CN104592267B - Double triazole M-phthalic acid cadmium complex of naphthalene with potential fluorescent material and preparation method thereof - Google Patents
Double triazole M-phthalic acid cadmium complex of naphthalene with potential fluorescent material and preparation method thereof Download PDFInfo
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- CN104592267B CN104592267B CN201510088026.0A CN201510088026A CN104592267B CN 104592267 B CN104592267 B CN 104592267B CN 201510088026 A CN201510088026 A CN 201510088026A CN 104592267 B CN104592267 B CN 104592267B
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- naphthalene
- triazole
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- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 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 25
- 150000003852 triazoles Chemical class 0.000 title claims abstract description 16
- 229910052793 cadmium Inorganic materials 0.000 title claims abstract description 15
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 239000000463 material Substances 0.000 title claims abstract description 8
- 239000013078 crystal Substances 0.000 claims abstract description 16
- 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
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 abstract description 11
- 238000000034 method Methods 0.000 abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 8
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 14
- 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 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 229960004643 cupric oxide Drugs 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
- 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
- 238000004220 aggregation Methods 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- MOFINMJRLYEONQ-UHFFFAOYSA-N [N].C=1C=CNC=1 Chemical class [N].C=1C=CNC=1 MOFINMJRLYEONQ-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- XIEPJMXMMWZAAV-UHFFFAOYSA-N cadmium nitrate Chemical compound [Cd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XIEPJMXMMWZAAV-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002447 crystallographic data 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
- 229910052757 nitrogen Inorganic materials 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- 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
- 206010070834 Sensitisation Diseases 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
- 229910052799 carbon Inorganic materials 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
- 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
- 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
- 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
- 239000002244 precipitate Substances 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
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000967 suction filtration 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
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Inorganic materials [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention discloses double triazole M-phthalic acid cadmium complex of naphthalene with potential fluorescent material and preparation method thereof, wherein double triazole M-phthalic acid cadmium complex { [Cd (L) (the ipa)] 0.25H of naphthalene2The structural motif of O} (1) is as shown in Figure 1.Also disclose { [Cd (L) (ipa)] 0.25H simultaneously2O} (1) (L=1 [7 (1H 1,2,4 triazole 1 base) naphthalene 2 base) 1H 1,2,4 triazole, ipa=M-phthalic acid) preparation method.It is to use " solvent-thermal method ", i.e. Cd (NO3)2·6H2O, ipa, L, DMF and water are 90oIt is slowly dropped to room temperature after reacting three days under C and obtains being suitable for the yellow bulk crystals of X ray single crystal diffraction.The present invention further discloses the double triazole M-phthalic acid cadmium complex of naphthalene as the application in terms of potential fluorescent material.
Description
The present invention obtains state natural sciences fund general project (21471113), young top-notch personnel's support plan, sky
Education Commission of Jinshi City general project (20140506), Tianjin Normal University's Middl-age and youth faculty Academic innovations advance planning item
(52XC1401), meter is cultivated by Tianjin State Scientific and Technological Commission general project (11JCYBJC03600) and Tianjin innovation team of institution of higher education
Draw the subsidy of (TD12-5038).
Technical field
The invention belongs to organic and Inorganic synthese technical field, relate to stating double triazole M-phthalic acid the cadmium complex { [Cd of naphthalene
(L)(ipa)]·0.25H2O} (1) (L=1-[7-(1H-1,2,4-triazole-1-base) naphthalene-2-base)-1H-1,2,4-three
Nitrogen azoles, ipa=M-phthalic acid) preparation method and as the application of potential fluorescent material.
Background technology
1,2,4-triazole and derivative thereof have the coordination feature of pyrazoles and imidazoles concurrently, are that the bridging that coordination ability is stronger is joined
Body, has synthesized and has characterized substantial amounts of monokaryon, multinuclear and multidimensional compound the most.These parts can be former with the nitrogen on 1,2
Son forms N1, N2-bridging pattern with metallic ion coordination, can be by 2,4 for 4 unsubstituted 1,2,4-triazole derivatives
On nitrogen-atoms formed N2, N4-bridging pattern, this N2, N4-bridging pattern is with the N1 of imidazoles in metalloenzyme, N3-bridging pattern
Similar.Specific use for triazole class compounds is also manifested by the design of molecular device, and synthesis has different dimension
Metal complex has been the vital step of device.
