CN104628747A - Green-fluorescence zinc N,N-bis(4-cyanophenyl) aminoacetate complex and preparation method thereof - Google Patents

Green-fluorescence zinc N,N-bis(4-cyanophenyl) aminoacetate complex and preparation method thereof Download PDF

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CN104628747A
CN104628747A CN201510047523.6A CN201510047523A CN104628747A CN 104628747 A CN104628747 A CN 104628747A CN 201510047523 A CN201510047523 A CN 201510047523A CN 104628747 A CN104628747 A CN 104628747A
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padil
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CN104628747B (en
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杨清香
陈志军
李�浩
王晓杰
赵倩倩
李银萍
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Zhengzhou University of Light Industry
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    • 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 System
    • C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic System without C-Metal linkages
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    • 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
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom

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  • Organic Chemistry (AREA)
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Abstract

The invention discloses a green-fluorescence zinc N,N-bis(4-cyanophenyl) aminoacetate complex and a preparation method thereof. The chemical formula of the complex is as follows: [Zn(L)2(bpe)(H2O)2]n, wherein L refers to an anionic ligand of N,N-bis(4-cyanophenyl) amino acetic acid, and bpe refers to 1,2-bis(4-pyridyl) ethane. The synthesis method of the complex is performed under a hydrothermal condition; the N,N-bis(4-cyanophenyl) amino acetic acid ligand, 1,2-bis(4-pyridyl) ethane and a metal zinc salt are dissolved in water to form a solution which is sealed in a reaction kettle; the solution is heated to a certain temperature at the rate of 10 DEG C per hour, and the temperature is maintained for 3 days and then reduced to the room temperature, and consequently, the green-fluorescence complex is obtained. The green-fluorescence complex has the advantages of good stability, simple preparation method, high yield and the like, and has potential application in the field of LED light-emitting materials as a novel light-emitting material.

