CN104592262B - There are two triazole M-phthalic acid Zn complexes of anthracene nucleus of potential fluorescent material and preparation method thereof - Google Patents
There are two triazole M-phthalic acid Zn complexes of anthracene nucleus of potential fluorescent material and preparation method thereof Download PDFInfo
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- CN104592262B CN104592262B CN201510088034.5A CN201510088034A CN104592262B CN 104592262 B CN104592262 B CN 104592262B CN 201510088034 A CN201510088034 A CN 201510088034A CN 104592262 B CN104592262 B CN 104592262B
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 150000003852 triazoles Chemical class 0.000 title claims abstract description 18
- 150000001454 anthracenes Chemical class 0.000 title claims abstract description 14
- 239000000463 material Substances 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title abstract description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 40
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 230000005260 alpha ray Effects 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
- 239000013078 crystal Substances 0.000 abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 6
- 238000000034 method Methods 0.000 abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 4
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 14
- 239000000975 dye Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 9
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 8
- 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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical class C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 229960004643 cupric oxide Drugs 0.000 description 6
- 229940072033 potash Drugs 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 235000015320 potassium carbonate Nutrition 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 5
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- CPIYEXXYOQSGAM-UHFFFAOYSA-N 1-[10-(1,2,4-triazol-1-yl)anthracen-9-yl]-1,2,4-triazole Chemical compound C1=NN(C=N1)C1=C2C=CC=CC2=C(N2C=NC=N2)C2=CC=CC=C12 CPIYEXXYOQSGAM-UHFFFAOYSA-N 0.000 description 2
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 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
- 238000002447 crystallographic data Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 238000005259 measurement Methods 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
- 238000012360 testing method Methods 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Inorganic materials [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 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
- 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
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000004429 atom Chemical group 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
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 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
- 238000011161 development Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte 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
- 235000008434 ginseng Nutrition 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 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
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 230000001795 light effect Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000001455 metallic ions Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 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
- 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
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 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
- 230000002441 reversible effect Effects 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
Abstract
The invention discloses two triazole M-phthalic acid Zn complexes of anthracene nucleus that have potential fluorescent material and preparation method thereof, wherein the two triazole M-phthalic acid Zn complexes of anthracene nucleus [Zn (L) (ipa)] 2DMF} (<b>1</b>) structural motif as shown in Figure 1. Also disclose [Zn (L) (ipa)] 2DMF} (simultaneously<b>1</b>) preparation method of (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 ˊ-dimethyl formamide). It is to adopt " solvent-thermal method ", i.e. Zn (NO3)2·6H2O, ipa, L, DMF and water are 90oUnder C, react the brown bulk crystals of being down to room temperature after three days and obtaining being applicable to X-ray single crystal diffraction. The present invention further discloses the application of the two triazole M-phthalic acid Zn complexes of anthracene nucleus as potential fluorescent material aspect.
Description
The present invention obtains state natural sciences fund general project (21471113), young top-notch personnel's support plan, skyEducation Commission of Jinshi City general project (20140506), the academic innovation of the young and middle-aged teacher of Tianjin Normal University 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 educationDraw the subsidy of (TD12-5038).
Technical field
The invention belongs to organic and inorganic synthesis technical field, relate to two triazole M-phthalic acid the Zn complex { [Zn of anthracene nucleus(L) (ipa)] 2DMF} (1) (L=1-[9-(1H-1,2,4-triazole-1-yl) anthracene-10-yl]-1H-1,2,4-, tri-nitrogenAzoles, ipa=M-phthalic acid, DMF=N, N'-dimethyl formamide) preparation method and as potential fluorescent materialApplication.
Background technology
1,2,4-triazole and derivative thereof have the coordination feature of pyrazoles and imidazoles concurrently, are that the bridging that coordination ability is stronger is joinedBody, has synthesized at present and has characterized a large amount of monokaryons, multinuclear and multidimensional compound. These parts can be former with the nitrogen on 1,2Son forms N1 with metallic ion coordination, N2-bridging pattern, for 4 unsubstituted 1,2,4-triazole derivative can pass through 2,4On nitrogen-atoms form N2, N4-bridging pattern, this N2, N4-bridging pattern is with the N1 of imidazoles in metalloenzyme, N3-bridging patternSimilar. Also show in the design of molecular device for the specific use of triazole class compounds, synthetic have different dimensionsMetal complex has been the vital step of device.
