CN104628749A - Tetraphenyl ethylene triazole zinc perchlorate complex with potential fluorescent material and preparation method of complex - Google Patents
Tetraphenyl ethylene triazole zinc perchlorate complex with potential fluorescent material and preparation method of complex Download PDFInfo
- Publication number
- CN104628749A CN104628749A CN201510088000.6A CN201510088000A CN104628749A CN 104628749 A CN104628749 A CN 104628749A CN 201510088000 A CN201510088000 A CN 201510088000A CN 104628749 A CN104628749 A CN 104628749A
- Authority
- CN
- China
- Prior art keywords
- triazole
- title complex
- zinc perchlorate
- complex
- tetraphenyl ethylene
- 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.)
- Pending
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 239000000463 material Substances 0.000 title claims abstract description 8
- LXGGXEACVVAXPO-UHFFFAOYSA-L zinc 2H-triazole 1,2,2-triphenylethenylbenzene diperchlorate Chemical compound Cl(=O)(=O)(=O)[O-].[Zn+2].N1N=NC=C1.C1(=CC=CC=C1)C(=C(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.Cl(=O)(=O)(=O)[O-] LXGGXEACVVAXPO-UHFFFAOYSA-L 0.000 title abstract 4
- 239000011701 zinc Substances 0.000 claims abstract description 20
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000013078 crystal Substances 0.000 claims abstract description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000012046 mixed solvent Substances 0.000 claims abstract description 6
- JLZUZNKTTIRERF-UHFFFAOYSA-N tetraphenylethylene Chemical group C1=CC=CC=C1C(C=1C=CC=CC=1)=C(C=1C=CC=CC=1)C1=CC=CC=C1 JLZUZNKTTIRERF-UHFFFAOYSA-N 0.000 claims description 12
- -1 triazole zinc perchlorate Chemical class 0.000 claims description 12
- 229910020366 ClO 4 Inorganic materials 0.000 claims description 11
- 239000000706 filtrate Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 5
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 10
- 229910001914 chlorine tetroxide Inorganic materials 0.000 abstract 3
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 abstract 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- 239000005977 Ethylene Substances 0.000 abstract 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 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
- BIRLDGKMJJEZRI-UHFFFAOYSA-N 1-bromo-4-[1,2,2-tris(4-bromophenyl)ethenyl]benzene Chemical compound C1=CC(Br)=CC=C1C(C=1C=CC(Br)=CC=1)=C(C=1C=CC(Br)=CC=1)C1=CC=C(Br)C=C1 BIRLDGKMJJEZRI-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 5
- 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
- 230000035484 reaction time Effects 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
- 150000003852 triazoles Chemical class 0.000 description 2
- NSPMIYGKQJPBQR-CVMUNTFWSA-N 1h-1,2,4-triazole Chemical class [13CH]=1[15N]=[13CH][15NH][15N]=1 NSPMIYGKQJPBQR-CVMUNTFWSA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
-
- 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 tetraphenyl ethylene triazole zinc perchlorate complex with a potential fluorescent material and a preparation method of the complex. Structure units of the tetraphenyl ethylene triazole zinc perchlorate complex [Zn(L)(ClO4)2](1) are shown in figure 1. The invention also discloses a preparation method of [Zn(L)(ClO4)2](1)(L=1,1,2,2-quadri[4-(1H-1,2,4-triazole-1-base) phenyl] ethylene). A normal-temperature volatilization method is adopted, i.e., L and Zn(ClO4)2.6H2O are stirred in a mixed solvent of CHCl3, CH3OH, water and DMF for half hour and then are filtered, and the filter solution is volatilized for two weeks at a normal temperature to obtain colorless block-shaped crystals which are suitable for the X-ray single crystal diffraction. The invention also discloses an application of the tetraphenyl ethylene triazole zinc perchlorate complex as a potential fluorescent material.
