Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Perfluoro-butyl substituted compound as well as preparation method and application thereof

A perfluorobutyl compound technology, which is applied in the field of perfluorobutyl substituted compounds and its preparation, can solve the problems of solubility, low stability, complex reaction steps, toxic by-products, etc., and eliminate the hazards of heavy metal catalysts , good air stability, beneficial to the effect of purification

Active Publication Date: 2019-08-30
SUN YAT SEN UNIV
View PDF6 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still many problems in this kind of compounds in n-type semiconductor materials, such as energy level mismatch, solubility and stability are not high
[0003] At present, the existing technology is usually to modify diketopyrrolopyrrole and isoindigo by introducing side groups on the aromatic ring or aromatic heterocycle. However, it is often necessary to generate a halogenated compound first, and then generate the final target product through a coupling reaction. The reaction steps are complex, the reaction yield is low, and the problem of polluting or toxic by-products is generated; therefore, it is imminent to find a simple and efficient synthesis method with relatively high yield

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Perfluoro-butyl substituted compound as well as preparation method and application thereof
  • Perfluoro-butyl substituted compound as well as preparation method and application thereof
  • Perfluoro-butyl substituted compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0104] A preparation method of a perfluorobutyl substituted pyrrolopyrrole diketopyrrole, comprising the steps of:

[0105] (1) Add 29g of potassium tert-butoxide into a three-necked round-bottomed flask, start degassing and then fill with nitrogen for three consecutive times, then add 179mL of tert-amyl alcohol, and stir at 110°C for 2h. Then 20mL of 3-cyanothiophene was added dropwise and stirred for 45min, and 9.4mL of dimethyl succinate and 29mL of tert-amyl alcohol solution were added dropwise with a dropping funnel, stirred, and continued to stir for 3h. After the reaction solution was cooled to 80°C, 108 mL of methanol and 29 mL of deionized water were added and stirred for 45 min. After the solution was cooled to room temperature, 57 mL of hydrochloric acid and 287 mL of methanol were added and stirred for 45 min. The treated reaction solution was filtered, and the filter residue was washed with 72mL of methanol to obtain compound (I). The quality of the obtained compo...

Embodiment 2

[0113] A kind of preparation method of the perfluorobutyl substituent of isoindigo, comprises the steps:

[0114] (1) Add 3.7754g isatin, 3.4472g 2-indolinone and 1mL hydrochloric acid into a round bottom flask, then add 150mL acetic acid, stir, and react at 115°C for 12h; filter the reacted solution and wash with methanol, water, Sodium bicarbonate solution and pentane wash filter residue, obtain solid compound (IV), the quality of compound is 4.8537g, productive rate is 79%; Its chemical reaction equation is as follows:

[0115]

[0116] (2) 1.5g of compound (IV) and 7.905g of potassium carbonate were added to the round-bottomed flask, degassed and then filled with nitrogen for three consecutive times, then added 30mLN,N-dimethylformamide (DMF), stirred, and then Add 2.76g bromoisooctane and react at 100°C for 24h. The obtained solution was distilled under reduced pressure first, and then purified by a chromatographic column. The ratio of the eluent dichloromethane to pe...

Embodiment 3

[0122] A preparation method of a perfluorobutyl substituted substance of thiophene isoindigo, comprising the steps of:

[0123] (1) Add 0.2g of cuprous iodide and 5.6g of potassium carbonate into a round bottom flask, start to degas and then fill with nitrogen for three consecutive times, then add 10mL of N,N-dimethylformamide (DMF), stir, and then Add 2mL of 3-bromothiophene, 5mL of isooctylamine, and 0.74g of 2-isobutyrylcyclohexanone, and react at 120°C for 12h. The resulting solution is first distilled under reduced pressure, and then passed through a flash chromatography column. The eluent is dichloromethane , to obtain 3-secondary aminothiophene; 0.75mL oxalyl chloride was added to a round bottom flask, 25mL dichloromethane was added, and 1.9939g 3-secondary aminothiophene and 11mL dichloromethane solution were mixed with 5.71mL triethylamine and 40mL of dichloromethane solution was added dropwise in the round-bottomed flask successively, stirred, and reacted at room tem...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a perfluoro-butyl substituted compound as well as a preparation method and application thereof. The compound is a perfluoro-butyl substituted compound of 3,6-di(2-thienyl)-2,5-dihydropyrrolo[3,4-c]pyrrole, isoindigo and thiophene indigo. The chemical structural formulas of the compound are respectively shown as formulas (III), (VI) and (X). In the formula, R represents branched alkane or straight-chain alkane having 8-16 carbon atoms. Moreover, the compound has excellent solubility, and the yield in each step is higher than 10%. Compared with a compound that is not substituted by fluoroalkyl, the perfluoro-butyl substituted compound has better air stability, LUMO (Lowest Unoccupied Molecular Orbital) and HOMO (Highest Occupied Molecular Orbital) energy levels of thecompound are reduced, and electron injection and transport can be facilitated. Furthermore, the maximum absorption wavelength exists in the visible field, and the compound has potential application prospects in the fields of organic field effect transistors (OFET) and organic photovoltaic cells (OPV).

Description

technical field [0001] The invention belongs to the technical field of organic semiconductor synthesis, and more specifically relates to a perfluorobutyl substituted compound and its preparation method and application. Background technique [0002] Materials such as diketopyrrolopyrrole, isoindigo and its derivatives are currently widely used organic semiconductor materials. The better planarity of diketopyrrolopyrrole and isoindigo and its derivatives can enhance their electron transport, so they are widely used in organic field-effect transistors (OFETs) and organic photovoltaic cells (OPVs). However, there are still many problems in this kind of compound in n-type semiconductor materials, such as energy level mismatch, solubility and stability are not high. [0003] At present, the existing technology is usually to modify diketopyrrolopyrrole and isoindigo by introducing side groups on the aromatic ring or aromatic heterocycle. However, it is often necessary to generate ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D487/04C07D519/00C07D209/34H01L51/30H01L51/46
CPCC07D487/04C07D519/00C07D209/34H10K85/655H10K85/6572H10K85/657Y02E10/549
Inventor 岳晚徐玉淳王亚洲
Owner SUN YAT SEN UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com