CN115094379A - One-dimensional polyfluorene chain and preparation method thereof - Google Patents
One-dimensional polyfluorene chain and preparation method thereof Download PDFInfo
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- CN115094379A CN115094379A CN202210780336.9A CN202210780336A CN115094379A CN 115094379 A CN115094379 A CN 115094379A CN 202210780336 A CN202210780336 A CN 202210780336A CN 115094379 A CN115094379 A CN 115094379A
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- 229920002098 polyfluorene Polymers 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 239000000758 substrate Substances 0.000 claims abstract description 34
- 239000002184 metal Substances 0.000 claims abstract description 15
- 229910052751 metal Inorganic materials 0.000 claims abstract description 15
- 239000002243 precursor Substances 0.000 claims abstract description 8
- 238000005859 coupling reaction Methods 0.000 claims abstract description 5
- 238000007256 debromination reaction Methods 0.000 claims abstract description 5
- 238000005516 engineering process Methods 0.000 claims abstract 2
- LCKDOHRDONNZTG-UHFFFAOYSA-N 1,2-dibromo-9h-fluorene Chemical compound C1=CC=C2CC3=C(Br)C(Br)=CC=C3C2=C1 LCKDOHRDONNZTG-UHFFFAOYSA-N 0.000 claims description 21
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 13
- 239000010931 gold Substances 0.000 claims description 13
- 229910052737 gold Inorganic materials 0.000 claims description 13
- 238000000137 annealing Methods 0.000 claims description 11
- 238000000151 deposition Methods 0.000 claims description 10
- 230000008021 deposition Effects 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 238000001451 molecular beam epitaxy Methods 0.000 claims 1
- 229910052709 silver Inorganic materials 0.000 claims 1
- 239000004332 silver Substances 0.000 claims 1
- 239000013078 crystal Substances 0.000 abstract description 11
- 238000000034 method Methods 0.000 abstract description 5
- 239000002105 nanoparticle Substances 0.000 abstract description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 230000005641 tunneling Effects 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 6
- 238000001000 micrograph Methods 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Substances [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000002086 nanomaterial Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000003775 Density Functional Theory Methods 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000002070 nanowire Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C14/00—Coating by vacuum evaporation, by sputtering or by ion implantation of the coating forming material
- C23C14/22—Coating by vacuum evaporation, by sputtering or by ion implantation of the coating forming material characterised by the process of coating
- C23C14/34—Sputtering
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B22—CASTING; POWDER METALLURGY
- B22F—WORKING METALLIC POWDER; MANUFACTURE OF ARTICLES FROM METALLIC POWDER; MAKING METALLIC POWDER; APPARATUS OR DEVICES SPECIALLY ADAPTED FOR METALLIC POWDER
- B22F1/00—Metallic powder; Treatment of metallic powder, e.g. to facilitate working or to improve properties
- B22F1/05—Metallic powder characterised by the size or surface area of the particles
- B22F1/054—Nanosized particles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y40/00—Manufacture or treatment of nanostructures
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
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- C—CHEMISTRY; METALLURGY
- C21—METALLURGY OF IRON
- C21D—MODIFYING THE PHYSICAL STRUCTURE OF FERROUS METALS; GENERAL DEVICES FOR HEAT TREATMENT OF FERROUS OR NON-FERROUS METALS OR ALLOYS; MAKING METAL MALLEABLE, e.g. BY DECARBURISATION OR TEMPERING
- C21D1/00—General methods or devices for heat treatment, e.g. annealing, hardening, quenching or tempering
- C21D1/26—Methods of annealing
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- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C14/00—Coating by vacuum evaporation, by sputtering or by ion implantation of the coating forming material
- C23C14/06—Coating by vacuum evaporation, by sputtering or by ion implantation of the coating forming material characterised by the coating material
- C23C14/12—Organic material
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/314—Condensed aromatic systems, e.g. perylene, anthracene or pyrene
- C08G2261/3142—Condensed aromatic systems, e.g. perylene, anthracene or pyrene fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
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Abstract
The invention discloses a one-dimensional polyfluorene chain and a preparation method thereof. In the preparation method, metal single crystal is selected as a substrate, precursor molecule dibromine fluorene is deposited on the surface of the substrate by a molecular beam epitaxial growth technology to obtain a sample, and then the sample is gradually annealed to induce the debromination and aryl coupling reaction among molecules, so that the one-dimensional polyfluorene chain structure with accurate atomic scale can be obtained. The method provides a new idea for preparing the nano-sized one-dimensional polyfluorene chain, and has higher scientific research value and wide application potential.