Description
Technical field
The invention belongs to organic and Inorganic synthese technical field, relate to and state tetraphenyl ethylene four triazole zinc perchlorate title complex [Zn (L) (ClO
4)
2] (
1) preparation method of (L=1,1,2,2-tetra-[4-(1H-1,2,4-triazole-1-base) phenyl] ethene) 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 Zn (ClO
4)
26H
2o is at CHCl
3, CH
3filter after stirring half an hour in the mixed solvent of OH, water and DMF, filtrate normal temperature obtains colourless bulk crystals [Zn (the L) (ClO of applicable X-ray single crystal diffraction after volatilizing two weeks
4)
2] (
1) (L=1,1,2,2-tetra-[4-(1H-1,2,4-triazole-1-base) phenyl] ethene).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 tetraphenyl ethylene four triazole zinc perchlorate title complex [Zn (L) (ClO
4)
2] (
1) (L=1,1,2,2-tetra-[4-(1H-1,2,4-triazole-1-base) phenyl] ethene) monocrystalline and preparation method thereof.
Current inventor provides following technical scheme for this reason:
Tetraphenyl ethylene four triazole zinc perchlorate title complex [Zn (L) (ClO
4)
2] (
1) (L=1,1,2,2-tetra-[4-(1H-1,2,4-triazole-1-base) phenyl] ethene) structural motif as shown in Figure 1.
The present invention further discloses tetraphenyl ethylene four triazole zinc perchlorate title complex [Zn (L) (ClO
4)
2] (
1) (L=1,1,2,2-tetra-[4-(1H-1,2,4-triazole-1-base) phenyl] ethene) 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
Tetraphenyl ethylene four triazole zinc perchlorate title complex [Zn (L) (ClO of the present invention
4)
2] (
1) preparation method of (L=1,1,2,2-tetra-[4-(1H-1,2,4-triazole-1-base) phenyl] ethene) monocrystalline, adopt " normal temperature volatilization method ", i.e. L and Zn (ClO
4)
26H
2o is at CHCl
3, CH
3filter after stirring half an hour in the mixed solvent of OH, water and DMF, filtrate normal temperature volatilizees two weeks to prepare this title complex
L。
The present invention's preferred example:
The preparation of 1,1,2,2-tetra-[4-(1H-1,2,4-triazole-1-base) phenyl] ethene (L)
Adopt " one kettle way " at polar solvent, 1,1,2,2-tetra-(4-bromophenyl) ethene, 1H-1,2,4-triazole, salt of wormwood and cupric oxide are reacted preparation in a heated condition; Wherein 1,1,2,2-tetra-(4-bromophenyl) ethene: 1H-1,2,4-triazole: salt of wormwood: the mol ratio of cupric oxide is 2:10-15:30:1; Temperature of reaction 80-200 DEG C, reaction times 12-120 hour;
1,1,2,2-tetra-(4-bromophenyl) ethene
1H-1,2,4-triazole
The present invention is 1,1,2,2-tetra-(4-bromophenyl) ethene: 1H-1,2,4-triazole preferably: 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 ", 1,1,2,2-tetra-(4-bromophenyl) ethene, 1H-1,2,4-triazole, salt of wormwood and cupric oxide are prepared this organic compound in a heated condition;
Another preferred embodiment of the present invention
1,1,2,2-tetra-[4-(1H-1,2,4-triazole-1-base) phenyl] ethene (L) (0.1 mmol) and Zn (ClO
4)
26H
2o (0.1 mmol) is at CHCl
3(1 mL), CH
3filter after stirring half an hour in the mixed solvent of OH (4 mL), water (4 mL) and DMF (10 mL), 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
37h
27cl
15n
14o
6zn) theoretical value (%): C, 37.29; H, 2.29; N, 16.23.Measured value: C, 37.17; H, 2.22; N, 16.34.
The present invention further discloses tetraphenyl ethylene four triazole zinc perchlorate title complex [Zn (L) (ClO
4)
2] (
1) (L=1,1,2,2-tetra-[4-(1H-1,2,4-triazole-1-base) phenyl] ethene) can be used as potential fluorescent material aspect and applied.
A kind of tetraphenyl ethylene four triazole zinc perchlorate title complex [Zn (L) (ClO disclosed by the invention
4)
2] (
1) advantage and disadvantage that has of (L=1,1,2,2-tetra-[4-(1H-1,2,4-triazole-1-base) phenyl] ethene) 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) [Zn (the L) (ClO prepared by the present invention
4)
2] (
1) (L=1,1,2,2-tetra-[4-(1H-1,2,4-triazole-1-base) phenyl] ethene) 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
1two-dimentional chain-like 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 1,1,2,2-tetra-(4-bromophenyl) ethene, 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
1,1,2,2-tetra-(4-bromophenyl) ethene: triazole: salt of wormwood: the mol ratio of cupric oxide is 2:10-15:30:1
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), 1,1,2,2-tetra-(4-bromophenyl) ethene (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, separates out and precipitates in a large number, suction filtration, collects filter cake, 1,1,2,2-tetra-[4-(1H-1,2,4-triazole-1-base) phenyl] ethene (L).Yield 60%.
