A kind of diphenol monomer containing asymmetric fluorophore structure and its preparation method and application

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

Active Publication Date: 2020-02-07
JILIN UNIV
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  • Description
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Problems solved by technology

Compared with electrochromic materials, the development of electroluminescent materials is slower due to unstable electrical activity and low fluorescence contrast.

Method used

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  • A kind of diphenol monomer containing asymmetric fluorophore structure and its preparation method and application
  • A kind of diphenol monomer containing asymmetric fluorophore structure and its preparation method and application
  • A kind of diphenol monomer containing asymmetric fluorophore structure and its preparation method and application

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preparation example Construction

[0041] The invention provides a preparation method of the diphenol monomer containing an asymmetric fluorophore structure, comprising the following steps:

[0042] 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;

[0043] 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;

[0044] 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;

[0045] Mix the compound with the structure shown in formula IV, p-iodoanisole, copper powder, 18-crown-6, potassium carbonate and o-dichlorobenz...

Embodiment 1

[0142] The preparation of N,N-bis(4-hydroxyphenyl)-N'-4-methylphenyl-N'-1-pyrenyl-1,4-phenylenediamine, its structural formula is as follows:

[0143]

[0144] 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% ;

[0145] 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 fil...

Embodiment 2

[0151] The preparation of N,N-bis(4-hydroxyphenyl)-N'-2-anthracenyl-N'-9-anthracenyl-1,4-phenylenediamine, its structural formula is as follows:

[0152]

[0153] 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 in 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 N-4-nitrophenyl-2-anthracenamine, yield 82 %;

[0154] Under nitrogen, add 7.8g (30.3mmol) of 9-bromoanthracene, 12.0g (36.3mmol) of N-4-nitrophenyl -2-Anthracene amine, 9.6g (151.5mmol) copper powder, 20.9g (151.5mmol) potassium carbonate, 5.6g (21.2mmol) 18-crown-6, then add 69.4ml of o-dichlorobenzene, 155°C Reaction for 14h; Suction filtration while hot, distilled o-dichlorobenzene under reduced pressure, the obtained crude product was r...

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Abstract

The invention provides a diphenol monomer containing an asymmetric fluorophore structure with the structure shown in formula I, and the polyarylate prepared by using it as a monomer has excellent electrochromic and electroluminescence properties; The amine structure not only endows the polyarylate with double discoloration, but also reduces the initial oxidation potential of the material, ensuring the stability of the single cation free radical; the asymmetric fluorophore structure can effectively weaken the stacking effect of the polymer molecular chain, which can significantly improve the dissolution performance, enhanced solid-state fluorescence intensity, and faster response times. According to the description of the examples, the electrochromic and electroluminescence properties of the polyarylate prepared from the diphenol monomer containing an asymmetric fluorophore structure provided by the present invention are significantly 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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Patent Type & Authority Patents(China)
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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