Description
Technical Field
The invention relates to the technical field of nano materials, in particular to a preparation method for synthesizing a one-dimensional polyfluorene chain by depositing dibromofluorene molecules on a metal substrate, gradually annealing the dibromofluorene molecules, and utilizing the catalytic action and the template effect of the substrate.
Background
Surface synthesis has proven to be an efficient and widespread method for preparing, from bottom to top, low-dimensional nanostructures (e.g., one-dimensional nanowires, oligomers or polymers, quantum lattices, and two-dimensional porous network structures, etc.) with precise covalent bonding at the atomic level.
Polycyclic aromatic hydrocarbons composed of a carbon aromatic ring and a hydrogen atom have been of great interest for decades because they exhibit different optical and chemical properties compared to conventional conjugated polymers. Wherein the introduction of the non-benzene heterocyclic ring can remarkably adjust the electronic structure and the aromaticity of the main chain. This would show potential applications in organic electronics, open shell magnetic systems with unpaired electrons, spintronics and optoelectronics. Polyfluorene is composed of 6-5-6 condensed ring complete conjugate array, and is considered to have strong potential in Organic Light Emitting Devices (OLED), fluorescence biosensors, organic photovoltaic devices (OPV), building modules of p-type semiconductors in transistors and other applications. Substitution of the two hydrogen atoms attached to the carbon atom at the top of the five-membered ring in the fluorene unit gives a series of highly processable polymer derivatives. However, the synthesis of pure polyfluorenes without bulky groups on the top carbon is not easy under traditional solution chemistry conditions due to their poor solubility, and the precise characterization of the polyfluorene structure at the surface atomic level is relatively lacking.
Disclosure of Invention
The invention aims to provide a one-dimensional polyfluorene chain and a preparation method thereof. Specifically, the method utilizes a strategy that dibromofluorene molecules can generate debromination coupling under the catalytic action of a metal substrate to deposit the dibromofluorene molecules on the surface of the metal substrate to obtain a porous self-assembled sample which is regular and ordered on the substrate; and gradually annealing the sample at the temperature for inducing the debromination coupling reaction to obtain a high-quality one-dimensional polyfluorene chain.
The invention can be realized by the following technical scheme: under the ultrahigh vacuum environment, firstly, the dibromo fluorene precursor molecules are deposited on the surface of a clean metal substrate at the temperature of 25-30 ℃, the deposition time is 60 seconds, and then the metal substrate loaded with the precursor molecules is subjected to gradual annealing treatment at a reaction triggering temperature to obtain a high-quality one-dimensional polyfluorene chain structure.
Preferably, the method for preparing a nano-sized one-dimensional polyfluorene chain further comprises the following steps: before the molecules of the precursor are deposited, the temperature is kept for 10 minutes at the evaporation temperature, so that the stability of the molecular beam current is ensured. After deposition, the metal substrate is annealed at room temperature for 10 minutes to ensure that the molecules are fully diffused, arranged and assembled on the substrate.
Preferably, the growth temperature is 160-200 ℃, and the time for keeping after the temperature is raised to the reaction temperature is 5-10 minutes. This step is also referred to as an "annealing" step in the present invention. By carrying out this step, the deposited dibromofluorene molecules can be made to react by diffusion sufficiently to form polyfluorene chains of higher quality.
