CN104592267B - Double triazole M-phthalic acid cadmium complex of naphthalene with potential fluorescent material and preparation method thereof - Google Patents

Double triazole M-phthalic acid cadmium complex of naphthalene with potential fluorescent material and preparation method thereof Download PDF

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CN104592267B
CN104592267B CN201510088026.0A CN201510088026A CN104592267B CN 104592267 B CN104592267 B CN 104592267B CN 201510088026 A CN201510088026 A CN 201510088026A CN 104592267 B CN104592267 B CN 104592267B
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naphthalene
triazole
phthalic acid
ipa
cadmium complex
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CN104592267A (en
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王英
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Tianjin Normal University
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    • C07F3/00Compounds containing elements of Groups 2 or 12 of the Periodic Table
    • C07F3/003Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
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    • C09K11/00Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/188Metal complexes of other metals not provided for in one of the previous groups

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Abstract

The invention discloses double triazole M-phthalic acid cadmium complex of naphthalene with potential fluorescent material and preparation method thereof, wherein double triazole M-phthalic acid cadmium complex { [Cd (L) (the ipa)] 0.25H of naphthalene2The structural motif of O} (1) is as shown in Figure 1.Also disclose { [Cd (L) (ipa)] 0.25H simultaneously2O} (1) (L=1 [7 (1H 1,2,4 triazole 1 base) naphthalene 2 base) 1H 1,2,4 triazole, ipa=M-phthalic acid) preparation method.It is to use " solvent-thermal method ", i.e. Cd (NO3)2·6H2O, ipa, L, DMF and water are 90oIt is slowly dropped to room temperature after reacting three days under C and obtains being suitable for the yellow bulk crystals of X ray single crystal diffraction.The present invention further discloses the double triazole M-phthalic acid cadmium complex of naphthalene as the application in terms of potential fluorescent material.

