A fluorescent material with piezochromic and lyochromic properties

A fluorescent material and piezochromic technology, applied in the field of fluorescent materials, can solve problems such as limited types and quantities, imperfect color change mechanism, and difficulties in designing and synthesizing such molecules

Active Publication Date: 2019-06-28
连城县奕斯科技服务中心
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the types and quantities of piezoluminescent materials are relatively limited, and the relevant color-changing mechanism is not yet perfect, and the aggregated state structure of fluorescent material samples under stress still needs further research, which also makes it difficult to design and synthesize such molecules.

Method used

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  • A fluorescent material with piezochromic and lyochromic properties
  • A fluorescent material with piezochromic and lyochromic properties
  • A fluorescent material with piezochromic and lyochromic properties

Examples

Experimental program
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Effect test

Embodiment 1

[0021] Example 1: Preparation of 8,8'-bisdimethylamino-10,10'-biphenylcoumarin-3,3'-dicarboxylic acid diethyl ester

[0022] a. Synthesis of intermediate 2,2'-bismethoxymethoxy-7,7'-bisdimethylamino-1,1'-binaphthyl

[0023]

[0024] Under ice-cooling, add 1.26g of sodium hydride (31.5mmol) into 10mL of DMF, then add 2.01g of 7,7'-bisdimethylaminobinaphthol (5.4mmol) to the solution, stir for about 10 minutes, and then 1.73 g of chloromethyl methyl ether (17.0 mmol) was added dropwise to the reaction solution, and the stirring was continued for 1 hour, then the ice-water bath was removed, and then the reaction was stirred at room temperature for 3 hours. After the reaction was complete, ethyl acetate (20 mL) and water (50 mL) were added to the reaction solution, and the organic phase was separated. The aqueous phase (2×15 mL) was extracted with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, filtered, spin-dried, and vacuum-dried to obt...

Embodiment 2

[0034] Example 2: The piezochromic ability of target 8,8'-bisdimethylamino-10,10'-biphenylcoumarin-3,3'-dicarboxylate diethyl ester

[0035] The compound 8,8'-bisdimethylamino-10,10'-biphenylcoumarin-3,3'-dicarboxylate diethyl ester exhibits orange-yellow fluorescence in the initial state, and it shows Fluorescent red. figure 2 It clearly shows that the solid fluorescence emission wavelength of the compound 8,8'-bisdimethylamino-10,10'-biphenylcoumarin-3,3'-dicarboxylate red-shifted from 579 nm to 610 nm, the wavelength red shift reaches 31 nm. The ground sample was fumigated with dichloromethane gas, and its solid fluorescence returned to the original orange-yellow fluorescence (emission wavelength 579 nm). This shows that such compounds have typical piezochromic properties.

Embodiment 3

[0036] Example 3: Lyochromic properties of target 8,8'-bisdimethylamino-10,10'-biphenylcoumarin-3,3'-dicarboxylate diethyl ester

[0037]Compound 8,8'-bisdimethylamino-10,10'-bibenzocoumarin-3,3'-dicarboxylated diethyl The ester concentration is 10 -5 mol / L of the solution to be tested. The fluorescent properties of the above solutions were tested with a Hitachi-F4500 fluorescence spectrophotometer, and the excitation wavelength was 440 nm. Such as figure 1 As shown, the maximum fluorescence emission wavelength of the compound 8,8'-bisdimethylamino-10,10'-biphenylcoumarin-3,3'-dicarboxylate in tetrahydrofuran solvent is 547 nm , 552 nm in dichloromethane, 564 nm in acetonitrile, and 569 nm in dimethylsulfoxide. The above data clearly show that the maximum fluorescence emission peak of the compound 8,8'-bisdimethylamino-10,10'-biphenylcoumarin-3,3'-dicarboxylate diethyl ester increases with the polarity of the solvent. Large gradual redshift. This shows that such compound...

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Abstract

The invention discloses a benzocoumarin compound with piezochromism and solvatochromism properties and a preparation method of the benzocoumarin compound, and belongs to the field of functional materials. The solid fluorescence of the benzocoumarin compound disclosed by the invention is orange-yellow in the initial state; the fluorescence emission wavelength of the ground material is shifted towards a long wavelength; after the material is fumigated with dichloromethane, the material restores solid fluorescence emission wavelength and has a piezochromism property. Meanwhile, with the polarityincrease of a solvent, the fluorescence emission peak of the compound is gradually subjected to red shift, which indicates that the fluorescent material has a solvatochromism property.

Description

【Technical field】 [0001] The invention relates to the technical field of fluorescent materials, in particular to a fluorescent material with piezochromic and lyochromic properties. 【Background technique】 [0002] Fluorescent materials have a wide range of applications in optoelectronic devices, environmental monitoring, biosensing and other fields (Chem. Rev., 2012, 112, 4391-4420; Angew. Chem. Int. Ed. 2016, 55, 2-44). Small organic molecular piezoluminescent materials have a distorted molecular conformation. When they are stimulated by the outside world, they will show different light-emitting behaviors due to the change of the intermolecular stacking method. They are a new type of smart materials. They are used in stress sensors, data storage, memory chips , trademark anti-counterfeiting and other fields have broad development prospects (Top.Curr.Chem.2015,369,345-375; Adv.Mater.2016,28,1073-1095; J.Mater.Chem.2011,21,8282-8291). At present, the types and quantities of p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/92C09K9/02C09K11/06
CPCC07D311/92C09K9/02C09K11/06C09K2211/1088
Inventor 胡志强陈绍晋王鲲鹏尚会师刘威葛兆海张文轩
Owner 连城县奕斯科技服务中心
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