The present invention adopts " solvent-thermal method ", i.e. Zn (NO3)2·6H2O, M-phthalic acid, L, DMF and water are 90oC hydro-thermalUnder condition, react the brown bulk crystals { [Zn (L) (ipa)] of being down to room temperature after three days and obtaining being applicable to X-ray single crystal diffraction2DMF} (1) (L=1-[9-(1H-1,2,4-triazole-1-yl) anthracene-10-yl]-1H-1,2,4-triazole, between ipa=Phthalic acid, DMF=N, N'-dimethyl formamide). This 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 anthracene nucleus two triazole M-phthalic acid Zn complex { [Zn (L)(ipa)] 2DMF} (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) monocrystalline and preparation method thereof.
The inventor provides following technical scheme for this reason:
The two triazole M-phthalic acid Zn complexes of anthracene nucleus [Zn (L) (ipa)] 2DMF} (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'-dimethylFormamide) structural motif as shown in Figure 1.
The present invention further discloses two triazole M-phthalic acid Zn complex { [Zn (L) (the ipa)] 2DMF} of anthracene nucleus(1) (L=1-[9-(1H-1,2,4-triazole-1-yl) anthracene-10-yl]-1H-1,2,4-triazole, ipa=isophthalic diformazanAcid, DMF=N, N'-dimethyl formamide) monocrystalline, it is characterized in that this mono-crystalline structures adopts APEXIICCD single crystal diffractionInstrument, using through the Mok alpha ray (λ=0.71073) of graphite monochromatization is incident radiation, collects with ω-2 θ scan modePoint diffraction, obtains cell parameter through least square refinement, utilizes SHELXL-97 direct from difference Fourier electron-density mapMethod solves monocrystalline data:
The crystallographic data of table 1. complex 1
Two triazole M-phthalic acid Zn complex { [Zn (L) (ipa)] 2DMF} (the 1) (L=of anthracene nucleus of the present invention1-[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) preparation method of monocrystalline, it is characterized in that adopting " solvent-thermal method ", i.e. Zn (NO3)2·6H2O,Phthalic acid, L, DMF and water are 90oUnder C hydrothermal condition, react and after three days, be down to room temperature and obtain being applicable to X-ray single crystal diffractionBrown bulk crystals. Filtrate normal temperature volatilizees one week to prepare this complex
Lipa。
Preferred example of the present invention:
1-[9-(1H-1,2,4-triazole-1-yl) anthracene-10-yl]-1H-1, the preparation of 2,4-triazole (L)
Adopt " one kettle way " at polar solvent, by 9,10-dibromoanthracene, 1H-1,2,4-triazole, potash and cupric oxide are addingReaction preparation under heat condition; Wherein 9,10-dibromoanthracene: 1H-1,2,4-triazole: potash: the mol ratio of cupric oxide is 2:10-15:30:1；
9,10-dibromoanthracene 1H-1,2,4-triazole
The present invention preferably 9,10-dibromoanthracene: 1H-1, and 2,4-triazole: potash: the mol ratio of cupric oxide is 2:10-15:30:1; 100 DEG C of reaction temperatures, 48 hours reaction time. In polar solvent, adopt " one kettle way ", by 9,10-dibromoanthracene, 1H-1,2,4-triazole, potash and cupric oxide are prepared this organic compound under heating condition;
Another preferred embodiment of the present invention
1-[9-(1H-1,2,4-triazole-1-yl) anthracene-10-yl]-1H-1,2,4-triazole (0.2mmol), Zn(NO3)2(0.2mmol), M-phthalic acid (0.1mmol), DMF (2mL) and H2O (6mL) is put into 23mL water heating kettleIn. 90oC heating is slowly down to room temperature in three days afterwards, opens the brown bulk crystals that has applicable X-ray single crystal diffraction after still. Productive rate:40%. Elementary analysis (C32H30N8O6Zn) theoretical value (%): C, 55.86; H, 4.40; N, 16.29. Measured value: C, 55.90; H,4.45；N，16.32。
The present invention further discloses two triazole M-phthalic acid Zn complex { [Zn (L) (the ipa)] 2DMF} of anthracene nucleus(1) (L=1-[9-(1H-1,2,4-triazole-1-yl) anthracene-10-yl]-1H-1,2,4-triazole, ipa=isophthalic diformazanAcid, DMF=N, N'-dimethyl formamide) can be used as potential fluorescent material aspect and applied.
