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
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The potential application of boron-nitrogen doped compounds in electronic devices has been widely studi...

Method used

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

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[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...

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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

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Application Information

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IPC IPC(8): C07F5/02C09K11/06
CPCC07B2200/13C07F5/02C09K11/06C09K2211/1055
Inventor 刘旭光自凌剑
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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