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A-D-A conjugated molecule based on thieno cyclopentanedione derivative and preparation method of A-D-A conjugated molecule

A technology of cyclopentadione and conjugated molecules, which is applied in the field of A-D-A conjugated molecules and its preparation, can solve the problems of difficult adjustment of absorption and energy levels, no absorption of visible light, and difficult purification, and achieve high open circuit voltage and fill factor, High photoelectric conversion efficiency and good solubility

Active Publication Date: 2017-06-23
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, fullerene derivatives also have problems such as no absorption of visible light, difficulty in adjusting absorption and energy levels, difficulty in purification, and high cost, making it difficult for practical application (Energy.Environ.Sci.2012,5,8343-8350)

Method used

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  • A-D-A conjugated molecule based on thieno cyclopentanedione derivative and preparation method of A-D-A conjugated molecule
  • A-D-A conjugated molecule based on thieno cyclopentanedione derivative and preparation method of A-D-A conjugated molecule
  • A-D-A conjugated molecule based on thieno cyclopentanedione derivative and preparation method of A-D-A conjugated molecule

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Experimental program
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Effect test

Embodiment 1

[0063] Embodiment 1: the preparation of compound 1

[0064]

[0065] Add compound a (96.3mg, 0.1mmol) and compound d (100mg, 0.5mmol) in a round bottom flask, repeatedly exhaust the gas in the reaction vessel and inject inert gas to get rid of the air in the reaction vessel, then add 10mL of chloroform and stir , add pyridine 0.1mL after completely dissolving; carry out stirring reaction at a temperature of 80°C for 12 hours, then cool to room temperature; the obtained reaction solution is rotary evaporated to remove the solvent, and the obtained solid product is subjected to silica gel (200-300 mesh) column chromatography For separation, the eluent was petroleum ether / dichloromethane (volume ratio 1:1), and the product was a dark blue solid (101 mg, 76%), which was the A-D-A conjugated molecule 1. Theoretical value of element analysis: C, 77.79; H, 5.92; N, 4.22; found value: C, 77.82; H, 5.94; N, 4.25;

Embodiment 2

[0066] Embodiment 2: the preparation of compound 3

[0067] Compound 3 was prepared using the same method as compound 1, except that compound a was replaced by the corresponding thienocyclopentanedione derivative. Elemental analysis theoretical value: C, 78.11; H, 6.26; N, 4.05; found value: C, 78.09; H, 6.24; N, 4.00;

Embodiment 3

[0068] Embodiment 3: the preparation of compound 6

[0069] Compound 6 was prepared using the same method as compound 1, except that compound a was replaced by the corresponding thienocyclopentanedione derivative. Theoretical value of element analysis: C, 77.79; H, 5.92; N, 4.22; found value: C, 77.81; H, 5.94; N, 4.25;

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Abstract

The invention relates to a type of A-D-A conjugated molecules adopting a thieno cyclopentanedione derivative as an end-capping group, homopolymerize quinary heterocyclic aromatic as a bridging unit and polycyclic trapezoidal conjugated molecule as a core, and a preparation method of the A-D-A conjugated molecule, and application of the molecule as an active layer electron receptor material in an organic photovoltaic cell (OPV). The A-D-A conjugated molecule is good in solubility, has an appropriate energy level, and has a better absorption spectrum. A solar cell device prepared based on the A-D-A conjugated molecule has extremely high energy conversion efficiency. The A-D-A conjugated molecule has the following general structure. (Shown in the description).

Description

technical field [0001] The present invention relates to a class of A-D-A conjugated molecules with thienocyclopentanedione derivatives as end-capping groups, homopolymerized five-membered aromatic heterocycles as bridging units, and polycyclic ladder-shaped conjugated molecules as cores and a preparation method thereof. And the application of this type of molecule as an electron acceptor material in the active layer in organic solar cells (OPV). Background technique [0002] An organic solar cell is a solar cell that uses organic matter as the light-absorbing active layer material. Compared with inorganic solar cells, organic solar cells have the advantages of low cost, light weight, flexible devices and solution processing, and have gradually been accepted by the academic community. And widespread concern in the industry (Chem.Rev.2007,107,1324-1338). The active layer of organic solar cells often adopts a bulk heterojunction structure to facilitate charge separation, which...

Claims

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Application Information

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IPC IPC(8): C07D495/04C07D495/22H01L51/42H01L51/46
CPCC07D495/04C07D495/22H10K85/649H10K85/655H10K85/6576H10K30/50Y02E10/549Y02P70/50
Inventor 杨楚罗谢东君高威罗正辉
Owner WUHAN UNIV
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