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Method for preparing polyphenylene vinylene derivative

A technology of polyphenylene vinylene and derivatives, which is applied in the field of preparation of polyphenylene vinylene derivatives, can solve problems such as difficulty in dissolving, little effect, and increased dispersion coefficient, so as to reduce the reaction temperature and shorten the reaction time. Time, the effect of increasing productivity

Inactive Publication Date: 2008-08-27
TSINGHUA UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When the molecular weight was larger, the intermolecular van der Waals force (addition) was very strong, and the existing solvent and the mechanical stirring used in the prior art could not overcome this force, showing that there was gel precipitation or suspension in the solution, and further The elimination reaction cannot occur, and the obtained polymer contains gel or mostly gel, which is difficult to dissolve
[0005] Among all PPV derivatives synthesized by the Gilch route, poly-2-methoxy-5-(2`-ethylhexyloxy)phenylene vinylene (MEHPPV) is considered to have the best solubility in common solvents , but still inevitably form gels or microgels (Neef, C.J.; Ferraris, J.P.; Macromolecules, 2000, 33, 2311), which leads to It is difficult to obtain a flat MEHPPV film
Chen Z.K. et al. believe that the reason for the above problems is that the kinetic chain growth rate is too fast in the polymerization reaction (Chen, Z.K.; Pan, J.Q.; Xiao, Y.; Lee, N.H.S.; Chua, S.J.; Huang, W.; Thin Solid Films, 2000,363,98; Neef, C.J.; Ferraris, J.P.; Macromolecules, 2000,33,2311), need to add chain stoppers (chain stoppers) to slow down the reaction, but the result of doing so MEHPPV molecular weight change Small and increased dispersion coefficient (Mw / Mn), resulting in poor machinability and performance of the material
Neef C.J. et al. tried to mechanistically solve the problem of gelation during MEHPPV polymerization (Neef, C.J.; Ferraris, J.P.; Macromolecules, 2000, 33, 2311), but all had little success

Method used

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  • Method for preparing polyphenylene vinylene derivative
  • Method for preparing polyphenylene vinylene derivative
  • Method for preparing polyphenylene vinylene derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Synthesis of poly(2-methoxy-5-octyloxy-1,4-phenylene vinylene) (MOOOPPV)

[0021] The first step: etherification reaction

[0022] Synthesis of 4-methoxy-1-octyloxybenzene (MOOOB)

[0023] The reaction proceeds as follows:

[0024]

[0025] Specific steps are as follows:

[0026] Installed with a reflux condenser, N 2 Add 70ml of absolute ethanol to the three-necked bottle of the trachea and thermometer, carefully add 5g (chopped) of accurately weighed metallic sodium, and 2 Under gas protection, use ultrasonic vibration to completely react the sodium metal. in N 2 Add 70ml of dehydrated ethanol solution of 1.20g4-methoxyphenol (MOPH) to the reactor under the protection of air, and after ultrasonic vibration for 5 minutes, add 20ml1-bromooctane at one time, and in N 2 Under gas protection, the reaction was ultrasonically oscillated at 54°C until no raw material point was monitored on a thin-layer chromatography (TLC) plate (developing solvent: hexane:ethyl acet...

Embodiment 2

[0073] Synthesis of poly(2-methoxy-5-(2`-ethylhexyloxy)-1,4-phenylene vinylene) (MEHPPV)

[0074] The first step: etherification reaction

[0075] Synthesis of 4-methoxy-1-(2`-ethylhexyloxy)benzene (MOEHOB)

[0076] The reaction proceeds as follows:

[0077]

[0078] Specific steps are as follows:

[0079] Installed with a reflux condenser, N 2 Add 70ml of absolute ethanol to the three-necked bottle of the trachea and thermometer, carefully add 5g (chopped) of accurately weighed metallic sodium, and 2 Under gas protection, use ultrasonic vibration to completely react the sodium metal. in N 2 Add the dehydrated ethanol (70ml) solution of 1.20g4-methoxyphenol (MOPH) to the reactor under the protection of air, and after ultrasonic vibration for 5 minutes, add 20ml 1-bromo-2-ethylhexane in one go, under N 2 Under gas protection, the reaction was ultrasonically oscillated at 70°C until no raw material point was monitored on a thin-layer chromatography (TLC) plate (developi...

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Abstract

A process for preparing phenylene ethylidene derivative from hydroquinone or p-methoxyphenol through etherifying, bihalomethylation and polymerizing under ultrasonic action. Its advantages are low reaction temp., short time and high output rate.

Description

technical field [0001] The present invention relates to a method for preparing polyphenylene vinylene derivatives. Background technique [0002] Conjugated polymer polyphenylene vinylene (PPV) derivatives, due to their excellent optical properties, electrical properties and photoconductive properties, can be widely used in optoelectronic devices, such as photovoltaic cells (photovoltaic cells), field-induced transistors (field effect transistors), light-emitting diodes (light-emitting diodes), photoelectrochemical cells (photoelectrochemical cells), etc. [0003] For the synthesis of PPV derivatives, the Wessling route (Wessling, R.A.; Zimmerman, R.G.; U.S.Patens 3,401,152, 1968and 3,532,643, 1970) and the Gilch route (Gilch, H.G.; wheelwright, W.L.; J.Polym.Sci., Part A) are mainly used at present. : Polym.Chem., 1966,4,1337), in addition to Wittig reaction (Gilch, H.G.; wheelwright, W.L.; J.Polym.Sci., Part A: Polym.Chem., 1966,4,1337), polycondensation Reaction (Yang Z....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/10
CPCC08G2261/312
Inventor 邱勇王立铎李银奎
Owner TSINGHUA UNIV