Flexible organic tribo-luminescent material based on benzothiophene oxide and preparation and use methods thereof

A benzothiophene and triboluminescence technology, which is applied in luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve the difficulty in monitoring the damage of stress sensing materials, and restrict the flexible development and practical application of organic triboluminescence materials. Difficult to prepare film and other problems, to achieve the effect of improving order, easy purification and simple process

Active Publication Date: 2020-11-03
NORTHWESTERN POLYTECHNICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, the triboluminescent phenomenon of organic materials can only occur in the non-centrosymmetric crystalline state, and it is difficult to prepare materials for film formation and flexible optoelectronic devices. For non-planar (non-planar under normal application conditions) stress sensing and Material damage monitoring is even more difficult to achieve, which seriously restricts the flexible development and practical application of organic triboluminescent materials.

Method used

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  • Flexible organic tribo-luminescent material based on benzothiophene oxide and preparation and use methods thereof
  • Flexible organic tribo-luminescent material based on benzothiophene oxide and preparation and use methods thereof
  • Flexible organic tribo-luminescent material based on benzothiophene oxide and preparation and use methods thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] (1) Synthesis of intermediate [3,3'-diiododibenzothiophene sulfone]

[0052]

[0053] Dissolve dibenzothiophene sulfone (5.00g, 23.12mmol) in 50mL acetic acid, add 5mL H 2 O and 5mLH 2 SO 4 , iodine (7.04 g, 27.75 mmol) and periodic acid (6.32 g, 27.75 mmol) were added with stirring. Raise the temperature to solvent reflux, stir and reflux for 16 hours, then cool the reaction solution, pour the reaction solution into water, filter with suction, and evaporate the filtrate to dryness with a rotary evaporator. Purification was carried out by silica gel column chromatography, and the eluent was a mixed solution of dichloromethane and n-hexane with a volume ratio of 1:1. 7.30 g of pure product was obtained with a yield of 67.5%.

[0054] (2) Synthesis of intermediate [3-diphenylamino-3'-iododibenzothiophene sulfone]

[0055]

[0056] Under nitrogen atmosphere, add diphenylamine (0.40g, 2.36mmol) into a 250mL dry three-necked flask, then add 3,3'-diiododibenzothiop...

Embodiment 2

[0061] (1) Synthesis of intermediate [3-carbazolyl-3'-iododibenzothiophene sulfone]

[0062]

[0063] With reference to step (2) in Example 1, carbazole was used instead of diphenylamine to synthesize 3-carbazolyl-3'-iododibenzothiophene sulfone. (yield is 55.2%)

[0064] (2) Synthesis of the target product [3-carbazolyl-3'-diphenylphosphinyl dibenzothiophene sulfone] (M2)

[0065]

[0066] With reference to step (3) in Example 1, use 3-carbazolyl-3'-iododibenzothiophene sulfone to replace 3-diphenylamino-3'-iododibenzothiophene sulfone to synthesize 3-carbazolyl- 3'-Diphenylphosphinyldibenzothiophene sulfone. (The yield is 60.8%)

[0067] To sum up, the material synthesized in the present invention has amorphous triboluminescent properties, is extremely sensitive to external stimulus and cracks of the substrate material, and is accompanied by an easily detectable fluorescent signal. The material synthesis method is simple, the luminescence quantum efficiency is high...

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Abstract

The invention relates to a flexible organic tribo-luminescent material based on benzothiophene oxide and a preparation and use method. The structural general formula of the flexible organic tribo-luminescent material is D-X-A, wherein the D is an electron donor group with a distorted configuration, A is an electron acceptor group with a distorted configuration, X is benzothiophene oxide, and the D, X and A are connected through covalent bonds. The synthesized material has amorphous state triboluminescence performance, is extremely sensitive to external force stimulation and crack induction ofa substrate material, and is accompanied by a fluorescence signal which is easy to detect. The material is simple in synthesis method, high in luminous quantum efficiency and excellent in triboluminescence property, can be prepared into a stress response type flexible device, and is applied to the fields of novel flexible stress sensors, high-precision damage monitoring of materials, micro-loss detection of precise instruments and aerospace equipment and the like.

Description

technical field [0001] The invention belongs to a flexible organic triboluminescent material and its preparation and use method, and relates to a flexible organic triboluminescent material based on oxybenzothiophene and its preparation and use method. The flexible organic triboluminescent material involved in the present invention has good triboluminescent properties and high fluorescence quantum efficiency in an amorphous state, and can be prepared as a stress-responsive flexible optoelectronic device, which is applied to high-precision damage monitoring of materials and precision instruments Micro-damage detection and other fields. Background technique [0002] Triboluminescence, also known as mechanoluminescence, refers to the process in which a solid material converts mechanical energy into light energy and releases it to the outside under the action of external forces (friction, stretching, extrusion, collision, etc.), see literature: N.C.Eddingsaas, K.S.Suslick, "Ligh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6553C07F9/6558C09K11/06A61B5/02A61B5/024
CPCC07F9/655354C07F9/65586C09K11/06A61B5/02A61B5/024C09K2211/1014C09K2211/1029C09K2211/1092Y02E10/549
Inventor 于涛谢宗良纪雷孙浩东王海兰黄成董孟阳黄维
Owner NORTHWESTERN POLYTECHNICAL UNIV
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