Description

There is the double triazole M-phthalic acid cadmium complex of naphthalene and the preparation thereof of potential fluorescent material Method
The present invention obtains state natural sciences fund general project (21471113), young top-notch personnel's support plan, sky Education Commission of Jinshi City general project (20140506), Tianjin Normal University's Middl-age and youth faculty Academic innovations advance planning item (52XC1401), meter is cultivated by Tianjin State Scientific and Technological Commission general project (11JCYBJC03600) and Tianjin innovation team of institution of higher education Draw the subsidy of (TD12-5038).
Technical field
The invention belongs to organic and Inorganic synthese technical field, relate to stating double triazole M-phthalic acid the cadmium complex { [Cd of naphthalene (L)(ipa)]·0.25H2O} (1) (L=1-[7-(1H-1,2,4-triazole-1-base) naphthalene-2-base)-1H-1,2,4-three Nitrogen azoles, ipa=M-phthalic acid) preparation method and as the application of potential fluorescent material.
Background technology
1,2,4-triazole and derivative thereof have the coordination feature of pyrazoles and imidazoles concurrently, are that the bridging that coordination ability is stronger is joined Body, has synthesized and has characterized substantial amounts of monokaryon, multinuclear and multidimensional compound the most.These parts can be former with the nitrogen on 1,2 Son forms N1, N2-bridging pattern with metallic ion coordination, can be by 2,4 for 4 unsubstituted 1,2,4-triazole derivatives On nitrogen-atoms formed N2, N4-bridging pattern, this N2, N4-bridging pattern is with the N1 of imidazoles in metalloenzyme, N3-bridging pattern Similar.Specific use for triazole class compounds is also manifested by the design of molecular device, and synthesis has different dimension Metal complex has been the vital step of device.
The present invention is i.e. to use " solvent-thermal method ", i.e. Cd (NO3)2·6H2O, ipa, L, DMF and water are 90oC hydrothermal condition Lower reaction is down to room temperature and is obtained being suitable for the yellow bulk crystals { [Cd (L) (ipa)] of X-ray single crystal diffraction after three days 0.25H2O} (1) (L=1-[7-(1H-1,2,4-triazole-1-bases) naphthalene-2-base)-1H-1,2,4-triazoles, ipa= M-phthalic acid).This complex is alternatively arranged as potential fluorescent material aspect and is applied.
Summary of the invention
Offer double triazole M-phthalic acid the cadmium complex { [Cd (L) of a kind of naphthalene is provided (ipa)]·0.25H2O} (1) (L=1-[7-(1H-1,2,4-triazole-1-base) naphthalene-2-base)-1H-1,2,4-three nitrogen Azoles, ipa=M-phthalic acid) monocrystalline and preparation method thereof.
Following technical scheme is current inventor provides for this:
Double triazole M-phthalic acid cadmium complex { [Cd (L) (the ipa)] 0.25H of naphthalene2O} (1) (L = 1-[7-(1H- 1,2,4-triazole-1-base) naphthalene-2-base)-1H-1,2,4-triazoles, ipa=M-phthalic acid) structural motif such as Fig. 1 institute Show.
The present invention further discloses double triazole M-phthalic acid cadmium complex { [Cd (L) (the ipa)] 0.25H of naphthalene2O} (1) (L=1-[7-(1H-1,2,4-triazole-1-bases) naphthalene-2-base)-1H-1,2,4-triazoles, ipa=isophthalic diformazan Acid) monocrystalline, it is characterised in that this mono-crystalline structures uses APEX II CCD single crystal diffractometer, uses through graphite monochromatised Mok alpha ray (λ=0.71073) is incident radiation, collects point diffraction with ω-2 θ scan mode, repaiies through least square method Just obtain cell parameter, utilize SHELXL-97 direct method to solve single crystal data from difference Fourier electron-density map:
The crystallographic data of table 1. complex 1
Double triazole M-phthalic acid cadmium complex { [Cd (L) (the ipa)] 0.25H of naphthalene of the present invention2O} (1) (L = 1-[7-(1H-1,2,4-triazole-1-bases) naphthalene-2-base)-1H-1,2,4-triazoles, ipa=M-phthalic acid) system of monocrystalline Preparation Method, its feature is using " solvent-thermal method ", Cd (NO3)2·6H2O, ipa, L, DMF and water are 90oAfter reacting three days under C It is down to room temperature to prepare this complex
L ipa。
One preferred example of the present invention:
1-[7-(1H-1,2,4-triazole-1-base) naphthalene-2-base) preparation of-1H-1,2,4-triazole (L)
1-of the present invention [7-(1H-1,2,4-triazole-1-base) naphthalene-2-base) the preparation side of-1H-1,2,4-triazole Method, its feature is using " one kettle way " at polar solvent, and by 2,7-dibromine naphthalene, 1H-1,2,4-triazoles, potassium carbonate and cupric oxide exist Prepare under heating condition;Wherein 2,7-dibromine naphthalene: 1H-1,2,4-triazole: potassium carbonate: the mol ratio of cupric oxide is 2:10-15: 30:1;
2,7-dibromine naphthalene 1H-1,2,4-triazole
The present invention preferred 2,7-dibromine naphthalene: 1H-1,2,4-triazole: potassium carbonate: the mol ratio of cupric oxide is 2:10-15:30: 1;Reaction temperature 100 DEG C, 48 hours reaction time.In polar solvent, use " one kettle way ", by 2,7-dibromine naphthalene, 1H-1, This organic compound prepared in a heated condition by 2,4-triazole, potassium carbonate and cupric oxide;
Presently preferred embodiment
1-[7-(1H-1,2,4-triazole-1-base) naphthalene-2-base)-1H-1,2,4-triazole (L) (0.1 mmol), ipa (0.1 mmol)、Cd(NO3)2·6H2O (0.2 mmo), 10 mL water and 6 mL DMF are put in 23 mL water heating kettles.90oC adds Heat was slowly dropped to room temperature after three days, obtained being suitable for the yellow bulk crystals of X-ray single crystal diffraction after driving still.Productivity: 40%.Element Analyze (C22H14.5CdN6O4.25) theoretical value (%): C, 48.64;H, 2.69;N, 15.47.Measured value: C, 48.68;H, 2.65;N, 15.26。
The present invention further discloses double triazole M-phthalic acid cadmium complex { [Cd (L) (the ipa)] 0.25H of naphthalene2O} (1) (L=1-[7-(1H-1,2,4-triazole-1-bases) naphthalene-2-base)-1H-1,2,4-triazoles, ipa=M-phthalic acid) Can be applied as potential fluorescent material aspect.
Double triazole M-phthalic acid cadmium complex { [Cd (L) (ipa)] 0.25H of a kind of naphthalene disclosed by the invention2O} (1) (L=1-[7-(1H-1,2,4-triazole-1-bases) naphthalene-2-base)-1H-1,2,4-triazoles, ipa=M-phthalic acid) single Brilliant have the advantage that and feature are:
(1) operation is simple and easy to do.
(2) reaction yield is high, and the purity of products obtained therefrom is high.
(3) { [Cd (L) (ipa)] 0.25H prepared by the present invention2O} (1) (L=1-[7-(1H-1,2,4-tri- Nitrogen azoles-1-base) naphthalene-2-base)-1H-1,2,4-triazoles, ipa=M-phthalic acid) production cost is low, and method is easy, is suitable for Large-scale production.
Accompanying drawing explanation
The crystal structure primitive figure of Fig. 1: complex 1;
The two-dimensional layered structure figure of Fig. 2: complex 1.
Detailed description of the invention
Below in conjunction with embodiment, the present invention is described further, and embodiment is only explanatory, is in no way intended to it Limit the scope of the present invention by any way.Raw materials used 2,7-dibromine naphthalene, 1H-1,2,4-triazole, potassium carbonate and cupric oxide Etc. being commercially available.All raw materials are all to buy from chemical reagents corporation both domestic and external, not through continuing to purify but straight Connect use.
Embodiment 1
2,7-dibromine naphthalene: 1H-1,2,4-triazole: potassium carbonate: the mol ratio of cupric oxide is 2:10:30:1
It is separately added into CuO (0.5 in equipped with 50 mL three neck round bottom flasks of magneton, reflux condenser and thermometer Mmol), potassium carbonate (15 mmol), 1H-1,2,4-triazole (5 mmol), 2,7-dibromine naphthalene (1 mmol) and 20 mL DMF.Start stirring 100oC, reacts 24 hours.After reaction terminates, reactant liquor being down to room temperature, filter, filtrate adds 100 ML water, separates out and precipitates in a large number, suction filtration, collection filter cake, and 1-[7-(1H-1,2,4-triazole-1-bases) naphthalene-2-base)-1H-1,2,4- Triazole (L).Yield 60%, yield 60%.
Embodiment 2
1-[7-(1H-1,2,4-triazole-1-base) naphthalene-2-base)-1H-1,2,4-triazole (L) (0.1 mmol), ipa (0.1 mmol)、Zn(NO3)2·6H2O (0.2 mmo), 10 mL water and 6 mL DMF are put in 23 mL water heating kettles.90oC adds Heat was slowly dropped to room temperature after three days, obtained being suitable for the yellow bulk crystals of X-ray single crystal diffraction after driving still.Productivity: 40%.Element Analyze (C22H14.5CdN6O4.25) theoretical value (%): C, 48.64;H, 2.69;N, 15.47.Measured value: C, 48.68;H, 2.65;N, 15.26。
Embodiment 3
Crystal structure determination uses APEX II CCD single crystal diffractometer, uses through graphite monochromatised Mok alpha ray (λ =0.71073) it is incident radiation, collects point diffraction with ω-2 θ scan mode, obtain structure cell ginseng through least square refinement Number, utilizes software to solve crystal structure from difference Fourier electron-density map, and through Lorentz lorentz and polarity effect correction.All of H atom is synthesized by difference Fourier and determines through preferable position calculation.Detailed axonometry data are shown in Table 1.Structural motif is shown in Fig. 1, two-dimensional layered structure is shown in Fig. 2.
The crystallographic data of table 1. complex 1
Embodiment 4
The concrete instance that dyestuff or luminous agent use
Method: differentiated pulse volt-ampere (DPV) the curve negotiating Princeton Applied Research Laboratory of dye solution is developed PARSTAT 2273 electrochemical workstation is measured.The DPV test of solution uses three-electrode system, and glass-carbon electrode is working electrode, Auxiliary electrode is platinum plate electrode, homemade Ag/AgNO3Electrode is reference electrode;Electrolyte is the acetonitrile of 0.1mol L-1TBAP Solution.With the Oxidation of Ferrocene reversible point of reduction to as internal standard, obtain the corrected value between test system and standard hydrogen electrode system.
Monochromatic incident light photoelectric transformation efficiency (IPCE) describes DSCs photoelectric transformation efficiency under monochromatic light effect, is to turn Move on to the electron number of external circuit and the ratio of incident light subnumber.During measurement, 500 W xenon lamps are used to pass through as light source, incident light The multifunctional assembled grating spectrograph of WDS-5 type obtains the monochromatic light under different wave length λ;Monochromatic light exposure is in the light sun of battery Pole, is read current value I by Keithley2400 digital sourcemeter.Monochromatic good fortune illumination is micro-by USB4000 plug-and-play Type light spectral instrument is measured.
Step: in order to have any actual knowledge of dyestuff at TiO2Adsorbance on film, by dye sensitization TiO2Nanometer crystal film (geometric surface Long-pending about 1 cm2) it is immersed in 10 mL 0.01 mol L-1NaOH methanol solution in overnight, treat that dyestuff desorbs completely The absorbance of rear mensuration solution.Wash one's face and rinse one's mouth according to absorbance and molar absorptivity and can calculate dyestuff on unit are nanometer crystal film Adsorbance.The adsorbance of this complex is 5.2 × 10-4 mol/cm2
Result: compared with the methanol solution of dyestuff, dyestuff is at TiO2Absorption spectrum on film the most substantially broadens and red shift.This Show that dye molecule is at TiO2Define the first and J-aggregation of tail.Say from the operation principle of DSCs, the light that dye aggregation causes Spectrum width and red shift are highly beneficial for the widening of photoelectric respone scope of dyestuff.But meanwhile, dye aggregation is known from experience It is substantially reduced its electron injection efficiency, thus causes the degraded performance of DSCs.So, in dye solution, generally add eutectoid content Agent suppresses the gathering of dyestuff.This complex is in methanol solution and at TiO2The fluorometric investigation of the purple solution on membrane electrode is adopted With 2.5 × 10-5The methanol solution of mol/L, maximum emission wavelength is positioned at 570 nm.
After the preferred embodiment described in detail, it is familiar with this skilled worker and is clearly understood that, without departing from above-mentioned Can carry out various change and amendment under claim and spirit, all technical spirit according to the present invention are to above example institute Any simple modification, equivalent variations and the modification made, belongs to the scope of technical solution of the present invention.And the present invention is not illustrated The restriction of example embodiment in book.