Two triazole M-phthalic acid Zn complex { [Zn (L) (the ipa)] 2DMF} (1) of a kind of anthracene nucleus disclosed by the invention(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) advantage and disadvantage that has of 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 { [Zn (L) (ipa)] 2DMF} (1) (L=1-[9-(1H-1,2,4-, tri-nitrogen of the present inventionAzoles-1-yl) anthracene-10-yl]-1H-1,2,4-triazole, ipa=M-phthalic acid, DMF=N, N'-dimethyl formamide) rawProduct cost is low, and method is easy, is applicable to large-scale production.
Brief description of the drawings
Fig. 1: the crystal structure primitive figure of complex 1;
Fig. 2: the two-dimensional layered structure figure of complex 1.
Detailed description of the invention
Below in conjunction with embodiment, the present invention is described further, and embodiment is only indicative, never means itLimit the scope of the invention by any way. All raw materials are for example: anthracene nucleus etc. are all to enter from chemical reagents corporation both domestic and externalRow buy, through continuation purify but directly use. Raw materials used 9,10-dibromoanthracene, 1H-1,2,4-triazole, carbonAcid potassium, cupric oxide etc. all have commercially available.
Embodiment 1
9,10-dibromoanthracene: 1H-1,2,4-triazole: potash: the mol ratio of cupric oxide is 2:10-15:30:1
In tri-mouthfuls of round-bottomed flasks of 50mL that magneton, reflux condenser and thermometer are housed, add respectively CuO (0.0398Mg, 0.5mmol), potash (2.0731g, 15mmol), triazole (0.345mg, 5mmol), 9,10-dibromoanthracene(0.3360g, 1mmol), 20mLDMF. Start and be stirred in 100oC, reacts 24 hours. After reaction finishes, reactant liquor is fallenTo room temperature, to filter, filtrate adds 100mL water, separates out a large amount of precipitations, and suction filtration is collected filter cake, 1-[9-(1H-1,2,4-, tri-nitrogenAzoles-1-yl) anthracene-10-yl]-1H-1,2,4-triazole (L), yield 60%.
Embodiment 2
1-[9-(1H-1,2,4-triazole-1-yl) anthracene-10-yl]-1H-1,2,4-triazole (0.2mmol), Zn(NO3)2(0.2mmol), M-phthalic acid (0.1mmol), DMF (2mL) and H2O (6mL) is put into 23mL water heating kettleIn. 90oC heating is slowly down to room temperature in three days afterwards, opens the brown bulk crystals that has applicable X-ray single crystal diffraction after still. Productive rate:40%. Elementary analysis (C32H30N8O6Zn) theoretical value (%): C, 55.86; H, 4.40; N, 16.29. Measured value: C, 55.90; H,4.45；N，16.32。
Embodiment 3
Crystal structure determination adopts APEXIICCD single crystal diffractometer, uses the Mok alpha ray (λ through graphite monochromatization=0.71073) be incident radiation, collect point diffraction with ω-2 θ scan mode, obtain structure cell ginseng through least square refinementNumber, utilizes software to solve crystal structure from difference Fourier electron-density map, and through Lorentz lorentz and polarity effect correction. AllH atom is synthesized by difference Fourier and determines through desirable position calculation. Detailed axonometry data are in table 1. Structural motif is shown inFig. 1, two-dimensional layered structure is shown in Fig. 2.
The crystallographic data of table 1. complex 1
Embodiment 4
The concrete instance that dyestuff or luminous agent use
Method: differentiated pulse volt-ampere (DPV) the curve negotiating Princeton Applied Research Laboratory development of dye solutionPARSTAT2273 electrochemical workstation is measured. The DPV test of solution adopts 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 0.1molL-1TBAPSolution. Reversible to as interior mark taking Oxidation of Ferrocene reduction, obtain the corrected value between test system and standard hydrogen electrode system.
Monochromatic incident light photoelectric transformation efficiency (IPCE) is described the photoelectric transformation efficiency of DSCs under monochromatic light effect, is to turnMove on to the electron number of external circuit and the ratio of incident light subnumber. When measurement, use 500W xenon lamp as light source, incident light processThe multifunctional assembled grating spectrograph of WDS-5 type obtains the monochromatic light under different wave length λ; Monochromatic light irradiates the light sun in batteryThe utmost point, by Keithley2400 digital sourcemeter reading current value I. Monochromatic good fortune illumination is micro-by USB4000plug-and-playType light spectrometer measurement.
