CN104558055A - Oxyether bistriazole nickel nitrate complex with potential fluorescent material and preparation method thereof - Google Patents

Oxyether bistriazole nickel nitrate complex with potential fluorescent material and preparation method thereof Download PDF

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CN104558055A
CN104558055A CN201510088211.XA CN201510088211A CN104558055A CN 104558055 A CN104558055 A CN 104558055A CN 201510088211 A CN201510088211 A CN 201510088211A CN 104558055 A CN104558055 A CN 104558055A
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triazole
title complex
chcl
phenyl
phenoxy group
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CN104558055B (en
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王英
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Tianjin Normal University
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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
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/04—Nickel compounds
    • C07F15/045—Nickel compounds without a metal-carbon linkage
    • 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
    • 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
    • C09K2211/187—Metal complexes of the iron group metals, i.e. Fe, Co or Ni

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Abstract

The invention discloses an oxyether bistriazole zinc chloride complex with a potential fluorescent material and a preparation method thereof. The oxyether bistriazole zinc chloride complex {[Ni(L)2(NO3)2].CHCl3} (1) has a structural element as shown in the Figure.1. The invention also discloses the preparation method of {[Ni(L)2(NO3)2].CHCl3} (1) (L is 1-(4-(4-(1H-1,2,4-triazole-1-yl)phenoxy) phenyl)-1H-1,2,4-triazole). A 'normal-temperature volatilization' method adopted in the invention comprises the following steps that L and Ni(NO3)2.6H2O are stirred in a mixed solvent of CHCl3, CH3OH and water and filtered to obtain a filtrate and the filtrate is subjected to normal-temperature volatilization for two weeks to obtain light green rod-like crystals applicable to X-ray diffraction. The invention further discloses an application of the oxyether bistriazole zinc chloride complex as the potential fluorescent material.

