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Bridged bis-benzimidazole salt as well as preparation method and application thereof

A kind of bisbenzimidazole and reaction technology, applied in the field of bridged bisbenzimidazole salt preparation, and can solve the problems such as wide application to be developed and the like

Active Publication Date: 2022-06-03
XI AN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although existing molecules show good redox properties, the widespread use of carbon-derived redox molecules in practical applications remains to be explored

Method used

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  • Bridged bis-benzimidazole salt as well as preparation method and application thereof
  • Bridged bis-benzimidazole salt as well as preparation method and application thereof
  • Bridged bis-benzimidazole salt as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] to N 1 ,N 2 To a solution of diisopropylbenzene-1,2-diamine (768 mg, 4.00 mmol) in dichloromethane (3 mL) was added terephthalaldehyde (1 mmol, 134 mg). Then 0.35 mL of glacial acetic acid was added, and the resulting mixed solution was stirred at 50 °C at a rate of 100 rpm for 16 hours, and the solvent was removed in vacuo under reduced pressure to obtain 1,4-bis(1,3-diisopropyl-2, Crude product of 3-dihydro-1H-benzimidazol)-2-yl)benzene.

[0074] To a solution of crude 1,4-bis(1,3-diisopropyl-2,3-dihydro-1H-benzimidazol-2-yl)benzene in tetrahydrofuran (6 mL) was added 2-bromoacetophenone (2.1 mmol, 418 mg) and stirred at room temperature for 20 hours. The filtrate was removed and the residue was purified by silica gel chromatography (methanol / dichloromethane volume ratio = 1:10) to give Ar ( i Pr)A 1 ·2Br - , (0.7 mmol, 334 mg).

[0075] Ar ( i Pr)A 1 ·2Br - and methyl trifluoromethanesulfonate (0.95 mmol, 156 mg) were mixed in dry dichloromethane (3 mL), an...

Embodiment 2

[0082] to N 1 ,N 2 -Diisopropylbenzene-1,2-diamine (768 mg, 4.00 mmol) in dichloromethane (3 mL) was added biphenyldicarbaldehyde (1 mmol, 210.2 mg). Then 0.35 mL of glacial acetic acid was added, and the resulting mixed solution was stirred at 50° C. at a rate of 100 rpm for 16 hours, and the solvent was removed under reduced pressure and vacuum to obtain 4,4′-bis(1,3-diisopropyl-2 ,3-dihydro-1H-benzimidazol-2-yl)-1,1'-biphenyl crude product.

[0083] To a solution of crude 4,4'-bis(1,3-diisopropyl-2,3-dihydro-1H-benzimidazol-2-yl)-1,1'-biphenyl in tetrahydrofuran (6 mL ) was added with 2-bromoacetophenone (2.1 mmol, 418 mg), followed by stirring at room temperature for 20 hours. The filtrate was removed and the residue was purified by silica gel chromatography (methanol / dichloromethane volume ratio = 1:10) to give Ar ( i Pr)A 2 ·2Br - (0.7 mmol, 502.3 mg).

[0084] Ar ( i Pr)A 2 ·2Br - and methyl trifluoromethanesulfonate (0.95 mmol, 156 mg) were mixed in dry dichl...

Embodiment 3

[0091] to N 1 ,N 2 - Diisopropylbenzene - 1,2-diamine (768 mg, 4.00 mmol) in dichloromethane (3 mL) was added terphenyl - 4,4" - dicarbaldehyde (1 mmol, 286.3 mg). Then 0.35 mL was added Glacial acetic acid, the resulting mixed solution was stirred at 50 °C at a rate of 100 rpm, reacted for 16 hours, and the solvent was removed under reduced pressure to obtain 4,4"-bis(1,3-diisopropyl-2,3-diisopropyl) Hydrogen-1H-benzimidazol-2-yl)-1,1':4',1"-crude product of terphenyl.

[0092] To 4,4"-bis(1,3-diisopropyl-2,3-dihydro-1H-benzimidazol-2-yl)-1,1':4',1"-terphenyl crude product 2-Bromoacetophenone (2.1 mmol, 418 mg) was added to the tetrahydrofuran solution (6 mL), and the mixture was stirred at room temperature for 20 hours. The filtrate was removed and the residue was purified by silica gel chromatography (methanol / dichloromethane volume ratio = 1:10) to give Ar ( i Pr)A 3 ·2Br - (0.7 mmol, 554.9 mg).

[0093] Ar ( i Pr)A 3 ·2Br - and methyl trifluoromethanesulfonate (...

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Abstract

According to the bridging bis-benzimidazole salt as well as the preparation method and the application thereof, compared with common imidazole salt, the imidazole salt has a bridging framework with a more rigid plane, an additional redox center and a narrower HOMO-LUMO energy gap. Due to the good oxidation-reduction property, the bridged bis-imidazolium salt can be better applied to a solution type electrochromic device, and a cross dehydrogenation coupling reaction of N-phenyl tetrahydroisoquinoline and diphenyl phosphine oxide can be promoted to form a carbon-phosphorus bond. The preparation method comprises the following steps: firstly, reacting N1, N2-disubstituted benzene-1, 2-diamine with diformaldehyde with different structures under the catalysis of glacial acetic acid to obtain an intermediate product A; reacting the intermediate product A with 2-bromoacetophenone in an organic solvent for 16-24 hours, and separating the product to obtain an intermediate product B; and finally, reacting the intermediate product B with methyl trifluoromethanesulfonate in an organic solvent, and then separating the product to obtain the bridged bis-benzimidazole salt.

Description

technical field [0001] The invention belongs to the field of preparation of bridged bisbenzimidazole salts, in particular to a class of bridged bisbenzimidazole salts and a preparation method and application thereof. Background technique [0002] In the early stage of the development of the electronics industry, most semiconductor materials were inorganic materials, such as silicon (Si), germanium (Ge), gallium arsenide (GaAs), etc., while organic materials were often used for insulation, passivation, sacrificial layers and patterns chemical material. [0003] Conventional wisdom holds that organic materials are carbon-atom-based insulators that generally do not possess the properties of conductors or semiconductors such as light, electricity, and magnetism. After several years of development, organic semiconductor materials have been widely and deeply used in electroluminescence, photovoltaic cells and other fields. Bridged bisbenzimidazole salts have redox properties and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/20C07D495/04B01J31/02C07F9/62C09K9/02G02F1/1516
CPCC07D235/20C07D495/04B01J31/0244B01J31/0271C07F9/62C09K9/02G02F1/1516C09K2211/1044C09K2211/1007C09K2211/1011C09K2211/1092B01J35/39Y02E10/549
Inventor 饶彬王静何奔李增辉何刚
Owner XI AN JIAOTONG UNIV
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