Anthracene-based mechanoluminescent organic material, and preparation method and application thereof

An organic material and luminescent technology, applied in luminescent materials, organic chemical methods, organic chemistry, etc.

Active Publication Date: 2021-05-28
JILIN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But this design strategy is only applicable to molecules with a twisted structure as the luminescent center

Method used

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  • Anthracene-based mechanoluminescent organic material, and preparation method and application thereof
  • Anthracene-based mechanoluminescent organic material, and preparation method and application thereof
  • Anthracene-based mechanoluminescent organic material, and preparation method and application thereof

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preparation example Construction

[0041] The present invention provides a method for preparing the mechanoluminescent organic material described in the above technical solution, comprising the following steps:

[0042] When R is hydrogen, mix 9-bromoanthracene, pinacol diborate, [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride, potassium acetate and the first organic solvent , carry out the Miyaura boronate reaction to obtain the mechanoluminescent organic material BN;

[0043] When R is p-nitrophenyl:

[0044] Miyaura Reaction, obtain 10-bromoanthracene boronate, denoted as compound 1;

[0045]Mix the compound 1, p-nitrophenylboronic acid, tetrakis(triphenylphosphine)palladium, potassium carbonate aqueous solution and a third organic solvent, and perform the first Suzuki reaction to obtain an anthracene-based mechanoluminescent organic material BO;

[0046] When R is thiophene or 2-methylthiophene, the compound 1, boronic acid-substituted thiophene compound, tetrakis(triphenylphosphine)palladium,...

Embodiment 1

[0078] Synthesis of compound 9-anthracene pinacol borate (BN):

[0079]

[0080] 9-Bromoanthracene (257.1 mg, 1 mmol), pinacol diboronate (380.9 mg, 1.5 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (24.5 mg, 0.03mmol) and potassium acetate (588.8mg, 6mmol) were dissolved in 10mL 1,4-dioxane, heated and stirred at 80°C under nitrogen for 24 hours, the cooled mixture was washed with water, and then two Chloromethane (DCM) extraction, anhydrous magnesium sulfate drying to remove solvent, and then using DCM / petroleum ether (1:4, v / v) as eluent, the resulting crude product was purified by silica gel column chromatography to obtain 9- Anthracene pinacol borate, denoted as BN, yield was 80.3%.

[0081] The NMR data of the compound BN prepared in this embodiment are: 1 H NMR (500MHz, DMSO), 8.67(s, 1H), 8.31(d, J=8.5Hz, 2H), 8.11(d, J=8.2Hz, 2H), 7.597.50(m, 4H), 1.52( s, 12H). MALDI-TOF-MS: 303.89.

Embodiment 2

[0083] Synthesis of 10-bromoanthracene borate (compound 1):

[0084]

[0085] 9,10-Dibromoanthracene (336.2mg, 1mmol), pinacol diborate (380.9mg, 1.5mmol), [1,1'-bis(diphenylphosphino)ferrocene] dichloride A mixture of palladium (24.5mg, 0.03mmol) and potassium acetate (588.8mg, 6mmol) was dissolved in 10mL of 1,4-dioxane gas, heated and stirred at 80°C for 24 hours, after cooling, the resulting mixture was washed with water, DCM Extract, then dry with anhydrous magnesium sulfate for 12h to remove the solvent, then use DCM / petroleum ether (1:4, v / v) as the eluent, and purify the obtained crude product by silica gel column chromatography to obtain compound 1. The rate is 85.3%, 325.5mg ( 1 H NMR (500MHz, DMSO), 8.50(t, J=8.2Hz, 2H), 8.29(t, J=8.2Hz, 2H), 7.827.61(m, 4H), 1.54(d, J=8.1Hz, 12H). MALDI-TOF-MS: 382.39);

[0086] Synthesis of 10-nitrophenyl anthracene boronate (BO):

[0087]

[0088] Add compound 1 (500mg, 1.31mmol), p-nitrophenylboronic acid (327mg, 1.96...

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Abstract

The invention provides an anthracene-based mechanoluminescent organic material, a preparation method and application thereof, and belongs to the technical field of organic luminescent materials. The anthracene-based mechanoluminescence organic material provided by the invention takes an anthracene borate group as a core unit, has high fluorescence quantum efficiency and better crystallization property, is stable in crystal structure, and still has high-brightness mechanoluminescence property under sunlight after being ground for more than one minute; and different heteroatom groups are connected to a 10-substituted site of an anthracene borate group, and the light color and the molecular stacking structure of the anthracene borate group are adjusted, so that mechanoluminescent organic materials with different light colors can be obtained.

Description

technical field [0001] The invention relates to the technical field of organic luminescent materials, in particular to an anthracene-based mechanoluminescent organic material and its preparation method and application. Background technique [0002] In addition to light, electricity, heat, force, etc. can also become the excitation source or driving force of the luminescent material. Among them, Mechanoluminescence (Mechanoluminescence), also known as "Mechanoluminescence" (ML) or "Triboluminescence" (TL), refers to a phenomenon in which a material emits light under the action of an external force without being excited by ultraviolet light. . Due to the special excitation method, high-brightness mechanoluminescent materials can be used in many fields such as display lighting, data storage, stress sensing and imaging. [0003] ML is induced by mechanical force on crystals or microcrystals to emit light. When a crystal is crushed, elastic and plastic deformation occurs. Dur...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06
CPCC07F5/025C09K11/06C09K2211/1088C09K2211/1092C09K2211/1011C07B2200/13
Inventor 张明缪俊张瞾霞
Owner JILIN UNIV
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