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Fluorescent conjugated polymer containing phenothiazine group, and synthesis method and application thereof

A conjugated polymer, phenothiazine-based technology, used in the field of fluorescent conjugated polymers and their synthesis, can solve problems such as difficult testing and processing, insoluble and infusible polymers, and achieve improved solubility and good thermal stability. , the effect of good application prospects

Inactive Publication Date: 2014-11-19
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The improved reaction conditions are mild and the yields are high, but the resulting polymers are mostly insoluble and infusible, making them difficult to test and process

Method used

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  • Fluorescent conjugated polymer containing phenothiazine group, and synthesis method and application thereof
  • Fluorescent conjugated polymer containing phenothiazine group, and synthesis method and application thereof
  • Fluorescent conjugated polymer containing phenothiazine group, and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1, the synthesis of N-octyl-3,6-two (ethynyl) phenothiazines:

[0040] 2g of 3,6-dibromo-N-octylphenothiazine (4.26mmol), 2mg of CuI, 60mg of Pd(Ph 3 P) 2 Cl 2 Sequentially add to a 100ml (19#) two-neck flask, under nitrogen protection, add 30ml of toluene, 30ml of triethylamine and 1.25ml of 3,3'-dimethyl-3-hydroxypropyne, heat to 110°C, React for 12 hours; filter the reaction product, wash with anhydrous ether, evaporate the solvent to dryness, and purify by column chromatography. The developer uses a mixed solvent of petroleum ether and ethyl acetate, and the volume ratio of petroleum ether and ethyl acetate is 3:1 , and purified to obtain 1.384 g of yellow solid, with a yield of 68%;

[0041] Take 0.35g of the yellow solid (0.73mmol) obtained in the above steps and 30mg of NaOH (0.73mmol) into a 100ml (19#) two-neck flask, under the protection of nitrogen, add 15ml of toluene, heat to 110°C to condense and reflux, and react 4h; the reaction mixture wa...

Embodiment 2

[0046] Embodiment 2, the synthesis of N-octyl-3,6-two (ethynyl) carbazoles:

[0047] 1 g of 3,6-diiodo-N-octylcarbazole (1.9 mmol), 1 mg of CuI (0.005 mmol), 30 mg of Pd(Ph 3 P) 2 Cl 2 Add to 100ml (19#) single-necked round bottom flask successively, under N 2 Under atmosphere, add 15ml of triethylamine, then add 0.6ml of 3,3'-dimethyl-3-hydroxypropyne, stir at room temperature for 16h; after the reaction stops, filter the reaction mixture and wash with anhydrous ether Atmospheric pressure distillation removes solvent, carries out column chromatography purification, developing agent adopts the mixed solvent of sherwood oil and ethyl acetate, and the volume ratio of sherwood oil and ethyl acetate is 3: 1, purifies and obtains light yellow solid 0.706g, productive rate 84.5%;

[0048] Take 0.5g of the light yellow solid (1.18mmol) obtained in the above steps and 0.047g of NaOH (1.18mmol) into a 100ml (19#) two-necked round bottom flask, add 15ml of toluene under nitrogen pro...

Embodiment 3

[0053] Embodiment 3, the synthesis of 4,7-diethynyl-2,1,3-benzothiaxazole:

[0054] 1g of 4,7-dibromobenzothiaxazole (3.4mmol), a small amount of CuI and 48mg of Pd(Ph 3 P) 2 Cl 2 (0.068mmol) was added to 100ml (19#) two-necked round bottom flask successively, under N 2 Under the atmosphere, add 15ml of toluene, 15ml of triethylamine and 1ml of 3,3'-dimethyl-3-hydroxypropyne, raise the temperature to 110°C, condense and reflux, and react for 16h; after the reaction is stopped, filter the reaction mixture and use Washing with anhydrous ether; distilled at normal pressure to remove the solvent, then purified by column chromatography, using a mixed solvent of petroleum ether and ethyl acetate as the developer, the volume ratio of petroleum ether and ethyl acetate was 2:1, and purified to obtain a light yellow solid of 0.761 g, yield 74.6%;

[0055] Take 0.5 g of the light yellow solid (1.67 mmol) obtained in the above steps and 0.067 g of NaOH (1.67 mmol) into a 100 ml (19#) ...

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Abstract

The invention belongs to the field of conjugated polymers, and discloses a fluorescent conjugated polymer containing a phenothiazine group, and a synthesis method and an application thereof. The synthesis method comprises the following steps: firstly, synthesizing an N-alkyl-3,6-bi(acetenyl) phenothiazine monomer, then completely dissolving the N-alkyl-3,6-bi(acetenyl) phenothiazine monomer and an N-octyl-3,6-bi(acetenyl) carbazole monomer or a 4,7-diacetenyl-2,1,3-benzothiazine oxazole monomer into orthodichlorobenzene, and carrying out reaction under stirring in a catalytic system containing CuCl and TMEDA; precipitating and filtering the mixture in a mixed solution of methyl alcohol and concentrated hydrochloric acid after reaction is ended, and carrying out vacuum drying, so as to obtain the fluorescent conjugated polymer containing the phenothiazine group. According to the fluorescent conjugated polymer, the solubility of the polymer is improved by introducing an alkyl chain into the phenothiazine group, the structure is improved by introducing groups with different electron donating and withdrawing effects, and the conjugated polymer with excellent photoelectric property, solubility and heat stability is provided.

Description

technical field [0001] The invention belongs to the field of conjugated polymers, and in particular relates to a fluorescent conjugated polymer containing phenothiazine groups, a synthesis method and application thereof. Background technique [0002] Conjugated polymers are a new type of functional material. Because they have the photoelectric properties of metal semiconductors, are easy to process, and have certain flexibility, they are widely used in the fields of solar cells, photoelectric conversion, and optical information materials. . Fluorescent conjugated polymers have strong fluorescence quantum yield and molar extinction coefficient due to their unique π-π* molecular wire structure. Compared with traditional small-molecule fluorescent materials, it has the advantages of adjustable structure, high sensitivity, direct spin-coating, and good stability, so it has attracted more and more attention. [0003] In 1869, Carl Glaser successfully synthesized 1,4-diphenyl-1,...

Claims

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Application Information

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IPC IPC(8): C08G61/12C09K11/06
Inventor 彭汉袁雪
Owner SOUTH CHINA UNIV OF TECH
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