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Synthesis method of benzoboron-nitrogen naphthalene thiophene derivative

A benzoborazine-naphthylthiophene and synthetic method technology, applied in chemical instruments and methods, compounds containing elements of group 3/13 of the periodic table, organic chemistry, etc., to achieve the effect of wide range of raw materials, small impact and simple reaction

Active Publication Date: 2020-09-04
JIUJIANG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The difficulty of synthesis limits the further application of such materials in the field of organic electronics

Method used

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  • Synthesis method of benzoboron-nitrogen naphthalene thiophene derivative
  • Synthesis method of benzoboron-nitrogen naphthalene thiophene derivative
  • Synthesis method of benzoboron-nitrogen naphthalene thiophene derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Synthesis of benzoborazine-naphthylthiophene derivatives:

[0017] Take 15 mL of dry Schlenk tube, evacuate and change argon three times, under the protection of argon, add bisbromoborazine (362 mg, 1 mmol), Na 2 S (156 mg, 2 mmol), CuI (19 mg, 10 mol %), 4,4'-di-tert-butyl-2,2'-dipyridine (54 mg, 20 mol %) Na 2 CO 3 (160 mg, 1.5 mmol), introduced into anhydrous and oxygen-free solvent DMF (5mL). Under the protection of argon, react at 120°C for about 8 h. After the reaction is completed, after the temperature of the system drops to room temperature, extract with dichloromethane (4*10 mL) and water (50 mL), combine the organic phases, and dry them with anhydrous sodium sulfate. , the solvent was removed under reduced pressure, and column chromatography (developing solvent: n-hexane: dichloromethane = 5:1) gave 160 mg of a yellow-green solid with a yield of 68%.

[0018] The 1H NMR spectrum, 13C, and 11B NMR spectrum were measured with a 400M superconducting nuclea...

Embodiment 2

[0022] Synthesis of benzoborazine-naphthylthiophene derivative compound 2:

[0023]

[0024] Take 15 mL of dry Schlenk tube, vacuumize and change argon three times, under the protection of argon, add monobromoborazin (297 mg, 1 mmol), Na 2 S (156 mg, 2 mmol), CuI (19 mg, 10 mol %), 4,4'-di-tert-butyl-2,2'-dipyridine (54 mg, 20 mol %), Na 2 CO 3 (160 mg, 1.5 mmol), introduced into anhydrous and oxygen-free solvent tetrahydrofuran (5 mL). Under the protection of argon, react at 140°C for about 6 h. After the reaction is completed, after the temperature of the system drops to room temperature, extract with dichloromethane (4*10 mL) and water (50 mL), combine the organic phases, and dry them with anhydrous sodium sulfate. , the solvent was removed under reduced pressure, and column chromatography (developing solvent: n-hexane: dichloromethane = 5:1) gave 181 mg of a yellow-green solid with a yield of 72%.

[0025] The nuclear magnetic analysis data of this compound are as f...

Embodiment 3

[0028] Synthesis of benzoborazine-naphthylthiophene derivative compound 3:

[0029]

[0030] Take 15 mL of dry Schlenk tube, vacuumize and change argon three times, under the protection of argon, add monobromoborazin (301 mg, 1 mmol), Na 2 S (156 mg, 2 mmol), CuI (19 mg, 10 mol %), 2,2'-bipyridine (32 mg, 20 mol %), Na 2 CO 3 (160 mg, 1.5 mmol), introduced into anhydrous and oxygen-free solvent tetrahydrofuran (5 mL). Under the protection of argon, react at 100°C for about 18 h. After the reaction is completed, after the temperature of the system drops to room temperature, extract with dichloromethane (4*10 mL) and water (50 mL), combine the organic phases, and dry over anhydrous sodium sulfate. The solvent was removed under reduced pressure and separated by column chromatography (developing solvent: n-hexane: dichloromethane = 5:1) to obtain 178 mg of a yellow-green solid with a yield of 70%.

[0031] The nuclear magnetic analysis data of this compound are as follows: ...

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Abstract

The invention provides a synthesis method of a benzoboron-nitrogen naphthalene thiophene derivative. The synthesis method comprises the following steps: taking bromo-boron-nitrogen naphthalene, sulfide, a catalyst and the like as raw materials, reacting for 8-24 hours at 90-140 DEG C, and then concentrating and purifying to obtain the benzoboron-nitrogen naphthalene thiophene derivative. The brominated boron-nitrogen-naphthalene is a boron-nitrogen-naphthalene monobromide or a boron-nitrogen-naphthalene dibromide; the sulfide is S8, K2S, Na2S or KSCN; the catalyst is palladium acetate, palladium bis (triphenylphosphine) dichloride, [1, 1-bis (diphenylphosphine) ferrocene] palladium dichloride, an allyl palladium chloride (II) dimer or cuprous iodide; the ligand is triphenylphosphine, 2-(di-tert-butylphosphine) biphenyl, 2, 2 '-dipyridine, 4, 4'-di-tert-butyl-2, 2 '-dipyridine or 1, 10-phenanthroline; and the alkaline salt is sodium carbonate, potassium carbonate, potassium acetate or sodium tert-butoxide. The method has the advantages of mild reaction conditions, wide raw material application range, specific reaction, high yield, small environmental pollution and the like.

Description

technical field [0001] The invention relates to a synthesis method of benzoborazine-naphthylthiophene derivatives, which belongs to the technical field of organic synthesis. Background technique [0002] Although the research on the application of borazine condensed ring molecules in organic electronics has just started, these molecules have shown good device performance. At present, the types and quantities of the materials are relatively small, which makes the research on the structure-activity relationship more difficult. Although theoretical chemistry can be used to predict the molecular orbitals and related properties of the boron nitrogen heterocondensed ring structure, it is still necessary to synthesize a large number of structures to summarize the rules after clarifying the effect of BN unit covalent intercalation on the electronic properties of organic π-conjugated materials. Despite nearly 60 years of hard work, the synthesis of borazaromatic fused ring compounds...

Claims

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Application Information

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IPC IPC(8): C07F5/02
CPCC07F5/02Y02E10/549
Inventor 黄华南周影刘国昌徐志雄
Owner JIUJIANG UNIVERSITY
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