CN104592265B - Double triazole phthalic acid cadmium complex of anthracene nucleus with potential fluorescent material and preparation method thereof - Google Patents
Double triazole phthalic acid cadmium complex of anthracene nucleus with potential fluorescent material and preparation method thereof Download PDFInfo
- Publication number
- CN104592265B CN104592265B CN201510088019.0A CN201510088019A CN104592265B CN 104592265 B CN104592265 B CN 104592265B CN 201510088019 A CN201510088019 A CN 201510088019A CN 104592265 B CN104592265 B CN 104592265B
- Authority
- CN
- China
- Prior art keywords
- triazole
- phthalic acid
- pta
- anthracene
- cadmium complex
- 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.)
- Expired - Fee Related
Links
- 150000003852 triazoles Chemical class 0.000 title claims abstract description 16
- JATDFGSGZLGMTA-UHFFFAOYSA-N cadmium;phthalic acid Chemical compound [Cd].OC(=O)C1=CC=CC=C1C(O)=O JATDFGSGZLGMTA-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 239000000463 material Substances 0.000 title claims abstract description 7
- 150000001454 anthracenes Chemical class 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title abstract description 8
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000013078 crystal Substances 0.000 claims abstract description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 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
- 230000005260 alpha ray Effects 0.000 claims description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical class C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 abstract description 14
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 8
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 abstract description 5
- 238000001027 hydrothermal synthesis Methods 0.000 abstract description 3
- 239000000975 dye Substances 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 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
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 7
- 239000005751 Copper oxide Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 229910000431 copper oxide Inorganic materials 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000005286 illumination Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002447 crystallographic data Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment 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
- 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
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(I) nitrate Inorganic materials [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 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
- 241000208340 Araliaceae Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- MOFINMJRLYEONQ-UHFFFAOYSA-N [N].C=1C=CNC=1 Chemical class [N].C=1C=CNC=1 MOFINMJRLYEONQ-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009286 beneficial effect Effects 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
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 238000005564 crystal structure determination Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000005516 engineering process Methods 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
- 239000000706 filtrate Substances 0.000 description 1
- 235000008434 ginseng Nutrition 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
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000001795 light effect Effects 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
- 150000001455 metallic ions Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 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
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction 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
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention discloses double triazole phthalic acid cadmium complex [Cd (pta) (the L) (H of anthracene nucleus2O)] structural motif of (1) is as shown in Figure 1.Also disclose [Cd (pta) (L) (H simultaneously2O)] the preparation method of (1) (L=1 [9 (1H 1,2,4 triazole 1 base) anthracene 10 base] 1H 1,2,4 triazole, pta=phthalic acid).It is to use " hydro-thermal method ", i.e. Cd (Ac)2·2H2O, pta, L and water are 90oIt is down to room temperature after reacting three days under C hydrothermal condition and obtains being suitable for the yellow bulk crystals of X ray single crystal diffraction.The present invention further discloses double triazole phthalic acid cadmium complex [Cd (pta) (the L) (H of anthracene nucleus2O)] (1) (L=1 [9 (1H 1,2,4 triazole 1 base) anthracene 10 base] 1H 1,2,4 triazole, pta=phthalic acid) is as the application in terms of potential fluorescent material.
Description
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 the double triazole phthalic acid cadmium complex of anthracene nucleus
[Cd(pta)(L)(H2O)] (1) (L=1-[9-(1H-1,2,4-triazole-1-base) anthracene-10-base]-1H-1,2,4-three nitrogen
Azoles, pta=phthalic acid) preparation method and as the application of potential fluorescent material.
Background technology
1,2,4-triazole and derivant 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 be i.e. it be use " hydro-thermal method ", i.e. Cd (Ac)2·2H2O, pta, L and water are 90oUnder C hydrothermal condition
It is down to room temperature after reacting three days and obtains being suitable for yellow bulk crystals [Cd (pta) (the L) (H of X-ray single crystal diffraction2O)] (1)
(L=1-[9-(1H-1,2,4-triazole-1-bases) anthracene-10-base]-1H-1,2,4-triazoles, pta=phthalic acid).