Description

A kind of green fluorescence N, N-bis-(4-cyano-phenyl) Padil Zn complex and preparation method thereof
Technical field
The invention belongs to luminescent material preparing technical field, be specifically related to a kind of N, N-bis-(4-cyano-phenyl) Padil Zn complex and preparation method thereof.
Background technology
Luminescent material is widely used in all trades and professions of society, Chinese scholars are also constantly goed deep into for the exploration of novel luminescent material, the plurality of advantages such as rare earth luminous title complex photoluminescent band is narrow, purity of color is high, light absorpting ability is strong, fluorescence lifetime is long, process based prediction model is stable are the focuses that people study always.But the features such as rare earth mining difficulty is large, environmental pollution is serious, expensive, which limits rare earth large-scale application in the material, so the Sustainable development of complex luminescent material to society of the transition metal of exploitation excellent property has important social effect and economic worth.
Metal coordinating polymer, simultaneously containing inorganic metal and organic ligand, makes it have higher stability than pure organic ligand, moreover due to the coordination of metal, the emission wavelength of organic ligand will obviously be affected.Its luminescent properties can be regulated and controled by changing the approach such as metal ion, part, synthesis condition, and the material of the efficient green fluorescence obtained by transition metal zine ion or rarely found, thus can advanced luminescent material be obtained, in the field of LED luminescent material, there is potential application.
Summary of the invention
The object of this invention is to provide a kind of green fluorescence N, N-bis-(4-cyano-phenyl) Padil Zn complex and preparation method thereof, this complexes stability is good, preparation method is simple and productive rate is high.
For achieving the above object, the present invention is by the following technical solutions:
Green fluorescence N, N-bis-(4-cyano-phenyl) Padil Zn complex of the present invention, the chemical formula of described N, N-bis-(4-cyano-phenyl) Padil Zn complex is [Zn (L) 2(bpe) (H 2o) 2] n, wherein L=N, N-bis-(4-cyano-phenyl) Padil anion ligand, skeleton symbol is as follows:
Bpe=1, two (4-pyridyl) ethane of 2-, skeleton symbol is as follows:
。
Described N, N-bis-(4-cyano-phenyl) Padil Zn complex crystal belongs to oblique system, spacer is Cc, unit cell parameters is a=17.470 (5), b=13.697 (4), c=16.955 (5), α=90 °, β=95.962 (4) °, γ=90 °, V=4035 (2) 3.
Described title complex basic structure is an one dimensional network structure, the ligancy of center zinc atom is 6, respectively with from two N, two Sauerstoffatoms of N-bis-(4-cyano-phenyl) Padil, two nitrogen-atoms of two 1,2-two (4-pyridyl) ethane and two water molecule coordination; A Sauerstoffatom and zinc atom coordination in the carboxyl of N, N-bis-(4-cyano-phenyl) Padil part; In title complex, two (4-pyridyl) the ethane part of 1,2-connects zinc atom and forms one-dimensional chain structure; One-dimensional chain structure is interacted by hydrogen bond and pi-pi bond and forms three-dimensional net structure.
Green fluorescence N of the present invention, the preparation method of N-bis-(4-cyano-phenyl) Padil Zn complex, step is as follows: under the condition of hydro-thermal, by N, N-bis-(4-cyano-phenyl) Padil, 1,2-(4-pyridyl) ethane and zinc nitrate mixing solutions of making soluble in water are enclosed in reactor, 80 ~ 120 DEG C are heated to the speed of 10 DEG C/h, be incubated 3 days, then be naturally down to room temperature, light yellow bulk crystals can be obtained, yellow bulk crystals is separated, successively through washing, drying treatment, obtain target product.
In described mixing solutions, the concentration of N, N-bis-(4-cyano-phenyl) Padil is 0.005 ~ 0.01 mol L – 1.
In described mixing solutions, the concentration of 1,2-two (4-pyridyl) ethane is 0.005 ~ 0.01 mol L – 1.
In described mixing solutions, nitric acid zinc concentration is 0.01 ~ 0.02 mol L -1.
Beneficial effect of the present invention: N of the present invention, N-bis-(4-cyano-phenyl) Padil Zn complex is a kind of green fluorescence title complex, its structure is simple, send strong fluorescence at 502 nm places, have satisfactory stability, the materials'use life-span is long, preparation technology is simple, reaction times is short, and aftertreatment is easy, productive rate advantages of higher.A kind of new fluorescence luminescent material may be become, and for making the field such as fluorescence radiation device, biological tracking, Optochemical sensor, anti-counterfeit printing, in the field of LED luminescent material, there is potential application as advanced luminescent material.
figure of description
Fig. 1 is the coordination environment figure of Zn (II) in the N of embodiment 1, N-bis-(4-cyano-phenyl) Padil Zn complex.
Fig. 2 is the one-dimensional chain structure iron of the N of embodiment 1, N-bis-(4-cyano-phenyl) Padil Zn complex.
Fig. 3 is the three-dimensional accumulation graph of the N of embodiment 1, N-bis-(4-cyano-phenyl) Padil Zn complex.
Fig. 4 is the solid state fluorescence spectrogram of the N of embodiment 1, N-bis-(4-cyano-phenyl) Padil Zn complex.