Step: understand dyestuff at TiO for definite2Adsorbance on film, by dye sensitization TiO2Nanometer crystal film (geometric surfaceThe long-pending 1cm that is about2) be immersed in 10mL0.01molL-1The methanol solution of NaOH in spend the night, treat that dyestuff desorbs completelyThe absorbance of rear mensuration solution. Wash one's face and rinse one's mouth and can calculate dyestuff on unit are nanometer crystal film according to absorbance and molar absorptivityAdsorbance. The adsorbance of this complex is 1.9 × 10-4mol/cm2。
Result: compared with the methanol solution of dyestuff, dyestuff is at TiO2Absorption spectrum on film all obviously broadens and red shift. ThisShow that dye molecule is at TiO2Form the J-aggregation of first and tail. From the operation principle of DSCs, dyestuff is assembled the light causingSpectrum width and red shift are very favourable for the widening of photoelectric respone scope of dyestuff. But meanwhile, dyestuff aggregation meetingGreatly reduce its electron injection efficiency, thereby cause the performance of DSCs low. So, conventionally in dye solution, add common absorptionAgent suppresses the gathering of dyestuff. This complex is in methanol solution and at TiO2The fluorometric investigation of the purple solution on membrane electrode is adoptedWith 2.5 × 10-5The methanol solution of mol/L, maximum emission wavelength is positioned at 670nm.
Describe in detail preferred embodiment after, being familiar with this technology personage can be well understood to, do not depart from above-mentionedUnder claim and spirit, can carry out various variations and amendment, all foundations technical spirit of the present invention is to above embodiment instituteAny simple modification, equivalent variations and the modification done, all belong to the scope of technical solution of the present invention. And the present invention is not also illustratedThe restriction of example embodiment in book.
Claims (2)
1. the two triazole M-phthalic acid Zn complex monocrystalline of anthracene nucleus, is characterized in that this mono-crystalline structures adopts APEXIICCD mono-Brilliant diffractometer, uses the Mok alpha ray through graphite monochromatization, and λ=0.71073 is incident radiation, with θ scanning side, ω-2Formula is collected point diffraction, obtains cell parameter through least square refinement, utilizes software solution from difference Fourier electron-density mapGo out monocrystalline data:
The molecular formula of the described two triazole M-phthalic acid Zn complex monocrystalline of anthracene nucleus: [Zn (L) (ipa)] 2DMF, wherein 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.
2. described in claim 1, the two triazole M-phthalic acid Zn complex monocrystalline of anthracene nucleus are being prepared as potential fluorescent material sideThe application of face; Wherein the maximum emission wavelength of the two triazole M-phthalic acid Zn complex monocrystalline of anthracene nucleus is positioned at 670nm.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510088034.5A CN104592262B (en) | 2015-02-26 | 2015-02-26 | There are two triazole M-phthalic acid Zn complexes of anthracene nucleus of potential fluorescent material and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510088034.5A CN104592262B (en) | 2015-02-26 | 2015-02-26 | There are two triazole M-phthalic acid Zn complexes of anthracene nucleus of potential fluorescent material and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104592262A CN104592262A (en) | 2015-05-06 |
| CN104592262B true CN104592262B (en) | 2016-05-18 |
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| 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 |
| 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 |
| CN105524095A (en) * | 2016-01-05 | 2016-04-27 | 天津师范大学 | One-dimensional morpholine cadmium complex single crystal and preparation method 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 |
| CN105524097A (en) * | 2016-01-05 | 2016-04-27 | 天津师范大学 | 1, 4-dimethyl-2, 5-dimethylene bistriazole inclusion 1-methyl-2-pyrrolidone cadmium complex single crystal |
| 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 |
| 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 |
| 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 |
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| CN102070659A (en) * | 2010-12-02 | 2011-05-25 | 南开大学 | Zinc organic complex as well as preparation method and application thereof |
| CN102942580A (en) * | 2012-12-06 | 2013-02-27 | 洛阳师范学院 | Zinc 5-methyl isophthalate complex and preparation method thereof |
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| CN102070659A (en) * | 2010-12-02 | 2011-05-25 | 南开大学 | Zinc organic complex as well as preparation method and application thereof |
| CN102942580A (en) * | 2012-12-06 | 2013-02-27 | 洛阳师范学院 | Zinc 5-methyl isophthalate complex and preparation method thereof |
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