This coordination compound is alternatively arranged as potential fluorescent material aspect and is applied.
Summary of the invention
The offer double triazole phthalic acid cadmium complex [Cd (pta) (L) of a kind of anthracene nucleus is provided
(H2O)] (1) (L=1-[9-(1H-1,2,4-triazole-1-bases) anthracene-10-base]-1H-1,2,4-triazoles, pta=neighbour
Phthalic acid) monocrystalline and preparation method thereof.
Following technical scheme is current inventor provides for this:
Double triazole phthalic acid cadmium complex [Cd (pta) (the L) (H of anthracene nucleus2O)] (1) (L = 1-[9-(1H-1,2,
4-triazole-1-base) anthracene-10-base]-1H-1,2,4-triazoles, pta=phthalic acid) structural motif as shown in Figure 1.
The present invention further discloses double triazole phthalic acid cadmium complex [Cd (pta) (the L) (H of anthracene nucleus2O)] (1)
(L=1-[9-(1H-1,2,4-triazole-1-bases) anthracene-10-base]-1H-1,2,4-triazoles, pta=phthalic acid) is single
Brilliant, it is characterised in that this mono-crystalline structures uses APEX II CCD single crystal diffractometer, use and penetrate through graphite monochromatised Mok α
Line (λ=0.71073) is incident radiation, collects point diffraction with ω-2 θ scan mode, obtains through least square refinement
Cell parameter, utilizes SHELXL-97 direct method to solve single crystal data from difference Fourier electron density map:
The crystallographic data of table 1. coordination compound 1
Double triazole phthalic acid cadmium complex [Cd (pta) (the L) (H of anthracene nucleus of the present invention2O)] (1) (L = 1-
[9-(1H-1,2,4-triazole-1-bases) anthracene-10-base]-1H-1,2,4-triazoles, pta=phthalic acid) system of monocrystalline
Preparation Method, its feature is using " hydro-thermal method ", i.e. Cd (Ac)2·2H2O, pta, L and water are 90oReact three days under C hydrothermal condition
After be down to room temperature to prepare this coordination compound
One preferred example of the present invention:
The preparation of 1-[9-(1H-1,2,4-triazole-1-base) anthracene-10-base]-1H-1,2,4-triazole (L)
Using " one kettle way " at polar solvent, by 9,10-dibromoanthracene, 1H-1,2,4-triazoles, potassium carbonate and copper oxide are adding
Reaction preparation under heat condition；Wherein 9,10-dibromoanthracene: 1H-1,2,4-triazole: potassium carbonate: the mol ratio of copper oxide is 2:10-
15:30:1；
9,10-dibromoanthracene 1H-1,2,4-triazole
The present invention preferred 9,10-dibromoanthracene: 1H-1,2,4-triazole: potassium carbonate: the mol ratio of copper oxide is 2:10-15:
30:1；Reaction temperature 100 DEG C, 48 hours response time.In polar solvent, use " one kettle way ", by 9,10-dibromoanthracene, 1H-
1,2,4-triazole, potassium carbonate and copper oxide prepare this organic compound in a heated condition；
Presently preferred embodiment
1-[9-(1H-1,2,4-triazole-1-base) anthracene-10-base]-1H-1,2,4-triazole (L) (0.1 mmol), neighbour
Phthalic acid (0.1 mmol), Cd (Ac)2·2H2O (0.1 mmo) and 4 mL water are put in 23 mL water heating kettles.90oC heats
It is slowly dropped to room temperature after three days, after driving still, has the yellow bulk crystals of applicable X-ray single crystal diffraction, productivity 40%.Elementary analysis
(C26H18CdN6O5) theoretical value (%): C, 51.46；H, 2.99；N, 13.85.Measured value: C, 51.55；H, 3.09；N, 13.82.
The present invention further discloses double triazole phthalic acid cadmium complex [Cd (pta) (the L) (H of anthracene nucleus2O)] (1)
(L=1-[9-(1H-1,2,4-triazole-1-bases) anthracene-10-base]-1H-1,2,4-triazoles, pta=phthalic acid) can
Applied as potential fluorescent material aspect.
