CN105418652A - 1,4-dibromo-2,5-dimethylene bis triazol hydroxyphenylacetic isophthalic acid zinc complex single crystal and application - Google Patents

1,4-dibromo-2,5-dimethylene bis triazol hydroxyphenylacetic isophthalic acid zinc complex single crystal and application Download PDF

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CN105418652A
CN105418652A CN201610001154.1A CN201610001154A CN105418652A CN 105418652 A CN105418652 A CN 105418652A CN 201610001154 A CN201610001154 A CN 201610001154A CN 105418652 A CN105418652 A CN 105418652A
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triazole
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王英
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Abstract

The invention discloses a 1,4-dibromo-2,5-dimethylene bis triazol hydroxyphenylacetic isophthalic acid zinc complex single crystal and application. The structure of the 1,4-dibromo-2,5-dimethylene bis triazol hydroxyphenylacetic isophthalic acid zinc complex single crystal is [Zn(L)(hipt)], wherein L=4-(4-((4H-1,2,4-triazole-4-yl)methyl)-2,5-bisbromomethyl, and hipt= hydroxyphenylacetic isophthalic acid. The invention further discloses a preparation method of the 1,4-dibromo-2,5-dimethylene bis triazol hydroxyphenylacetic isophthalic acid zinc complex single crystal. The method comprises the steps that a normal temperature volatilization method is adopted, L, hipt and Cd(NO3)2.4H2O are stirred in water for half an hour and filtered, and a filtrate is volatilized at normal temperature for two weeks to obtain the colorless bulk crystal suitable for X-ray single-crystal diffraction, wherein the molar ratio of L to hipt to Zn(NO3)2.6H2O is 1:1:1. The invention further discloses the application of the 1,4-dibromo-2,5-dimethylene bis triazol hydroxyphenylacetic isophthalic acid zinc complex single crystal as a potential fluorescent material on the aspect of detecting the adsorbing capacity of dye or an illuminating agent.

