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Synthesis method of intramolecular exciton splitting material with anti-aromaticity and quinonoid structure, preparation method of thin film and single crystal

A synthetic method and aromatic technology, which is applied in the synthesis, thin film preparation and single crystal preparation of intramolecular exciton splitting materials with antiaromaticity and quinone structure, and can solve the problems of chromophore sensitivity and limited development

Active Publication Date: 2021-07-20
CAPITAL NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Materials with exciton splitting properties discovered so far include naphthacene, pentacene and other acene compounds, polythiophenes, carotenoid polymers, perylene imides, covalently bonded dimers, 1, 3-Diphenylisobenzofuran, etc. Most of the exciton splitting materials discovered so far are intermolecular exciton splitting materials, and their properties are highly sensitive to the crystal packing of chromophores and the morphology of the active layer, which limits their further development. development, scientists are committed to designing intramolecular exciton splitting materials and polymers to effectively overcome this drawback

Method used

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  • Synthesis method of intramolecular exciton splitting material with anti-aromaticity and quinonoid structure, preparation method of thin film and single crystal
  • Synthesis method of intramolecular exciton splitting material with anti-aromaticity and quinonoid structure, preparation method of thin film and single crystal
  • Synthesis method of intramolecular exciton splitting material with anti-aromaticity and quinonoid structure, preparation method of thin film and single crystal

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preparation example Construction

[0027] A method for synthesizing a material with intramolecular exciton splitting properties, comprising the following steps:

[0028] Synthesize diketopyrrolopyrrole (BDPP) as the molecular skeleton and introduce different alkyl chain substituents on the nitrogen atom of the amide bond.

[0029] For example, 1,5-dihexyl-3,7-diphenylpyrrolopyrrole-2,6-dione (designated BDPP-C6) was synthesized. The BDPP-C6 molecule is taken as an example for illustration below.

[0030] A method for preparing a thin film of a material with an intramolecular exciton splitting property, comprising synthesizing the above molecule and preparing a thin film of the molecule by vacuum vapor deposition.

[0031] For example, to prepare BDPP-C6 molecules, a thin film of BDPP-C6 molecules is prepared by vacuum vapor deposition.

[0032] A method for preparing a single crystal of an intramolecular exciton splitting material, comprising synthesizing the above molecules: dissolving a small amount of mole...

Embodiment 1

[0039] Embodiment one: if figure 1 The synthesis route of the BDPP skeleton shown is illustrated by taking BDPP-C6 as an example.

[0040] Synthesis of BDPP-C6 molecule: ①Add p-phenylenediamine and mandelic acid to chlorobenzene, react at a certain temperature (for example, 130°C) for several hours, such as 18 hours, cool to room temperature, filter the precipitate, and wash with ethanol , dried to obtain a white solid BP molecule (C 22 h 20 N 2 o 4 ). 2. Add BP molecules into concentrated sulfuric acid, stir at room temperature for example for 20 hours, pour into ice water after the reaction is over, filter the precipitate, wash with water, and dry to obtain light red solid BDP molecules (C 22 h 16 N 2 o 2 ). ③ Add sodium hydroxide solution dropwise to the ethanol suspension of BDP molecules, then add aqueous potassium persulfate solution, heat and reflux at, for example, 78°C for 2 hours, and after cooling, filter the precipitate, wash with water, and dry to obtain ...

Embodiment 2

[0042] Example 2: Preparation and characterization of BDPP-C6 molecular film:

[0043] Preparation of BDPP-C6 molecular film: at 1×10 -5 mbar vacuum condition, to BDPP-C6 molecular film was prepared by vacuum vapor deposition method on sapphire or quartz substrate, and the evaporated molecular film was 100-120nm.

[0044] figure 2 Shown are the absorption emission spectrum of BDPP-C6 solution and the absorption spectrum of film. The maximum absorption peak of BDPP-C6 molecule in solution is at the wavelength of 456nm, and the highest emission peak is at the wavelength of 532nm. The maximum absorption peak of the BDPP-C6 molecular film has an obvious red shift compared with the solution, the absorption band edge is at 530nm, and the band gap is about 2.4eV.

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Abstract

The invention discloses a synthesis method of an intramolecular exciton splitting material with anti-aromaticity and a quinonoid structure and a preparation method of a thin film and a single crystal. The synthesis method of the intramolecular exciton splitting material comprises the following steps: synthesizing a molecule which takes benzopyrrolopyrroledione (BDPP) as a molecular skeleton and introduces different alkyl chain substituent groups on an amido bond nitrogen atom, wherein the skeleton has relatively strong blue-green light absorption, excellent air and light stability and appropriate triplet state energy. The invention discloses characterization means of the molecular solution and the thin film spectrum. The intramolecular exciton splitting material has an ultrafast-scale exciton splitting rate and a relatively high triplet state exciton yield, so that possibility is provided for application of a novel organic photovoltaic device to a great extent. The intramolecular exciton splitting (iSF) process in the BDPP molecule hardly depends on intermolecular orientation and electronic coupling, and the BDPP molecule has great potential to be integrated into an SF-based organic photovoltaic device.

Description

technical field [0001] The invention relates to the technical field of preparation of materials with certain special photoelectric properties. Specifically, we designed and synthesized an intramolecular exciton splitting material with antiaromaticity and quinoid structure, which has ultrafast exciton splitting rate and high triplet exciton yield , independent of intermolecular orientation and electronic coupling, has great potential for integration into SF-based organic photovoltaic devices. Background technique [0002] Singlet exciton splitting is a process in which the spin of a singlet exciton allows the generation of two triplet excitons of altered multiplicity. In organic materials, singlet splitting refers to the transformation of a singlet exciton generated by photoexcitation into two triplets on an ultrafast scale when the energy of the singlet excitons is greater than twice the energy of the triplet excitons. Exciton process. It is different from the intersystem...

Claims

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Application Information

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IPC IPC(8): C07D487/04C30B29/54C30B7/06
CPCC07D487/04C30B29/54C30B7/06C07B2200/13
Inventor 付红兵谢少华吴义室廖清王龙
Owner CAPITAL NORMAL UNIVERSITY
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