Double triazole phthalic acid cadmium complex [Cd (pta) (the L) (H of a kind of anthracene nucleus disclosed by the invention2O)] (1) (L
=1-[9-(1H-1,2,4-triazole-1-bases) anthracene-10-base]-1H-1,2,4-triazoles, pta=phthalic acid) monocrystalline
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 (pta) (the L) (H prepared by the present invention2O)] (1) (L=1-[9-(1H-1,2,4-triazole-1-
Base) anthracene-10-base]-1H-1,2,4-triazoles, pta=phthalic acid) production cost is low, and method is easy, is suitable for extensive
Produce.
Accompanying drawing explanation
The crystal structure primitive figure of Fig. 1: coordination compound 1；
The one-dimensional catenary structure figure of Fig. 2: coordination compound 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.All of raw material is such as: anthracene nucleus etc. are all to enter from chemical reagents corporation both domestic and external
Row is bought, and through continuation purification but does not directly use.Raw materials used 9,10-dibromoanthracene, 1H-1,2,4-triazole, carbon
Acid potassium, copper oxide etc. are commercially available.
Embodiment 1
9,10-dibromoanthracene: 1H-1,2,4-triazole: potassium carbonate: the mol ratio of copper oxide is 2:10-15:30:1
It is separately added into CuO (0.0398 in equipped with 50 mL three neck round bottom flasks of magneton, reflux condenser and thermometer
Mg, 0.5 mmol), potassium carbonate (2.0731 g, 15 mmol), triazole (0.345 mg, 5 mmol), 9,10-dibromoanthracenes
(0.3360 g, 1 mmol), 20 mL DMF.Start stirring 100oC, reacts 24 hours.After reaction terminates, reactant liquor is dropped
To room temperature, filtering, filtrate adds 100 mL water, separates out a large amount of precipitation, sucking filtration, collects filter cake, yield 60%.
Embodiment 2
1-[9-(1H-1,2,4-triazole-1-base) anthracene-10-base]-1H-1,2,4-triazole (L) (0.1 mmol), neighbour
Phthalic acid (0.1 mmol), Cd (Ac)2·2H2O (0.1 mmo) and 4 mL water are put in 23 mL water heating kettles.90oC heats
It is slowly dropped to room temperature after three days, after driving still, has the yellow bulk crystals of applicable X-ray single crystal diffraction, productivity 40%.Elementary analysis
(C26H18CdN6O5) theoretical value (%): C, 51.46；H, 2.99；N, 13.85.Measured value: C, 51.55；H, 3.09；N, 13.82.
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, one-dimensional catenary structure is shown in Fig. 2.
The crystallographic data of table 1. coordination compound 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 illumination 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 illumination subnumber.During measurement, 500 W xenon lamps are used to pass through as light source, incident illumination
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-1Sodium hydroxide 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 coordination compound is 1.9 × 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, generally add co-adsorption in dye solution
Agent suppresses the gathering of dyestuff.This coordination compound 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 560 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 phthalic acid cadmium complex of anthracene nucleus, it is characterised in that this mono-crystalline structures uses APEX II CCD
Single crystal diffractometer, uses through graphite monochromatised Mok alpha ray, and λ=0.71073 is incident radiation, with ω-2 θ scanning side
Formula collects point diffraction, obtains cell parameter through least square refinement, utilizes software solution from difference Fourier electron density map
Go out single crystal data:
The molecular formula of the double triazole phthalic acid cadmium complex monocrystalline of described anthracene nucleus: [Cd (pta) (L) (H2O)], wherein: L=1-
[9-(1H-1,2,4-triazole-1-bases) anthracene-10-base]-1H-1,2,4-triazoles, pta=phthalic acid.
