CN104628750A - Anthracene ring bis-triazole zinc complex with potential fluorescent material and preparation method thereof - Google Patents
Anthracene ring bis-triazole zinc complex with potential fluorescent material and preparation method thereof Download PDFInfo
- Publication number
- CN104628750A CN104628750A CN201510088008.2A CN201510088008A CN104628750A CN 104628750 A CN104628750 A CN 104628750A CN 201510088008 A CN201510088008 A CN 201510088008A CN 104628750 A CN104628750 A CN 104628750A
- Authority
- CN
- China
- Prior art keywords
- triazole
- ipa
- dmf
- anthracene
- base
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 239000000463 material Substances 0.000 title claims abstract description 7
- SIFAPWXAIHQOMZ-UHFFFAOYSA-N [Zn].N1=NC(N=C1)=C1N=NC=N1 Chemical compound [Zn].N1=NC(N=C1)=C1N=NC=N1 SIFAPWXAIHQOMZ-UHFFFAOYSA-N 0.000 title abstract 3
- 125000005577 anthracene group Chemical group 0.000 title abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 86
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000013078 crystal Substances 0.000 claims abstract description 14
- 239000000706 filtrate Substances 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 6
- 239000012046 mixed solvent Substances 0.000 claims abstract description 6
- 238000003756 stirring Methods 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001454 anthracenes Chemical class 0.000 claims description 13
- 150000003852 triazoles Chemical class 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 230000005260 alpha ray Effects 0.000 claims description 3
- 238000002447 crystallographic data Methods 0.000 claims description 3
- 229910002804 graphite Inorganic materials 0.000 claims description 3
- 239000010439 graphite Substances 0.000 claims description 3
- 230000005855 radiation Effects 0.000 claims description 3
- 239000011701 zinc Substances 0.000 abstract 4
- 238000001704 evaporation Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 14
- 239000000975 dye Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- BRUOAURMAFDGLP-UHFFFAOYSA-N 9,10-dibromoanthracene Chemical compound C1=CC=C2C(Br)=C(C=CC=C3)C3=C(Br)C2=C1 BRUOAURMAFDGLP-UHFFFAOYSA-N 0.000 description 8
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
- 235000015320 potassium carbonate Nutrition 0.000 description 7
- 229960004643 cupric oxide Drugs 0.000 description 6
- 229910010413 TiO 2 Inorganic materials 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- NSPMIYGKQJPBQR-CVMUNTFWSA-N 1h-1,2,4-triazole Chemical class [13CH]=1[15N]=[13CH][15NH][15N]=1 NSPMIYGKQJPBQR-CVMUNTFWSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- 230000000274 adsorptive effect Effects 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 101710134784 Agnoprotein Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000019771 cognition Effects 0.000 description 1
- 238000005564 crystal structure determination Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000001455 metallic ions Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- GRONZTPUWOOUFQ-UHFFFAOYSA-M sodium;methanol;hydroxide Chemical compound [OH-].[Na+].OC GRONZTPUWOOUFQ-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/06—Zinc compounds
-
- 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
- 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
- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
Abstract
The invention discloses a structure element of an anthracene ring bis-triazole zinc complex Zn(L)(DMF)(ipa) (1) expressed by the formula 1 and discloses a preparation method of Zn(L)(DMF)(ipa) (1) (L=1-[9-(1H-1,2,4-triazole-1-yl) anthracene-10-yl]-1H-1,2,4-triazole, ipa=m-phthalic acid, DMF=N,N'-dimethyl formamide). The method adopts the normal temperature evaporation method, and comprises the steps of stirring Zn(NO3)2.6H2O, ipa and L in the mixed solvent of DMF and water for half an hour and filtering, and volatilizing the filtrate for a week at normal temperature to obtain the yellow rod crystal which is suitable for X-ray single crystal diffraction. The application of the anthracene ring bis-triazole zinc complex Zn(L)(DMF)(ipa) (1) (L=1-[9-(1H-1,2,4-triazole-1-yl) anthracene-10-yl]-1H-1,2,4-triazole, ipa=m-phthalic acid, DMF=N,N'-dimethyl formamide) as the potential fluorescent material is also disclosed.
