Synthesis method of boron aza-naphthalene thiophthene hetero arene and derivative thereof

A synthesis method and a technology for heteroaromatic hydrocarbons are applied in the field of synthesis of boraza naphthothiophene heteroaromatic hydrocarbons and derivatives thereof, and can solve the problems that potential application characteristics are not widely developed and the like

Inactive Publication Date: 2019-05-24
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The potential applications of boron-nitrogen-doped compounds in electronic devices have been widely studi...

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  • Synthesis method of boron aza-naphthalene thiophthene hetero arene and derivative thereof
  • Synthesis method of boron aza-naphthalene thiophthene hetero arene and derivative thereof
  • Synthesis method of boron aza-naphthalene thiophthene hetero arene and derivative thereof

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[0031] An overall synthesis method of borazabenzothiophene heteroaromatic derivatives of the present invention comprises the following synthesis route and steps:

[0032]

[0033] Some of the above-mentioned compounds are given examples, and the details are as follows:

Embodiment 1

[0034] Embodiment 1: the synthesis of double 1,2-azaborinaphthothiophene compound 1

[0035] 1) Synthesis of Compound 4: Accurately weigh 2,5-dibromo-3,4-dinitrothiophene (1.00equiv, 5mmol, 1.66g), phenylboronic acid (2.10equiv, 11.5mmol, 1.48g), potassium carbonate (2.00equiv, 10.0mmol, 1.38g) and tetrakistriphenylphosphine palladium (0.05equiv, 0.25mmol, 0.30g) were added to a 100mL round-bottomed flask, and the system was evacuated using a vacuum oil pump, and the Schlenk Line was used to introduce High-purity nitrogen, repeated three times, added solvent tetrahydrofuran and water (volume ratio 4:1, 40mL), heated the reaction system to 100°C for reaction, and reacted overnight. The next day, TLC monitoring, rotary evaporator to remove solvent, dichloromethane and water extraction three times, combined organic phase, added anhydrous magnesium sulfate to dry for five minutes, then suction filtered, liquid phase was removed by rotary evaporator, and the residue was washed with...

Embodiment 2

[0041] Example 2: Synthesis of two 1,2-azaborinaphthothiophene compound derivatives 2

[0042] 5) Synthesis of Compound 6: Weigh Compound 5 (1.00equiv, 0.63mmol, 170.00mg), add sodium carbonate (4.00equiv, 2.40mmol, 260.00mg) into a round bottom flask, add a stir bar, connect a spherical condenser, add Rubber stopper, vacuumize the system, use the Schlenk Line to feed high-purity nitrogen, repeat three times, connect a nitrogen balloon as a buffer, slowly add 40wt% glyoxal aqueous solution (1.10equiv, 0.71mmol, 0.13mL), Add solvent ethanol 10mL, react overnight at room temperature. TLC monitoring, rotary evaporation to remove solvent, dichloromethane and water extraction three times, combined organic phases, adding anhydrous magnesium sulfate to dry for five minutes, and suction filtration, liquid phase was removed by rotary evaporator, the residue was dissolved with a small amount of toluene, and used The silica gel chromatography column was subjected to column chromatograph...

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Abstract

The invention relates to a synthesis method of boron aza-naphthalene thiophthene hetero arene and a derivative thereof. The photophysical properties and single crystal diffraction structures of the compounds are tested, and the potential application value of the organic material in organic electrochemistry is further researched. According to the structural formula of the compound, R1, R2, R3 and R4 are independent substituted or non-substituted groups which comprise alkyl and aryl (benzene ring, thiophene ring, furan ring, pyrrole, pyridine, benzothiophene, benzofuran, benzopyrrole, quinoline,naphthalene ring, anthracene ring, phenalene, naphthacene, pyrene, a compound shown in the description, linear or angled pentacene, hexacene, indene, fluorene and the like). R3 and R4 can also be used as a single substituted halogen atom X : F, Cl, Br and I. The formula is shown in the description.

Description

technical field [0001] The present invention relates to a kind of synthesis method of borazine naphthothiophene heteroaromatics and derivatives thereof, using commercially available reagents as raw materials, through Suzuki coupling, metal reduction, Lewis base-guided electrophilic boronization reaction. Borazabenzothiophene heteroaromatics and derivatives thereof are obtained. 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] Conjugated polycyclic aromatic hydrocarbons have a large π-electron system, so they are often used as functional optoelectronic materials. Common applications include: field-effect transistors (OFETs), photovoltaic cells (OPVs), organic light-emitting diodes (OLEDs), etc. The π-electron system of conjugated polycyclic aromatic hydrocarbons can adjust the conjugated structure by intro...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06H01L51/54
Inventor 刘旭光张乾崔培培
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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