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Oligothiophene derivative and preparation method thereof

A technology of oligothiophene and derivatives, applied in chemical instruments and methods, color-changing fluorescent materials, organic chemistry, etc., can solve problems such as unstable color changes

Active Publication Date: 2013-10-30
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to provide an oligothiophene derivative with stable color change for the existing organic electrochromic materials that have unstable color changes when a voltage is applied

Method used

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  • Oligothiophene derivative and preparation method thereof
  • Oligothiophene derivative and preparation method thereof
  • Oligothiophene derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1: Preparation of 1,3,5-tri[5',2"-(3",4"-dioxyethylene-thienyl)-2'-thienyl]benzene (3TB-3EDOT)

[0019] The first step is to add 1,3,5-tris(2′-thienyl)-benzene (3TB) into the Erlenmeyer flask, dissolve it with dichloromethane, and add N-bromosuccinimide under magnetic stirring (NBS), reacted at room temperature for 20 hours. The solvent was removed to give a crude product of 1,3,5-tris(5'-bromo-2'-thienyl)benzene (3TB-3Br). Using petroleum ether as a flushing liquid, the purer 3TB-3Br is obtained by separation with a chromatographic column, and then recrystallized to obtain pure 3TB-3Br.

[0020] In the second step, under the protection of nitrogen, 3,4-dioxyethylenethiophene (EDOT) and anhydrous tetrahydrofuran were added into a three-necked flask, and the reaction temperature was controlled at -78°C. After the temperature was stabilized, n-butyllithium was added dropwise, and after the dropwise addition, the temperature was raised to room temperature, and th...

Embodiment 2

[0027] Example 2: Preparation of 1,3,5-tris[5',2"-(3",4"-dioxyethylene-thienyl)-2'-thienyl]benzene (3TB-3EDOT)

[0028] The first step is to add 1,3,5-tris(2′-thienyl)-benzene (3TB) into the Erlenmeyer flask, dissolve it with dichloromethane, and slowly add N-bromosuccinyl under magnetic stirring imine (NBS), reacted at room temperature for 20 hours. The solvent was removed to give a crude product of 1,3,5-tris(5'-bromo-2'-thienyl)benzene (3TB-3Br). Using petroleum ether as a flushing liquid, the purer 3TB-3Br is obtained by separation with a chromatographic column, and then recrystallized to obtain pure 3TB-3Br.

[0029] In the second step, under the protection of nitrogen, 3,4-dioxyethylenethiophene (EDOT) and anhydrous tetrahydrofuran were added into a three-necked flask, and the reaction temperature was controlled at -78°C. After the temperature stabilized, n-butyllithium was slowly added dropwise, and after the dropwise addition, it was raised to room temperature, and t...

Embodiment 3

[0036] Example 3: Preparation of 1,3,5-tri[5',2"-(3",4"-dioxyethylene-thienyl)-2'-thienyl]benzene (3TB-3EDOT)

[0037]The first step is to add 1,3,5-tris(2′-thienyl)-benzene (3TB) into the Erlenmeyer flask, dissolve it with dichloromethane, and slowly add N-bromosuccinyl under magnetic stirring imine (NBS), reacted at room temperature for 20 hours. The solvent was removed to give a crude product of 1,3,5-tris(5'-bromo-2'-thienyl)benzene (3TB-3Br). Using petroleum ether as a flushing liquid, separate with a chromatographic column to obtain relatively pure 3TB-3Br, and then recrystallize to obtain pure 3TB-3Br.

[0038] In the second step, under the protection of nitrogen, 3,4-dioxyethylenethiophene (EDOT) and anhydrous tetrahydrofuran were added into a three-necked flask, and the reaction temperature was controlled at -78°C. After the temperature stabilized, n-butyllithium was slowly added dropwise, and after the dropwise addition, the temperature was raised to room temperatu...

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Abstract

The invention relates to an oligothiophene derivative and a preparation method thereof. The preparation method of the oligothiophene derivative mainly comprises the following steps of: dissolving 3TB into dichloromethane, adding NBS (N-bromosuccinimide), stirring and reacting so as to obtain 3TB-3Br; adding EDOT (3,4-ethylenedioxythiophene) and tetrahydrofuran into a three-neck flask, controlling the reaction temperature to be minus 78 DEG C, dropwise adding n-butyllithium, gradually raising to be room temperature after the dropwise adding, and continuously reacting; subsequently decreasing the reaction temperature to be minus 78 DEG C, dropwise adding tributyl stannic chloride, gradually raising to be the room temperature after the dripping, and reacting to obtain an EDOT tin reagent; under the protection of nitrogen, adding methylbenzene into the three-neck flask, further adding the 3TB-3Br and the EDOT tin reagent, carrying out backflow reaction so as to obtain a 3TB-3Br crude product, thus obtaining pure 3TB-3EDOT through separation. As cation (or anion) free radicals generated in electrochemical doping are stable, the oligothiophene derivative can be used as a novel organic electrochromic material.

Description

technical field [0001] The invention relates to the technical field of organic polymer optical and electrical materials, in particular to oligothiophene derivatives; the invention also relates to a preparation method of oligothiophene derivatives. Background technique [0002] High-purity oligothiophene with definite molecular weight, whose degree of polymerization and polymerization position can be controlled, is not only a "model" compound for studying polythiophene, but also an electronically conjugated compound with excellent optical and electrical properties. Due to its excellent optical and electrical properties, it has been researched and developed as a functional organic material in recent years. So far, various oligothiophene derivatives have been designed and synthesized according to the research and development goal of oligothiophene as an optoelectronic information functional organic material. These derivatives are mainly used in the research of the following as...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00C09K9/02
Inventor 刘平高金明
Owner SOUTH CHINA UNIV OF TECH
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