Description
Technical field
The invention belongs to organic and Inorganic synthese technical field, relate to the two triazole Zn complex [Zn (L) (DMF) (ipa)] of anthracene nucleus (
1) (L=1-[9-(1H-1,2,4-triazole-1-base) anthracene-10-base]-1H-1,2,4-triazole, ipa=m-phthalic acid, DMF=N, N'-dimethyl formamide) preparation method and 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 selects Zn (NO
3)
26H
2o, ipa and L filter stir half an hour in the mixed solvent of DMF and water after, filtrate normal temperature obtain after volatilizing one week applicable X-ray single crystal diffraction yellow rhabdolith [Zn (L) (DMF) (ipa)] (
1) (L=1-[9-(1H-1,2,4-triazole-1-base) anthracene-10-base]-1H-1,2,4-triazole, ipa=m-phthalic acid, DMF=N, N'-dimethyl formamide).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 be to provide the two triazole Zn complex [Zn (L) (DMF) (ipa)] of a kind of anthracene nucleus (
1) (L=1-[9-(1H-1,2,4-triazole-1-base) anthracene-10-base]-1H-1,2,4-triazole, ipa=m-phthalic acid, DMF=N, N'-dimethyl formamide) monocrystalline and preparation method thereof.
Current inventor provides following technical scheme for this reason:
The two triazole Zn complex [Zn (L) (DMF) (ipa)] of anthracene nucleus (
1) (L=1-[9-(1H-1,2,4-triazole-1-base) anthracene-10-base]-1H-1,2,4-triazole, ipa=m-phthalic acid, DMF=N, N'-dimethyl formamide) structural motif as shown in Figure 1.
The present invention further discloses the two triazole Zn complex [Zn (L) (DMF) (ipa)] of anthracene nucleus (
1) (L=1-[9-(1H-1,2,4-triazole-1-base) anthracene-10-base]-1H-1,2,4-triazole, ipa=m-phthalic acid, DMF=N, N'-dimethyl formamide) 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
The two triazole Zn complex [Zn (L) (DMF) (ipa)] of anthracene nucleus of the present invention (
1) (L=1-[9-(1H-1,2,4-triazole-1-base) anthracene-10-base]-1H-1,2,4-triazole, ipa=m-phthalic acid, DMF=N, N'-dimethyl formamide) preparation method of monocrystalline, its feature is at employing " normal temperature volatilization method ", i.e. Zn (NO
3)
26H
2o, ipa and L filter stir half an hour in the mixed solvent of DMF and water after, and filtrate normal temperature volatilizees one week to prepare this title complex
The present invention's preferred example:
The preparation of 1-[9-(1H-1,2,4-triazole-1-base) anthracene-10-base]-1H-1,2,4-triazole (L)
" one kettle way " is adopted at polar solvent, by 9,10-dibromoanthracene, 1H-1,2,4-triazole, salt of wormwood and cupric oxide react preparation in a heated condition; Wherein 9,10-dibromoanthracenes: 1H-1,2,4-triazole: salt of wormwood: the mol ratio of cupric oxide is 2:10-15:30:1;
9,10-dibromoanthracene
1H-1,2,4-triazole
The present invention is 9,10-dibromoanthracenes preferably: 1H-1,2,4-triazole: salt of wormwood: the mol ratio of cupric oxide is 2:10-15:30:1; Temperature of reaction 100 DEG C, 48 hours reaction times.In polar solvent, adopt " one kettle way ", by 9,10-dibromoanthracene, 1H-1,2,4-triazole, this organic compound prepared in a heated condition by salt of wormwood and cupric oxide;
Another preferred embodiment of the present invention
L (0.2 mmol), Zn (NO
3)
2(0.2 mmol) and m-phthalic acid (0.1 mmol) are at DMF (2 mL) and H
2filter after stirring half an hour in the mixed solvent of O (6 mL), filtrate is yellow, and normal temperature has the yellow rhabdolith of applicable X-ray single crystal diffraction after volatilizing one week.Productive rate: 45%.Ultimate analysis (C
29h
23n
7o
5zn) theoretical value (%): C, 56.64; H, 3.77; N, 15.94.Measured value: C, 56.55; H, 3.80; N, 15.89.
The present invention further discloses the two triazole Zn complex [Zn (L) (DMF) (ipa)] of anthracene nucleus (
1) (L=1-[9-(1H-1,2,4-triazole-1-base) anthracene-10-base]-1H-1,2,4-triazole, ipa=m-phthalic acid, DMF=N, N'-dimethyl formamide) can be used as potential fluorescent material aspect and applied.