Preferably, the step of evaporating and depositing the dibromofluorene molecules onto a metal substrate is to evaporate and deposit the dibromofluorene molecules onto the metal substrate by thermoresistive heating.
In certain embodiments of the invention, the dibromofluorene molecules are evaporated at an evaporation temperature of 25 ℃ to 30 ℃. For example, in the case where the evaporation temperature is selected to be 30 ℃, a good deposition effect can be obtained.
In certain embodiments of the invention, better sample quality may be achieved by annealing at 160 ℃ for 5 minutes first, followed by a 10 minute continuation at 160 ℃, followed by a 5 minute anneal at 180 ℃, and finally a 200 ℃ anneal.
In certain embodiments of the present invention, the metal substrate is prepared by a method comprising: a. performing argon ion sputtering on the metal substrate in an ultrahigh vacuum chamber; b. the metal substrate was heated and held at 450 ℃ for 10-30 minutes. c. The metal substrate was slowly cooled down to 260 c at an annealing rate of 6 c/min and then allowed to cool down naturally.
Drawings
Embodiments of the invention are described in detail below with reference to the attached drawing figures, wherein:
FIG. 1 shows a schematic diagram of polyfluorene chain synthesis according to an embodiment of the present invention;
fig. 2 shows a scanning tunneling microscope image and a cell structure of a two-dimensional porous nano-network formed by self-assembly of dibromofluorene molecules, and an optimized structure of a scanning tunneling microscope key resolution image and density functional theory calculation according to an embodiment of the present invention;
FIG. 3 shows scanning tunneling microscope images obtained by successive annealing at different temperatures on a single-crystal gold substrate according to an embodiment of the present invention;
FIG. 4 shows scanning tunneling microscope and bond-resolved scanning tunneling microscope images of high quality closely-packed polyfluorene chain and single, longer polyfluorene chain samples, and corresponding chemical structural formulae, in accordance with embodiments of the present invention;
FIG. 5 shows an electrical property characterization of a one-dimensional polyfluorene chain according to an embodiment of the present invention;
Detailed Description
The present invention is described in further detail below with reference to specific embodiments, which are given by way of illustration only and are not intended to limit the scope of the present invention.
Test instruments and equipment:
low-temperature scanning tunnel microscope: from omitron, germany.
K-cell molecular evaporation source: from Omicron, Germany.
An argon ion gun: from omitron, germany.
Raw materials:
dibromofluorene molecules: purchased from chemson, 99% pure.
Single crystal gold substrate: purchased from MaTecK, 99.999% pure.
Examples
Preparation of single crystal gold substrate: and (3) carrying out argon ion sputtering treatment on the gold single crystal by using an argon ion gun in an ultrahigh vacuum chamber to obtain a gold substrate, heating the gold substrate, keeping the temperature at 450 ℃ for 10-30 minutes, and obtaining a clean and flat single crystal gold substrate.
After the single crystal gold substrate is prepared, under an ultrahigh vacuum environment, dibromofluorene molecules are evaporated and deposited on the surface of the single crystal gold substrate kept at room temperature by using a thermal resistance type K-cell molecular evaporation source at the evaporation temperature of 30 ℃, the deposition time of the dibromofluorene molecules is 60 seconds, and after the deposition is finished, the single crystal gold substrate and the dibromofluorene molecules on the substrate are kept at the annealing temperature of 30 ℃ for 10 minutes. The aim is to allow the molecules to diffuse, align and assemble sufficiently. The sample was heated to 160 ℃ and held at the reaction temperature for 10 minutes. This step is also referred to as an "annealing" step in the present invention. By performing this step, the deposited dibromofluorene molecules can undergo a debromination coupling reaction under the catalysis of the single-crystal gold substrate.
