CN105336866A - Metalloporphyrin coordination compound and preparation method and application thereof - Google Patents
Metalloporphyrin coordination compound and preparation method and application thereof Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 150000001875 compounds Chemical class 0.000 title abstract 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 22
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000003446 ligand Substances 0.000 claims abstract description 10
- -1 4-carboxyl phenyl Chemical group 0.000 claims abstract description 9
- 239000000758 substrate Substances 0.000 claims abstract description 8
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 230000005693 optoelectronics Effects 0.000 claims description 14
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000011521 glass Substances 0.000 claims description 6
- 238000009413 insulation Methods 0.000 claims description 6
- 230000006837 decompression Effects 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims description 3
- BHWUCEATHBXPOV-UHFFFAOYSA-N 2-triethoxysilylethanamine Chemical compound CCO[Si](CCN)(OCC)OCC BHWUCEATHBXPOV-UHFFFAOYSA-N 0.000 claims description 3
- MWVTWFVJZLCBMC-UHFFFAOYSA-N 4,4'-bipyridine Chemical compound C1=NC=CC(C=2C=CN=CC=2)=C1 MWVTWFVJZLCBMC-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- JILBPZJGIGDIGK-UHFFFAOYSA-N 5-triethoxysilylpentan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCCCN JILBPZJGIGDIGK-UHFFFAOYSA-N 0.000 claims description 2
- RNGSTWPRDROEIW-UHFFFAOYSA-N [Ni].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 Chemical compound [Ni].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 RNGSTWPRDROEIW-UHFFFAOYSA-N 0.000 claims description 2
- 239000005357 flat glass Substances 0.000 claims description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 claims description 2
- ROWWCTUMLAVVQB-UHFFFAOYSA-N triethoxysilylmethanamine Chemical compound CCO[Si](CN)(OCC)OCC ROWWCTUMLAVVQB-UHFFFAOYSA-N 0.000 claims description 2
- 238000010792 warming Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 10
- 238000010992 reflux Methods 0.000 abstract description 5
- 230000005540 biological transmission Effects 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- 238000005660 chlorination reaction Methods 0.000 abstract 2
- 239000000376 reactant Substances 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 150000004032 porphyrins Chemical class 0.000 description 14
- 239000000463 material Substances 0.000 description 9
- 239000000178 monomer Substances 0.000 description 5
- 239000002800 charge carrier Substances 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 3
- 239000010453 quartz Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 244000208060 Lawsonia inermis Species 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical class Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- LGAILEFNHXWAJP-BMEPFDOTSA-N macrocycle Chemical group N([C@H]1[C@@H](C)CC)C(=O)C(N=2)=CSC=2CNC(=O)C(=C(O2)C)N=C2[C@H]([C@@H](C)CC)NC(=O)C2=CSC1=N2 LGAILEFNHXWAJP-BMEPFDOTSA-N 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
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 238000002444 silanisation Methods 0.000 description 1
- 239000003115 supporting electrolyte Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Photovoltaic Devices (AREA)
- Hybrid Cells (AREA)
Abstract
The invention provides a metalloporphyrin coordination compound with a structural formula described in the description and a preparation method thereof. The preparation method comprises preparing acylating chlorination metalloporphyrin by using 5,10,15,20-four (4-carboxyl phenyl) metalloporphyrin and thionyl chloride as reactants; adding amino silane into the acylating chlorination metalloporphyrin; and performing circulation reflux to obtain the metalloporphyrin coordination compound. The invention also provides a preparation method of a three-dimensional ordered photoelectric film. The metalloporphyrin coordination compound, bridging bidentate ligand, and hydrochloric acid are dissolved in tetrahydrofuran according to a certain stoichiometric ratio and a substrate is coated with the obtained solution to be subjected self-guided assembly so that the three-dimensional ordered photoelectric film is obtained. The method achieves carrier transmission between multiple self-assembled organic thin layers so as to improve the photoelectric effect of the organic film.
Description
Technical field
The invention belongs to organic photoelectrical material field, relate to a kind of Metalloporphyrins, specifically a kind of Metalloporphyrins and its preparation method and application.
Background technology
Organic photoelectrical material is a kind of new material, and in photovoltaic solar cell application, there is larger application prospect in the fields such as OLED, become the focus of current field of new research.In field of photovoltaic materials, no matter be photovoltaic cell field, or OLED, photoelectric material is all prepare photoelectric device with plural layers form.But in traditional plural layers photoelectric device, the transmission of charge carrier is mainly transmitted in the film of same layer, then seldom transmits, limits the transmittability of charge carrier to a certain extent, have impact on the performance of photoelectric material performance between the different layers of film.