The present invention is i.e. to use " solvent-thermal method ", i.e. Cd (NO3)2·6H2O, ipa, L, DMF and water are 90oC hydrothermal condition
Lower reaction is down to room temperature and is obtained being suitable for the yellow bulk crystals { [Cd (L) (ipa)] of X-ray single crystal diffraction after three days
0.25H2O} (1) (L=1-[7-(1H-1,2,4-triazole-1-bases) naphthalene-2-base)-1H-1,2,4-triazoles, ipa=
M-phthalic acid).This complex is alternatively arranged as potential fluorescent material aspect and is applied.
Summary of the invention
Offer double triazole M-phthalic acid the cadmium complex { [Cd (L) of a kind of naphthalene is provided
(ipa)]·0.25H2O} (1) (L=1-[7-(1H-1,2,4-triazole-1-base) naphthalene-2-base)-1H-1,2,4-three nitrogen
Azoles, ipa=M-phthalic acid) monocrystalline and preparation method thereof.
Following technical scheme is current inventor provides for this:
Double triazole M-phthalic acid cadmium complex { [Cd (L) (the ipa)] 0.25H of naphthalene2O} (1) (L = 1-[7-(1H-
1,2,4-triazole-1-base) naphthalene-2-base)-1H-1,2,4-triazoles, ipa=M-phthalic acid) structural motif such as Fig. 1 institute
Show.
The present invention further discloses double triazole M-phthalic acid cadmium complex { [Cd (L) (the ipa)] 0.25H of naphthalene2O}
(1) (L=1-[7-(1H-1,2,4-triazole-1-bases) naphthalene-2-base)-1H-1,2,4-triazoles, ipa=isophthalic diformazan
Acid) monocrystalline, it is characterised in that this mono-crystalline structures uses APEX II CCD single crystal diffractometer, uses through graphite monochromatised
Mok alpha ray (λ=0.71073) is incident radiation, collects point diffraction with ω-2 θ scan mode, repaiies through least square method
Just obtain cell parameter, utilize SHELXL-97 direct method to solve single crystal data from difference Fourier electron-density map:
The crystallographic data of table 1. complex 1
Double triazole M-phthalic acid cadmium complex { [Cd (L) (the ipa)] 0.25H of naphthalene of the present invention2O} (1) (L =
1-[7-(1H-1,2,4-triazole-1-bases) naphthalene-2-base)-1H-1,2,4-triazoles, ipa=M-phthalic acid) system of monocrystalline
Preparation Method, its feature is using " solvent-thermal method ", Cd (NO3)2·6H2O, ipa, L, DMF and water are 90oAfter reacting three days under C
It is down to room temperature to prepare this complex
L ipa。
One preferred example of the present invention:
1-[7-(1H-1,2,4-triazole-1-base) naphthalene-2-base) preparation of-1H-1,2,4-triazole (L)
1-of the present invention [7-(1H-1,2,4-triazole-1-base) naphthalene-2-base) the preparation side of-1H-1,2,4-triazole
Method, its feature is using " one kettle way " at polar solvent, and by 2,7-dibromine naphthalene, 1H-1,2,4-triazoles, potassium carbonate and cupric oxide exist
Prepare under heating condition；Wherein 2,7-dibromine naphthalene: 1H-1,2,4-triazole: potassium carbonate: the mol ratio of cupric oxide is 2:10-15:
30:1；
2,7-dibromine naphthalene 1H-1,2,4-triazole
The present invention preferred 2,7-dibromine naphthalene: 1H-1,2,4-triazole: potassium carbonate: the mol ratio of cupric oxide is 2:10-15:30:
