D-A-D type organic photo-thermal small molecular material and preparation method thereof

A D-A-D, small molecule technology, applied in organic chemistry and other directions, can solve problems such as poor dispersibility and stability, low nanoparticle concentration, and use restrictions, and achieve mild reaction conditions, good dispersibility, and simple operation.

Inactive Publication Date: 2020-04-03
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A problem of its own is that organic conjugated polymers that can convert light into heat usually have a large rigid structure, poor solubility in solvents, and the corresponding low concentration, poor dispersion and stability of nanoparticles make them suitable for biological applications. , energy and other fields are restricted

Method used

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  • D-A-D type organic photo-thermal small molecular material and preparation method thereof
  • D-A-D type organic photo-thermal small molecular material and preparation method thereof
  • D-A-D type organic photo-thermal small molecular material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] 1) Add sodium tert-amyloxide (3.00g, 27.2mmol) and 20mL of tert-amyl alcohol to a 250mL three-necked round-bottomed flask. After stirring evenly, add 2-cyanothiophene (2.67g, 24.5mmol), and finally Add diisopropyl succinate (1.66g, 8.2mmol), and react under reflux at 90°C. After reacting for 12h, cool to 60°C, add 30mL of methanol, cool to room temperature, spin to dry the solvent, then water, a small amount of methanol, di After washing with methyl chloride and suction filtration, 2.14 g of pure compound (I) was obtained with a yield of 87.0%. 1 H NMR (DMSO, 600MHz) δ: 8.27(s, 2H), 8.03(d, 2H), 7.35(s, 2H), 3.35(s, 2H);

[0032] 2) Add compound (I) (1.00g, 3.33mmol), bromoisoctane (5.14g, 26.7mmol), cesium carbonate (6.43g, 19.7mmol) in a 250mL three-neck round bottom flask, and then add 50mL of acetonitrile , reflux at 90°C for 15 hours. After the reaction, spin the acetonitrile to dryness, extract with a large amount of water and dichloromethane, spin the organic ph...

Embodiment 2

[0036] 1) Add sodium tert-amylate (0.59g, 5.4mmol) and 5mL of tert-amyl alcohol to a 250mL three-necked round-bottomed flask. After stirring evenly, add 2-cyanothiophene (0.53g, 4.9mmol), and finally Add diisopropyl succinate (0.32g, 1.6mmol), and react under reflux at 90°C. After reacting for 12h, cool to 60°C, add 20mL of methanol, cool to room temperature, spin to dry the solvent, water, a small amount of methanol, di After washing with methyl chloride and suction filtration, 0.35 g of pure compound (I) was obtained with a yield of 72.8%. 1 H NMR (DMSO, 600MHz) δ: 8.27(s, 1H), 8.03(d, 1H), 7.35(s, 2H), 3.35(s, 2H);

[0037] 2) with embodiment 1;

[0038] 3) In a 250mL single-necked round bottom flask, add compound (II) (1.00g, 1.91mmol), then add 70mL of chloroform, and then add N-bromobutyl dissolved in 20mL of chloroform drop by drop with a constant pressure dropping funnel Diimide (0.53g, 2.98mmol), react at room temperature for 3h, stop the reaction, spin the solvent ...

Embodiment 3

[0041] 1) with embodiment 1;

[0042] 2) Add compound (I) (1.00g, 3.33mmol), bromoisoctane (5.14g, 26.6mmol), potassium carbonate (2.72g, 19.7mmol) in a 250mL three-neck round bottom flask, and then add 50mL of acetonitrile , reflux at 90°C for 15 hours. After the reaction, spin the acetonitrile to dryness, extract with a large amount of water and dichloromethane, spin the organic phase to dryness, and then use a mixture of dichloromethane and petroleum ether with a volume ratio of 1:1. column, and the pure product point was collected to obtain 0.55 g of compound (II), with a yield of 31.5%. 1 H NMR (CDCl 3 ,600MHz)δ:8.90(m,2H),7.63(m,2H),7.28(m,2H),4.03(m,4H),1.85(m,2H),1.23-1.42(br,16H),0.84 -1.01(br,12H);

[0043] 3) In a 250mL single-necked round bottom flask, add compound (II) (1.00g, 1.91mmol), then add 70mL of chloroform, and then add N-bromosuccinimide (0.40g, 2.25mmol), react at room temperature for 3h, stop the reaction, spin the solvent to dryness, extract with ...

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Abstract

The invention provides a D-A-D type organic photo-thermal small molecular material and a preparation method thereof. The D-A-D type organic photo-thermal small molecular material contains an electronwithdrawing group 2,1,3-benzothiadiazole and an electron donating group 3,6-di(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c] pyrrole-1,4-dione. The preparation method comprises the steps: substituting H ona thiophene ring of bromo-isooctane substituted 3,6-di(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione with N-bromo-succinimide, and carrying out a reaction with 2,1,3-benzothiadiazole-4,7-bis(pinacol borate) through Suzuki reaction to obtain the target product. With the introduction of an alkyl chain on the side chain of the electron donating group, the solubility of the organic photo-thermal material in the organic solvent is improved, the problem of poor solubility of the organic polymer is overcome, and favorable light stability is achieved.

Description

technical field [0001] The invention relates to an organic photothermal material, in particular to a D-A-D type organic photothermal small molecule material and a preparation method. Background technique [0002] As a clean and friendly energy source, light is widely used in biology, medical treatment, energy and other fields. Due to the controllability of light, many people use light to produce some physical or chemical properties to achieve the desired effect, such as using light to generate active oxygen or heat to treat bacterial infections and cancer. In recent decades, the research of organic photothermal materials has attracted more and more attention. Organic photothermal materials are mainly modified organic conjugated polymer nanoparticles. A problem of its own is that organic conjugated polymers that can convert light into heat usually have a large rigid structure, poor solubility in solvents, and the corresponding low concentration, poor dispersion and stabilit...

Claims

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Application Information

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IPC IPC(8): C07D519/00
CPCC07D519/00
Inventor 王皓萍张慧冯丽恒
Owner SHANXI UNIV
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