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Aza-tetracene analogue of pyrrole-monoketone and preparation method and application thereof

A technology of pyrrole monoketone and tetracene, which is applied in semiconductor/solid-state device manufacturing, photovoltaic power generation, electrical components, etc., can solve the problems of complex synthesis steps and low yield, and achieve simple synthesis methods, easy purification, high air The effect of stabilizing performance

Active Publication Date: 2019-01-04
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no report on one side of the imide being substituted by an alkyl group and the other side is not modified by an alkyl group, and the existing derivatives of diketopyrrolopyrrole often have problems such as complex synthesis steps and low yields.

Method used

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  • Aza-tetracene analogue of pyrrole-monoketone and preparation method and application thereof
  • Aza-tetracene analogue of pyrrole-monoketone and preparation method and application thereof
  • Aza-tetracene analogue of pyrrole-monoketone and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] A method for preparing an aza-tetracene analogue of pyrrole monoketone, comprising the steps of:

[0068] (1) Mix 3.00 g 3,6-di(2-thienyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione (I) and 2.9 g tert-butanol Potassium was added to a three-necked round-bottomed flask, degassed and then filled with nitrogen for three consecutive times, then added 50 mL N,N-dimethylformamide (DMF), stirred, and then added C 16 h 33 Br (1-bromohexadecane) 4.6 mL, react at room temperature for 4 h. The obtained solution was rotary evaporated first, and then purified by a chromatographic column. The ratio of the eluent dichloromethane to petroleum ether was 1:2. Compound II could be obtained by distillation under reduced pressure. The quality of the obtained compound was 1.57 g. The rate is 30%; figure 2 It is the 1HNMR spectrogram of compound II, and the synthesized compound can be proved to be structure II by hydrogen nuclear magnetic resonance spectrum.

[0069] (2) Add 1.00 g of com...

Embodiment 2

[0072] A method for preparing an aza-tetracene analogue of pyrrole monoketone, comprising the steps of:

[0073] (1) Mix 3.00 g 3,6-di(2-thienyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione (I) and 2.9 g tert-butanol Potassium was added to a three-necked round-bottomed flask, degassed and then filled with nitrogen for three consecutive times, then added 50 mL N,N-dimethylformamide (DMF), stirred, and then added C 7 h 15 Br (bromoisoctane) 2.67 mL, react at room temperature for 4.5 h. The obtained solution was distilled under reduced pressure first, and then purified by a chromatographic column. The ratio of the eluent to dichloromethane and petroleum ether was 1:2. Compound II could be obtained by distillation under reduced pressure, and the quality of the obtained compound was 1.60 g. Yield is 40%; Figure 11 It is the 1H NMR spectrogram of compound II, and the synthesized compound can be proved to be structure II by proton nuclear magnetic resonance spectrum.

[0074] (2)...

Embodiment 3

[0077] (1) Mix 3.00 g 3,6-di(2-thienyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione (I) and 2.9 g tert-butanol Potassium was added to a three-necked round-bottomed flask, degassed and then filled with nitrogen for three consecutive times, then added 50 mL N,N-dimethylformamide (DMF), stirred, and then added C 8 h 17 Br 4.6 mL, react at room temperature for 4 h. The obtained solution was rotary-evaporated first, and then purified by a chromatographic column. The ratio of eluent dichloromethane to petroleum ether was 1:2, and compound II could be obtained by distillation under reduced pressure.

[0078] (2) Add 1.00 g of compound (II), 1.05 g of potassium carbonate and 0.63 g of 3-nitro-4-fluorobenzocyanide into a round bottom flask, then add 40 mL of N,N dimethylformamide, and heat at 80 °C, react for 24 h. , and finally the precipitated solid was filtered and then the solvent was distilled off under reduced pressure, and purified by a chromatography column, wherein the volum...

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Abstract

The invention discloses an aza-tetracene analogue of pyrrole-monoketone and a preparation method and application thereof. The novel monoketopyrrolopyrrole tetracene analogue is synthesized by a simplemethod, and the chemical structure formula is shown as formula (I), wherein R is straight-chain or branched-chain paraffin with 7-16 carbon atoms. Besides, the compound has good solubility. Comparedwith other acene structures, the synthesized acene analogue has a high yield, and the yield in each step is higher than 20%; compared with ketopyrrolopyrrole, the analogue has a larger conjugated structure, electron transport is better facilitated, and the maximum absorption wavelength enables the analogue to have potential application prospects in the visible light field and the fields of organicfield effect transistors (OFETs) and organic photovoltaic cells (OPVs).

Description

technical field [0001] The invention belongs to the technical field of organic semiconductors, and more specifically relates to an azatetracene analogue of pyrrole monoketone, a preparation method and application thereof. Background technique [0002] Diketopyrrolopyrrole derivatives are important organic semiconductor materials because of their larger conjugated structures, smaller dihedral angles, lower LUMO energy levels, and higher air stability. It has been widely used in organic field effect transistor (OEFT), organic photovoltaic cell (OPV), organic light emitting diode (OLED) and other fields. Therefore, using diketopyrrolopyrrole as a raw material to synthesize novel derivatives of pyrrolopyrrole through a simple and efficient method has important research and application value. [0003] So far, most of the modification positions for diketopyrrolopyrrole have focused on the substitution of the alkyl chain of the imide, or the modification of the double bond on the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/14H01L51/42H01L51/46H01L51/05H01L51/30
CPCC07D487/14H10K85/655H10K10/00H10K85/6572H10K30/00Y02E10/549
Inventor 岳晚王亚洲徐玉淳
Owner SUN YAT SEN UNIV
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