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

Synthesis method of diboron azatriphenylene and derivative thereof

A synthesis method and a derivative technology, which are applied in the field of synthesis of bisboraphenanthroline and its derivatives, can solve the problems that potential application characteristics have not been widely developed and the like

Inactive Publication Date: 2019-12-03
TIANJIN UNIVERSITY OF TECHNOLOGY
View PDF5 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The potential application of boron-nitrogen doped compounds in electronic devices has been widely studied, but their potential application characteristics in light-emitting materials have not been widely developed

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
  • Synthesis method of diboron azatriphenylene and derivative thereof
  • Synthesis method of diboron azatriphenylene and derivative thereof
  • Synthesis method of diboron azatriphenylene and derivative thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0026] A kind of overall synthetic method of borazine phenanthrene and its derivatives of the present invention comprises the following synthetic routes and steps:

[0027]

[0028] Some of the above-mentioned compounds are given examples, and the details are as follows:

Embodiment 1

[0029] Example 1: Synthesis of 2,9-diphenyl-1,2,9,10-azaboraphenanthrene compound 3

[0030] 1) Synthesis of compound 2: Weigh 3,6-dibromo-1,2 phenylenediamine (1.0equiv, 22.8mmol, 6g), tetrakistriphenylphosphine palladium (0.02equiv, 0.456mmol, 524mg) and pump gas Three times, under nitrogen protection, tri-n-butylvinyltin (3.0 equiv, 68.4 mmol, 21.7 g) was added and anhydrous toluene was added to reflux at 110° C. for 24 h. After the reaction was complete, it was filtered, spin-dried toluene, and quickly analyzed by column chromatography to obtain the yellow target compound.

[0031] 2) Synthesis of compound 3a: Add 3,6-divinyl-1,2-phenylenediamine (1.0equiv, 1.87mmol, 300mg) into a 100mL flask, add anhydrous toluene under nitrogen protection, and place at -30°C Add (3.0equiv, 5.6mmol5.6mL) boron trichloride, reflux for 24 hours, remove the solvent after the reaction, add anhydrous diethyl ether, add (3.0equiv, 1.87 mmol, 71mg) lithium aluminum hydride at -30°C, Stir at ro...

Embodiment 2

[0033] Example 2: Synthesis of 2,9-diphenyl-1,2,9,10-azaboraphenanthrene derivatives

[0034] 4) Synthesis of compound 4-2Br: Weigh 2,9-diphenyl-1,2,9,10-azaboraphenanthrene (1.0equiv, 0.142mmol, 46mg), add dichloromethane to dissolve it completely Stir at 0°C for 15min, add 1mol / L liquid bromine-dichloromethane solution (2.1equiv, 0.299mmol, 299ul), stir for 15min, take it out and stir at room temperature for 0.5h, after the reaction is complete, add water and dichloromethane to extract , dried with anhydrous magnesium sulfate, filtered, spin-dried, and separated by column chromatography to obtain the white target compound.

[0035] 5) Synthesis of compound 4-4Br: Weigh 2,9-diphenyl-1,2,9,10-azaboraphenanthrene (1.0equiv, 0.210mmol, 70mg), add dichloromethane to dissolve it completely Stir at 0°C for 15min, add 1mol / L liquid bromine-dichloromethane solution (6.0equiv, 0.1.264mmol, 1.264ml), stir for 15min, take it out and stir at room temperature for 12h, when the reaction i...

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 relates to a synthesis method of diboron azatriphenylene and a derivative thereof, tests the photoelectric physical properties of the compounds and further researches potential application values of the organic materials on the aspect of organic electrochemistry. The compound has a structural formula as shown in the specification, wherein each of R1, R2, R3, R4, R5, R6, R7 and R8 isan independent substituted or non-substituted group and comprises an alkyl and an aryl (a benzene ring, a thiophene ring, a furan ring, pyrrole, pyridine, benzothiophene, benzofuran, benzopyrrole, benzopyridine, a naphthalene ring, an anthracene ring, phenalene, naphthacene, pyrene, jue as shown in the specification, linear or angular pentacene, hexacene, indene, fluorene and the like), wherein R1, R2, R3 and R4 may also be single substituted halogen atom X: F, Cl, Br and I.

Description

technical field [0001] The present invention relates to a kind of synthesis method of bis-borazine phenanthrene and its derivatives, using commercially available 2,1,3-benzothiadiazole as raw material, through Stille coupling reaction, Lewis base-guided electrophilic boron Cyclization reaction, Suzuki coupling reaction can obtain bis-borazine phenanthrene and its derivatives. The synthesis method has the characteristics of simple operation, mild reaction conditions, short reaction path, etc., and the compound can be applied in the field of organic photoelectric materials. Background technique [0002] Polycyclic aromatic hydrocarbons (PAHs) have attracted widespread attention due to their unique electronic properties and supramolecular properties, making them attractive candidates for organic semiconductor devices such as organic field-effect transistors (OFETs). S ), organic photovoltaic devices (OPV S ) and Organic Light Emitting Diodes (OLEDs S )) candidates. [0003]...

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): C07F5/02C09K11/06
CPCC07B2200/13C07F5/02C09K11/06C09K2211/1055
Inventor 刘旭光自凌剑
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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