Chiral light-emitting liquid crystal polymer with circular polarization light-emitting property and preparation method thereof

A technology of liquid crystal polymers and circular polarization, applied in the direction of luminescent materials, liquid crystal materials, chemical instruments and methods, etc., to achieve the effects of rich types, obvious aggregation-induced fluorescence enhancement properties, and simple structure

Pending Publication Date: 2020-05-15
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, how to design and synthesize new AIE-type chiral light-emitting liquid crystal polymers with low cost, excellent performance and high circularly polarized luminous intensity is a difficult problem in front of us, which is very challenging.

Method used

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  • Chiral light-emitting liquid crystal polymer with circular polarization light-emitting property and preparation method thereof
  • Chiral light-emitting liquid crystal polymer with circular polarization light-emitting property and preparation method thereof
  • Chiral light-emitting liquid crystal polymer with circular polarization light-emitting property and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] (1) Synthesis of benzaldehyde derivatives

[0056] Add p-Hydroxybenzaldehyde (8.0g, 65.6mmol) and bromoethanol (10.7g, 85.7mmol) successively in the single-necked bottle, then add 100mL of DMF, stir to dissolve the raw materials, then add anhydrous potassium carbonate (27.2g, 197.0 mmol), reacted at 100 DEG C for 8h, after the completion of the reaction, suction filtered potassium carbonate while hot to obtain the crude product filtrate, and the filtrate was concentrated under reduced pressure with ethyl acetate and sherwood oil mixed solvent as eluent (wherein the volume ratio was 1.5: 1) Column separation, collecting the target component liquid, spin-drying, and obtaining a colorless liquid product after vacuum drying.

[0057] (2) Synthesis of phenylacetonitrile derivatives

[0058] P-Hydroxybenzonitrile (4.0g, 30.1mmol), 1,6-dibromohexane (14.7g, 60.2mmol), anhydrous potassium carbonate (12.5g, 90.3mmol) and 200mL of acetone were sequentially added to the single-ne...

Embodiment 2

[0067] (1) Synthesis of benzaldehyde derivatives

[0068] With the step (1) in the embodiment 1.

[0069] (2) Synthesis of phenylacetonitrile derivatives

[0070] P-Hydroxybenzonitrile (4.0g, 30.1mmol), 1,10-dibromodecane (16.2g, 60.2mmol), anhydrous potassium carbonate (12.5g, 90.3mmol) and 200mL of acetone were sequentially added to a single-necked flask, Stir to dissolve the raw materials, and reflux at 75°C for 10 hours. After the reaction was completed, the anhydrous potassium carbonate was removed by suction filtration, the filter cake was washed 3 times with acetone, the filtrate was collected, and the crude product was obtained after rotary evaporation. The crude product was washed with a mixed solvent of dichloromethane and petroleum ether (volume ratio=1:1). Remove the agent and separate through the column, collect the target component liquid, spin dry, and obtain the pure product after vacuum drying.

[0071] (3) Synthesis of cyano-stilbene derivatives

[0072] ...

Embodiment 3

[0080] (1) Synthesis of benzaldehyde derivatives

[0081] With the step (1) in the embodiment 1.

[0082] (2) Synthesis of phenylacetonitrile derivatives

[0083] Add p-hydroxybenzonitrile (4.0g, 30.1mmol), 1,12-dibromododecane (18.1g, 60.2mmol), anhydrous potassium carbonate (12.5g, 90.3mmol) and 200mL of acetone to the single-necked flask successively , stirred to dissolve the raw materials, and reflux at 75°C for 10h. After the reaction was completed, the anhydrous potassium carbonate was removed by suction filtration, the filter cake was washed 3 times with acetone, the filtrate was collected, and the crude product was obtained after rotary evaporation. The crude product was washed with a mixed solvent of dichloromethane and petroleum ether (volume ratio=1:1). Remove the agent and separate through the column, collect the target component liquid, spin dry, and obtain the pure product after vacuum drying.

[0084] (3) Synthesis of cyano-stilbene derivatives

[0085] Add ...

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Abstract

The invention discloses a chiral light-emitting liquid crystal polymer with a circular polarization light-emitting property and a preparation method thereof. The preparation method comprises the following steps: firstly, reacting 4-hydroxybenzaldehyde or 4-hydroxybiphenyl formaldehyde with bromine alcohol to generate benzene or a biphenyl formaldehyde derivative; preparing benzene or a derivativeof biphenyl acetonitrile from 4-hydroxyphenylacetonitrile or 4-hydroxybiphenyl acetonitrile and dihaloalkane; carrying out a Knoevenagel reaction on two derivatives to generate a cyano-stilbene derivative, carrying out a reaction on the obtained derivative and cholesteryl formyl chloride to generate a cyano-stilbene derivative containing a cholesteric chiral structure, and carrying out a reactionon the derivative and (meth)acrylic acid to generate a polymerizable monomer. The monomer can be subjected to free radical polymerization to obtain a polymer taking poly(meth)acrylic acid as a main chain, and can also be subjected to hydrosilylation reaction with polysiloxane to obtain a polymer taking polysiloxane as a main chain. The obtained polymer has liquid crystallinity, an aggregation-induced fluorescence enhanced property and a circular polarization luminescence property, and has a good application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic polymer light-emitting materials, and in particular relates to a chiral light-emitting liquid crystal polymer with circularly polarized light-emitting properties and a preparation method thereof. Background technique [0002] Circularly polarized luminescence (CPL) refers to the special optical properties of a chiral luminescent system, which can reflect the structural information of the excited state of chiral fluorescent molecules. Circularly polarized luminescent materials have received extensive attention in recent years due to their broad application prospects in asymmetric synthesis, biological / chemical probes, 3D optical displays, liquid crystal lasers, and especially backlit liquid crystal displays. [0003] From a structural point of view, circularly polarized fluorescent materials are usually composed of chiral groups and fluorescent chromophores. Under the induction of chiral groups, th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K19/38C09K19/40C09K11/06C08F120/36C08F283/12C08F220/36
CPCC09K19/3866C09K19/408C09K11/06C08F120/36C08F283/12C09K2211/1416C09K2211/1425C08F220/36
Inventor 袁勇杰张海良陈友德卢鹏
Owner XIANGTAN UNIV
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