Description

Two triazole nickelous nitrate title complex of oxygen ether with potential fluorescent material and preparation method thereof
The present invention obtains state natural sciences fund general project (21471113), young top-notch personnel's support plan, Tianjin Education Commission general project (20140506), Tianjin Normal University Middl-age and youth faculty Academic innovations advance planning item (52XC1401), the subsidy of Tianjin State Scientific and Technological Commission general project (11JCYBJC03600) and Tianjin innovation team of institution of higher education training plan (TD12-5038).
Technical field
The invention belongs to organic and Inorganic synthese technical field, relate to two triazole nickelous nitrate the title complex { [Ni (L) of oxygen ether 2(NO 3) 2] CHCl 3( 1) preparation method of (L=1-(4-(4-(1H-1,2,4-triazole-1-base) phenoxy group) phenyl)-1H-1,2,4-triazole) and the application as potential fluorescent material.
Background technology
1,2,4-triazole and derivative thereof have the coordination feature of pyrazoles and imidazoles concurrently, are the bridgingligands that coordination ability is stronger, have synthesized at present and have characterized a large amount of monokaryons, multinuclear and multidimensional compound.These parts can with 1, nitrogen-atoms on 2 and metallic ion coordination form N1, N2-bridging pattern, for 4 unsubstituted 1,2,4-triazole derivative is by 2, nitrogen-atoms on 4 forms N2, N4-bridging pattern, this N2, N4-bridging pattern is with the N1 of imidazoles in metalloenzyme, and N3-bridging mode class seemingly.Special purpose for triazole class compounds also shows in the design of molecular device, and the metal complexes that synthesis has different dimension has been the vital step of device.
The present invention adopts " normal temperature volatilization method ", i.e. L and Ni (NO 3) 26H 2o is at CHCl 3, CH 3filter after stirring half an hour in the mixed solvent of OH and water, filtrate normal temperature volatilizees light green the rhabdolith { [Ni (L) obtaining applicable X-ray single crystal diffraction for two weeks 2(NO 3) 2] CHCl 3( 1) (L=1-(4-(4-(1H-1,2,4-triazole-1-base) phenoxy group) phenyl)-1H-1,2,4-triazole).This title complex also can be used as potential fluorescent material aspect and is applied.
Summary of the invention
Another object of the present invention is to provide a kind of oxygen ether two triazole nickelous nitrate title complex { [Ni (L) 2(NO 3) 2] CHCl 3( 1) (L=1-(4-(4-(1H-1,2,4-triazole-1-base) phenoxy group) phenyl)-1H-1,2,4-triazole) monocrystalline and preparation method thereof.
Current inventor provides following technical scheme for this reason:
Two triazole nickelous nitrate the title complex { [Ni (L) of oxygen ether 2(NO 3) 2] CHCl 3( 1) (L=1-(4-(4-(1H-1,2,4-triazole-1-base) phenoxy group) phenyl)-1H-1,2,4-triazole) structural motif as shown in Figure 1.
The present invention further discloses two triazole nickelous nitrate the title complex { [Ni (L) of oxygen ether 2(NO 3) 2] CHCl 3( 1) (L=1-(4-(4-(1H-1,2,4-triazole-1-base) phenoxy group) phenyl)-1H-1,2,4-triazole) monocrystalline, it is characterized in that this single crystal structure adopts APEX II CCD single crystal diffractometer, use through graphite monochromatised Mok alpha-ray (λ=0.71073) be incident radiation, with ω-2 θscan mode collects point diffraction, obtains unit cell parameters, utilize SHELXL-97 direct method to solve single crystal data from difference Fourier electron density map through least-squares refinement:
Table 1. title complex 1crystallographic data
Two triazole nickelous nitrate the title complex { [Ni (L) of oxygen ether of the present invention 2(NO 3) 2] CHCl 3( 1) (L=1-(4-(4-(1H-1,2,4-triazole-1-base) phenoxy group) phenyl)-1H-1,2,4-triazole) preparation method of monocrystalline, its feature is at employing " normal temperature volatilization method ", i.e. L and Ni (NO 3) 26H 2o is at CHCl 3, CH 3filter after stirring half an hour in the mixed solvent of OH and water, to prepare this title complex after filtrate normal temperature volatilizees two weeks
L。
The present invention's preferred example:
The preparation of 1-(4-(4-(1H-1,2,4-triazole-1-base) phenoxy group) phenyl)-1H-1,2,4-triazole (L)
Adopt " one kettle way " at polar solvent, by 4,4 '-dibromodiphenyl ether, 1H-1,2,4-triazole, salt of wormwood and cupric oxide are prepared in a heated condition; The wherein bromo-4-of 1-(4-bromine phenoxy group) benzene: 1H-1,2,4-triazole: salt of wormwood: the mol ratio of cupric oxide is 2:10:30:1;
4,4 '-dibromodiphenyl ether 1H-1,2,4-triazole
The present invention preferably 4,4 '-dibromodiphenyl ether: 1H-1,2,4-triazole: salt of wormwood: the mol ratio of cupric oxide is 2:10:30:1; Temperature of reaction 80-200 DEG C, reaction times 12-120 hour.In polar solvent, adopt " one kettle way ", by 4,4 '-dibromodiphenyl ether, 1H-1, this organic compound prepared in a heated condition by 2,4-triazole, salt of wormwood and cupric oxide;
Another preferred embodiment of the present invention
1-(4-(4-(1H-1,2,4-triazole-1-base) phenoxy group) phenyl)-1H-1,2,4-triazole (L) (0.1 mmol) and Ni (NO 3) 26H 2o (0.2 mmol) is at CHCl 3(10 mL), CH 3oH (8 mL) and H 2filter after stirring half an hour in the mixed solvent of O (1 mL), filtrate normal temperature obtains the light green bulk crystals of X-ray single crystal diffraction after volatilizing two weeks.Productive rate: 40%.Ultimate analysis (C 33h 25cl 3n 14niO 8) theoretical value (%): C, 43.52; H, 2.77; N, 21.53.Measured value: C, 43.58; H, 2.82; N, 21.49.
The present invention further discloses two triazole nickelous nitrate the title complex { [Ni (L) of oxygen ether 2(NO 3) 2] CHCl 3( 1) (L=1-(4-(4-(1H-1,2,4-triazole-1-base) phenoxy group) phenyl)-1H-1,2,4-triazole) can be used as potential fluorescent material aspect and applied.
Two triazole nickelous nitrate the title complex { [Ni (L) of a kind of oxygen ether disclosed by the invention 2(NO 3) 2] CHCl 3( 1) advantage and disadvantage that has of (L=1-(4-(4-(1H-1,2,4-triazole-1-base) phenoxy group) phenyl)-1H-1,2,4-triazole) monocrystalline is:
(1) operation is simple and easy to do.
(2) reaction yield is high, and the purity of products obtained therefrom is high.
