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Ester-substituted heterocyclic aromatic conjugated skeleton and polymer material and application thereof

A technology of conjugated polymers and aromatic heterocycles, applied in photovoltaic power generation, organic chemistry, etc., can solve the problems of inability to perform 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: 2021-08-17
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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  • Ester-substituted heterocyclic aromatic conjugated skeleton and polymer material and application thereof
  • Ester-substituted heterocyclic aromatic conjugated skeleton and polymer material and application thereof
  • Ester-substituted heterocyclic aromatic conjugated skeleton and polymer material and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0052] Synthesis of a conjugated skeleton of aromatic heterocyclic ring containing ester group substitution:

[0053] Its synthetic route is as follows figure 2 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, Keeping the temperature 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 showed disappearance of the starting material, and the reaction mixture was slowly poured into a beaker with ice / water, and 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, and a light...

Embodiment 2

[0061] A kind of synthesis of aromatic heterocyclic conjugated polymer (PATQ-T) containing ester group substitution:

[0062] Its synthetic route is as follows Figure 7 As shown, under the protection of nitrogen, the product (M1) (0.1mmol, 110.7mg) prepared in Example 1 and 2,5-bis(trimethyltin)thiophene (0.1mmol, 41mg), tri(dimethoxy Benzylacetone) Dipalladium (Pd 2 (dba) 3 ) (2.75mg, 0.003mmol) and three (o-methylphenyl) phosphorus (P (o-Tol) 3 ) (3.65mg, 0.012mmol) was dissolved in 5mL of chlorobenzene solution. Under the protection of nitrogen, the reaction was refluxed for 24 hours. After cooling to room temperature, the reaction liquid was dropped into 150 mL of methanol solution to precipitate, and filtered to obtain a green solid. After extracting with acetone for 24 hours in a Soxhlet extractor, the final polymer was washed with tetrahydrofuran, cooled and filtered through a 0.45 μm organic membrane, precipitated in methanol, filtered, and vacuum-dried. The dark...

Embodiment 3

[0064] A kind of synthesis of aromatic heterocyclic conjugated polymer (PATQ-Se) containing ester group substitution:

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

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Abstract

The invention belongs to the technical field of conjugated polymers, and particularly relates to an ester-substituted aromatic heterocyclic conjugated skeleton and a polymer material and application thereof. The ester-substituted heterocyclic aromatic conjugated skeleton and the polymer material thereof have a larger conjugated plane structure and are more beneficial to intramolecular charge transfer, and compared with the traditional heterocyclic aromatic polymer material, the ester-substituted heterocyclic aromatic conjugated skeleton has the advantages that on the basis of the original chemical structure of the polymer, two strong electron-withdrawing functional groups, namely ester groups, are introduced, so that the aromatic heterocyclic conjugated skeleton has stronger electron-withdrawing capability, the polymer has lower LUMO energy level, redder absorption spectrum and excellent long-wave range light absorption performance, and the ester-substituted aromatic heterocyclic conjugated skeleton and the polymer material thereof are used as photothermal conversion materials to be applied to the field of photoacoustic imaging, and have the advantages of higher photothermal conversion efficiency, better light stability, better imaging effect and the like.

Description

technical field [0001] 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. 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 technologies have more or less 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 ...

Claims

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Application Information

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Patent Type & Authority Applications(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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