The two triazole Zn complex of a kind of anthracene nucleus disclosed by the invention [Zn (L) (DMF) (ipa)] (
1) advantage and disadvantage that has of (L=1-[9-(1H-1,2,4-triazole-1-base) anthracene-10-base]-1H-1,2,4-triazole, ipa=m-phthalic acid, DMF=N, N'-dimethyl formamide) 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) prepared by the present invention [Zn (L) (DMF) (ipa)] (
1) (L=1-[9-(1H-1,2,4-triazole-1-base) anthracene-10-base]-1H-1,2,4-triazole, ipa=m-phthalic acid, DMF=N, N'-dimethyl formamide) production cost is low, and method is easy, is applicable to scale operation.
Accompanying drawing explanation
Fig. 1: title complex
1crystalline structure primitive figure;
Fig. 2: title complex
1tomograph.
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.All raw materials are such as: anthracene nucleus etc. are all buy from chemical reagents corporation both domestic and external, through continuing to purify but directly use.Raw materials used 9,10-dibromoanthracenes, 1H-1,2,4-triazole, salt of wormwood, cupric oxide etc. all have commercially available.
Embodiment 1
9,10-dibromoanthracene: 1H-1,2,4-triazole: salt of wormwood: the mol ratio of cupric oxide is 2:10-15:30:1
CuO (0.0398 mg is added respectively in 50 mL, tri-mouthfuls of round-bottomed flasks that magneton, reflux exchanger and thermometer are housed, 0.5 mmol), salt of wormwood (2.0731 g, 15 mmol), 1H-1,2,4-triazole (0.345 mg, 5 mmol), 9,10-dibromoanthracene (0.3360 g, 1 mmol), 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, separates out and precipitates in a large number, suction filtration, collects filter cake, (L)=1-[9-(1H-1,2,4-triazole-1-base) anthracene-10-base]-1H-1,2,4-triazole, yield 60%.
Embodiment 2
1-[9-(1H-1,2,4-triazole-1-base) anthracene-10-base]-1H-1,2,4-triazole (L) (0.2 mmol), Zn (NO
3)
26H
2o (0.2 mmol) and ipa (0.1 mmol) is at DMF (2 mL) and H
2filter after stirring half an hour in the mixed solvent of O (6 mL), filtrate is yellow, and normal temperature has the yellow rhabdolith of applicable X-ray single crystal diffraction after volatilizing one week.Productive rate: 45%.Ultimate analysis (C
29h
23n
7o
5zn) theoretical value (%): C, 56.64; H, 3.77; N, 15.94.Measured value: C, 56.55; H, 3.80; N, 15.89.
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 three-dimensional frame 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 1.3 × 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 560 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. the two triazole Zn complex [Zn (L) (DMF) (ipa)] of anthracene nucleus (
1) structural motif as shown in Figure 1:
L=1-[9-(1H-1,2,4-triazole-1-base) anthracene-10-base]-1H-1,2,4-triazole, ipa=m-phthalic acid, DMF=N, N'-dimethyl formamide.
2. the monocrystalline of the two triazole Zn complex of anthracene nucleus 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. the two triazole Zn complex [Zn (L) (DMF) (ipa)] of anthracene nucleus described in claim 1 (
1) (L=1-[9-(1H-1,2,4-triazole-1-base) anthracene-10-base]-1H-1,2,4-triazole, ipa=m-phthalic acid, DMF=N, N'-dimethyl formamide) preparation method, it is characterized in that it be adopt " normal temperature volatilization method ", i.e. Zn (NO
3)
26H
2o, ipa and L filter stir half an hour in the mixed solvent of DMF and water after, and filtrate normal temperature volatilizees one week to prepare this title complex
L ipa。
4. the two triazole Zn complex [Zn (L) (DMF) (ipa)] of anthracene nucleus described in claim 1 (
1) (L=1-[9-(1H-1,2,4-triazole-1-base) anthracene-10-base]-1H-1,2,4-triazole, ipa=m-phthalic acid, DMF=N, N'-dimethyl formamide) as the application of potential fluorescent material aspect.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510088008.2A CN104628750B (en) | 2015-02-26 | 2015-02-26 | A kind of double; two triazole Zn complex of anthracene nucleus with potential fluorescent material and preparation method thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510088008.2A CN104628750B (en) | 2015-02-26 | 2015-02-26 | A kind of double; two triazole Zn complex of anthracene nucleus with potential fluorescent material and preparation method thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