(3) { [Ni (L) prepared by the present invention 2(NO 3) 2] CHCl 3( 1) (L=1-(4-(4-(1H-1,2,4-triazole-1-base) phenoxy group) phenyl)-1H-1,2,4-triazole) production cost is low, method is easy, is applicable to scale operation.
Accompanying drawing explanation
Fig. 1: title complex 1crystalline structure primitive figure;
Fig. 2: title complex 1one-dimensional catenary structure figure.
Embodiment
Below in conjunction with embodiment, the present invention is described further, and embodiment is only indicative, never means that it limits the scope of the invention by any way.Raw materials used 4,4 '-dibromodiphenyl ether, 1H-1,2,4-triazole, salt of wormwood and cupric oxide etc. all have commercially available.All raw materials are all buy from chemical reagents corporation both domestic and external, through continuation purify but directly use.
Embodiment 1
4,4 '-dibromodiphenyl ether: 1H-1,2,4-triazole: salt of wormwood: the mol ratio of cupric oxide is 2:10:30:1
CuO (0.5 mmol), salt of wormwood (15 mmol), 1H-1 is added respectively in 50 mL, tri-mouthfuls of round-bottomed flasks that magneton, reflux exchanger and thermometer are housed, 2,4-triazole (5 mmol), 4,4 '-dibromodiphenyl ether (1 mmol) and 20 mL DMF.Start and be stirred in 100 oc, reacts 24 hours.After reaction terminates, reaction solution is down to room temperature, filter, filtrate adds 100 mL water, separate out a large amount of precipitation, suction filtration, collect filter cake, 1-(4-(4-(1H-1,2,4-triazole-1-base) phenoxy group) phenyl)-1H-1,2,4-triazole (L).Yield 60%.
Embodiment 2
1-(4-(4-(1H-1,2,4-triazole-1-base) phenoxy group) phenyl)-1H-1,2,4-triazole (L) (0.1 mmol) and Ni (NO 3) 26H 2o (0.2 mmol) is at CHCl 3(10 mL), CH 3oH (8 mL) and H 2filter after stirring half an hour in the mixed solvent of O (1 mL), filtrate normal temperature obtains the light green bulk crystals of X-ray single crystal diffraction after volatilizing two weeks.Productive rate: 40%.Ultimate analysis (C 33h 25cl 3n 14niO 8) theoretical value (%): C, 43.52; H, 2.77; N, 21.53.Measured value: C, 43.58; H, 2.82; N, 21.49.
Embodiment 3
Crystal structure determination adopts APEX II CCD single crystal diffractometer, use through graphite monochromatised Mok alpha-ray (λ=0.71073) be incident radiation, with ω-2 θscan mode collects point diffraction, obtains unit cell parameters, utilize software to solve crystalline structure from difference Fourier electron density map through least-squares refinement, and through Lorentz lorentz and polarizing effect correction.All H atom are synthesized by difference Fourier and are determined through desirable position calculation.Detailed axonometry data are in table 1.Structural motif is shown in Fig. 1, and one-dimensional catenary structure is shown in Fig. 2.
Table 1. title complex 1crystallographic data
Embodiment 4
The concrete instance that dyestuff or luminous agent use
Method: PARSTAT 2273 electrochemical workstation of differentiated pulse volt-ampere (DPV) the curve negotiating Princeton Applied Research Laboratory development of dye solution is measured.The DPV test of solution adopts three-electrode system, and glass-carbon electrode is working electrode, and supporting electrode is platinum plate electrode, homemade Ag/AgNO 3electrode is reference electrode; Electrolytic solution is the acetonitrile solution of 0.1molL-1TBAP.Reduce reversible point to for interior mark with Oxidation of Ferrocene, obtains the correction value between test system and standard hydrogen electrode system.
Monochromatic incident light photoelectric transformation efficiency (IPCE) describes the photoelectric transformation efficiency of DSCs under monochromatic ray effect, is transfer to the electronic number of external circuit and the ratio of incident light subnumber.During measurement, use 500 W xenon lamps as light source, the monochromatic ray of incident light under the multifunctional assembled grating spectrograph of WDS-5 type obtains different wave length λ; Monochromatic light exposure, in the light anode of battery, reads current value I by Keithley2400 digital sourcemeter.Monochromatic good fortune illumination is measured by USB4000 plug-and-play Miniature optical linear light spectrometer.
Step: in order to definitely understand dyestuff at TiO 2adsorptive capacity on film, by dye sensitization TiO 2(geometric area is about 1 cm to nanometer crystal film 2) be immersed in 10 mL 0.01 molL -1sodium hydroxide methanol solution in spend the night, treat that the absorbancy of attached mensuration solution separated completely by dyestuff.Wash one's face and rinse one's mouth according to absorbancy and molar absorptivity and can calculate the adsorptive capacity of dyestuff on unit surface nanometer crystal film.The adsorptive capacity of this title complex is 6.3 × 10 -4mol/cm 2.
Result: compared with the methanol solution of dyestuff, dyestuff is at TiO 2absorption spectrum on film all obviously broadens and red shift.This shows that dye molecule is at TiO 2define the J-aggregate of first also tail.From the principle of work of DSCs, the spectrum broadening that dye aggregation causes and red shift are very favourable for the widening of photoelectric response scope of dyestuff.But meanwhile, dye aggregation cognition reduces its electron injection efficiency greatly, thus causes the degraded performance of DSCs.So, in dye solution, usually add coadsorbent to suppress the gathering of dyestuff.This title complex is in methanol solution and at TiO 2the fluorometric investigation of the purple solution on membrane electrode adopts 2.5 × 10 -5the methanol solution of mol/L, maximum emission wavelength is positioned at 588 nm.
After the preferred embodiment described in detail, be familiar with this technology personage can be well understood to, do not departing under above-mentioned claim and spirit and can carry out various change and amendment, all above embodiment is done according to technical spirit of the present invention any simple modification, equivalent variations and modification, all belong to the scope of technical solution of the present invention.And the present invention is not also by the restriction of example embodiment in specification sheets.