1；Reaction temperature 100 DEG C, 48 hours reaction time.In polar solvent, use " one kettle way ", by 2,7-dibromine naphthalene, 1H-1,
This organic compound prepared in a heated condition by 2,4-triazole, potassium carbonate and cupric oxide；
Presently preferred embodiment
1-[7-(1H-1,2,4-triazole-1-base) naphthalene-2-base)-1H-1,2,4-triazole (L) (0.1 mmol), ipa
(0.1 mmol)、Cd(NO3)2·6H2O (0.2 mmo), 10 mL water and 6 mL DMF are put in 23 mL water heating kettles.90oC adds
Heat was slowly dropped to room temperature after three days, obtained being suitable for the yellow bulk crystals of X-ray single crystal diffraction after driving still.Productivity: 40%.Element
Analyze (C22H14.5CdN6O4.25) theoretical value (%): C, 48.64；H, 2.69；N, 15.47.Measured value: C, 48.68；H, 2.65；N,
15.26。
The present invention further discloses double triazole M-phthalic acid cadmium complex { [Cd (L) (the ipa)] 0.25H of naphthalene2O}
(1) (L=1-[7-(1H-1,2,4-triazole-1-bases) naphthalene-2-base)-1H-1,2,4-triazoles, ipa=M-phthalic acid)
Can be applied as potential fluorescent material aspect.
Double triazole M-phthalic acid cadmium complex { [Cd (L) (ipa)] 0.25H of a kind of naphthalene disclosed by the invention2O} (1)
(L=1-[7-(1H-1,2,4-triazole-1-bases) naphthalene-2-base)-1H-1,2,4-triazoles, ipa=M-phthalic acid) single
Brilliant have the advantage that and feature are:
(1) operation is simple and easy to do.
(2) reaction yield is high, and the purity of products obtained therefrom is high.
(3) { [Cd (L) (ipa)] 0.25H prepared by the present invention2O} (1) (L=1-[7-(1H-1,2,4-tri-
Nitrogen azoles-1-base) naphthalene-2-base)-1H-1,2,4-triazoles, ipa=M-phthalic acid) production cost is low, and method is easy, is suitable for
Large-scale production.
Accompanying drawing explanation
The crystal structure primitive figure of Fig. 1: complex 1；
The two-dimensional layered structure figure of Fig. 2: complex 1.
Detailed description of the invention
Below in conjunction with embodiment, the present invention is described further, and embodiment is only explanatory, is in no way intended to it
Limit the scope of the present invention by any way.Raw materials used 2,7-dibromine naphthalene, 1H-1,2,4-triazole, potassium carbonate and cupric oxide
Etc. being commercially available.All raw materials are all to buy from chemical reagents corporation both domestic and external, not through continuing to purify but straight
Connect use.
Embodiment 1
2,7-dibromine naphthalene: 1H-1,2,4-triazole: potassium carbonate: the mol ratio of cupric oxide is 2:10:30:1
It is separately added into CuO (0.5 in equipped with 50 mL three neck round bottom flasks of magneton, reflux condenser and thermometer
Mmol), potassium carbonate (15 mmol), 1H-1,2,4-triazole (5 mmol), 2,7-dibromine naphthalene (1 mmol) and 20 mL
DMF.Start stirring 100oC, reacts 24 hours.After reaction terminates, reactant liquor being down to room temperature, filter, filtrate adds 100
ML water, separates out and precipitates in a large number, suction filtration, collection filter cake, and 1-[7-(1H-1,2,4-triazole-1-bases) naphthalene-2-base)-1H-1,2,4-
Triazole (L).Yield 60%, yield 60%.