Fig. 5 is the test of the powdery diffractometry (XPRD) of the N of embodiment 1, N-bis-(4-cyano-phenyl) Padil Zn complex and theoretical contrast figure.
Embodiment
The present invention is set forth further below in conjunction with concrete embodiment.
Embodiment 1
By N, N-bis-(4-cyano-phenyl) Padil (0.05 mmol, 14.0 mg), 1, two (4-pyridyl) ethane part (0.05 mmol of 2-, 9.0 mg) with zinc nitrate (0.15 mmol, 28.4mg) be dissolved in water (8 mL) stir 5 minutes after enclose in the hydrothermal reaction kettle of 25mL.Again reaction mixture is heated to 80 DEG C with 10 DEG C per hour, maintains this temperature 3 days, be then down to room temperature, can obtain colourless bulk crystals, separated by this monocrystalline, successively through washing, drying treatment, obtain target product, productive rate is about 45%.
The structure determination of the N of the present embodiment, N-bis-(4-cyano-phenyl) Padil Zn complex:
(1) crystal structure determination of title complex
The monocrystalline choosing suitable size under the microscope at room temperature carries out X – ray diffraction experiments.On Xcalibur, Eos, Gemini diffractometer, collect diffraction data by Mo – Ka ray (l=0.71073) through graphite monochromator monochromatization, Yi φ – ω mode.Reduction of data is carried out by CrysAlisPro, Agilent Technologies, Version 1.171.35.15 program.The diffraction data SADABS program of part-structure carries out absorption correction.Crystalline structure is solved in conjunction with difference Fourier synthesis by direct method.Whole non-hydrogen atom coordinate and anisotropic parameters carry out complete matrix least-squares refinement, and hydrogen atom position is determined by theoretical mode computation.The method process of difference Fourier peak-seeking of hydrogen atom on partial solvent water and methyl alcohol.Detailed axonometry data are in table 1.Crystalline structure is shown in Fig. 1, Fig. 2 and Fig. 3.
The predominant crystal data of table 1 title complex
(2) the solid fluorescence performance study of title complex
Complex crystal sample after enrichment process, through further milled processed, carries out the test of solid fluorescence: title complex excites at 360 nm places, obtains an emission peak, see Fig. 4 at 502 nm places.(INSTRUMENT MODEL: HITACHI/F – 7000).
(3) the XPRD phase purity of title complex characterizes
The XPRD sign of title complex shows it and has reliable phase purity, for its application as fluorescent material provides guarantee, sees Fig. 5.(INSTRUMENT MODEL: Bruker/D8 Advance).
Embodiment 2
By N, N-bis-(4-cyano-phenyl) Padil (0.1 mmol, 27.7 mg), 1, two (4-pyridyl) ethane part (0.05 mmol of 2-, 9.0 mg) with zinc nitrate (0.15 mmol, 28.4mg) be dissolved in water (10 mL) stir 5 minutes after enclose in the hydrothermal reaction kettle of 25ml.Again reaction mixture is heated to 80 DEG C with 10 DEG C per hour, maintains this temperature 3 days, be then down to room temperature, can obtain colourless bulk crystals, separated by this monocrystalline, successively through washing, drying treatment, obtain target product, productive rate is about 55%.
Embodiment 3
By N, N-bis-(4-cyano-phenyl) Padil (0.05 mmol, 14.0 mg), 1, two (4-pyridyl) ethane part (0.1 mmol of 2-, 18.0 mg) with zinc nitrate (0.15 mmol, 28.4mg) be dissolved in water (8 mL) stir 5 minutes after enclose in the hydrothermal reaction kettle of 25ml.Be heated at 100 DEG C by reaction mixture with 10 DEG C per hour again, maintain this temperature 3 days, be then down to room temperature, can obtain colourless bulk crystals, separated by this monocrystalline, successively through washing, drying treatment, obtain target product, productive rate is about 65%.
Embodiment 4
By N, N-bis-(4-cyano-phenyl) Padil (0.1 mmol, 27.7 mg), 1, two (4-pyridyl) ethane part (0.1 mmol of 2-, 18.0 mg) with zinc nitrate (0.15 mmol, 28.4mg) be dissolved in water (10 mL) stir 5 minutes after enclose in the hydrothermal reaction kettle of 25ml.Be heated at 100 DEG C by reaction mixture with 10 DEG C per hour again, maintain this temperature 3 days, be then down to room temperature, can obtain colourless bulk crystals, separated by this monocrystalline, successively through washing, drying treatment, obtain target product, productive rate is about 60%.
Embodiment 5
Under the condition of hydro-thermal, by N, N-bis-(4-cyano-phenyl) Padil (0.1 mmol, 27.7 mg), 1, two (4-pyridyl) ethane part (0.1 mmol of 2-, 18.0 mg) and zinc nitrate (0.2 mmol, 37.8mg) being dissolved in water (10 mL) to stir enclosed in the hydrothermal reaction kettle of 25m L after 5 minutes, 120 DEG C are heated to the speed of 10 DEG C/h, be incubated 3 days, then naturally room temperature is down to, light yellow bulk crystals can be obtained, yellow bulk crystals is separated, successively through washing, drying treatment, obtain target product, productive rate is 58%.
Embodiment 6
Under the condition of hydro-thermal, by N, N-bis-(4-cyano-phenyl) Padil (0.05 mmol, 14.0 mg), 1, two (4-pyridyl) ethane part (0.05 mmol of 2-, 9.0 mg) and zinc nitrate (0.1 mmol, 18.9mg) being dissolved in water (10 mL) to stir enclosed in the hydrothermal reaction kettle of 25mL after 5 minutes, be heated to 90 DEG C with the speed of 10 DEG C/h, be incubated 3 days, be then naturally down to room temperature, light yellow bulk crystals can be obtained, yellow bulk crystals is separated, successively through washing, drying treatment, obtains target product.