Embodiment 2
1,1,2,2-tetra-[4-(1H-1,2,4-triazole-1-base) phenyl] ethene (L) (0.1 mmol) and Zn (ClO
4)
26H
2o (0.1 mmol) is at CHCl
3(1 mL), CH
3filter after stirring half an hour in the mixed solvent of OH (4 mL), water (4 mL) and DMF (10 mL), 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
37h
27cl
15n
14o
6zn) theoretical value (%): C, 37.29; H, 2.29; N, 16.23.Measured value: C, 37.17; H, 2.22; N, 16.34.
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 two-dimensional layered 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 569 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. tetraphenyl ethylene four triazole zinc perchlorate title complex [Zn (L) (ClO
4)
2] (
1) structural motif as shown in Figure 1:
L=1,1,2,2-tetra-[4-(1H-1,2,4-triazole-1-base) phenyl] ethene.
2. the monocrystalline of tetraphenyl ethylene four triazole zinc perchlorate title complex described in claim 1, 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 software to solve single crystal data from difference Fourier electron density map through least-squares refinement:
Table 1. title complex
1crystallographic data
。
3. tetraphenyl ethylene four triazole zinc perchlorate title complex [Zn (L) (ClO described in claim 1
4)
2] (
1) preparation method of (L=1,1,2,2-tetra-[4-(1H-1,2,4-triazole-1-base) phenyl] ethene), it is characterized in that it adopts " normal temperature volatilization method ", i.e. L and Zn (ClO
4)
26H
2o is at CHCl
3, CH
3filter after stirring half an hour in the mixed solvent of OH, water and DMF, filtrate normal temperature volatilizees two weeks to prepare this title complex
L。
4. tetraphenyl ethylene four triazole zinc perchlorate title complex [Zn (L) (ClO described in claim 1
4)
2] (
1) (L=1,1,2,2-tetra-[4-(1H-1,2,4-triazole-1-base) phenyl] ethene) as the application of potential fluorescent material aspect.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510088000.6A CN104628749A (en) | 2015-02-26 | 2015-02-26 | Tetraphenyl ethylene triazole zinc perchlorate complex with potential fluorescent material and preparation method of complex |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510088000.6A CN104628749A (en) | 2015-02-26 | 2015-02-26 | Tetraphenyl ethylene triazole zinc perchlorate complex with potential fluorescent material and preparation method of complex |
Publications (1)
Publication Number | Publication Date |
---|---|
CN104628749A true CN104628749A (en) | 2015-05-20 |
Family
ID=53208035
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201510088000.6A Pending CN104628749A (en) | 2015-02-26 | 2015-02-26 | Tetraphenyl ethylene triazole zinc perchlorate complex with potential fluorescent material and preparation method of complex |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN104628749A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105418650A (en) * | 2016-01-05 | 2016-03-23 | 天津师范大学 | Potential fluorescent material tetraphenyl ethylene tetratriazole zinc bromide complex and preparing method thereof |
CN105418651A (en) * | 2016-01-05 | 2016-03-23 | 天津师范大学 | Potential fluorescent material tetraphenyl ethylene tetratriazole zinc silicofluoride complex and preparing method thereof |
CN105622648A (en) * | 2016-01-05 | 2016-06-01 | 天津师范大学 | Tetraphenyl ethylene tetra-triazole included methanol zinc perchlorate complex with potential fluorescent material and preparation method thereof |
CN105669717A (en) * | 2016-01-05 | 2016-06-15 | 天津师范大学 | 1,4-Dibromo-2,5-dimethylenebistriazol zinc complex monocrystal and application thereof |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104230996A (en) * | 2014-09-25 | 2014-12-24 | 天津师范大学 | Tetraphenyl ethylene manganese coordination compound, preparation method thereof, as well as application thereof as cadmium ion fluorescence probe |
CN104277074A (en) * | 2014-09-25 | 2015-01-14 | 天津师范大学 | Tetraphenyl ethylene manganese complex and application of complex in cadmium ion and zinc ion fluorescent probes |
-
2015