Embodiment 2
1-[7-(1H-1,2,4-triazole-1-base) naphthalene-2-base)-1H-1,2,4-triazole (L) (0.1 mmol), ipa
(0.1 mmol)、Zn(NO3)2·6H2O (0.2 mmo), 10 mL water and 6 mL DMF are put in 23 mL water heating kettles.90oC adds
Heat was slowly dropped to room temperature after three days, obtained being suitable for the yellow bulk crystals of X-ray single crystal diffraction after driving still.Productivity: 40%.Element
Analyze (C22H14.5CdN6O4.25) theoretical value (%): C, 48.64；H, 2.69；N, 15.47.Measured value: C, 48.68；H, 2.65；N,
15.26。
Embodiment 3
Crystal structure determination uses APEX II CCD single crystal diffractometer, uses through graphite monochromatised Mok alpha ray (λ
=0.71073) it is incident radiation, collects point diffraction with ω-2 θ scan mode, obtain structure cell ginseng through least square refinement
Number, utilizes software to solve crystal structure from difference Fourier electron-density map, and through Lorentz lorentz and polarity effect correction.All of
H atom is synthesized by difference Fourier and determines through preferable position calculation.Detailed axonometry data are shown in Table 1.Structural motif is shown in
Fig. 1, two-dimensional layered structure is shown in Fig. 2.
The crystallographic data of table 1. complex 1
Embodiment 4
The concrete instance that dyestuff or luminous agent use
Method: differentiated pulse volt-ampere (DPV) the curve negotiating Princeton Applied Research Laboratory of dye solution is developed
PARSTAT 2273 electrochemical workstation is measured.The DPV test of solution uses three-electrode system, and glass-carbon electrode is working electrode,
Auxiliary electrode is platinum plate electrode, homemade Ag/AgNO3Electrode is reference electrode；Electrolyte is the acetonitrile of 0.1mol L-1TBAP
Solution.With the Oxidation of Ferrocene reversible point of reduction to as internal standard, obtain the corrected value between test system and standard hydrogen electrode system.
Monochromatic incident light photoelectric transformation efficiency (IPCE) describes DSCs photoelectric transformation efficiency under monochromatic light effect, is to turn
Move on to the electron number of external circuit and the ratio of incident light subnumber.During measurement, 500 W xenon lamps are used to pass through as light source, incident light
The multifunctional assembled grating spectrograph of WDS-5 type obtains the monochromatic light under different wave length λ；Monochromatic light exposure is in the light sun of battery
Pole, is read current value I by Keithley2400 digital sourcemeter.Monochromatic good fortune illumination is micro-by USB4000 plug-and-play
Type light spectral instrument is measured.
Step: in order to have any actual knowledge of dyestuff at TiO2Adsorbance on film, by dye sensitization TiO2Nanometer crystal film (geometric surface
Long-pending about 1 cm2) it is immersed in 10 mL 0.01 mol L-1NaOH methanol solution in overnight, treat that dyestuff desorbs completely
The absorbance of rear mensuration solution.Wash one's face and rinse one's mouth according to absorbance and molar absorptivity and can calculate dyestuff on unit are nanometer crystal film
Adsorbance.The adsorbance of this complex is 5.2 × 10-4 mol/cm2。
Result: compared with the methanol solution of dyestuff, dyestuff is at TiO2Absorption spectrum on film the most substantially broadens and red shift.This
Show that dye molecule is at TiO2Define the first and J-aggregation of tail.Say from the operation principle of DSCs, the light that dye aggregation causes
Spectrum width and red shift are highly beneficial for the widening of photoelectric respone scope of dyestuff.But meanwhile, dye aggregation is known from experience
It is substantially reduced its electron injection efficiency, thus causes the degraded performance of DSCs.So, in dye solution, generally add eutectoid content
Agent suppresses the gathering of dyestuff.This complex is in methanol solution and at TiO2The fluorometric investigation of the purple solution on membrane electrode is adopted
With 2.5 × 10-5The methanol solution of mol/L, maximum emission wavelength is positioned at 570 nm.
After the preferred embodiment described in detail, it is familiar with this skilled worker and is clearly understood that, without departing from above-mentioned
Can carry out various change and amendment under claim and spirit, all technical spirit according to the present invention are to above example institute
Any simple modification, equivalent variations and the modification made, belongs to the scope of technical solution of the present invention.And the present invention is not illustrated
The restriction of example embodiment in book.