Fig. 1 shows a schematic diagram of a preparation method according to an embodiment of the present invention, the different colors of the five-membered rings representing different orientations of the connecting units due to carbon-carbon single bond rotation. Wherein the rotational arrows mark the rotational nature of the carbon-carbon single bond. Fig. 2 shows a scanning tunneling microscope image and a bond-resolved scanning tunneling microscope image of a high-density nano-sized two-dimensional porous nano-network assembled from dibromofluorene molecules, and corresponding structural model images thereof. Fig. 3 shows scanning tunneling microscope images obtained by annealing under different temperature conditions on a single-crystal gold substrate according to an embodiment of the manufacturing method of the present invention. The polyfluorene chain samples prepared according to the preparation method of the embodiment of the present invention can be dynamically and effectively observed. Figure 4 shows a close-packed polyfluorene chain and a longer single polyfluorene chain structure prepared according to an example preparation method of the present invention. The polyfluorene chains are represented by the staggered arrangement and the equidirectional arrangement of molecular units, and the polyfluorene chains prepared by the preparation method provided by the embodiment of the invention are judged to have a linear chain structure and a chain structure with a certain curvature. Fig. 5 shows the electrical property characterization of a single straight fluorene chain, and experimental and computational results indicate that the single polyfluorene chain structure has a band gap of 2.25 ± 0.05 eV and a density of states distributed at the armchair boundary of the cell molecule at 2200 meV energy. Has excellent semiconductor properties.
Claims (6)
1. A preparation method of a one-dimensional polyfluorene chain is characterized by comprising the following steps: depositing a precursor molecule of dibromofluorene on the surface of a metal substrate by a molecular beam epitaxy technology to obtain a sample carrying the dibromofluorene molecules; and then heating the sample to a certain temperature for gradual annealing treatment to obtain the one-dimensional polyfluorene chain.
2. The one-dimensional polyfluorene chain and the preparation method thereof according to claim 1, wherein: the deposition temperature of the precursor molecule of the dibromofluorene is 30 ℃.
3. The method for producing a one-dimensional polyfluorene chain according to claim 1, wherein: the deposition time of the precursor molecule of dibromofluorene is 60 seconds.
4. The method for producing a one-dimensional polyfluorene chain according to claim 1, wherein: the temperature of the precursor molecule dibromofluorene for debromination coupling reaction is 160 ℃.
5. The method for producing a one-dimensional polyfluorene chain according to claim 1, wherein: the growth temperature of the sample is 160-200 ℃.
6. The method for producing a one-dimensional polyfluorene chain according to claim 1, wherein: the metal substrate is a gold substrate, a silver substrate and a copper substrate.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009051560A1 (en) * | 2007-10-17 | 2009-04-23 | Agengy For Science, Technology And Research | Water-soluble fluorescent material with balanced hydrophilicity and hydrophobicity |
| CN103130985A (en) * | 2011-11-23 | 2013-06-05 | 张勇 | Novel surface polymerization method and application in preparation of organic electronic device thereof |
| CN113564529A (en) * | 2021-07-29 | 2021-10-29 | 南京理工大学 | Method for controlling selectivity of reaction product on surface of oxygen-containing organic precursor |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009051560A1 (en) * | 2007-10-17 | 2009-04-23 | Agengy For Science, Technology And Research | Water-soluble fluorescent material with balanced hydrophilicity and hydrophobicity |
| CN103130985A (en) * | 2011-11-23 | 2013-06-05 | 张勇 | Novel surface polymerization method and application in preparation of organic electronic device thereof |
| CN113564529A (en) * | 2021-07-29 | 2021-10-29 | 南京理工大学 | Method for controlling selectivity of reaction product on surface of oxygen-containing organic precursor |
Non-Patent Citations (2)
| Title |
|---|
| T. TUNNO等: "Matrix-assisted pulsed laser evaporation of polyfluorene thin films", 《APPLIED SURFACE SCIENCE》, vol. 253, no. 15, pages 6461, XP022066274, DOI: 10.1016/j.apsusc.2007.01.024 * |
| 赵前进 等: "金刚烷双溴化物改性聚芴的Suzuki偶联聚合 及光致发光性能", 《精细化工》, vol. 26, no. 3, pages 209 - 212 * |
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