Claims (4)

1. two triazole nickelous nitrate the title complex { [Ni (L) of oxygen ether 2(NO 3) 2] CHCl 3( 1) structural motif, wherein L=1-(4-(4-(1H-1,2,4-triazole-1-base) phenoxy group) phenyl)-1H-1,2,4-triazole.
2. the monocrystalline of the two triazole nickelous nitrate title complex of oxygen ether described in claim 1, is characterized in that this single crystal structure adopts APEX II CCD single crystal diffractometer, use through graphite monochromatised Mok alpha-ray (λ=0.71073) be incident radiation, with ω-2 θscan mode collects point diffraction, obtains unit cell parameters, utilize software to solve single crystal data from difference Fourier electron density map through least-squares refinement:
Table 1. title complex 1crystallographic data
。
3. two triazole nickelous nitrate the title complex { [Ni (L) of oxygen ether described in claim 1 2(NO 3) 2] CHCl 3( 1) (L=1-(4-(4-(1H-1,2,4-triazole-1-base) phenoxy group) phenyl)-1H-1,2,4-triazole) preparation method, it is characterized in that it be adopt " normal temperature volatilization method ", i.e. L and Ni (NO 3) 26H 2o is at CHCl 3, CH 3filter after stirring half an hour in the mixed solvent of OH and water, to prepare this title complex after filtrate normal temperature volatilizees two weeks
L。
4. two triazole nickelous nitrate the title complex { [Ni (L) of oxygen ether described in claim 1 2(NO 3) 2] CHCl 3( 1) (L=1-(4-(4-(1H-1,2,4-triazole-1-base) phenoxy group) phenyl)-1H-1,2,4-triazole) as the application of potential fluorescent material aspect.
CN201510088211.XA 2015-02-26 2015-02-26 There is oxygen ether pair triazole nitric acid nickel complex of potential fluorescent material and preparation method thereof Expired - Fee Related CN104558055B (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105524123A (en) * 2016-01-05 2016-04-27 天津师范大学 1, 4-dimethyl-2, 5-dimethylene bistriazole nickel complex single crystal and application thereof
CN105524120A (en) * 2016-01-05 2016-04-27 天津师范大学 1, 4-dimethyl-2, 5-dimethylene bistriazole two-dimensional nickel complex single crystal and application thereof
CN105693639A (en) * 2016-03-29 2016-06-22 广西师范大学 High nuclear nickel cluster based on sulphur-containing triazole ligand and preparation method thereof

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CN103772305A (en) * 2014-01-14 2014-05-07 天津师范大学 Oxyether triazole compound, and preparation method and application thereof
CN104370839A (en) * 2014-11-10 2015-02-25 天津师范大学 Oxygen ether-4-substituted bitriazole compound as well as preparation method and application of oxygen ether-4-substituted bitriazole compound

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CN103772305A (en) * 2014-01-14 2014-05-07 天津师范大学 Oxyether triazole compound, and preparation method and application thereof
CN104370839A (en) * 2014-11-10 2015-02-25 天津师范大学 Oxygen ether-4-substituted bitriazole compound as well as preparation method and application of oxygen ether-4-substituted bitriazole compound

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SHAO-BIN MIAO ET AL，: "Synthesis, Crystal Structure, and Properties of a 3D Cu(I) Coordination Polymer Based on Cu3(CN)2 Clusters and 1,3-Di-(1,2,4-Triazole-4-yl) Benzene", 《J CLUST SCI》 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105524123A (en) * 2016-01-05 2016-04-27 天津师范大学 1, 4-dimethyl-2, 5-dimethylene bistriazole nickel complex single crystal and application thereof
CN105524120A (en) * 2016-01-05 2016-04-27 天津师范大学 1, 4-dimethyl-2, 5-dimethylene bistriazole two-dimensional nickel complex single crystal and application thereof
CN105693639A (en) * 2016-03-29 2016-06-22 广西师范大学 High nuclear nickel cluster based on sulphur-containing triazole ligand and preparation method thereof
CN105693639B (en) * 2016-03-29 2018-07-31 广西师范大学 A kind of high core nickel cluster compound and preparation method thereof based on sulfur-bearing Triazole ligand

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