CN104628750A true CN104628750A (en) | 2015-05-20 |
CN104628750B CN104628750B (en) | 2016-06-08 |
Family
ID=53208036
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201510088008.2A Expired - Fee Related CN104628750B (en) | 2015-02-26 | 2015-02-26 | A kind of double; two triazole Zn complex of anthracene nucleus with potential fluorescent material and preparation method thereof |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN104628750B (en) |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105503910A (en) * | 2016-01-05 | 2016-04-20 | 天津师范大学 | 1, 4-dimethyl-2, 5-dimethylene bis triazole two-dimensional zinc m-phthalate complex single crystal and application |
CN105524090A (en) * | 2016-01-05 | 2016-04-27 | 天津师范大学 | 1, 4-dimethyl-2, 5-dimethylene bistriazole two-dimensional layered zinc complex single crystal and application thereof |
CN105524084A (en) * | 2016-01-05 | 2016-04-27 | 天津师范大学 | One-dimensional zinc complex single crystal and preparation method and application thereof |
CN105524091A (en) * | 2016-01-05 | 2016-04-27 | 天津师范大学 | 1, 4-dimethyl-2, 5-dimethylene bistriazole zinc complex single crystal and application thereof |
CN105524089A (en) * | 2016-01-05 | 2016-04-27 | 天津师范大学 | 1, 4-dimethyl-2, 5-dimethylene bistriazole three-dimensional zinc complex single crystal and preparation method and application thereof |
CN105524098A (en) * | 2016-01-05 | 2016-04-27 | 天津师范大学 | 1, 4-dimethyl-2, 5-dimethylene bistriazole isophthalic acid cadmium complex single crystal and application thereof |
CN105524085A (en) * | 2016-01-05 | 2016-04-27 | 天津师范大学 | 1, 4-dimethyl-2, 5-dimethylene bistriazole terephthalic acid three-dimensional zinc complex single crystal and application thereof |
CN105601655A (en) * | 2016-01-05 | 2016-05-25 | 天津师范大学 | 1,4-dimethyl-2,5-dimethylene bis-triazole two-dimensional zinc complex single crystals and application |
CN105601654A (en) * | 2016-01-05 | 2016-05-25 | 天津师范大学 | 1,4-dibromo-2,5-dimethylene bis-triazole two-dimensional zinc complex single crystals and application |
CN105622651A (en) * | 2016-01-05 | 2016-06-01 | 天津师范大学 | 1,4-dimethyl-2,5-dimethylene bistriazole inclusion diethyl formamide two-dimensional zinc complex single crystal and application thereof |
CN105622650A (en) * | 2016-01-05 | 2016-06-01 | 天津师范大学 | 1,2,4,5-tetramethyl benzene bistriazole two-dimensional zinc complex single crystal and application thereof |
CN105622649A (en) * | 2016-01-05 | 2016-06-01 | 天津师范大学 | Anthracycline bis(triazol) isophthalic acid-included zinc dimethylacetamide complex single crystal and application thereof |
CN105622652A (en) * | 2016-01-05 | 2016-06-01 | 天津师范大学 | 1,4-dimethyl-2,5-dimethylene bistriazole isophthalic acid zinc complex single crystal and application thereof |
CN105669719A (en) * | 2016-01-05 | 2016-06-15 | 天津师范大学 | Zinc 1,4-dimethyl-2,5-dimethylenebistriazolyl-5-methyl-m-phthalate complex monocrystal and application thereof |
CN105669720A (en) * | 2016-01-05 | 2016-06-15 | 天津师范大学 | 1,4-Dimethyl-2,5-dimethylenebistriazol layered zinc complex monocrystal and application thereof |
CN111410646A (en) * | 2019-12-26 | 2020-07-14 | 江西科技师范大学 | 9, 10-dipyrrolyl anthracene fluorescent compound and preparation method and application thereof |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103772418A (en) * | 2014-01-13 | 2014-05-07 | 刘国政 | Coordination polymer with mixed ligand and preparation method thereof |
CN103772303A (en) * | 2014-01-14 | 2014-05-07 | 天津师范大学 | Anthracene ring triazole compound, and preparation method and application thereof |
-
2015
- 2015-02-26 CN CN201510088008.2A patent/CN104628750B/en not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103772418A (en) * | 2014-01-13 | 2014-05-07 | 刘国政 | Coordination polymer with mixed ligand and preparation method thereof |
