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

A kind of synthetic method of phenanthrene borazine and its derivatives

A synthetic method and a phenanthrene technology, which is applied in the field of synthesis of borazaphenanthrene and its derivatives, can solve the problems that the potential application characteristics have not been widely developed.

Inactive Publication Date: 2021-04-20
TIANJIN UNIVERSITY OF TECHNOLOGY
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The potential applications of boron-nitrogen-doped compounds in electronic devices have 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
  • A kind of synthetic method of phenanthrene borazine and its derivatives
  • A kind of synthetic method of phenanthrene borazine and its derivatives
  • A kind of synthetic method of phenanthrene borazine and its derivatives

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0033] A kind of overall synthetic method of borazine phenanthrene and its derivatives of the present invention comprises the following synthetic routes and steps:

[0034]

[0035] Some of the above-mentioned compounds are given examples, and the details are as follows:

Embodiment 1

[0036] Embodiment 1: the synthesis of 1,2-azaboraphenanthrene compound 1

[0037] 1) Synthesis of compound 4: Weigh 2-nitro-1-naphthol (1.0equiv, 27mmol, 5.07g) and add trifluoromethanesulfonic anhydride (1.25equiv, 34mmol, 9.5g) at 0°C, triethylamine (2.4equiv, 65mmol, 6.5g) was stirred at room temperature for 12h. After the reaction was complete, water and dichloromethane were added for extraction, the organic layers were combined, and dried over anhydrous magnesium sulfate, filtered, spin-dried, and quickly separated by column chromatography to obtain the target compound as a yellow solid (7.4 g, yield 85%);

[0038] 1 HNMR (400MHz, CDCl 3 ):δ8.26-8.30(m,1H,Ar),8.08(d,J=9.2Hz,1H,Ar),7.98-8.02(m,2H,Ar),7.78-7.83(m,2H,Ar) .

[0039] 2) Synthesis of Compound 5: Weigh 2-nitro-1-trifluoromethanesulfonic naphthalene (1.0equiv, 18.4mmol, 5.93g), tetrakistriphenylphosphine palladium (0.1equiv, 1.8mmol, 2.08g) , sodium carbonate (5.0equiv, 91.8mmol, 9.7g) was pumped for three t...

Embodiment 2

[0045] Embodiment 2: Synthesis of 1,2-azaboraphenanthrene derivatives

[0046] 5) Synthesis of Compound 12: Weigh 2-amino-1-vinylnaphthalene (1.0equiv, 5.0mmol, 850mg), add chlorobenzene in the glove box and stir to dissolve, then add triethylamine (1.5equiv, 7.5mmol, 1.05mL) and dichlorophenylborane (1.25equiv, 6.28mmol, 0.68mL) were placed at 130°C and heated to reflux for 12 hours. After the reaction was completed, water and dichloromethane were added for extraction. The organic layers were combined and dried over anhydrous magnesium sulfate. Filtration, spin-drying, and separation by column chromatography gave the white target compound (1.27 g, yield 99%).

[0047] 1 HNMR (400MHz, CDCl 3 ):δ9.10(d,J=12.0Hz,1H,Ar),8.58(d,J=8.8Hz,1H,Ar),8.41(br,1H,NH),7.98(dd,J 1 =8.0Hz,J 2 =2.0Hz, 2H, Ar), 7.89(t, J=6.8Hz, 2H, Ar), 7.64-7.67(m, 1H, Ar), 7.45-7.52(m, 6H, Ar).

[0048] 6) Synthesis of compound 13: Weigh 2-phenyl-1,2-azaborine (1.0equiv, 1.37mmol, 350mg), add dichlorometh...

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 present invention relates to a synthetic method of borazine phenanthrene and its derivatives, and tested the photoelectric physical properties of these compounds, and further studied the potential application value of this type of organic material in organic electrochemistry. The structural formula of this compound is: wherein R 1 , R 2 , R 3 , R 4 They are independently substituted or unsubstituted groups, including alkyl, aryl (benzene ring, thiophene ring, furan ring, pyrrole, pyridine, benzothiophene, benzofuran, benzopyrrole, benzopyridine, naphthalene ring , anthracycline, phenacene, tetracene, pyrene, linear or angled pentacene, hexacene, indene, fluorene, etc.). where R 1 , R 2 It can also be a single substituted halogen atom X: F, Cl, Br, I.

Description

technical field [0001] The present invention relates to a synthetic method of borazine phenanthrene and its derivatives. Using commercially available double-substituted naphthalene as raw material, boron nitrogen can be obtained through Suzuki coupling, metal reduction, and Lewis base-directed electrophilic borocyclization reaction. Heterophenanthrene compounds. The synthesis method has the characteristics of simple operation, mild reaction conditions, high yield, etc., and the compound can be applied to the field of organic photoelectric materials. Background technique [0002] Due to the unique space electronic structure of polycyclic aromatic hydrocarbons, it has many good application prospects in the field of optoelectronic materials such as organic field-effect transistors, organic light-emitting diodes, and organic photovoltaic cells. By introducing different heteroatoms such as B, N, P, O, S, Si, etc. into the full-carbon PAH skeleton, different optoelectronic proper...

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): C07F5/02
CPCC07F5/02
Inventor 刘旭光张晨崔培培薛松
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