Description

Hydroxy M Phthalic Acid Zn complex monocrystalline and application between bromo-2, the 5-dimethylenes of Isosorbide-5-Nitrae-two two triazole
The present invention obtains the subsidy that state natural sciences fund general project (21471113), Tianjin Education Commission general project (20140506) and Tianjin Normal University's Middl-age and youth faculty Academic innovations advance planning item (52XC1401).
Technical field
The invention belongs to organic and Inorganic synthese technical field, relate to 1, the preparation method of Hydroxy M Phthalic Acid Zn complex monocrystalline [Zn (L) (hipt)] and the application as potential fluorescent material between bromo-2, the 5-dimethylenes of 4-bis-two triazole, wherein, L=4-(4-((4H-1,2,4-triazole-4-yl) methyl)-2,5-bis-brooethyls)-4H-1,2,4-triazole; Hydroxy M Phthalic Acid between hipt=.
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, hipt and Zn (NO 3) 26H 2o filters stir half an hour in water after, filtrate normal temperature obtains the colourless bulk crystal structure of applicable X-ray single crystal diffraction for [Zn (L) (hipt)] after volatilizing two weeks, wherein, L=4-(4-((4H-1,2,4-triazole-4-yl) methyl)-2,5-bis-brooethyls)-4H-1,2,4-triazole; Hydroxy M Phthalic Acid between hipt=.This title complex also can be used as potential fluorescent material aspect and is applied.
Summary of the invention
Current inventor provides following technical scheme for this reason:
A kind of 1,4-bis-bromo-2, the monocrystalline of Hydroxy M Phthalic Acid Zn complex between 5-dimethylene two triazole, it is characterized in that this single crystal structure adopts APEXIICZN single crystal diffractometer, use through graphite monochromatised Mok alpha-ray, λ=0.71073 is incident radiation, collects point diffraction with ω-2 θ scan mode, obtain unit cell parameters through least-squares refinement, utilize software to solve single crystal data from difference Fourier electron density map:
Its structure is as follows:
[Zn (L) (hipt)], wherein
L=4-(4-((4H-1,2,4-triazole-4-yl) methyl)-2,5-bis-brooethyls)-4H-1,2,4-triazole;
Hydroxy M Phthalic Acid between hipt=.
The present invention further discloses the preparation method of Hydroxy M Phthalic Acid Zn complex monocrystalline between bromo-2, the 5-dimethylenes of Isosorbide-5-Nitrae-two two triazole, it is characterized in that it adopts normal temperature volatilization method, by L, hipt and Zn (NO 3) 26H 2o filters stir half an hour in water after, and filtrate normal temperature obtains the colourless bulk crystals of applicable X-ray single crystal diffraction after volatilizing two weeks; Wherein L:hipt:Zn (NO 3) 26H 2the mol ratio of O is 1:1:1;
Between bromo-2, the 5-dimethylenes of Isosorbide-5-Nitrae-two two triazole, the structure of Hydroxy M Phthalic Acid Zn complex monocrystalline is [Zn (L) (hipt) (H 2o) 2]; Wherein L=4-(4-((4H-1,2,4-triazole-4-yl) methyl)-2,5-bis-brooethyls)-4H-1,2,4-triazole; Hydroxy M Phthalic Acid between hipt=;
Lhipt。
The present invention further discloses between bromo-2, the 5-dimethylenes of Isosorbide-5-Nitrae-two two triazole that Hydroxy M Phthalic Acid Zn complex monocrystalline is as the application of potential fluorescent material in the adsorptive capacity detecting dyestuff or luminous agent, and experimental result shows:
(1) complex monocrystal in embodiment 2 has good selectivity and susceptibility to dyestuff, and detectability reaches 0.1ppm.
(2) can detect the luminous agent of trace, detection limit reaches 5.0 μ g/L.
(3) complex monocrystal that prepared by embodiment 2 is 1.4 × 10 for the adsorptive capacity of dyestuff -3mol/cm 2.
The present invention's preferred example:
The preparation of 4-(4-((4H-1,2,4-triazole-4-yl) methyl)-2,5-bis-brooethyls)-4H-1,2,4-triazole (L)
Bromo-2, the 5-dimethyl benzenes of Isosorbide-5-Nitrae-two: the mol ratio of two formyl hydrazine is 1:4
In 50mL tri-mouthfuls of round-bottomed flasks that magneton, reflux exchanger and thermometer are housed, add bromo-2, the 5-dimethyl benzenes (1mmol) of Isosorbide-5-Nitrae-two and two formyl hydrazine (4mmol) respectively, start and be stirred in 150 oc, reacts 24 hours.After reaction terminates, reaction solution is down to room temperature, the precipitation obtained is added 100mL hot methanol, after stirring and dissolving, filter, filtrate is slowly volatilized and is obtained white solid, yield 85%.Ultimate analysis (C 12n 6h 10br 2) theoretical value (%): C, 36.21; H, 2.53; N, 21.11.Measured value: C, 36.24; H, 2.55; N, 21.05;
The two formyl hydrazine of bromo-2, the 5-dimethyl benzenes of Isosorbide-5-Nitrae-two.
Bromo-2, the 5-dimethyl benzenes of the preferred Isosorbide-5-Nitrae of the present invention-two: the mol ratio of two formyl hydrazine is 1:4, temperature of reaction 150 DEG C, 24 hours reaction times.Adopt " one kettle way ", by bromo-for Isosorbide-5-Nitrae-two 2,5-dimethyl benzene and two formyl hydrazine prepare 4-(4-((4H-1,2,4-triazole-4-yl) methyl)-2 in a heated condition, 5-bis-brooethyl)-4H-1,2,4-triazole (L).
Another preferred embodiment of the present invention
4-(4-((4H-1,2,4-triazole-4-yl) methyl)-2,5-bis-brooethyls)-4H-1,2,4-triazole (L) (0.1mmol), a Hydroxy M Phthalic Acid (hipt) (0.1mmol) and Zn (NO 3) 26H 2o (0.1mmol) filters stir half an hour in water (10mL) after, and filtrate normal temperature obtains the colourless bulk crystals of applicable X-ray single crystal diffraction after volatilizing two weeks.Productive rate: 40%.Ultimate analysis (C 20h 14br 2n 6o 5zn) theoretical value (%): C, 37.33; H, 2.19; N, 13.06.Measured value: C, 37.25; H, 2.14; N, 13.09.
