A class of triphenyl dioxazinimide diploid derivatives and preparation method thereof

A technology of triphenyldioxazinimide and its derivatives, applied in the field of diploid derivatives of triphenyldioxazinimide and its preparation, to achieve the effects of high molar extinction coefficient, low cost, and high electron-accepting ability

Active Publication Date: 2022-06-17
DALIAN UNIV OF TECH
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In 2017, our research group designed and synthesized a conjugated bridged triphenyldioxazinimide diploid structure, but the known triphenyldioxazinimide diploid structures all contain conjugated bridge phases. Connection, does not involve the study of triphenyldioxazinimide diploids directly connected by C-C single bonds. The diploid structure directly connected by C-C single bonds can produce steric torsion to inhibit molecular aggregation, through chemical modification of its structure , is expected to obtain N-type semiconductor materials with excellent photoelectric performance
So far, there are no diploid derivatives of triphenyldioxazine imides directly connected by C-C bonds

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
  • A class of triphenyl dioxazinimide diploid derivatives and preparation method thereof
  • A class of triphenyl dioxazinimide diploid derivatives and preparation method thereof
  • A class of triphenyl dioxazinimide diploid derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020]

[0021] 1 g of bromotriphenyl dioxazine imide and 987.52 mg of Cu powder were weighed into a reaction flask, 25 ml of dimethyl sulfoxide was added, and the reaction was stirred at 120° C. for 18 hours. When the reaction was completed, the reaction solution was spin-dried under reduced pressure, and 0.4 g of product was obtained by column chromatography, with a yield of 45%, HRMS: found 1127.1800.

Embodiment 2

[0023]

[0024] 1 g of bromotriphenyl dioxazine imide and 782.76 mg of Cu powder were weighed into a reaction flask, 25 ml of dimethyl sulfoxide was added, and the reaction was stirred at 110° C. for 15 hours. When the reaction was complete, the reaction solution was spin-dried under reduced pressure, and 0.5 g of product was obtained by column chromatography, with a yield of 55%, HRMS: found 1463.8280.

Embodiment 3

[0026]

[0027] 1 g of bromotriphenyl dioxazine imide and 782.76 mg of Cu powder were weighed into a reaction flask, 25 ml of nitrogen methylpyrrolidone was added, and the mixture was stirred and refluxed at 140° C. for 8 hours. When the reaction was complete, the reaction solution was spin-dried under reduced pressure, and 0.45 g of product was obtained by column chromatography, with a yield of 49%, HRMS: found 1688.2600.

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

A class of diploid derivatives of triphenyldioxazinimide and a preparation method thereof belong to the technical field of organic synthesis. The material is a triphenyldioxazinimide derivative with large conjugation and space distortion. It adopts monobrominated triphenyl dioxazinimide, under the catalysis of copper powder, synthesized by C-C single bond coupling method. Triphenyldioxazinimide diploid semiconductor materials have excellent solubility in common organic solvents, strong absorption in the visible light region, high molar extinction coefficient, and good redox characteristics and electron transport properties. Applied in the field of organic optoelectronics.

Description

technical field [0001] The invention relates to a class of triphenyl dioxazine imide diploid derivatives and a preparation method, which belong to the field of organic synthesis. Background technique [0002] The whole molecule of triphenyl dioxazine imide is composed of central triphenyl dioxazine skeleton and two sides of biscarboxyimide. Its advantages are: strong absorption in the visible light region, high molar extinction coefficient, fluorescence quantum yield, good photostability and thermal stability, etc., it is a kind of organic semiconductor material with excellent performance. The 6- and 14-positions of triphenyldioxazinide are affected by the electron withdrawing groups on both sides of the imide, and the reactivity is strong, which is prone to aromatic electrophilic substitution reaction, which can introduce halogen into triphenyldioxazinyl. imines, more complex chemical modifications to the parent. [0003] In 2017, our group designed and synthesized a conj...

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
Patent Type & Authority Patents(China)
IPC IPC(8): C07D519/00H01L51/30H01L51/46H01L51/54
CPCC07D519/00H10K85/615H10K85/626H10K85/654H10K85/655H10K85/657H10K85/6572Y02E10/549
Inventor 陈令成李萌肖义
Owner DALIAN UNIV OF TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap