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Strong two-photon absorption conjugated polymer based on S,S-dioxo-dibenzothiophene unit and preparing method and application of strong two-photon absorption conjugated polymer

A two-photon absorption, dibenzothiophene technology, applied in the directions of phototherapy, chemical instruments and methods, luminescent materials, etc., can solve the problem of weak two-photon absorption ability, achieve high two-photon absorption cross-section value, and improve two-photon absorption. Responsive and flat effect

Inactive Publication Date: 2018-01-05
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the two-photon absorption ability of existing materials is weak, so the development of strong two-photon absorption materials with market value has been widely valued by many research institutions and scientific research teams in the world

Method used

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  • Strong two-photon absorption conjugated polymer based on S,S-dioxo-dibenzothiophene unit and preparing method and application of strong two-photon absorption conjugated polymer
  • Strong two-photon absorption conjugated polymer based on S,S-dioxo-dibenzothiophene unit and preparing method and application of strong two-photon absorption conjugated polymer
  • Strong two-photon absorption conjugated polymer based on S,S-dioxo-dibenzothiophene unit and preparing method and application of strong two-photon absorption conjugated polymer

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Experimental program
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Effect test

Embodiment 1

[0050] Synthesis of 4-n-octyltriphenylamine:

[0051] Dissolve 4-octylbromobenzene (2.69g, 10mmol) and aniline (0.93g, 23mmol) in 150ml of toluene solution, then add sodium tert-butyl alkoxide (3.94g, 41mmol) and palladium acetate (96mg, 0.5mmol) , under the protection of argon, the temperature of the oil bath was raised to 85°C, and a toluene solution of tri-tert-butylphosphine (1.0mol / L, 0.5mL) was added; after 12 hours of reaction, water was added to the reaction solution to quench the reaction, Extracted with dichloromethane three times, the organic phase was washed three times with deionized water, dried, concentrated, the crude product was separated and purified by silica gel column chromatography, and pure petroleum ether was used as eluent to obtain a white solid. Yield 82%. 1 H NMR, 13 C NMR, MS and elemental analysis results show that the compound obtained is the target product, and the chemical reaction equation is as follows:

[0052]

Embodiment 2

[0054] Synthesis of 4,4'-dibromo-4"-octyltriphenylamine:

[0055]Dissolve 4-n-octyltriphenylamine (2.50g, 7mmol) completely with 20ml N,N-dimethylformamide, and add N-bromosuccinimide dropwise under ice-bath conditions (0°C) (NBS, 2.74g, 15.4mmol) of N,N-dimethylformamide solution, reacted for 4 hours under dark conditions; after the reaction, pour the reaction solution into water, stir, filter, and filter the cake with silica gel Separation and purification by column chromatography using pure petroleum ether as eluent to obtain a white solid. Yield 78%. 1 H NMR, 13 C NMR, MS and elemental analysis results show that the compound obtained is the target product, and the chemical reaction equation is as follows:

[0056]

Embodiment 3

[0058] Synthesis of 4,4'-bis(4,4',5,5'-tetramethyl-1,3,2-dioxaborolane-diyl)-phenyl)-4”-octyltriphenylamine :

[0059] 4,4'-dibromo-4"-octyltriphenylamine (2.58 g, 5 mmol) was completely dissolved in 100 ml of anhydrous tetrahydrofuran (THF) solution, and under the protection of argon, the temperature was lowered to -78°C, and 5.3 The n-hexane solution of n-butyllithium of ml (concentration is 2.4mol L -1 ), after reacting for 1 hour, add 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-ethylenedioxy borate (2.6g, 14mmol) in one go, continue Stir for 2 hours; the reaction system was gradually raised to room temperature and reacted for 24 hours; the reaction solution was concentrated, extracted three times with ethyl acetate, the organic phase was washed three times with deionized water, dried, concentrated, and the crude product was separated and purified by silica gel column chromatography , a mixed solvent of petroleum ether / ethyl acetate (5 / 1, v / v) was used as eluent to obtain a wh...

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Abstract

The invention discloses a strong two-photon absorption conjugated polymer based on a S,S-dioxo-dibenzothiophene unit and a preparing method and application of the strong two-photon absorption conjugated polymer. The strong two-photon absorption conjugated polymer based on the S,S-dioxo-dibenzothiophene unit is prepared through a Suzuki reaction. The strong two-photon absorption conjugated polymerbased on the S,S-dioxo-dibenzothiophene unit has high electronegativity, and has a high capability of withdrawing electrons; meanwhile, the polymer has good planarity, and is connected with a strong electron donator, which is beneficial to enhancing of the intramolecular charge transfer effect and improvement of two-photon absorption performance of the conjugated polymer. The strong two-photon absorption conjugated polymer has a large development potential and a great prospect in the field of non-linear optics and the field of two-photon fluorescence imaging.

Description

technical field [0001] The invention belongs to the field of two-photon fluorescent polymers, and specifically relates to a strong two-photon absorption conjugated polymer containing S,S-dioxo-dibenzothiophene units, a preparation method and application thereof. Background technique [0002] Organic two-photon absorbing materials have the advantages of simple device structure, convenient use, fast response, and high linear transmittance, making them useful in two-photon up-conversion lasers, two-photon absorption light limiting, three-dimensional optical information storage, two-photon fluorescence microscopy, Photodynamic therapy and other aspects have great potential application prospects. However, the two-photon absorption ability of existing materials is weak, so the development of strong two-photon absorption materials with market value has been widely valued by many research institutions and scientific research teams in the world. [0003] The Journal of Organic Chemi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12A61N5/06C09K11/06
Inventor 应磊胡黎文郭婷杨伟彭俊彪曹镛
Owner SOUTH CHINA UNIV OF TECH
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