The advantage and disadvantage that between bromo-2, the 5-dimethylenes of a kind of Isosorbide-5-Nitrae-two disclosed by the invention two triazole, Hydroxy M Phthalic Acid Zn complex monocrystalline has is:
(1) operation is simple and easy to do.
(2) reaction yield is high, and the purity of products obtained therefrom is high.
(3) Hydroxy M Phthalic Acid Zn complex monocrystalline between bromo-2, the 5-dimethylenes of the Isosorbide-5-Nitrae-two prepared by the present invention two triazole, production cost is low, and method is easy, is applicable to scale operation.The photoelectric response range problem widening dyestuff can be solved at dyestuff or luminous agent application aspect.
Accompanying drawing explanation
Fig. 1: the crystalline structure figure of complex monocrystal;
Fig. 2: the two-dimensional layered structure figure of complex monocrystal.
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 all have commercially available.The raw materials such as all raw materials are all buy from chemical reagents corporation both domestic and external, such as bromo-2, the 5-dimethyl benzenes of Isosorbide-5-Nitrae-two, through continuation purify but directly use.
Embodiment 1
The preparation of 4-(4-((4H-1,2,4-triazole-4-yl) methyl)-2,5-bis-brooethyls)-4H-1,2,4-triazole (L)
Bromo-2, the 5-dimethyl benzenes of Isosorbide-5-Nitrae-two: the mol ratio of two formyl hydrazine is 1:4
In 50mL tri-mouthfuls of round-bottomed flasks that magneton, reflux exchanger and thermometer are housed, add bromo-2, the 5-dimethyl benzenes (1mmol) of Isosorbide-5-Nitrae-two and two formyl hydrazine (4mmol) respectively, start and be stirred in 150 oc, reacts 24 hours.After reaction terminates, reaction solution is down to room temperature, the precipitation obtained is added 100mL hot methanol, after stirring and dissolving, filter, filtrate is slowly volatilized and is obtained white solid, yield 85%.Ultimate analysis (C 12n 6h 10br 2) theoretical value (%): C, 36.21; H, 2.53; N, 21.11.Measured value: C, 36.24; H, 2.55; N, 21.05;
The two formyl hydrazine of bromo-2, the 5-dimethyl benzenes of Isosorbide-5-Nitrae-two.
Bromo-2, the 5-dimethyl benzenes of the preferred Isosorbide-5-Nitrae of the present invention-two: the mol ratio of two formyl hydrazine is 1:4, temperature of reaction 150 DEG C, 24 hours reaction times.Adopt " one kettle way ", by bromo-for Isosorbide-5-Nitrae-two 2,5-dimethyl benzene and two formyl hydrazine prepare 4-(4-((4H-1,2,4-triazole-4-yl) methyl)-2 in a heated condition, 5-bis-brooethyl)-4H-1,2,4-triazole (L).
Embodiment 2
4-(4-((4H-1,2,4-triazole-4-yl) methyl)-2,5-bis-brooethyls)-4H-1,2,4-triazole (L) (0.1mmol), a Hydroxy M Phthalic Acid (hipt) (0.1mmol) and Zn (NO 3) 26H 2o (0.1mmol) filters stir half an hour in water (10mL) after, and filtrate normal temperature obtains the colourless bulk crystals of applicable X-ray single crystal diffraction after volatilizing two weeks.Productive rate: 40%.Ultimate analysis (C 20h 14br 2n 6o 5zn) theoretical value (%): C, 37.33; H, 2.19; N, 13.06.Measured value: C, 37.25; H, 2.14; N, 13.09.
Embodiment 3
Crystal structure determination adopts APEXIICZN single crystal diffractometer, use through graphite monochromatised Mok alpha-ray, λ=0.71073 is incident radiation, point diffraction is collected with ω-2 θ scan mode, unit cell parameters is obtained through least-squares refinement, software is utilized to solve crystalline structure from difference Fourier electron density map, 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:
Embodiment 4
The concrete instance that dyestuff or luminous agent use
Method: the PARSTAT2273 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 500W xenon lamp 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 USB4000plug-and-play Miniature optical linear light spectrometer.
Step: in order to definitely understand dyestuff at TiO 2adsorptive capacity on film, complex monocrystal dye sensitization TiO prepared by embodiment 2 2(geometric area is about 1cm to nanometer crystal film 2) be immersed in 10mL0.01molL -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 complex monocrystal is 1.4 × 10 -3mol/cm 2.
Result: compared with the methanol solution of dyestuff, complex monocrystal 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 complex monocrystal 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 500nm.
Embodiment 5
Between bromo-2, the 5-dimethylenes of Isosorbide-5-Nitrae-two two triazole, Hydroxy M Phthalic Acid Zn complex monocrystalline is as the application preparing luminescent material.
Method: by spectrophotofluorometer, carries out the excitation wavelength of this compound monocrystal (embodiment 2) and the scanning of emission wavelength respectively, selects and determine optimal wavelength.
Conclusion: excitation wavelength and the emission wavelength of this compound are respectively 340nm and 500nm.
Step: Hydroxy M Phthalic Acid Zn complex monocrystalline grinding compressing tablet between two for bromo-for Isosorbide-5-Nitrae-two 2,5-dimethylenes triazole is become the sheet sample that external diameter is 27mm, thickness is about 3mm, and the sample pool putting into MPF-4 fluorescence spectrophotometer is measured.
Result: the excitation wavelength lambda of this compound ex=340nm, emission wavelength lambda em=500nm.
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 (3)

