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An aromatic heterocyclic conjugated skeleton substituted with an ester group and its polymer material and application

A technology of conjugated polymers and aromatic heterocycles, applied in organic chemistry, photovoltaic power generation, etc., can solve the problems of inability to carry out photoacoustic imaging and low LUMO energy level, and achieve excellent light absorption performance in the long-wave range, excellent imaging effect, The effect of high solubility

Active Publication Date: 2022-05-27
SOUTH CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are relatively few narrow-bandgap conjugated polymers with strong absorption at NIR-II
When the aromatic heterocyclic acceptor unit is polymerized with donor units such as thiophene, fused thiophene, bithiophene, selenophene, benzodithiophene, etc., the polymer absorption stays at the NIR level because the LUMO energy level of the polymer is not low enough. -I interval cannot perform higher resolution NIR-II photoacoustic imaging

Method used

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  • An aromatic heterocyclic conjugated skeleton substituted with an ester group and its polymer material and application
  • An aromatic heterocyclic conjugated skeleton substituted with an ester group and its polymer material and application
  • An aromatic heterocyclic conjugated skeleton substituted with an ester group and its polymer material and application

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Effect test

Embodiment 1

[0052] A kind of synthesis of aromatic heterocyclic conjugated skeleton substituted with ester group:

[0053] Its synthetic route is as figure 2 As shown, the reaction steps are as follows:

[0054] 1) Synthesis of product (2) 4,7-dibromo-5,6-dinitrobenzothiadiazole: add (15 mL) fuming trifluoromethanesulfonic acid to a round-bottomed flask equipped with a stirring bar, The temperature was kept at 0°C, 4,7-dibromobenzothiadiazole (1.000 g, 3.40 mmol) was added in small amounts, and finally fuming nitric acid (15 mL) was added dropwise. The reaction was warmed to room temperature and stirred overnight;

[0055] Analysis by thin layer chromatography indicated disappearance of starting material, the reaction mixture was poured slowly into a beaker with ice / water, the solid precipitate was recovered by filtration, washed several times with water and dried under reduced pressure. The crude product was purified by silica gel column chromatography to obtain a pale yellow solid (...

Embodiment 2

[0061] Synthesis of an ester-substituted aromatic heterocyclic conjugated polymer (PATQ-T):

[0062] Its synthetic route is as Figure 7 As shown, under the protection of nitrogen, the product (M1) (0.1 mmol, 110.7 mg) prepared in Example 1 and 2,5-bis(trimethyltin)thiophene (0.1 mmol, 41 mg), tris(diagne) benzylacetone)dipalladium (Pd 2 (dba) 3 ) (2.75 mg, 0.003 mmol) and tris(o-methylphenyl)phosphorus (P(o-Tol) 3 ) (3.65 mg, 0.012 mmol) was dissolved in 5 mL of chlorobenzene solution. Under nitrogen protection, the reaction was refluxed for 24 hours. After cooling to room temperature, the reaction was dropped into 150 mL methanol solution for precipitation, and a green solid was obtained by filtration. After extraction with acetone in a Soxhlet extractor for 24 hours, finally the polymer was washed with tetrahydrofuran, cooled, filtered through a 0.45 μm organic filter, precipitated in methanol, filtered and dried in vacuo. The dark green solid polymer PATQ-T (101 mg) w...

Embodiment 3

[0064] Synthesis of an ester-substituted aromatic heterocyclic conjugated polymer (PATQ-Se):

[0065] Its synthetic route is as Figure 8 As shown, the product (M1) and 2,5-bis(trimethyltin)selenophene obtained in Example 1 were selected as polymerization monomers, and the other specific operations were the same as in Example 2 to obtain dark green solid polymer PATQ-Se , the yield was 92%.

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Abstract

The invention belongs to the technical field of conjugated polymers, and in particular relates to an aromatic heterocyclic conjugated skeleton substituted with an ester group and its polymer material and application. The ester group-substituted aromatic heterocyclic conjugated skeleton and its polymer material have a larger conjugated planar structure, which is more conducive to intramolecular charge transfer. Compared with traditional aromatic heterocyclic polymer materials, this The invented ester-substituted aromatic heterocyclic conjugated polymer is based on the chemical structure of the original polymer, and introduces two strong electron-withdrawing functional ester groups, which have stronger electron-withdrawing ability, so that the polymer has a lower LUMO energy level, redder absorption spectrum, and excellent light absorption performance in the long-wave range. The ester-containing aromatic heterocyclic conjugated skeleton and its polymer materials are used as photothermal conversion materials in the field of photoacoustic imaging. It can have the advantages of higher photothermal conversion efficiency, better photostability, and better imaging effect.

Description

technical field [0001] The invention belongs to the technical field of conjugated polymers, and in particular relates to an ester group-substituted aromatic heterocyclic conjugated skeleton and its polymer material and application. Background technique [0002] With the development of science and technology, more and more medical imaging technologies have been widely used in the detection and prevention of diseases, such as traditional positron emission computed tomography (CT), magnetic resonance imaging (MRI), optical coherence tomography Imaging Technology (OCT) and Ultrasound Imaging, etc. However, these traditional imaging techniques have more or less some existing defects, such as too slow image acquisition rate and low imaging resolution. Based on this, photoacoustic imaging, an emerging imaging technology, has become a new star in today's medical imaging technology due to its high imaging resolution, high imaging contrast, low cost, and strong imaging tracking abili...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D498/04C07D513/04C07D517/04C08G61/12
CPCC07D498/04C07D513/04C07D517/04C08G61/126C08G61/123C08G2261/124C08G2261/3223C08G2261/3246C08G2261/3241C08G2261/1426C08G2261/414Y02E10/549
Inventor 刘升建罗英桐蔡跃鹏
Owner SOUTH CHINA NORMAL UNIVERSITY
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