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A-pi-D-pi-A type organic small molecule based on diindenopyrazine as well as preparation method and application thereof

A technology of indenopyrazine and small molecules, applied in the field of A-π-D-π-A type organic small molecules and their preparation, to achieve the effects of wide supply of raw materials, high promotion, and high short-circuit current

Inactive Publication Date: 2020-02-21
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the electron-deficient system fused with multiple aromatic rings as the central D-unit wide bandgap acceptor material has rarely been reported.
Especially the electron-deficient IPY unit as the central core (D), the electron-withdrawing unit (such as 3-(dicyanomethylene)inden-1-one, etc.) as the terminal A, and the thiophene unit as the π-conjugated bridge A -π-D-π-A type small molecule acceptor material and its preparation method and photovoltaic application have not yet been reported

Method used

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  • A-pi-D-pi-A type organic small molecule based on diindenopyrazine as well as preparation method and application thereof
  • A-pi-D-pi-A type organic small molecule based on diindenopyrazine as well as preparation method and application thereof
  • A-pi-D-pi-A type organic small molecule based on diindenopyrazine as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] An A-π-D-π-A type organic small molecule CLS1 based on bis-indenopyrazine (IPY), with the electron-donating IPY unit as the central core D, thiophene as the π-conjugated bridge, 3-(dicyano Methylene) inden-1-one is the electron-withdrawing terminal A.

[0063] CLS1 has the general structural formula of Formula I:

[0064]

[0065] Wherein, R is n-octyl, and A is 3-(dicyanomethylene)inden-1-one.

[0066] The specific chemical structural formula of the small molecule CLS1 is:

[0067]

[0068] A preparation method of CLS1 of this embodiment, see the synthetic route figure 1 , the specific preparation method comprises the following steps:

[0069] (1) Synthesis of 5-bromo-2-oximino-2,3-dihydro-1-indanone (compound 2).

[0070] 1.1. Under argon atmosphere, add 5.00 g of 5-bromo-indanone (23.69 mmol) (compound 1) and 100 mL of toluene into a 250 mL three-necked flask.

[0071] 1.2. Bubble dry HCl gas into the reaction system for 5 minutes.

[0072] 1.3. Pass the ...

Embodiment 2

[0125] An A-π-D-π-A small molecule CLS2 based on the indenopyrazine (IPY) unit, with the electron-donating IPY unit as the central core D, thiophene as the π-conjugated bridge, and 5,6-di Chloro-3-(dicyanomethylene)inden-1-one is the electron-withdrawing terminal A.

[0126] CLS2 has the general structural formula of Formula I:

[0127]

[0128] Among them, R is n-octyl, A is 5,6-dichloro-3-(dicyanomethylene)inden-1-one, and the specific chemical structure formula of the small molecule CLS2 is as follows:

[0129]

[0130] A preparation method of CLS2 of this embodiment, see the synthetic route figure 1 , the specific preparation method comprises the following steps:

[0131] (1) Intermediate M1 5,5'-(6,6,12,12-tetraoctyl-6,12-dihydroindeno[1,2-b:1',2'-e]pyridine Synthesis of oxazine-2,8-diyl)bis(thiophene-2-carbaldehyde): same as Example 1.

[0132] (2) Synthesis of CLS2: under argon atmosphere, in a 100mL three-neck flask, add 0.60g of intermediate M1 (0.65mmol), 0...

Embodiment 3

[0145] An A-π-D-π-A type small molecule CLS3 based on an IPY unit: with the electron-donating IPY unit as the central core D, thiophene as the π-conjugated bridge, 5,6-difluoro-3-(dicyano Methylene) inden-1-one is the electron-withdrawing terminal A.

[0146] CLS3 has the general structural formula of I formula:

[0147]

[0148] Wherein, R is n-octyl, A is 5,6-difluoro-3-(dicyanomethylene)inden-1-one, and the specific chemical structural formula of the small molecule CLS3 is as follows:

[0149]

[0150] A preparation method of CLS3 of this embodiment, see the synthetic route figure 1 , the specific preparation method comprises the following steps:

[0151] (1) Intermediate M1 5,5'-(6,6,12,12-tetraoctyl-6,12-dihydroindeno[1,2-b:1',2'-e]pyridine Synthesis of oxazine-2,8-diyl)bis(thiophene-2-carbaldehyde): same as Example 1.

[0152] (2) Synthesis of CLS3: Add 0.67g of intermediate M1 (0.72mmol) and 0.66g of 5,6-difluoro-3-(dicyanomethylene) into a 100mL three-neck fl...

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Abstract

The invention discloses an A-pi-D-pi-A type organic small molecule based on diindenopyrazine as well as a preparation method and application of the A-pi-D-pi-A type organic small molecule. In the A-pi-D-pi-A type organic small molecule, an IPY unit for electron donating is used as a central core D, thiophene is used as a pi conjugate bridge, and 3-(dicyanomethylene) indene-1-one or 5, 6-dichloro-3-(dicyanomethylene) indene-1-one or 5, 6-difluoro-3-(dicyanomethylene) indene-1-one is used as an electron withdrawing terminal A. The preparation method comprises the step of carrying out Knoevenagelcondensation reaction on intermediate M1 and A under the action of a solvent and a catalyst. By changing the different electron withdrawing terminal A, regulation and control of the A-pi-D-pi-A typeorganic small molecule on photoelectric properties such as a small molecular structure, an absorption spectrum, a band gap and a proline molecular orbital energy level can be realized, a small molecular photoelectric functional material with excellent photoelectric properties is prepared, and the small molecular photoelectric functional material can be applied to preparation of organic solar cells.

Description

technical field [0001] The invention relates to the technical field of organic solar cells, in particular to an A-π-D-π-A type organic small molecule based on a bisindenopyrazine unit and a preparation method and application thereof. Background technique [0002] Organic solar cells (OSCs) are devices based on organic compounds that directly convert solar energy into electrical energy using the photovoltaic effect. It has the advantages of light weight, cheap price, simple preparation process, and good controllability of the chemical structure of the material, and has obvious advantages in future applications. At present, the power conversion efficiency (PCE) of laminated OSCs based on acceptor-donor-acceptor (A-D-A) type small molecule receptors has exceeded 17% (Meng L, Zhang Y, Wan X, et al.Science, 2018, 361, 1094-1098). The PCE of single-junction OSCs based on small molecule receptor materials has also exceeded 16% (B.Fan, F.Huang, Y.Cao.et al.Sci.China Chem., 2019, 6...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/14H01L51/42H01L51/46H01L51/48
CPCC07D409/14H10K71/12H10K85/626H10K85/655H10K30/00H10K85/6572Y02E10/549
Inventor 沈平陈丽曾敏翁超
Owner XIANGTAN UNIV
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