1. one kind 1,4-bis-bromo-2, the monocrystalline of Hydroxy M Phthalic Acid Zn complex between 5-dimethylene two triazole, it is characterized in that this single crystal structure adopts APEXIICZN single crystal diffractometer, use through graphite monochromatised Mok alpha-ray, λ=0.71073 is incident radiation, collects point diffraction with ω-2 θ scan mode, obtain unit cell parameters through least-squares refinement, utilize software to solve single crystal data from difference Fourier electron density map:
Its structure is as follows:
[Zn (L) (hipt)], wherein
L=4-(4-((4H-1,2,4-triazole-4-yl) methyl)-2,5-bis-brooethyls)-4H-1,2,4-triazole;
Hydroxy M Phthalic Acid between hipt=.
2. the preparation method of Hydroxy M Phthalic Acid Zn complex monocrystalline between bromo-2, the 5-dimethylenes of Isosorbide-5-Nitrae-two described in claim 1 two triazole, is characterized in that it adopts normal temperature volatilization method, by L, hipt and Zn (NO 3) 26H 2o filters stir half an hour in water after, and filtrate normal temperature obtains the colourless bulk crystals of applicable X-ray single crystal diffraction after volatilizing two weeks; Wherein L:hipt:Zn (NO 3) 26H 2the mol ratio of O is 1:1:1;
Between bromo-2, the 5-dimethylenes of Isosorbide-5-Nitrae-two two triazole, the structure of Hydroxy M Phthalic Acid Zn complex monocrystalline is [Zn (L) (hipt)]; Wherein L=4-(4-((4H-1,2,4-triazole-4-yl) methyl)-2,5-bis-brooethyls)-4H-1,2,4-triazole; Hydroxy M Phthalic Acid between hipt=;
Lhipt。
3. between bromo-2, the 5-dimethylenes of Isosorbide-5-Nitrae-two described in claim 1 two triazole Hydroxy M Phthalic Acid Zn complex monocrystalline as the application of potential fluorescent material in the adsorptive capacity detecting dyestuff or luminous agent.
CN201610001154.1A 2016-01-05 2016-01-05 1,4-dibromo-2,5-dimethylene bis triazol hydroxyphenylacetic isophthalic acid zinc complex single crystal and application Pending CN105418652A (en)

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CN110885450A (en) * 2019-12-09 2020-03-17 重庆师范大学 Green fluorescent cadmium-organic coordination polymer and preparation method and application thereof

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CN103588797A (en) * 2013-11-22 2014-02-19 淮南师范学院 Novel triazole fluorescent coordination polymer as well as preparation method and application thereof

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Application publication date: 20160323