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Aryl containing diacetylene conjugated polymer and synthesis thereof

An aryl diacetylene-containing and conjugated polymer technology is applied in the field of aryl diacetylene-containing macromolecular polymers and their synthesis, which can solve the problems of low molecular weight and the like, and achieve high yield and molecular weight and good thermal stability. Effect

Inactive Publication Date: 2008-07-16
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the introduction of flexible alkoxy side chains, the solubility of the polymer is improved. This type of polymer is soluble in common organic solvents such as chloroform and tetrahydrofuran. The disadvantage is that the molecular weight of the product is low

Method used

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  • Aryl containing diacetylene conjugated polymer and synthesis thereof
  • Aryl containing diacetylene conjugated polymer and synthesis thereof
  • Aryl containing diacetylene conjugated polymer and synthesis thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033]

[0034] Synthesis of N-octylcarbazole:

[0035] Carbazole (6g, 35.9mmol), tetrabutylammonium bromide (1g, 3.1mmol), toluene (80ml), KOH solution (50%, 100ml), bromooctane (8.116ml) were added to 250ml (19#) In a two-necked round bottom flask, heat to reflux, stop the reaction after 30h. Extract with toluene, wash with water until neutral, add anhydrous Na 2 SO 4 After drying, filtering and rotary evaporation, 9.779 g of white viscous liquid was obtained, with a yield of 97.0%.

[0036] Synthesis of 3,6-diiodo-N-octylcarbazole:

[0037] N-octylcarbazole (3.767g, 13.5mmol), KI (4.001g, 24.1mmol), KIO 3 (4.836g, 22.6mmol), HOAc (35ml) was added to a 250ml (24#) three-neck round bottom flask, the oil bath was heated to 90°C in advance, and then the flask was immersed in the oil bath, and the temperature was rapidly raised to 120°C, the acetic acid Reflux, stop the reaction after 1h. Extracted with chloroform, followed by Na 2 S 2 o 3 The solution was washed wit...

Embodiment 2

[0046]

[0047] Synthesis of 2,7-dibromo-9,9-ditrianilinofluorene:

[0048] Add dibromofluorenone (2.46g, 7.38mmol) and triphenylamine (25g, 102mmol) into a 100ml three-necked round-bottomed flask, add 0.47ml of methanesulfonic acid with a syringe, heat to 150°C in a sand bath, and react for 7 hours. The reaction was stopped, extracted with dichloromethane, and the solvent was distilled off under reduced pressure, followed by column chromatography purification (developing solvent: petroleum ether) to obtain 2.8 g of a white powdery solid with a yield of 47%.

[0049] Synthesis of 2,7-bis(3,3-dimethyl-3-hydroxy-propynyl)-9,9-ditriphenylaminofluorene:

[0050] 2,7-dibromo-9,9-bistriphenylaminofluorene (0.86g, 1mmol), CuI trace, Pd(Ph 3 P) 2 Cl 2 (15mg, 0.02mmol) was sequentially added to a 100ml (19#) single-necked round bottom flask, and under nitrogen protection, Et 3 N (15ml) and toluene (10ml) were added, and 3,3'-dimethyl-3-hydroxypropyne (0.4ml) was added. The reac...

Embodiment 3

[0057]

[0058] Bis-(4-iodophenyl)-4-octyloxyaniline:

[0059] Diphenyl-4-octyloxyaniline (1.4g, 3.75mmol), KI (0.834g, 5.03mmol), KIO 3 (0.803g, 3.75mmol), HOAc (25ml) was added to a 250ml (24#) three-necked round-bottomed flask, the oil bath was heated to 90°C in advance, and then the flask was immersed in the oil bath, and the temperature was rapidly raised to 120°C. Reflux, stop the reaction after 1h. Extracted with chloroform, followed by Na 2 S 2 o 3 The solution was washed with chloroform to remove excess iodine, and anhydrous MgSO was added 4 Dry, filter, and purify by column chromatography (developing solvent: petroleum ether) to obtain 1.377 g of white crystals with a yield of 63.4%.

[0060] Di-[4-(3,3-dimethyl-3-hydroxy-propynyl)]phenyl-4-octyloxyaniline:

[0061] Bis-(4-iodophenyl)-4-octyloxyaniline (1.37g, 2.19mmol), CuI trace, Pd(Ph 3 P) 2 Cl 2 (16mg) was added to a 250ml single-necked round bottom flask in sequence, and under nitrogen protection, Et...

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Abstract

The invention discloses a conjugated polymer containing aromatic radical diacetylene and the synthesis method thereof. The constitutional formula of the polymer is (I)formula, wherein, R1 is aryl of carbazole, fluorine, triphenylamine and nitrogen heterocyclic ring, R2 is aryl of benzene, thiophene, biphenyl and carbazole, X is between 2 and 300, and Y is between 4 and 500; formula (II) is diacetylene structure. When in preparation, monomer synthesis is firstly done, and then polymer synthesis is done; the monomer is firstly dissolved in dichloro benzene and is stirred for 15 minutes at the temperature between room temperature and 60 DEG C until the monomer is fully dissolved, then the solvent is transferred to a catalytic system containing cuprous chloride and TMEDA for reaction for 20 to 60 minutes, and after the reaction solution is precipitated, filtered, washed with methanol and vacuum-dried, the conjugated polymer containing aromatic radical diacetylene is obtained. The polymer synthesized by the invention has comparatively high yield and molecular weight, good thermal stability and electroluminescent or photoluminescent properties.

Description

technical field [0001] The invention relates to the field of conjugated polymers, in particular to a macromolecular polymer containing aryl diacetylene synthesized by Glaser-Hay reaction and a synthesis method thereof. Background technique [0002] Diacetylenic polymers containing aryl groups are a class of conjugated polymers with many excellent properties. Because its internal alkyne bond does not contain any hydrogen atoms, it is easy to prepare polymers with high carbon structure, which can be used as high temperature resistant materials; the existence of two parallel carbon-carbon triple bonds in the polymer makes this type of polymer have the same properties as The performance of metal chelation, the metal chelate formed with metal chelation is magnetic; if a flexible chain group is introduced into the polymer side chain, the material is expected to exhibit liquid crystallinity and so on. Therefore, based on the special optical, electrical, and magnetic properties of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F38/02
Inventor 彭汉常迪王松钊
Owner SOUTH CHINA UNIV OF TECH
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