Porphyrin alkali is the important organic macrocycle part of a class, has planar structure and the chromophore of height conjugation, is the light-sensitive material of excellent performance, is all widely used in different field such as photoelectric device, catalysis, molecular recognition.At present, have for the common method of constructing porphyrin film: solvent-thermal method, layer assembly method, growth layer by layer and Langmuir-Blodgett (LBL) combination method.In these methods, although solvent-thermal method or LBL method can obtain the film of three-dimensional order or partial order, to reaction condition or environmental requirement higher, and be difficult to obtain at short notice the film of multilayer order.And the porphyrin being modified with organic siloxane with periphery is for monomer carries out self-steering assembling, and to prepare the research of porphyrin laminated film at the early-stage, and be only two-dimensional structure, rete spacing and the number of plies are also difficult to control.Not yet relate to and utilize the structure of porphyrin self and reaction characteristics to construct the report of three-dimensional order porphyrin complex film by simple process self-steering assembling completely.
Summary of the invention
For above-mentioned technical problem of the prior art, the invention provides a kind of Metalloporphyrins and its preparation method and application, it is limited that described this Metalloporphyrins and its preparation method and application solves carrier transport ability in plural layers photoelectric device of the prior art, affects the technical problem of photoelectric material performance.
The invention provides a kind of Metalloporphyrins, its structural formula is as follows:
Wherein M is Co
3+, Ni
2+, or Fe
3+, R is-CONH (CH
2)
nsi (OEt)
3, n=1 ~ 5.
This corproporphyrin monomer has following design feature: porphyrin ring center has the metal ion of axial coordination ability, as transitional metal ion Co
3+, Fe
3+deng, and-the cagelike silsesquioxane (carbon chain lengths is adjustable) of polymerization reaction that can be spontaneously hydrolyzed is had in porphyrin ring periphery meso position.
The synthetic method of described Metalloporphyrins is as follows:
M in compd A is Co
3+ni
2+, Fe
3+deng metal ion, R in Compound C
1for-NH (CH
2)
nsi (OEt)
3, n is 1 ~ 5.
Present invention also offers the preparation method of above-mentioned Metalloporphyrins, comprise the steps:
1) by 5,10,15,20 – tetra-(4 – carboxyl phenyl) Metalloporphyrins are dissolved in oxolane, add thionyl chloride, 5, the mol ratio of 10,15,20 – tetra-(4 – carboxyl phenyl) Metalloporphyrins and thionyl chloride is 1:120 ~ 1:100, be heated to oxolane backflow, react 1 ~ 3 hour;
2) decompression distillation removes excessive thionyl chloride, add amino silane, 5,10,15, the mol ratio of 20 – tetra-(4 – carboxyl phenyl) Metalloporphyrins and amino silane is 1:3 ~ 5, continues back flow reaction 5 ~ 10h, obtains a kind of Metalloporphyrins according to claim 1.
Further, described 5,10,15,20 – tetra-(4 – carboxyl phenyl) Metalloporphyrins are 5,10,15,20 – tetra-(4 – carboxyl phenyl) Cob altporphyrin complexs or 5,10,15,20 – tetra-(4 – carboxyl phenyl) ferriporphyrin complexs or 5, any one in the Metalloporphyrins such as 10,15,20 – tetra-(4 – carboxyl phenyl) nickel-porphyrin complexs.
Further, described amino silane compounds is any one in aminomethyl triethoxysilane, 2-amino-ethyl triethoxysilane, APTES, 4-ammobutyltriethoxysilane or 5-Aminopentyl triethoxysilane.
Present invention also offers a kind of preparation method of three-dimensional order optoelectronic film, by Compound C and bridging bidentate ligand (4,4 '-bipyridine, alkynyl bipyridine or pyridine radicals porphyrin) be dissolved in oxolane, the mol ratio of Compound C and bridging bidentate ligand is 1:4, add hydrochloric acid solution (mol ratio between Metalloporphyrins, bridging bidentate ligand and hydrochloric acid is 1:4:1.3 ~ 1:4:2), be warming up to 50 ~ 70 DEG C, insulation 2 ~ 6h, is coated in sheet glass, the FTO (SnO of doped with fluorine by gained solution
2transparent conducting glass), on the substrate such as ITO (indium tin oxide transparent conducting glass) or silicon chip, the optoelectronic film of three-dimensional order after oxolane volatilization, can be obtained.
Further, described bridging bidentate ligand is 4,4'-Bipyridine, alkynyl bipyridine, the one in pyridine radicals porphyrin.