CN103772303A (en) * | 2014-01-14 | 2014-05-07 | 天津师范大学 | Anthracene ring triazole compound, and preparation method and application thereof |
Non-Patent Citations (3)
Title |
---|
FU-HONG LIU 等: "Pillared metal organic frameworks for the luminescence sensing of small molecules and metal ions in aqueous solutions", 《DALTON TRANSACTIONS》, vol. 44, 17 November 2014 (2014-11-17) * |
JU-YAN LIU等: "Anion-Exchange and Anthracene-Encapsulation within Copper(II) and Manganese(II)-Triazole Metal-Organic Confined Space in a Single Crystal-to-Single Crystal Transformation Fashion", 《INORGANIC CHEMISTRY》, vol. 53, 27 May 2014 (2014-05-27), pages 5972 - 5985 * |
苗少斌: "基于1,2,4-三氮唑配体的配位聚合物的合成、结构和性能研究", 《中国博士学位论文全文数据库 工程科技Ⅰ辑》, no. 2, 15 February 2015 (2015-02-15) * |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105503910A (en) * | 2016-01-05 | 2016-04-20 | 天津师范大学 | 1, 4-dimethyl-2, 5-dimethylene bis triazole two-dimensional zinc m-phthalate complex single crystal and application |
CN105524090A (en) * | 2016-01-05 | 2016-04-27 | 天津师范大学 | 1, 4-dimethyl-2, 5-dimethylene bistriazole two-dimensional layered zinc complex single crystal and application thereof |
CN105524084A (en) * | 2016-01-05 | 2016-04-27 | 天津师范大学 | One-dimensional zinc complex single crystal and preparation method and application thereof |
CN105524091A (en) * | 2016-01-05 | 2016-04-27 | 天津师范大学 | 1, 4-dimethyl-2, 5-dimethylene bistriazole zinc complex single crystal and application thereof |
CN105524089A (en) * | 2016-01-05 | 2016-04-27 | 天津师范大学 | 1, 4-dimethyl-2, 5-dimethylene bistriazole three-dimensional zinc complex single crystal and preparation method and application thereof |
CN105524098A (en) * | 2016-01-05 | 2016-04-27 | 天津师范大学 | 1, 4-dimethyl-2, 5-dimethylene bistriazole isophthalic acid cadmium complex single crystal and application thereof |
CN105524085A (en) * | 2016-01-05 | 2016-04-27 | 天津师范大学 | 1, 4-dimethyl-2, 5-dimethylene bistriazole terephthalic acid three-dimensional zinc complex single crystal and application thereof |
CN105601655A (en) * | 2016-01-05 | 2016-05-25 | 天津师范大学 | 1,4-dimethyl-2,5-dimethylene bis-triazole two-dimensional zinc complex single crystals and application |
CN105601654A (en) * | 2016-01-05 | 2016-05-25 | 天津师范大学 | 1,4-dibromo-2,5-dimethylene bis-triazole two-dimensional zinc complex single crystals and application |
CN105622651A (en) * | 2016-01-05 | 2016-06-01 | 天津师范大学 | 1,4-dimethyl-2,5-dimethylene bistriazole inclusion diethyl formamide two-dimensional zinc complex single crystal and application thereof |
CN105622650A (en) * | 2016-01-05 | 2016-06-01 | 天津师范大学 | 1,2,4,5-tetramethyl benzene bistriazole two-dimensional zinc complex single crystal and application thereof |
CN105622649A (en) * | 2016-01-05 | 2016-06-01 | 天津师范大学 | Anthracycline bis(triazol) isophthalic acid-included zinc dimethylacetamide complex single crystal and application thereof |
CN105622652A (en) * | 2016-01-05 | 2016-06-01 | 天津师范大学 | 1,4-dimethyl-2,5-dimethylene bistriazole isophthalic acid zinc complex single crystal and application thereof |
CN105669719A (en) * | 2016-01-05 | 2016-06-15 | 天津师范大学 | Zinc 1,4-dimethyl-2,5-dimethylenebistriazolyl-5-methyl-m-phthalate complex monocrystal and application thereof |
CN105669720A (en) * | 2016-01-05 | 2016-06-15 | 天津师范大学 | 1,4-Dimethyl-2,5-dimethylenebistriazol layered zinc complex monocrystal and application thereof |
CN111410646A (en) * | 2019-12-26 | 2020-07-14 | 江西科技师范大学 | 9, 10-dipyrrolyl anthracene fluorescent compound and preparation method and application thereof |
Also Published As
Publication number | Publication date |
---|---|
CN104628750B (en) | 2016-06-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN104628750A (en) | Anthracene ring bis-triazole zinc complex with potential fluorescent material and preparation method thereof | |
CN104610302A (en) | Antharcycline bis-triazole terephthalic acid zinc complex with potential fluorescent material and preparation method of antharcycline bis-triazole terephthalic acid zinc complex | |
