Phenothiazine organic small molecule donor and preparation method thereof

A technology of small molecule donor and phenothiazine, which is applied in the field of phenothiazine organic small molecule donor and its preparation, can solve the problems of rare application and low efficiency of solar cells, and achieves narrow band gap and solubility The effect of good sex and high matching degree

Active Publication Date: 2016-02-03
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Phenothiazine contains electron-rich sulfur atoms and oxygen atoms. It is a well-known strong electron-donating component and is often used as a hole transport material. It has great potential in the field of solar cells, but its application in solar cells is not More common and less efficient

Method used

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  • Phenothiazine organic small molecule donor and preparation method thereof
  • Phenothiazine organic small molecule donor and preparation method thereof
  • Phenothiazine organic small molecule donor and preparation method thereof

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preparation example Construction

[0029] The preparation process of the phenothiazine organic small molecule donor of the present invention is as follows:

[0030] 1) Substitution of aldehyde groups at positions 3 and 10 of the core unit by Vilsmeier reaction: N 2 Add POCl to N,N-dimethylformamide (DMF) under atmosphere 3 Stir the reaction; add 7,14-dialkyl-benzo[1,4]thiazino[2,3-b]phenothiazine in DMF solution, heat up to reflux reaction, wash with water and filter to remove DMF and POCl 3 , and separated by column chromatography after drying to obtain intermediate 1 yellow powder 7,14-dialkyl-benzo[1,4]thiazino[2,3-b]phenothiazine-3,10-dialdehyde; DMF with POCl 3 The molar ratio is 1:(0.9-1.1); 7,14-dialkyl-benzo[1,4]thiazino[2,3-b]phenothiazine and POCl 3 The molar ratio of DMF and POCl3 is 1: (15-25); the condition of stirring reaction between DMF and POCl3 is 0-20°C and stirring for half an hour, then return to 25-35°C and stir. After 1-3 hours, return to 0-20°C; heat up and reflux reaction temperatur...

Embodiment 1

[0037] N 2 Under atmosphere and stirring, POCl was added dropwise to DMF (20eq, 80mmol, 6.2mL) at 0°C 3 (20eq, 80mmol, 7.4mL), after the addition, stirred at 0°C for half an hour, then returned to room temperature and stirred. After 2h, return to 0°C, add intermediate 7,14-di(2-octyldodecyl)-benzo[1,4]thiazino[2,3-b]phenothiazine to the reaction system (4mmol, 3.53g) of DMF solution (30mL), after the addition, the temperature of the reaction system was raised to 90°C, and after reflux reaction for 24h, the reaction solution was poured into ice water, a small amount of ammonium acetate was added to promote hydrolysis, stirred, and after the precipitation was complete , suction filtration, and drying the obtained solid crude sample to conduct column chromatography separation with dichloromethane / n-hexane (v / v=2 / 1) as the eluent, and finally obtain intermediate 1, yellow powder 7,14-dialkyl -Benzo[1,4]thiazino[2,3-b]phenothiazine-3,10-dialdehyde 1.45 g, yield 38.7%.

[0038] T...

Embodiment 2

[0041] The intermediate 7,14-bis(2-octyldodecyl)-benzo[1,4]thiazino[2,3-b]phenothiazine (4mmol, 3.53g) was dissolved in chloroform / In acetic acid (100mL / 100mL) solution, down to 0°C, N 2 Under a protective atmosphere, NBS (3eq, 12mmol, 2.14g) was added in five batches to the stirred reaction system. After the addition, it was gradually raised to room temperature, and reacted for 24h. The reaction solution was extracted three times with water / dichloromethane system, and finally the combined Anhydrous MgSO for organic phase 4 Dry overnight, filter, and spin dry the organic phase. The resulting crude sample is separated by column chromatography using n-hexane as the eluent to finally obtain intermediate 2, a yellow oily substance 3,10-dibromo-7,14-dialkyl - Benzo[1,4]thiazino[2,3-b]phenothiazine 2.07 g, yield 49.8%.

[0042] Intermediate 2 (2mmol, 2.07g) and 2-(4-hexyl-2-thienyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3eq, 6mmol, 1.77g) into the 25ml two-necked flask, with ...

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Abstract

The present invention discloses a phenothiazine organic small molecule donor and a preparation method thereof. The preparation method comprises: under a N2 atmosphere, adding POCl3 to N,N-dimethylformamide (DMF), carrying out a stirring reaction, adding a DMF solution of 7,14-dialkyl-benzo[1,4]-thiazino[2,3-b]phenothiazine, carrying out a heating reflux reaction, carrying out water washing filtration to remove the DMF and the POCl3, drying, carrying out column chromatography separation to obtain an intermediate 1, taking the intermediate 1, ammonium acetate and 3-alkyl rhodanine, dissolving in acetic acid, carrying out a reflux reaction, pouring the reaction liquid into cold water after completing the reaction, extracting with methylene chloride, carrying out rotating drying on the organic phase, and carrying out column chromatography separation to obtain the target product. According to the present invention, the donor small molecule has characteristics of large conjugating structure, good hole-transporting property, narrow band gap, good light absorption performance, good solubility, high energy level and PCBM matching degree, and the like.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a phenothiazine organic small molecule donor and a preparation method thereof. Background technique [0002] Solar cell technology is an effective means to solve the energy shortage in the world today. Phenothiazine contains electron-rich sulfur atoms and oxygen atoms. It is a well-known strong electron-donating component and is often used as a hole transport material. It has great potential in the field of solar cells, but its application in solar cells is not More common and less efficient. Contents of the invention [0003] The purpose of the present invention is to provide a phenothiazine organic small molecule donor and a preparation method thereof, and provide a hole transport material with higher efficiency. [0004] In order to achieve the above purpose, the following technical solutions are adopted: [0005] A phenothiazine organic small molecule donor h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/04
Inventor 刘治田柳斌吴瑶张旗高翔
Owner WUHAN INSTITUTE OF TECHNOLOGY
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