Claims (2)
1. the monocrystalline of the double triazole M-phthalic acid cadmium complex of naphthalene, it is characterised in that this mono-crystalline structures uses APEX II CCD mono-
Brilliant diffractometer, uses through graphite monochromatised Mok alpha ray, and λ=0.71073 is incident radiation, with ω-2 θ scan mode
Collect point diffraction, obtain cell parameter through least square refinement, utilize software to solve from difference Fourier electron-density map
Single crystal data:
The structure of the double triazole M-phthalic acid cadmium complex monocrystalline of described naphthalene: { [Cd (L) (ipa)] 0.25H2O}；Wherein L=
1-[7-(1H-1,2,4-triazole-1-bases) naphthalene-2-base)-1H-1,2,4-triazoles, ipa=M-phthalic acid.
2. the double triazole M-phthalic acid cadmium complex monocrystalline of naphthalene described in claim 1 is in terms of preparation is as potential fluorescent material
Application.
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| CN105418657A (en) * | 2016-01-05 | 2016-03-23 | 天津师范大学 | 1,4-dimethyl-2,5-dimethylene bis(triazole)isophthalic acid-included dimethylacetamide cadimium complex single crystal and application |
| CN105418654A (en) * | 2016-01-05 | 2016-03-23 | 天津师范大学 | 1,4-dimethyl-2,5-dimethylene bis(triazole) 5-methyl isophthalic acid cadimium complex single crystal and application |
| CN105418658A (en) * | 2016-01-05 | 2016-03-23 | 天津师范大学 | 1,4-dimethyl-2,5-dimethylene bis triazol one-dimensional cadmium complex single crystal and application |
| CN105418660A (en) * | 2016-01-05 | 2016-03-23 | 天津师范大学 | 1,4-dimethyl-2,5-dimethylene bis(triazole)cadimium complex single crystal and application |
| CN105541881A (en) * | 2016-01-05 | 2016-05-04 | 天津师范大学 | 1,4-dimethyl-2,5-dimethylene bis(triazole) three-dimensional cadmium complex single crystal and application |
| CN105524094A (en) * | 2016-01-05 | 2016-04-27 | 天津师范大学 | 1, 4-dimethyl-2, 5-dimethylene bistriazole inclusion N, N'-diethyl acetamide cadmium complex single crystal |
| CN105503913A (en) * | 2016-01-05 | 2016-04-20 | 天津师范大学 | 1, 4-dimethyl-2, 5-dimethylene bis triazole cadmium terephthalate complex single crystal and application |
| CN105418659A (en) * | 2016-01-05 | 2016-03-23 | 天津师范大学 | 1,4-dimethyl-2,5-dimethylene bis triazol hydroxyphenylacetic isophthalic acid cadmium complex single crystal and application |
| CN105524096A (en) * | 2016-01-05 | 2016-04-27 | 天津师范大学 | 1, 4-dimethyl-2, 5-dimethylene bistriazole isophthalic acid inclusion diethyl formamide cadmium complex single crystal and application thereof |
| CN112592358B (en) * | 2020-12-18 | 2022-12-13 | 闽都创新实验室 | Blue light luminescent crystal material and preparation method and application thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101250264A (en) * | 2008-03-26 | 2008-08-27 | 天津师范大学 | High nuclear zinc coordination polymer as well as preparation method and uses thereof |
-
2015
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101250264A (en) * | 2008-03-26 | 2008-08-27 | 天津师范大学 | High nuclear zinc coordination polymer as well as preparation method and uses thereof |
Non-Patent Citations (2)
| Title |
|---|
| "Hydrothermal syntheses and characterization of a series of luminescent Cd(II) frameworks with pyridine-based and benzene-based bis-triazole ligands";Bin Ding et al.;《CrystEngComm》;20130114;第15卷;第2490-2503页 * |
| "基于1,2,4-三氮唑配体的配位聚合物的合成、结构和性能研究";苗少斌;《中国博士学位论文全文数据库 工程科技Ⅰ辑》;20150215(第2期);第B014-22页 * |
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