Concrete, the concentration of described hydrochloric acid solution is 0.01 ~ 3mol/L, is preferably 0.1mol/L.
Optoelectronic film prepared by this method, utilize the siloxanes of Metalloporphyrins side chain that Metalloporphyrins is connected into network structure, utilize the coordination of bridging bidentate ligand and porphyrin central metal simultaneously, the multichannel transmission of charge carrier is achieved in the direction perpendicular to film, meet the application requirement of optoelectronic film, be conducive to the raising of photoelectric respone.
The present invention is by the porphyrin monomer of design, synthesizing new and utilize the design feature of monomer self, the number of plies is controlled, the porphyrin complex film of three-dimensional order to induce the assembling of porphyrin monomer self-steering to construct by bridging bidentate ligand, realize perpendicular to film carrier transport between layers on substrate direction, improve the carrier transport ability of film, and then improve the photoelectric respone of material.
The present invention compares with prior art, and its technological progress is significant.Present invention achieves multilayer self assembly organic film carrier transport between layers, thus improve the photoelectric effect of organic film.
Accompanying drawing explanation
Fig. 1 is 5, the infrared spectrum (b) of 10,15,20 – tetra-(4 – cocamidopropyl triethoxysilicane) Cob altporphyrin complex (a) and porphyrin film.
Embodiment
Below in conjunction with specific embodiment, the present invention is described in further detail, but should not regard limitation of the present invention as.
Embodiment 1
1) 5,10, the synthesis 5,10 of 15,20 – tetra-(4 – cocamidopropyl triethoxysilicane) Cob altporphyrin complexs, 15,20 – tetra-(4 – carboxyl phenyl) Cob altporphyrin complex 10.3g, are dissolved in 1000mL oxolane, then add 100mL thionyl chloride, be heated to oxolane reflux temperature, reaction 2h.Decompression distillation removes excessive thionyl chloride, obtains dark violet red solid.Add APTES 10mL wherein again, be heated to reflux temperature, reaction 8h, obtains henna product, i.e. 5,10,15,20 – tetra-(4 – cocamidopropyl triethoxysilicane) Cob altporphyrin complexs.The infrared contrast collection of illustrative plates of 5,10,15,20 – tetra-(4 – carboxyl phenyl) Cob altporphyrin complexs before above-claimed cpd and silanization as shown in Figure 1.
2) preparation method of optoelectronic film
Get 7.84g5,10,15,20 – tetra-(4 – cocamidopropyl triethoxysilicane) Cob altporphyrin complex and 2.9g bipyridines, are dissolved in 1000mL oxolane, add 100mL0.1molL
-1hydrochloric acid solution.Solution is heated to 60 DEG C, insulation 5h.Gained solution is coated on the substrate such as silicon chip, FTO, the optoelectronic film of three-dimensional order after oxolane volatilization, can be obtained.
Embodiment 2
1) synthesis of 5,10,15,20 – tetra-(4 – acylamino-ethyl triethoxy silicane) ferriporphyrin complexs
By 5,10,15,20 – tetra-(4 – carboxyl phenyl) ferriporphyrin complex 8.2g, are dissolved in 850mL oxolane, then add 85mL thionyl chloride, be heated to oxolane reflux temperature, reaction 2h.Decompression distillation removes excessive thionyl chloride, obtains dark violet red solid.Add 2-amino-ethyl triethoxysilane 10mL more wherein, be heated to reflux temperature, reaction 8h, obtains henna product, i.e. 5,10,15,20 – tetra-(4 – acylamino-ethyl triethoxy silicane) ferriporphyrin complexs.
2) preparation method of optoelectronic film
Get 15.6g5,10,15,20 – tetra-(4 – acylamino-ethyl triethoxy silicane) ferriporphyrin complex and 5.849g pyridine radicals porphyrins, are dissolved in 1500mL oxolane, add 150mL0.1molL
-1hydrochloric acid solution.Solution is heated to 60 DEG C, insulation 5h.Gained solution is coated on the substrate such as ITO or quartz, the optoelectronic film of three-dimensional order after oxolane volatilization, can be obtained.
Comparative example 1
Get 3.9g5,10,15,20 – tetra-(4 – acylamino-ethyl triethoxy silicane) porphyrin and 2.9g bipyridines, are dissolved in 500mL oxolane, add 50mL0.1molL
-1hydrochloric acid solution.Solution is heated to 60 DEG C, insulation 5h.Gained solution is coated on the substrate such as ITO or quartz, after oxolane volatilization, can optoelectronic film be obtained.
