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

The technology of diamine monomer and fluorophore is applied in the field of diamine monomer containing asymmetric fluorophore structure and its preparation, and can solve the problems of difficulty in having electronically controlled fluorescence performance, weak triphenylamine fluorescence, high driving voltage and the like, Achieve enhanced solubility and solid-state fluorescence, improved contrast, and faster response times

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

AI Technical Summary

Problems solved by technology

[0004] However, the fluorescence of triphenylamine is weak, and its cationic radicals require a high driving voltage, coupled with a long response time, making it difficult to have excellent electronically controlled fluorescence properties.

Method used

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

Examples

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preparation example Construction

[0048] The present invention also provides a preparation method of the diamine monomer containing an asymmetric fluorophore structure, comprising the following steps:

[0049] 4-fluoronitrobenzene, R 2 -NH 2 , triethylamine and dimethyl sulfoxide are mixed, nucleophilic substitution reaction I occurs, and a compound having the structure shown in formula II is obtained;

[0050] 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 Ullman reaction occurs to obtain a compound with the structure shown in formula III; the R 1 X in -X is Cl, Br or I;

[0051] Mix the compound having the structure shown in formula III, Pd / C, hydrazine hydrate and dioxane, and undergo reduction reaction I to obtain the compound having the structure shown in formula IV;

[0052] Mix the compound having the structure shown in formula IV, 4-fluoronitrobenzene, cesium fluoride and dimethyl sulfoxide, and unde...

Embodiment 1

[0168] The preparation of N,N-bis(4-aminophenyl)-N'-4-methoxyphenyl-N'-1-aminopyrene-1,4-phenylenediamine, its structural formula is as follows:

[0169]

[0170] Under nitrogen, add 35.3g (250mmol) of 4-fluoronitrobenzene, 40.0g (325mmol) of p-methoxyaniline, 32.9g (325mmol) of triethyl amine, then added 273 mL of dimethyl sulfoxide, and reacted at 85°C for 36h. Discharge in ice-water mixture at room temperature, filter with suction, and recrystallize the filter cake with ethanol and N,N-dimethylformamide to obtain 4-nitro-4'-methoxydiphenylamine in orange-red needle-like crystals 45g, yield 74%;

[0171]Under nitrogen, add 10.0 g (35.6 mmol) of 1-bromopyrene, 9.2 g (37.4 mmol) of 4-nitro-4'- Methoxydiphenylamine, 9.0g (142.2mmol) of copper powder, 19.6g (142.2mmol) of potassium carbonate, 4.7g (17.8mmol) of 18-crown-6, then add 60ml of o-dichlorobenzene and react at 160°C 18h; Suction filtration while hot, and o-dichlorobenzene was distilled off under reduced pressure,...

Embodiment 2

[0178] Preparation of N,N-bis(4-aminophenyl)-N'-4-methoxyphenyl-N'-2-amino-9,9'-spirobifluorene-1,4-phenylenediamine, The N,N-bis(4-aminophenyl)-N'-4-methoxyphenyl-N'-2-amino-9,9'-spirobifluorene-1,4-phenylenediamine The structural formula is:

[0179]

[0180] The preparation of 4-nitro-4'-methoxydiphenylamine is the same as in Example 1;

[0181] Under nitrogen, 9 g (22.8 mmol) of 2-bromo-9,9'-spirobifluorene, 6.2 g (25.2 mmol) of 4 -Nitro-4'-methoxydiphenylamine, 5.7g (91.2mmol) of copper powder, 12.6g (91.2mmol) of potassium carbonate, 3.0g (11.4mmol) of 18-crown-6, and then add 48mL of Dichlorobenzene, reacted at 160°C for 18 hours; suction filtered while it was hot, distilled o-dichlorobenzene under reduced pressure, and recrystallized the obtained crude product with ethanol and N,N-dimethylacetamide (V:V=1:1), Obtained 9.9 g of 4-nitrophenyl-4'-methoxyphenyl-2-amino-9,9'-spirobifluorene with a yield of 78%;

[0182] Add 9.0 g (16.2 mmol) of 4-nitrophenyl-4'-metho...

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Abstract

The invention provides a diamine monomer containing an asymmetric fluorophore structure. The diamine monomer has a structure shown as a formula (I); semi-aromatic polyamide or semi-aromatic polyimideprepared by the monomer is capable of maintaining thermal stability of polymer, improving dissolvability and film-forming property and giving excellent electrically-controlled fluorescence property ofthe polymer; specifically, the p-phenylenediamine in the diamine monomer containing the asymmetric fluorophore structure can ensure that the polymer has stable electroactivity; fluorophore is introduced into the polymer, so that the fluorescence intensity of the polymer can be improved, and the fluorescent switching contrast is improved; the asymmetric structure is capable of effectively reducingthe accumulation action of the polymer; the dissolvability and the solid fluorescence are enhanced; the response speed is accelerated; meanwhile, aliphatic diacid and aliphatic dianhydride inhibit the charge transfer action and reduce the occurrence probability of nonradiative jump; the fluorescence of the semi-aromatic polymer is obviously improved. According to the record of the embodiment, theelectrically-controlled fluorescence property of semi-aromatic polyamide or semi-aromatic polyimide prepared from the diamine monomer containing the asymmetric fluorophore structure provided by the invention is obviously improved.

Description

technical field [0001] The invention relates to the technical field of electronically controlled fluorescence, in particular to a diamine monomer containing an asymmetric fluorophore structure and a preparation method and application thereof. Background technique [0002] Electronically controlled fluorescence refers to the phenomenon that the fluorescence of materials undergoes reversible switching or discoloration under the action of an external electric field. Because of its good controllability, good reversibility, and environmental friendliness, it is widely used in optical display, information encryption, and information communication. have potential applications. [0003] Since Lehn reported the first electronically controlled fluorescent material in 1993, other electrically controlled fluorescent materials have been studied successively, mainly including two / multi-component systems constructed by electroactive groups and fluorophores, conjugated polymers and electroa...

Claims

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Application Information

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IPC IPC(8): C07C217/84C07C211/61C09K11/06C07C213/00C07C209/68H01L51/54C08G69/26C08G73/10
CPCC09K11/06C07C211/61C07C217/84C08G69/26C08G73/1078C07C2603/54C07C2603/24C07C2603/50C09K2211/1408H10K85/615H10K85/624H10K85/626H10K85/633
Inventor 陈春海苏凯欣王大明孙宁伟周宏伟赵晓刚
Owner JILIN UNIV
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