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Pure organic phosphorescence small molecule material used for methanol solvent identification, and preparation method for pure organic phosphorescence small molecule material

A phosphorescent molecule and organophosphorus technology, which is applied in the analysis of materials, luminescent materials, and material analysis by optical means, can solve the problems of lack of solvent and other small molecule selectivity, reduced material sensitivity, and scarcity of sensors, etc. The effect of reusability, easy availability of raw materials, and broadening application prospects

Active Publication Date: 2020-05-29
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, sensors based on phosphorescence excitation are very rare, mainly because stable emission of phosphorescence requires a rigid microenvironment, but the rigid structure will also reduce the sensitivity of the material to external stimuli.
At the same time, the rigidification process of most phosphorescent materials lacks selectivity for small molecules such as solvents.

Method used

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  • Pure organic phosphorescence small molecule material used for methanol solvent identification, and preparation method for pure organic phosphorescence small molecule material
  • Pure organic phosphorescence small molecule material used for methanol solvent identification, and preparation method for pure organic phosphorescence small molecule material
  • Pure organic phosphorescence small molecule material used for methanol solvent identification, and preparation method for pure organic phosphorescence small molecule material

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Experimental program
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Embodiment 1

[0059] This embodiment provides a pure organic phosphorescence small molecule material for methanol solvent recognition, its general structural formula is:

[0060]

[0061] Among them, n represents the length of the alkyl chain, and its value is 1 or 2; R 1 Represents a series of monosaccharide substituent structures; R 2 It represents a class of phosphorescent molecular groups with a biphenyl skeleton structure.

[0062] The phosphorescent molecular group having a biphenyl skeleton structure includes the following basic structures:

[0063]

[0064] Wherein, X is a halogen heavy atom. The heavy halogen atom is one of Cl, Br and I.

[0065] The phosphorescent molecular group having a biphenyl skeleton structure is a biphenyl structural skeleton that can undergo structural twisting.

Embodiment 2

[0067] This embodiment provides a pure organic phosphorescent small molecule material, the general structural formula of which is:

[0068]

[0069] Among them, n=1, monosaccharide structure R 1 is the structure of β-D-galactose, R 2 is a halogen heavy atom modified biphenyl, X is Cl, Br, or I.

[0070] The preparation method of the pure organic phosphorescent small molecule material comprises the following steps:

[0071] Modification of phosphorescent groups containing biphenol skeleton: Add biphenol modified by heavy halogen atoms, 3-bromopropyne and anhydrous potassium carbonate into anhydrous acetonitrile and heat the reaction under the protection of inert gas for 12-24 hours until the reaction is complete. Separation and purification by column chromatography to obtain biphenyl with propargyl group modified at the end;

[0072] Acquisition of intermediates: Disperse the above-mentioned propargyl-modified biphenyl and β-substituted galactose azide in an organic solve...

Embodiment 3

[0078] In this embodiment, a pure organic phosphorescent small molecule material has a structural formula:

[0079]

[0080] Among them, n=1, monosaccharide structure R 1 is the structure of β-D-galactose, R 2 is a halogen heavy atom modified biphenyl, and X is Br.

[0081] The preparation method of the pure organic phosphorescent small molecule material comprises the following steps:

[0082] React 4'-bromo-[1,1'-biphenyl]-4-ol, 3-bromopropyne and anhydrous potassium carbonate in anhydrous acetonitrile under the protection of inert gas at 40-60°C for 12-24 hours to The reaction is complete, and then separated and purified by column chromatography to obtain 4-bromo-4'-(2-propargyl-1-oxyl)-1,1'-biphenyl;

[0083] Add tetraacetyl-α-D-bromogalactose and excess sodium azide to anhydrous N,N'-dimethylformamide, stir at 40°C for 6 hours, filter, and wash the product in the filtrate with silica gel Purified by column chromatography to obtain tetraacetyl-β-D-azidogalactose;

...

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Abstract

The invention discloses a pure organic phosphorescence small molecule material used for methanol solvent identification, and a preparation method for the pure organic phosphorescence small molecule material. The pure organic phosphorescence small molecule material is characterized in that only methanol can be used for activating room-temperature phosphorescence emission. In the pure organic phosphorescence small molecule material, a high-selectivity co-crystallization function between organic small molecules and methanol molecules can be used to form a solvate crystal, the rigidity of a systemeffectively inhibits the non-radiative transition of triplet state energy, and therefore, the selective activation of a phosphorescence emission solvent is realized.

Description

technical field [0001] The invention relates to the technical field of organic luminescence, in particular to a pure organic phosphorescence small molecule material used for methanol solvent recognition and a preparation method thereof. Background technique [0002] At present, pure organic room-temperature phosphorescent materials have been widely used in anti-counterfeiting materials, organic light-emitting diodes and sensors. However, as sensor materials, room-temperature phosphorescent materials have the advantages of low background and large Stokes shift, but at the same time, the application of pure organic room-temperature phosphorescent materials is very limited. At present, the phosphorescence sensor is mainly based on the quenching of phosphorescence, which utilizes the sensitivity of triplet energy to temperature and oxygen, and is used to detect temperature and oxygen. Sensors based on phosphorescence excitation are very rare, mainly because stable emission of p...

Claims

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Application Information

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IPC IPC(8): C07H19/056C07H1/00C09K11/06G01N21/64
CPCC07H19/056C07H1/00C09K11/06G01N21/643C09K2211/1059C09K2211/1088
Inventor 马骧袁志毅田禾
Owner EAST CHINA UNIV OF SCI & TECH
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