CN104592271A (en) | Cadmium isophthalate anthracene cyclo-bis(triazolyl) complex used as potential fluorescent material and preparation method of cadmium isophthalate anthracene cyclo-bis(triazolyl) complex | |
CN104592267A (en) | Cadmium naphthalene bis(triazolyl) isophthalate complex used as potential fluorescent material and preparation method of cadmium naphthalene bis(triazolyl) isophthalate complex | |
CN104592262A (en) | Zinc anthracene cyclo-bis(triazolyl) isophthalate complex used as potential fluorescent material and preparation method of zinc anthracene cyclo-bis(triazolyl) isophthalate complex | |
CN104610315A (en) | Cadmium oxyether bistriazol isophthalate complex with potential fluorescent material and preparation method of complex | |
CN104610295A (en) | Potential fluorescent material containing tetraphenylethylene tetra-triazole zinc terephthalate complex and preparation method thereof | |
CN104610290A (en) | Tetraphenyl ethylene 4-triazole zinc chloride complex serving as potential fluorescent material and preparation method thereof | |
CN104557991A (en) | Oxyether bistriazole zinc chloride complex with potential fluorescent material and preparation method thereof | |
CN104610320A (en) | Fluorescent material containing tetraphenylethylene-4-triazole three-dimensional cadmium complex and preparation method thereof | |
CN104628749A (en) | Tetraphenyl ethylene triazole zinc perchlorate complex with potential fluorescent material and preparation method of complex | |
CN104610299A (en) | Zinc naphthalene bistriazole terephthalic acid complex used as potential fluorescent material and preparation method thereof | |
CN104592270A (en) | Cadmium isophthalate anthracene cyclo-bis(triazolyl) nitrate complex used as potential fluorescent material and preparation method of cadmium isophthalate anthracene cyclo-bis(triazolyl) nitrate complex | |
CN104557992A (en) | Naphthalene bistriazole trimesinic acid cadmium complex with potential fluorescent material and preparation method thereof | |
CN104610378A (en) | Oxygen ether double-triazole nickle complex with potential fluorescent material and preparation method thereof | |
CN104610287A (en) | Oxygen ether double-triazole one-dimensional copper complex with potential fluorescent material and preparation method thereof | |
CN104610313B (en) | Two triazole cadmium complex of oxygen ether with potential fluorescent material and preparation method thereof | |
CN104610292A (en) | Tetraphenyl ethylene tetra-triazole zinc nitrate complex with potential fluorescent material and preparation method of complex | |
CN104592260A (en) | Zinc anthracene cyclo-bis(triazolyl) perchlorate complex used as potential fluorescent material and preparation method of zinc anthracene cyclo-bis(triazolyl) perchlorate complex | |
CN104610304A (en) | Oxygen ether double-triazole zinc complex with potential fluorescent material and preparation method thereof | |
CN104592265A (en) | Cadmium phthalate anthracene cyclo-bis(triazolyl) complex used as potential fluorescent material and preparation method of cadmium phthalate anthracene cyclo-bis(triazolyl) complex | |
CN104610319A (en) | Tetraphenylethylene 4-triazole cadmium perchlorate complex with potential fluorescence material and preparation method of tetraphenylethylene 4-triazole cadmium perchlorate complex | |
CN104592272A (en) | Cadmium tetraphenyl ethylene-tetra(triazolyl) bromide complex used as potential fluorescent material and preparation method of cadmium tetraphenyl ethylene-tetra(triazolyl) bromide complex | |
CN104610380A (en) | Potential fluorescent material containing tri-iodo-aniline-3,3-azole terephthalic cobalt complex and preparation method thereof | |
CN104610293A (en) | Naphthalene bistriazole trimesic acid zinc complex with potential fluorescent material and preparation method thereof |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20160608 Termination date: 20170226 |
|
CF01 | Termination of patent right due to non-payment of annual fee |