Diphenol monomer containing asymmetric fluorophore structure as well as preparation method and application thereof

A fluorophore, asymmetric technology, applied in the field of electrochromism and electronically controlled fluorescence, can solve the problems of unstable electrical activity, slow, low fluorescence contrast development of electronically controlled fluorescent materials, etc., to reduce the degree of aggregation quenching and accumulation Action, effect of electrochromic and electroluminescent performance enhancement

Active Publication Date: 2018-11-23
JILIN UNIV
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

Compared with electrochromic materials, the development of electroluminescent mate

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  • Diphenol monomer containing asymmetric fluorophore structure as well as preparation method and application thereof
  • Diphenol monomer containing asymmetric fluorophore structure as well as preparation method and application thereof
  • Diphenol monomer containing asymmetric fluorophore structure as well as preparation method and application thereof

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preparation example Construction

[0042] The invention provides a preparation method of the diphenol monomer containing an asymmetric fluorophore structure, comprising the following steps:

[0043] 4-fluoronitrobenzene, R 2 -NH 2 , triethylamine and dimethyl sulfoxide are mixed, and a nucleophilic substitution reaction occurs to obtain a compound having a structure shown in formula II;

[0044] The compound having the structure shown in formula II, copper powder, potassium carbonate, 18-crown-6, R 1 -X is mixed with o-dichlorobenzene, and Ullmann reaction I occurs to obtain a compound with the structure shown in formula III; the R 1 X in -X is Cl, Br or I;

[0045] mixing the compound having the structure shown in formula III, Pd / C, hydrazine hydrate and dioxane, and performing a reduction reaction to obtain the compound having the structure shown in formula IV;

[0046] Mix the compound with the structure shown in formula IV, p-iodoanisole, copper powder, 18-crown-6, potassium carbonate and o-dichlorobenz...

Embodiment 1

[0144] The preparation of N,N-bis(4-hydroxyphenyl)-N'-4-methylphenyl-N'-1-aminopyrene-1,4-phenylenediamine, its structural formula is as follows:

[0145]

[0146] Under nitrogen, add 16.9g (120mmol) of 4-fluoronitrobenzene, 16.7g (156mmol) of p-methylaniline, 15.8g (156mmol) of triethylamine in a 250mL three-necked flask equipped with mechanical stirring , adding 130 mL of dimethyl sulfoxide as a solvent, and reacting at 85° C. for 36 h. Discharge in ice-water mixture at room temperature, filter with suction, and recrystallize the filter cake with ethanol and N,N-dimethylformamide to obtain 21.9 g of 4-nitro-4'-methyldiphenylamine with a yield of 80% ;

[0147] Under nitrogen, add 10.0 g (35.6 mmol) of 1-bromopyrene, 9.0 g (37.4 mmol) of 4-nitro-4'- Copper powder of methyl diphenylamine, 9.0g (142.2mmol), 19.6g (142.2mmol) of potassium carbonate, 4.7g (17.8mmol) of 18-crown-6 are raw materials, add 60mL of o-dichlorobenzene as solvent, 160 Reaction at ℃ for 18h; Suction...

Embodiment 2

[0153] The preparation of N,N-bis(4-hydroxyphenyl)-N'-9-anthracenyl-N'-2-aminoanthracene-1,4-phenylenediamine, its structural formula is as follows:

[0154]

[0155] Under nitrogen, add 7.1g (50.0mmol) of 4-fluoronitrobenzene, 14.5g (75.0mmol) of 2-aminoanthracene, 7.6g (75.0mmol) of Triethylamine was then added to 58.9 mL of dimethyl sulfoxide, and reacted at 95°C for 42h. Discharge into ice-water mixture at room temperature, filter with suction, and recrystallize the filter cake with ethanol and N,N-dimethylformamide to obtain 12.9 g of 4-nitrophenyl-2-aminoanthracene with a yield of 82%;

[0156] Under nitrogen, add 7.8g (30.3mmol) of 9-bromoanthracene, 12.0g (36.3mmol) of 4-nitrophenyl-2 -Aminoanthracene, 9.6g (151.5mmol) copper powder, 20.9g (151.5mmol) potassium carbonate, 5.6g (21.2mmol) 18-crown-6, then add 69.4ml o-dichlorobenzene, react at 155°C for 14h ; Suction filtration while it was hot, distilled o-dichlorobenzene under reduced pressure, the resulting crud...

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Abstract

The invention provides a diphenol monomer containing an asymmetric fluorophore structure. The diphenol monomer has a structure shown as a formula (I). Polyarylester prepared from the monomer has excellent electrochromism and electrically-controlled fluorescence property; a p-phenylenediamine structure is capable of giving dual chromism to polyarylester, simultaneously reducing initial oxidation potential of the material and ensuring the stability of monocation free radicals; the asymmetric fluorophore structure is capable of effectively reducing the accumulation action of polymer molecular chains, obviously improving the dissolvability, enhancing solid fluorescence strength and accelerating response time. According to the record of the embodiment, the electrochromism and electrically-controlled fluorescence property of the polyarylester prepared from the diphenol monomer containing the asymmetric fluorophore structure provided by the invention are obviously improved.

Description

technical field [0001] The invention relates to the technical fields of electrochromism and electroluminescence, in particular to a diphenol monomer containing an asymmetric fluorophore structure and a preparation method and application thereof. Background technique [0002] Polyarylates are widely used in the automotive, aerospace and electronics industries due to their high optical transparency, outstanding mechanical properties and high thermal stability. However, the poor solubility and high glass transition temperature of polyarylate limit its application range. The introduction of bulky, propeller-structured triphenylamine into the polyarylate backbone is an effective solution to endow the polymer with optoelectronic properties while improving its solubility and processability. [0003] Electrochromism refers to the phenomenon that the optical properties of materials undergo reversible color changes under the action of an external electric field. It is widely used in ...

Claims

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Application Information

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IPC IPC(8): C07C215/82C07C213/00C09K11/06C09K9/02H01L51/54C08G63/685C08G63/688
CPCC09K9/02C09K11/06C07C215/82C08G63/6856C08G63/6886C07C2603/24C07C2603/18C07C2603/50C09K2211/1425C09K2211/1433C09K2211/1416C09K2211/1011C09K2211/1014C09K2211/1007H10K85/615H10K85/622H10K85/624
Inventor 陈春海田栩舟王大明苏凯欣周宏伟赵晓刚
Owner JILIN UNIV
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