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Synthetic method of bis-pyrrole fused boron naphthazine and derivatives of bis-pyrrole fused boron naphthazine

A synthesis method and technology of bispyrrole, applied in the field of synthesis of bispyrrole-fused borazanthene and its derivatives

Inactive Publication Date: 2019-11-01
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the synthesis of boron-nitrogen-doped polycyclic aromatic hydrocarbons with novel structures and their practical applications are still a great challenge.

Method used

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  • Synthetic method of bis-pyrrole fused boron naphthazine and derivatives of bis-pyrrole fused boron naphthazine
  • Synthetic method of bis-pyrrole fused boron naphthazine and derivatives of bis-pyrrole fused boron naphthazine
  • Synthetic method of bis-pyrrole fused boron naphthazine and derivatives of bis-pyrrole fused boron naphthazine

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[0032] An overall synthesis method of bispyrrole-fused borazanthene and derivatives thereof of the present invention comprises the following synthesis route and steps:

[0033]

[0034] Some of the above-mentioned compounds are given examples, and the details are as follows:

Embodiment 1

[0035] Embodiment 1: the synthesis of compound 1

[0036] 1) Synthesis of Compound 4: Weigh 1,5-difluoro-2,4-dinitrobenzene (1.00equiv, 29.40mmol, 6.00g) and sodium hydroxide (2.20equiv, 64.68mmol, 2.59g), The gas was exchanged three times, protected by nitrogen, and 50 mL of dimethyl sulfoxide solution was added, followed by pyrrole (2.20 equiv, 64.68 mmol, 4487 μl), and stirred at room temperature for 12 h. After the reaction was complete, water and ethyl acetate were added to extract, the organic layers were combined, dried over anhydrous magnesium sulfate, filtered, spin-dried, and quickly separated by column chromatography to obtain the yellow solid target compound 4 (5.75 g, yield 65%).

[0037] 1 H NMR (400MHz, CDCl 3 ): δ8.47(s, 1H, Ar), 7.54(s, 1H, Ar), 6.83(t, J=2.4Hz, 4H, Ar), 6.45(t, J=2.4Hz, 4H, Ar).

[0038] 2) Synthesis of compound 5: Weigh 1,5-dipyrrole-2,4-dinitrobenzene (1.0equiv, 1.97mmol, 586mg) and dissolve it in 20mL ethanol solution, add bismuth chlor...

Embodiment 2

[0042] Embodiment 2: the synthesis of compound 2

[0043] 5) Synthesis of compound 6: Weigh 1,5-dipyrrole-2,4-diaminobenzene (1.00equiv, 2.10mmol, 500mg), ventilate 3 times, protect with nitrogen, add 10mL of tetrahydrofuran solution, in -78 Add n-butyllithium (2.10equiv, 4.41mmol, 1.76mL, 2.5mol / L in hexane), 0.68mL) at ℃, stir at -78℃ for 1h, add hexyl bromide (4.00equiv, 8.40mmol, 1.39 g), then heated at 66°C under reflux for 4 hours, after the reaction was complete, the solvent was spin-dried, extracted with water and ethyl acetate, the organic layers were combined, dried with anhydrous magnesium sulfate, filtered, spin-dried, and quickly carried out column chromatography After separation, the target compound 6 (436 mg, yield 51%) was obtained as brown-red oily liquid.

[0044] 1 H NMR (400MHz, CDCl 3 ): δ6.97(s, 1H, Ar), 6.75(t, J=2.0Hz, 4H, Ar), 6.31(t, J=2.0Hz, 4H, Ar), 5.98(s, 1H, Ar), 3.72 (br, 2H, NH 2 ), 3.12(t, J=6.8Hz, 4H, CH 2 ), 1.53-1.56 (m, 4H, CH 2 ), ...

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Abstract

The invention relates to a synthetic method of bis-pyrrole fused boron naphthazine and derivatives of bis-pyrrole fused boron naphthazine. The photoelectric physical properties of the compounds are tested and studied, and study on application value of the organic materials in preparation of OLED devices is carried out. The structure formula of the compounds is disclosed in the invention, wherein R1, R2, R4, and R5 are respectively used for representing independent substituent groups or non-substituent groups including alkyl, aryl (phenyl ring, thiophene ring, furan ring, pyrrole, pyridine, benzothiophene, benzofuran, benzopyrrole, quinoline, naphthalene ring, anthracene nucleus, phenalene, tetracene, pyrene, linear or angled pentacene, hexacene, indene, fluorine, and the like), and R3 is used for representing alkyl, acyl, nitro, sulfonic group, aldehyde group, diazo group, or single substitution halogen atom X, F, Cl, Br, and I.

Description

technical field [0001] The present invention relates to a synthesis method of bispyrrole-fused borazanthane and its derivatives. The commercially available 1,5-difluoro-2,4-dinitrobenzene is used as a raw material, through the nucleophilic substitution of pyrrole reaction, reduction, and Lewis base-directed electrophilic borocyclization to give a series of bispyrrole-fused borazanthene compounds. The synthesis method is simple and easy to operate, has mild reaction conditions, fast reaction rate and high yield, and the compound has potential application value in the field of organic photoelectric materials. Background technique [0002] Polycyclic aromatic hydrocarbons are rich in carbon atoms, have large conjugated systems and outstanding electronic properties, and have received more and more attention in new organic optoelectronic materials, such as organic light-emitting diodes, organic semiconductor materials, solar cells (OPVs) and Field effect transistors (OFETs) have...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02
CPCC07F5/027
Inventor 刘旭光刘美艳
Owner TIANJIN UNIVERSITY OF TECHNOLOGY