Claims (7)

1. a green fluorescence N, N-bis-(4-cyano-phenyl) Padil Zn complex, is characterized in that: the chemical formula of described N, N-bis-(4-cyano-phenyl) Padil Zn complex is [Zn (L) 2(bpe) (H 2o) 2] n, wherein L=N, N-bis-(4-cyano-phenyl) Padil anion ligand, skeleton symbol is as follows:
Bpe=1, two (4-pyridyl) ethane of 2-, skeleton symbol is as follows:
。
2. green fluorescence N according to claim 1, N-bis-(4-cyano-phenyl) Padil Zn complex, it is characterized in that: described N, N-bis-(4-cyano-phenyl) Padil Zn complex crystal belongs to oblique system, spacer is Cc, unit cell parameters is a=17.470 (5), b=13.697 (4), c=16.955 (5), α=90 °, β=95.962 (4) °, γ=90 °, V=4035 (2) 3.
3. according to the green fluorescence N described in claim 1, N-bis-(4-cyano-phenyl) Padil Zn complex, it is characterized in that: described title complex basic structure is an one dimensional network structure, the ligancy of center zinc atom is 6, respectively with from two N, two Sauerstoffatoms of N-bis-(4-cyano-phenyl) Padil, two nitrogen-atoms of two 1,2-two (4-pyridyl) ethane and two water molecule coordination; A Sauerstoffatom and zinc atom coordination in the carboxyl of N, N-bis-(4-cyano-phenyl) Padil part; In title complex, two (4-pyridyl) the ethane part of 1,2-connects zinc atom and forms one-dimensional chain structure; One-dimensional chain structure is interacted by hydrogen bond and pi-pi bond and forms three-dimensional net structure.
4. the green fluorescence N described in claim 1, the preparation method of N-bis-(4-cyano-phenyl) Padil Zn complex, it is characterized in that step is as follows: under the condition of hydro-thermal, by N, N-bis-(4-cyano-phenyl) Padil, 1, two (4-pyridyl) ethane of 2-and zinc nitrate mixing solutions of making soluble in water are enclosed in reactor, 80 ~ 120 DEG C are heated to the speed of 10 DEG C/h, be incubated 3 days, then naturally room temperature is down to, light yellow bulk crystals can be obtained, yellow bulk crystals is separated, successively through washing, drying treatment, obtain target product.
5. according to the green fluorescence N described in claim 4, the preparation method of N-bis-(4-cyano-phenyl) Padil Zn complex, it is characterized in that: in described mixing solutions, the concentration of N, N-bis-(4-cyano-phenyl) Padil is 0.005 ~ 0.01 mol L – 1.
6. according to the green fluorescence N described in claim 4, the preparation method of N-bis-(4-cyano-phenyl) Padil Zn complex, it is characterized in that: in described mixing solutions, the concentration of 1,2-two (4-pyridyl) ethane is 0.005 ~ 0.01 mol L – 1.
7. according to the preparation method of the green fluorescence N described in claim 4, N-bis-(4-cyano-phenyl) Padil Zn complex, it is characterized in that: in described mixing solutions, nitric acid zinc concentration is 0.01 ~ 0.02 mol L -1.
CN201510047523.6A 2015-01-30 2015-01-30 A kind of green fluorescence N, N-bis-(4-cyano-phenyl) Padil Zn complex and preparation method thereof Expired - Fee Related CN104628747B (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114605659A (en) * 2022-04-06 2022-06-10 中原工学院 Cd-MOF material with double-spiral structure and preparation method and application thereof
CN114621744A (en) * 2022-04-15 2022-06-14 淮阴师范学院 Photochromic material and preparation method and application thereof

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JP2007135459A (en) * 2005-11-17 2007-06-07 Maruyama Mfg Co Ltd Elevator for boom sprayer
WO2007100082A1 (en) * 2006-03-03 2007-09-07 The University Of Tokyo Fluorescent probe
CN102241974A (en) * 2011-05-04 2011-11-16 宁波大学 Near blue fluorescent material and preparation method thereof
CN104262369A (en) * 2014-10-12 2015-01-07 刘国政 Coordination polymer for hydrolysis regulation of nitrile ligand and preparation method of coordination polymer

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007135459A (en) * 2005-11-17 2007-06-07 Maruyama Mfg Co Ltd Elevator for boom sprayer
WO2007100082A1 (en) * 2006-03-03 2007-09-07 The University Of Tokyo Fluorescent probe
CN102241974A (en) * 2011-05-04 2011-11-16 宁波大学 Near blue fluorescent material and preparation method thereof
CN104262369A (en) * 2014-10-12 2015-01-07 刘国政 Coordination polymer for hydrolysis regulation of nitrile ligand and preparation method of coordination polymer

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114605659A (en) * 2022-04-06 2022-06-10 中原工学院 Cd-MOF material with double-spiral structure and preparation method and application thereof
CN114605659B (en) * 2022-04-06 2023-03-14 中原工学院 Cd-MOF material with double-spiral structure and preparation method and application thereof
CN114621744A (en) * 2022-04-15 2022-06-14 淮阴师范学院 Photochromic material and preparation method and application thereof
CN114621744B (en) * 2022-04-15 2024-02-06 淮阴师范学院 Photochromic material and preparation method and application thereof

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