Claims (2)

1. the monocrystalline of the double triazole M-phthalic acid cadmium complex of naphthalene, it is characterised in that this mono-crystalline structures uses APEX II CCD mono- Brilliant diffractometer, uses through graphite monochromatised Mok alpha ray, and λ=0.71073 is incident radiation, with ω-2 θ scan mode Collect point diffraction, obtain cell parameter through least square refinement, utilize software to solve from difference Fourier electron-density map Single crystal data:
The structure of the double triazole M-phthalic acid cadmium complex monocrystalline of described naphthalene: { [Cd (L) (ipa)] 0.25H2O};Wherein L= 1-[7-(1H-1,2,4-triazole-1-bases) naphthalene-2-base)-1H-1,2,4-triazoles, ipa=M-phthalic acid.
2. the double triazole M-phthalic acid cadmium complex monocrystalline of naphthalene described in claim 1 is in terms of preparation is as potential fluorescent material Application.
CN201510088026.0A 2015-02-26 2015-02-26 Double triazole M-phthalic acid cadmium complex of naphthalene with potential fluorescent material and preparation method thereof Expired - Fee Related CN104592267B (en)

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CN105524094A (en) * 2016-01-05 2016-04-27 天津师范大学 1, 4-dimethyl-2, 5-dimethylene bistriazole inclusion N, N'-diethyl acetamide cadmium complex single crystal
CN105418660A (en) * 2016-01-05 2016-03-23 天津师范大学 1,4-dimethyl-2,5-dimethylene bis(triazole)cadimium complex single crystal and application
CN105418657A (en) * 2016-01-05 2016-03-23 天津师范大学 1,4-dimethyl-2,5-dimethylene bis(triazole)isophthalic acid-included dimethylacetamide cadimium complex single crystal and application
CN105503913A (en) * 2016-01-05 2016-04-20 天津师范大学 1, 4-dimethyl-2, 5-dimethylene bis triazole cadmium terephthalate complex single crystal and application
CN105524096A (en) * 2016-01-05 2016-04-27 天津师范大学 1, 4-dimethyl-2, 5-dimethylene bistriazole isophthalic acid inclusion diethyl formamide cadmium complex single crystal and application thereof
CN105541881A (en) * 2016-01-05 2016-05-04 天津师范大学 1,4-dimethyl-2,5-dimethylene bis(triazole) three-dimensional cadmium complex single crystal and application
CN105418658A (en) * 2016-01-05 2016-03-23 天津师范大学 1,4-dimethyl-2,5-dimethylene bis triazol one-dimensional cadmium complex single crystal and application
CN105418654A (en) * 2016-01-05 2016-03-23 天津师范大学 1,4-dimethyl-2,5-dimethylene bis(triazole) 5-methyl isophthalic acid cadimium complex single crystal and application
CN105418659A (en) * 2016-01-05 2016-03-23 天津师范大学 1,4-dimethyl-2,5-dimethylene bis triazol hydroxyphenylacetic isophthalic acid cadmium complex single crystal and application
CN112592358B (en) * 2020-12-18 2022-12-13 闽都创新实验室 Blue light luminescent crystal material and preparation method and application thereof

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