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Thiophene and pyrrole quinoid compound and preparation method thereof

A technology of thiophene quinone compound, which is applied in the field of preparation of thienopyrrole quinone compound, to achieve narrow band gap, strong light absorption ability, and beneficial to solution processing

Active Publication Date: 2016-08-10
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Tetracyanoquinone compounds with a larger ring system as the molecular skeleton have not yet been reported

Method used

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  • Thiophene and pyrrole quinoid compound and preparation method thereof
  • Thiophene and pyrrole quinoid compound and preparation method thereof
  • Thiophene and pyrrole quinoid compound and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] The preparation of embodiment 1 compound Ia

[0054]

[0055] Under nitrogen protection at -78°C, n-butyl lithium (1.6M in hexane, 188 μL, 0.30 mmol) was slowly added dropwise to a 10 mL three-necked flask containing compound IVa (113.0 mg, 0.12 mmol) and tetrahydrofuran (2 mL), Keep the reaction at -78°C for 30 minutes, add elemental iodine (76.1mg, 0.30mmol), rise to room temperature and react for 2 hours, add saturated sodium thiosulfate solution (5mL) to quench, and extract with ether (30mL×3), The organic phases were combined and washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation to obtain the crude compound IIa, which was directly used in the next reaction.

[0056] At 0°C, under nitrogen protection, malononitrile (39.6 mg, 0.60mmol), after the foam disappeared, it was raised to room temperature and reacted for 30 minutes. The resulting malononitrile anion solution was transferred via cannula...

Embodiment 2

[0057] The preparation of embodiment 2 compound IVa

[0058]

[0059] Add compound IIV (279.0mg, 0.5mmol), sodium tert-butoxide (768.8mg, 8.0mmol), tris(dibenzylideneacetone) dipalladium (457.9mg, 0.5mmol), 2,2' - Bis-(diphenylphosphino)-1,1'-binaphthyl (BINAP, 1.25g, 2.0mmol) and toluene (10mL), after stirring at 25°C for 20 minutes, compound IIIV (707.4mg, 2.0mmol) was added , heated to 120°C for 24 hours. After cooling to room temperature, water (20 mL) was added, extracted with ether (30 mL×3), the combined organic phases were washed with saturated brine, dried over anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, and the residue was separated by silica gel column chromatography (washing Compound IVa (white solid, 277.0 mg, yield: 80%) was obtained after removal of solvent: petroleum ether). 1 H NMR (400MHz, CDCl 3 )δ7.59(s,2H),7.34(d,J=5.2Hz,2H),7.05(d,J=5.2Hz,2H),4.16(d,J=7.2Hz,4H),2.17(m, 2H), 1.38–1.23(m, 80H), 0.88(m, 12H); 13 C NMR ...

Embodiment 3

[0060] The preparation of embodiment 3 compound 1b

[0061]

[0062] N-bromosuccinimide (NBS, 64.1mg, 0.36 mmol), kept at -78°C for 1 hour, extracted with ether (10mL×3), combined the organic phases and dried with anhydrous magnesium sulfate, and removed the organic solvent by rotary evaporation to obtain the crude product compound IIb, which was directly used in the following One step reaction.

[0063] At 0°C, under nitrogen protection, malononitrile (39.6 mg, 0.6 mmol), after the foam disappeared, the reaction was raised to room temperature for 30 minutes. The prepared malononitrile anion solution was transferred via cannula to a container containing compound IIb, tetrakis(triphenylphosphine)palladium (13.9 mg, 0.012 mmol) and 1,2-dimethoxyethane (5 mL). In a 50 mL three-necked flask, the reaction was heated under reflux for 3 hours under the protection of nitrogen. Then the reaction was cooled to room temperature and exposed to the air, dilute hydrochloric acid (10m...

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Abstract

The invention belongs to the technical field of the preparation of near-infrared dye, and relates to a preparation method of thiophene and pyrrole quinoidcompound. The dye has good stability in air, strong light absorbing capability in the near infrared region, maximum absorption wavelength at 709-880 nm, low LUMO energy level, narrow HOMO-LUMO energy level bandgap, wide range of conjugated system, excellent flatness, strong self-assembly capacity and good solubility, and is in favor of solution processing. The dye has great value in the fields of biological imaging, optical recording, organic solar cells and organic field effect transistors.

Description

technical field [0001] The invention belongs to the technical field of preparation of near-infrared dyes, and relates to a preparation method of a thienopyrrole quinone compound. Background technique [0002] Near-infrared dyes refer to a class of dyes that can perform optical absorption or fluorescence emission in the 700-2000 nm region. Such dyes have great application value in the fields of biological imaging, optical recording, organic solar cells and organic field effect transistors. It is of great practical significance to develop new structural near-infrared dyes. [0003] The molecular skeleton of the quinone structure compound has good planarity and strong rigidity. The LUMO energy level of this type of compound is usually lower than -4eV, so it is not sensitive to oxygen and water, and its stability is very good. At the same time, its narrow energy band gap and large molar absorptivity make it a class of organic materials with great application value. In partic...

Claims

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Application Information

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IPC IPC(8): C09B57/00C07D495/22H01L51/30
CPCC07D495/22C09B57/00H10K85/657H10K10/46Y02E10/549
Inventor 于晓强江华包明冯秀娟
Owner DALIAN UNIV OF TECH
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