Fluorescent liquid crystal monomer and polymer containing α-cyano-stilbene structure and preparation method thereof

A technology containing cyano stilbene and liquid crystal monomers, applied in liquid crystal materials, chemical instruments and methods, luminescent materials, etc., can solve the problems of increasing the complexity and difficulty of devices, poor film-forming properties of small molecular materials, etc.

Active Publication Date: 2022-04-15
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the fluorescent properties of small molecular solid materials are affected by their own aggregated structure, changes in temperature and humidity in the external environment will affect the fluorescence responsiveness. In addition, small molecular materials have poor film-forming properties, which increases the time required for device preparation and optimization. complexity and difficulty

Method used

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  • Fluorescent liquid crystal monomer and polymer containing α-cyano-stilbene structure and preparation method thereof
  • Fluorescent liquid crystal monomer and polymer containing α-cyano-stilbene structure and preparation method thereof
  • Fluorescent liquid crystal monomer and polymer containing α-cyano-stilbene structure and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] See attached figure 1 , it is the synthesis route diagram of the fluorescent liquid crystal monomer and polymer of alpha-cyano-stilbene structure of the present invention; In this embodiment, the fluorescent liquid crystal monomer and polymer of alpha-cyano-stilbene structure Prepared to R 1 =R 2 =R 3 = OC 12 h 25 The corresponding monomers and polymers are taken as examples, mainly including the following steps:

[0062] Step 1, preparation of compound A: 2.00 (11.62 mmol) of 3,4,5-trihydroxybenzaldehyde was dissolved in 40 mL of dry N, N-dimethylformamide, 5.62 g (40.66 mmol) of potassium carbonate was added and Potassium iodide (amount of catalyst), at 80 o 11.24 mL of bromododecane (46.48 mmol) was added dropwise under stirring, and the reaction was continued for 24 h after the addition was complete. After the reaction, when the system was down to room temperature, the mixture was poured into brine and stirred continuously, then extracted with dichlorometha...

Embodiment 2

[0076] For the monomers and polymers prepared in Example 1, take 1 mg samples and place them between two cell slides for polarizing microscope testing. Raise the samples to the isotropic temperature and take photos during the cooling process. For the results, see the attached Figure 4 ,all Z -isomer, whether it is a polymer or a monomer, they all have a liquid crystal texture, indicating that they have liquid crystallinity, and for E -isomer, no liquid crystal texture appeared during the whole cooling process, indicating no liquid crystallinity.

Embodiment 3

[0078] With the polymer prepared in Example 1, take 5 mg samples and wrap them in aluminum foil for small angle X-ray scattering test, the results are shown in the attached Figure 5 . P-( Z )-345 placed at 170 o The samples were piled up on the hot stage C, and then the hot stage was turned off to allow it to gradually cool down to room temperature, and the values ​​of the scattering vectors that appeared were 1.00, 1.76, and 2.00 nm in turn -1 , and their ratio is 1: : 2, is a hexagonal columnar phase structure. P-( Z )-34 placed at 200 o The samples were piled up on the hot stage C, and then the hot stage was turned off to allow it to gradually cool down to room temperature, and the values ​​of the scattering vectors that appeared were 1.01, 2.03 nm in turn -1 , and their ratio is 1:2, which is a smectic phase structure. P-( Z )-35 placed at 120 o The samples were piled up on the hot stage C, and then the hot stage was turned off to allow it to gradually cool down...

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Abstract

The invention discloses a fluorescent liquid crystal monomer and a polymer containing an α-cyano-stilbene structure and a preparation method thereof. Firstly, a fluorescent liquid crystal monomer containing α-cyano-stilbene structure is obtained through a series of syntheses. Since there is a norbornene structure in the monomer structure, the ROMP method can be used to quickly obtain the target polymer. The fluorescent liquid crystal monomer provided by the present invention can produce multiple fluorescent response behaviors under force, temperature and solvent; the fluorescent liquid crystal polymer provided can regulate the liquid crystal phase structure of the polymer by regulating the substitution position and number of alkyl chains, Thereby changing the fluorescent properties of polymers; under 365 nm and 254 nm UV light, fluorescent liquid crystal monomers and polymers can achieve reversible changes in fluorescence, which are suitable for microelectronics and chemical sensing, functional soft materials and other fields.

Description

technical field [0001] The invention relates to a monomer, a polymer and a preparation method of a cyano-stilbene derivative. Background technique [0002] Stimuli-responsive materials undergo reversible changes in structure, phase state, electrical, magnetic, mechanical, etc. response behavior when external stimuli are applied or removed (e.g., changing temperature, ionic strength, pH, electric field, magnetic field, force field), These materials have potential smart applications in sensors, actuators, electro-optic devices, etc. (see literature: J. Mater. Chem., 2008, 18, 5011-5018). Among the many materials, stimuli-responsive fluorescent materials have attracted the attention of researchers due to their sensitive signal and easy imaging characteristics (see literature: ACS Appl. Mater. Interfaces 2015, 7, 9904-9910). [0003] As a new type of stimuli-responsive fluorescent material, α-cyano-stilbene derivatives can exhibit multiple fluorescence response behaviors and ag...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/76C08G61/08C09K11/06C09K19/34C09K19/38
CPCC07D209/76C08G61/08C09K11/06C09K19/3477C09K19/3823C08G2261/11C08G2261/143C08G2261/3325C08G2261/418C08G2261/522C09K2211/1029C09K2211/1466C09K2211/1425C09K2211/1007
Inventor 陈小芳吴怡瑾
Owner SUZHOU UNIV
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