- 2015-02-26 CN CN201510088000.6A patent/CN104628749A/en active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104230996A (en) * | 2014-09-25 | 2014-12-24 | 天津师范大学 | Tetraphenyl ethylene manganese coordination compound, preparation method thereof, as well as application thereof as cadmium ion fluorescence probe |
CN104277074A (en) * | 2014-09-25 | 2015-01-14 | 天津师范大学 | Tetraphenyl ethylene manganese complex and application of complex in cadmium ion and zinc ion fluorescent probes |
Non-Patent Citations (1)
Title |
---|
WANG Y. ET AL,: ""Turn-On Fluorescence and Unprecedented Encapsulation of Large Aromatic Molecules within a Manganese(II)–Triazole Metal–Organic Confined Space"", 《CHEMISTRY A EUROPEAN JOURNAL》 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105418650A (en) * | 2016-01-05 | 2016-03-23 | 天津师范大学 | Potential fluorescent material tetraphenyl ethylene tetratriazole zinc bromide complex and preparing method thereof |
CN105418651A (en) * | 2016-01-05 | 2016-03-23 | 天津师范大学 | Potential fluorescent material tetraphenyl ethylene tetratriazole zinc silicofluoride complex and preparing method thereof |
CN105622648A (en) * | 2016-01-05 | 2016-06-01 | 天津师范大学 | Tetraphenyl ethylene tetra-triazole included methanol zinc perchlorate complex with potential fluorescent material and preparation method thereof |
CN105669717A (en) * | 2016-01-05 | 2016-06-15 | 天津师范大学 | 1,4-Dibromo-2,5-dimethylenebistriazol zinc complex monocrystal and application thereof |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN104628750A (en) | Anthracene ring bis-triazole zinc complex with potential fluorescent material and preparation method thereof | |
CN104610286B (en) | Two triazole cupric bromide title complex of oxygen ether with potential fluorescent material and preparation method thereof | |
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 | |
CN104610320A (en) | Fluorescent material containing tetraphenylethylene-4-triazole three-dimensional cadmium complex and preparation method thereof | |
CN104557991A (en) | Oxyether bistriazole zinc chloride complex with potential fluorescent material and preparation method thereof | |
CN104628749A (en) | Tetraphenyl ethylene triazole zinc perchlorate complex with potential fluorescent material and preparation method of complex | |
CN104610378A (en) | Oxygen ether double-triazole nickle complex with potential fluorescent material and preparation method thereof | |
CN104610299A (en) | Zinc naphthalene bistriazole terephthalic acid complex used as potential fluorescent material and preparation method thereof | |
CN104610313B (en) | Two triazole cadmium complex of oxygen ether with potential fluorescent material and preparation method thereof | |
CN104610322A (en) | Tetraphenyl ethylene tetratriazolyl cadmium acetate complex with potential fluorescent material and preparation method thereof | |
CN104610314A (en) | Oxygen ether bitriazol cadmium chloride complex with potential fluorescent material and preparation method of complex | |
CN104610321A (en) | Tetraphenyl ethylene four triazole terephthalic acid cadmium complex 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 | |
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 | |
CN104610304A (en) | Oxygen ether double-triazole zinc complex with potential fluorescent material and preparation method thereof | |
CN104610307A (en) | Zinc oxyether bistriazol acetate 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 | |
CN104610312A (en) | Tetraphenyl ethylene 4-triazole cadmium isophthalate complex serving as potential fluorescent material and preparation method thereof | |
CN104610380A (en) | Potential fluorescent material containing tri-iodo-aniline-3,3-azole terephthalic cobalt complex and preparation method thereof | |
CN104610368A (en) | Oxygen ether double-triazole manganese complex with potential fluorescent material and preparation method thereof | |
CN104628752A (en) | Tetraphenyl ethylene tetratriazole cadmium complex with potential fluorescent material 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 | ||
RJ01 | Rejection of invention patent application after publication |
Application publication date: 20150520 |
|
RJ01 | Rejection of invention patent application after publication |