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Donor-acceptor type fluorenyl nanometer grid material, preparation method and application thereof

A nano-lattice, donor-acceptor-type technology, which is applied in the field of donor-acceptor-type fluorenyl nano-lattice materials and its preparation, can solve the problems of low reactivity of acceptor fragments, low ring-forming yield of cyclic molecules, and difficulty in separation. , achieve the effects of reducing film solvent dependence, modular synthesis, and high scalability

Inactive Publication Date: 2017-03-22
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the tight π-π stacking of some structures, it exhibits excellent carrier mobility compared with general organics, and has potential application prospects in the field of optoelectronic devices, but its inability to be processed by solution limits its further application in optoelectronic devices
Another class of new cyclic compounds that have just begun to be studied in recent years, such as pillar aromatics (Pillalarene), Kekulene (kekulene), [n] cyclo-p-phenylene ([n] CPPs) and graphene-like or Carbon nanotube-like cyclic small molecules or polymers, which have a rigid skeleton structure and the advantages of soluble processing, have initially shown fascinating application prospects in the field of optoelectronic materials, but such materials that can be flexibly processed rarely have a skeleton At the same time, it contains molecular configuration reports for the alternate arrangement of receptor fragments. The introduction of receptor fragments is usually achieved by bridging macrocyclic skeletons, mainly due to the low yield of ring-forming ring molecules, difficulty in separation, and the reaction of receptor fragments. Difficult to achieve due to low activity
Therefore, it is impossible to effectively control the photoelectric property parameters such as band gap and energy level of cyclic compounds.
At the same time, the precise control of the nanoscale pore size of cyclic compounds and the introduction of high-performance optoelectronic groups are also facing a series of challenges. The application research in the field of optoelectronic materials has just started and is not deep enough.

Method used

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  • Donor-acceptor type fluorenyl nanometer grid material, preparation method and application thereof
  • Donor-acceptor type fluorenyl nanometer grid material, preparation method and application thereof
  • Donor-acceptor type fluorenyl nanometer grid material, preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0061] When W is C; Ar 1 、Ar 2 For p-bromooctyloxybenzene, Ar 3 For dithiophene or triple thiophene, Ar 4 It is benzothiadiazole, G1 and G2 are both hydrogen, and the lattice molecular structures are as follows:

[0062]

[0063] The reaction scheme is as follows:

[0064]

[0065] The specific preparation method is as follows: dithiophene and tertiary thiophene are obtained by coupling thiophene monomers under the catalysis of Pd / C; bisbromobenzobithiazole is borated at high temperature to obtain compound 3; –Crafts reaction to obtain compound 5, compound 3, 4, 5 in Pd(PPh 3 ) 4 Catalyst, alkaline solution choose K 2 CO 3 Under Suzuki coupling under / KF conditions, the monosubstituted L-shaped precursor can be obtained efficiently. The L-shaped precursor is located in Et through its own double active site tertiary alcohol group and the 2-position of thiophene 2 O·BF 3 Catalyzed Friedel–Crafts reaction ring closure to obtain the acceptor-type fluorenyl lattice ...

Embodiment 2

[0077] Thermogravimetric analysis (TGA) was performed on a Shimadzu DTG-60H thermogravimetric analyzer with a heating scan rate of 10 °C / min and a nitrogen flow rate of 20 cm 3 / min. Differential scanning calorimetry (DSC) was carried out on a Shimadzu DSC-60A tester. The sample was first heated at a rate of 10°C / min to a state ten degrees lower than the decomposition temperature of the sample, and then, under liquid nitrogen conditions The temperature was lowered back to the starting temperature, and the temperature was scanned at a rate of 10°C / min for the second time. From the TGA experiment, the temperature (T d ) are 355°C and 320°C, respectively. DSC experiments showed no obvious glass transition temperature.

Embodiment 3

[0079] Prepare the nanogrids G1 and G2 into accurate 1 μM dichloromethane dilute solutions respectively, and flush with argon gas to remove oxygen. The absorption and emission spectra were measured by Shimadzu UV-3150 ultraviolet-visible spectrometer and RF-530XPC fluorescence spectrometer.

[0080] Such as Figure 5 , 6 As shown, the peaks of the ultraviolet absorption spectrum and fluorescence spectrum of the nano-lattice G1 in dichloromethane are 381nm and 530nm, respectively. The peaks of the ultraviolet absorption spectrum and fluorescence spectrum of nano-lattice G2 in dichloromethane are 408nm and 534nm, respectively.

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Abstract

The invention discloses a donor-acceptor type fluorenyl nanometer grid material, a preparation method and application thereof. The nanometer grid material is of a square-ring-shaped rigid structure formed through alternative arrangement of fluorenyl ramification regarded as electron donor units and electron acceptor units. The preparation method comprises the following steps that a precursor with tertiary alcohol and aromatic nucleus terminal based hydrogen inhibitor dual binding sites is dissolved in organic solvent; at the room temperature, a catalyst is added, and stirring and reacting are conducted; and the reaction is conducted for 5 min-12 h, and products are obtained through chromatogram column separation. The donor-acceptor type fluorenyl nanometer grid material has the advantages that the compounding method is modularized, extensibility and stability of thermology, electrochemistry and photology are high; dependency of thin film solvent is reduced; large-area soluble processing is achieved; the size of apertures is accurately regulated and controlled; and accurate regulation an control of band gaps and energy level arrangement are achieved. The donor-acceptor type fluorenyl nanometer grid material has potential application prospects in the fields of photoelectric function materials of organic solar cells, storage and memory resistor, sensing, detecting and the like.

Description

technical field [0001] The invention belongs to the technical field of organic semiconductor materials, and in particular relates to a solution-processable donor-acceptor-type fluorenyl-based nano-lattice material with a nanoscale pore size and a preparation method thereof, and relates to the application of these materials in organic electricity storage, organic electromagnetism Applications in luminescence, photovoltaic cells, light detection, chemical and biological sensing, and organic lasers. Background technique [0002] Due to the advantages of low production cost, simple manufacturing process, and the ability to prepare flexible large-area devices, organic optoelectronic devices have become a hot research topic for scientists at home and abroad. Organic small molecule materials have been widely used in organic solar cells, organic electroluminescence, organic photodetection, organic storage, organic laser and other fields due to their definite molecular structure and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/22C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D513/22C09K2211/1092C09K2211/1051H10K85/657H10K50/15H10K50/18H10K50/11Y02E10/549
Inventor 解令海卞临沂章杨李腾飞余洋刘宁仪明东黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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