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 spectrum figure。
Fig. 5 is the present invention [Cu (tibc)2]nElectrochemiluminescence spectrogram。
Detailed description of the invention
Embodiment 1:
[the Cu (tibc) that the present invention relates to2]nMolecular formula be: C18H10CuBr4N8O2, molecular weight is: 797.70g/mol, Htibc are 3,5-Dibromosalicylaldehyde contracting 4-amino-1, and 2,4 triazole schiff bases, crystal structural data is in Table one, and bond distance's bond angle data are in Table two。
[Cu(tibc)2]nSynthetic method concretely comprise the following steps:
(1) by analytically pure for 2.79g 3,5-Dibromosalicylaldehyde and the analytically pure 4-amino-1 of 0.841g, 2,4-triazole, is dissolved in 30mL analytical pure alcoholic solution, is heated to reflux and has solid to precipitate out after stirring two hours, filter, by 10mL analytical pure washing with alcohol three times, dry at placing 50 DEG C, obtain part Htibc。Yield: 3.214g, productivity 94%。Dried for 0.069g Htibc and 0.040g analytical pure copper acetate is dissolved in 5mL analytical pure N, in N '-dimethyl Methanamide, it is placed in micro-reaction bulb, adds 5mL distilled water, 80 DEG C of baking ovens stand three days, has red crystals to generate i.e. [Cu (tibc)2]n。Yield: 0.039g, productivity 43%。[Cu (tibc) is measured by single crystal diffractometer2]nStructure, crystal structural data is in Table one, and bond distance's bond angle data are in Table two。
(2) step (1) gained [Cu (tibc) is taken2]nBeing dissolved in analytical pure N, being made into concentration in N '-dimethyl formamide solvent is 5.0 × 10-5The solution of mol/L, carries out fluorometric investigation, [Cu (tibc)2]nThe fluorescence of the 520nm of 193.7a.u. intensity is produced under the incident illumination of 450nm irradiates；Under the photomultiplier tube of 800V, the amplification coefficient of 3 times, take the 100 above-mentioned solution prepared of μ L and be placed in 1mol/L potassium persulfate solution (conducting medium), create the luminescence of 2750a.u. intensity, and with this understanding, can continue and stabilized illumination。
Embodiment 2:
[the Cu (tibc) that the present invention relates to2]nMolecular formula be: C18H10CuBr4N8O2, molecular weight is: 797.70g/mol, Htibc are 3,5-Dibromosalicylaldehyde contracting 4-amino-1, and 2,4 triazole schiff bases, crystal structural data is in Table one, and bond distance's bond angle data are in Table two。
[Cu(tibc)2]nSynthetic method concretely comprise the following steps:
(1) by analytically pure for 2.79g 3,5-Dibromosalicylaldehyde and the analytically pure 4-amino-1 of 0.841g, 2,4-triazole, is dissolved in 30mL analytical pure alcoholic solution, is heated to reflux and has solid to precipitate out after stirring two hours, filter, by 10mL analytical pure washing with alcohol three times, dry at placing 50 DEG C, obtain part Htibc。Yield: 3.214g, productivity 94%。Dried for 0.138g Htibc and 0.080g analytical pure copper acetate is dissolved in 5mL analytical pure N, in N '-dimethyl Methanamide, it is placed in micro-reaction bulb, adds 5mL distilled water, 80 DEG C of baking ovens stand three days, has red crystals to generate i.e. [Cu (tibc)2]n。Yield: 0.078g, productivity 43%。By single crystal diffractometer mensuration-[Cu (tibc)2]n-structure, crystal structural data is in Table one, and bond distance's bond angle data are in Table two。
(2) step (1) gained [Cu (tibc) is taken2]nBeing dissolved in analytical pure N, being made into concentration in N '-dimethyl formamide solvent is 5.0 × 10-5The solution of mol/L, carries out fluorometric investigation, [Cu (tibc)2]nThe fluorescence of the 520nm of 193.7a.u. intensity is produced under the incident illumination of 450nm irradiates；Under the photomultiplier tube of 800V, the amplification coefficient of 3 times, take the 100 above-mentioned solution prepared of μ L and be placed in 1mol/L potassium persulfate solution (conducting medium), create the luminescence of 2750a.u. intensity, and with this understanding, can continue and stabilized illumination。
Claims (1)
1. a luminescent material [Cu (tibc)2]n, it is characterised in that [Cu (tibc)2]nMonomer molecule formula be: C18H10CuBr4N8O2, molecular weight is: 797.70g/mol, Htibc are 3,5-Dibromosalicylaldehyde contracting 4-amino-1, and 2,4 triazole schiff bases, crystal structural data is in Table one, and bond distance's bond angle data are in Table two；The fluorescence of the 520nm of 193.7a.u. intensity is produced under the incident illumination of 450nm irradiates；Under the photomultiplier tube of 800V, the amplification coefficient of 3 times, in conducting medium 1mol/L potassium persulfate solution, produce 2750a.u. intensity and stable luminescence；
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 °
Symmetrycodes:(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.
Described [Cu (tibc)2]nSynthetic method concretely comprise the following steps:
By analytically pure for 2.79g 3,5-Dibromosalicylaldehyde and the analytically pure 4-amino-1 of 0.841g, 2,4-triazole, is dissolved in 30mL analytical pure alcoholic solution, is heated to reflux and has solid to precipitate out after stirring two hours, filter, by 10mL analytical pure washing with alcohol three times, dry at placing 50 DEG C, obtain part Htibc；Dried for 0.069-0.138g Htibc and 0.040-0.080g analytical pure copper acetate is dissolved in 5mL analytical pure N, in N '-dimethyl Methanamide, it is placed in micro-reaction bulb, adds 5mL distilled water, 80 DEG C of baking ovens stand three days, has red crystals to generate i.e. [Cu (tibc)2]n。
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| 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 |
| CN111992185A (en) * | 2020-09-21 | 2020-11-27 | 桂林理工大学 | Cu-MOF, modified adsorption material thereof and preparation method |
-
2016
- 2016-03-23 CN CN201610171246.4A patent/CN105693637B/en not_active Expired - Fee Related
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| 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 |
| CN111992185A (en) * | 2020-09-21 | 2020-11-27 | 桂林理工大学 | Cu-MOF, modified adsorption material thereof and preparation 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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