2. the double triazole phthalic acid cadmium complex monocrystalline of anthracene nucleus described in claim 1 is being prepared as potential fluorescent material side
The application in face.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510088019.0A CN104592265B (en) | 2015-02-26 | 2015-02-26 | Double triazole phthalic acid cadmium complex of anthracene nucleus with potential fluorescent material and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510088019.0A CN104592265B (en) | 2015-02-26 | 2015-02-26 | Double triazole phthalic acid cadmium complex of anthracene nucleus with potential fluorescent material and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104592265A CN104592265A (en) | 2015-05-06 |
| CN104592265B true CN104592265B (en) | 2016-08-17 |
Family
ID=53118360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510088019.0A Expired - Fee Related CN104592265B (en) | 2015-02-26 | 2015-02-26 | Double triazole phthalic acid cadmium complex of anthracene nucleus with potential fluorescent material and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104592265B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105669725A (en) * | 2016-01-05 | 2016-06-15 | 天津师范大学 | Anthracylbistriazolyl-m-phthalic acid inclusion dimethylacetamide cadmium complex monocrystal and application thereof |
| CN105418656A (en) * | 2016-01-05 | 2016-03-23 | 天津师范大学 | Anthracene nucleus di-triazole isophthalic acid included diethyl formamide cadmium complex single crystal and application |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101250264B (en) * | 2008-03-26 | 2011-02-02 | 天津师范大学 | High nuclear zinc coordination polymer as well as preparation method and uses thereof |
-
2015
- 2015-02-26 CN CN201510088019.0A patent/CN104592265B/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN104592265A (en) | 2015-05-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104610302B (en) | Double triazole p-phthalic acid Zn complex of anthracene nucleus with potential fluorescent material and preparation method thereof | |
| CN104592267B (en) | Double triazole M-phthalic acid cadmium complex of naphthalene with potential fluorescent material and preparation method thereof | |
| CN104628750B (en) | A kind of double; two triazole Zn complex of anthracene nucleus with potential fluorescent material and preparation method thereof | |
| CN104592262B (en) | There are two triazole M-phthalic acid Zn complexes of anthracene nucleus of potential fluorescent material and preparation method thereof | |
| CN104610315B (en) | Double; two triazole M-phthalic acid cadmium complex of oxygen ether with potential fluorescent material and preparation method thereof | |
| 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 | |
| CN104557991B (en) | Double triazole zinc chloride complex of oxygen ether with potential fluorescent material and preparation method thereof | |
| CN104557992B (en) | Double triazole trimesic acid cadmium complex of naphthalene with potential fluorescent material and preparation method thereof | |
| CN104610320B (en) | Tetraphenyl ethylene four triazole three-dimensional cadmium complex with potential fluorescent material and preparation method thereof | |
| CN104610378B (en) | Double triazole nickel complexes of oxygen ether 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 | |
| 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 | |
| CN104558055B (en) | There is oxygen ether pair triazole nitric acid nickel complex of potential fluorescent material and preparation method thereof | |
| CN104592265B (en) | Double triazole phthalic acid cadmium complex of anthracene nucleus with potential fluorescent material and preparation method thereof | |
| CN104610319B (en) | Tetraphenyl ethylene four triazole cadmium perchlorate coordination compound with potential fluorescent material and preparation method thereof | |
| CN104610322A (en) | Tetraphenyl ethylene tetratriazolyl cadmium acetate complex with potential fluorescent material and preparation method thereof | |
| CN104610304B (en) | Oxygen ether double-triazole zinc complex with potential fluorescent material and preparation method thereof | |
| CN104610321A (en) | Tetraphenyl ethylene four triazole terephthalic acid cadmium complex with potential fluorescent material and preparation method thereof | |
| CN104592269B (en) | Double triazole cadmium iodide complex of oxygen ether with potential fluorescent material and preparation method thereof | |
| CN104592273B (en) | Double triazole cadmium acetate complex of oxygen ether with potential fluorescent material and preparation method thereof | |
| CN104610288B (en) | A kind of phenyl triazole silver complex with potential fluorescent material and preparation method thereof | |
| CN104592305B (en) | There is oxygen ether pair triazole chlorination manganese complex of potential fluorescent material and preparation method thereof | |
| CN104610344B (en) | Oxygen ether bitriazol lead complex with potential fluorescent material and preparation method of complex | |
| CN104610301B (en) | There are two triazole M-phthalic acid Zn complexes of naphthalene of potential fluorescent material and preparation method thereof | |
| CN104610376B (en) | Double triazole iron complexes of oxygen ether 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 | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20160817 Termination date: 20170226 |