Comparative example 2
Get 3.9g5,10,15,20 – tetra-(4 – acylamino-ethyl triethoxy silicane) Cob altporphyrin, are dissolved in 500mL oxolane, add 50mL0.1molL
-1hydrochloric acid solution.Solution is heated to 60 DEG C, insulation 5h.Gained solution is coated on the substrate such as ITO or quartz, after oxolane volatilization, can optoelectronic film be obtained.
Photoelectric properties are tested
By the photoelectric properties of three-electrode system test membrane, supporting electrolyte is PBS (PBS, pH=7.4).Be coated with the FTO glass (SnO of doped with fluorine of porphyrin optoelectronic film
2transparent conducting glass) as work electrode, Pt silk is as to electrode, and saturated calomel electrode is as reference electrode.Light source is the xenon lamp (λ=200 – 1800nm) of 150W, and the irradiated area of light is about 1cm
2, bias voltage is controlled in 0.30V, and all photoelectric properties tests are carried out at about 25 DEG C.
Table 1 photoelectric properties compare
Claims (6)
1. a Metalloporphyrins, is characterized in that, its structural formula is as follows:
wherein M is Co
3+, Ni
2+or Fe
3+, R is-CONH (CH
2)
nsi (OEt)
3, n=1 ~ 5.
2. the preparation method of a kind of Metalloporphyrins according to claim 1, is characterized in that comprising the steps:
1) by 5,10,15,20 – tetra-(4 – carboxyl phenyl) Metalloporphyrins are dissolved in oxolane, add thionyl chloride, 5, the mol ratio of 10,15,20 – tetra-(4 – carboxyl phenyl) Metalloporphyrins and thionyl chloride is 1:120 ~ 1:100, be heated to oxolane backflow, react 1 ~ 3 hour;
2) decompression distillation removes excessive thionyl chloride, add amino silane, 5,10,15, the mol ratio of 20 – tetra-(4 – carboxyl phenyl) Metalloporphyrins and amino silane is 1:3 ~ 5, continues back flow reaction 5 ~ 10h, obtains a kind of Metalloporphyrins according to claim 1.
3. the preparation method of a kind of Metalloporphyrins according to claim 2, it is characterized in that: described 5,10,15,20 – tetra-(4 – carboxyl phenyl) Metalloporphyrins are 5,10,15,20 – tetra-(4 – carboxyl phenyl) Cob altporphyrin complexs or 5,10,15,20 – tetra-(4 – carboxyl phenyl) ferriporphyrin complexs or 5, any one in the Metalloporphyrins such as 10,15,20 – tetra-(4 – carboxyl phenyl) nickel-porphyrin complexs.
4. the preparation method of a kind of Metalloporphyrins according to claim 2, is characterized in that: described amino silane compounds is any one in aminomethyl triethoxysilane, 2-amino-ethyl triethoxysilane, APTES, 4-ammobutyltriethoxysilane or 5-Aminopentyl triethoxysilane.
5. the preparation method of a three-dimensional order optoelectronic film, it is characterized in that: a kind of Metalloporphyrins according to claim 1 and bridging bidentate ligand are dissolved in oxolane, add hydrochloric acid solution wherein, mol ratio between Metalloporphyrins, bridging bidentate ligand and hydrochloric acid is 1:4:1.3 ~ 1:4:2, be warming up to 50 ~ 70 DEG C, insulation 2 ~ 6h, is coated in the SnO of sheet glass, doped with fluorine by gained solution
2on transparent conducting glass, indium tin oxide transparent conducting glass or silicon chip substrate, the optoelectronic film of three-dimensional order after oxolane volatilization, can be obtained.
6. the preparation method of a kind of three-dimensional order optoelectronic film according to claim 5, is characterized in that: described bridging bidentate ligand is 4,4'-Bipyridine, alkynyl bipyridine, the one in pyridine radicals porphyrin.
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| CN109575068A (en) * | 2018-10-31 | 2019-04-05 | 泰山学院 | A kind of solvent regulation prepares the method and application of the porphyrin-POSS aggregation of different-shape |
| CN110527107A (en) * | 2019-08-27 | 2019-12-03 | 深圳大学 | A kind of orderly two-dimentional electroconductive molecule monolayer array preparation method and photoelectric device |
| CN110615793A (en) * | 2019-10-04 | 2019-12-27 | 吉林工程技术师范学院 | Metalloporphyrin complex and organic electroluminescent device thereof |
| CN115040446A (en) * | 2022-06-24 | 2022-09-13 | 曾会明 | SOD plant extract skin care composition, skin care product and preparation method thereof |
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| CN115040446A (en) * | 2022-06-24 | 2022-09-13 | 曾会明 | SOD plant extract skin care composition, skin care product and preparation method thereof |
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