Phenoxazine two-dimensional covalent organic framework material and preparation method and application thereof

A covalent organic framework, phenoxazine technology, applied in luminescent materials, analytical materials, material excitation analysis, etc., can solve the problems of precursor design difficulty, few examples of COFs powder crystal, difficult crystallinity of COFs, etc., and achieve good application Prospect, high crystallinity, good thermal stability

Active Publication Date: 2021-08-24
NANJING UNIV OF TECH
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

However, there are very few examples of COFs powder crystals currently used in the detection of moisture content in organic solvents. On the one hand, it is because of the great difficulty in the design of material structures, especially the design of precursors; on the other hand, it is because of the high crystallinity of COFs. It is more difficult and requires a large number of conditional screening
Therefore, the development of new COFs that can be applied to the detection of water content in organic solvents is of great significance and is extremely challenging.

Method used

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  • Phenoxazine two-dimensional covalent organic framework material and preparation method and application thereof
  • Phenoxazine two-dimensional covalent organic framework material and preparation method and application thereof
  • Phenoxazine two-dimensional covalent organic framework material and preparation method and application thereof

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preparation example Construction

[0034] Another aspect of the embodiments of the present invention also provides a method for preparing a phenoxazine-based two-dimensional covalent organic framework material, which includes:

[0035] Under a protective atmosphere, react a uniformly mixed reaction system comprising 10-methylphenoxazine-2,7-diamine, aryl aldehydes, acetic acid aqueous solution and solvent at 100-150°C for 3-7 days to prepare A two-dimensional covalent organic framework based on phenoxazine was obtained.

[0036] In some more specific embodiments, the aryl aldehydes include 1,3,5-tris(4-formylphenyl)benzene, 1,3,5-tris(4-formylphenyl)triazine any of the

[0037] Further, the concentration of the aqueous acetic acid solution is 3-9 mol / L.

[0038] Further, the solvent is a high boiling point solvent with a boiling point range of 80-180°C.

[0039] Further, the solvent includes any one or both of N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, dioxane, mesitylene, ortho-dichlorobenz...

Embodiment 1

[0058] Preparation of phenoxazine-based two-dimensional covalent organic framework material TFPB-DAPO-COF:

[0059] Add 20.4 mg of 10-methylphenoxazine-2,7-diamine, 23.4 mg of 1,3,5-tris(4-formylphenyl)benzene into a 10 mL Slack tube, then add 1 mL of acetonitrile, and sonicate After dissolving, add 0.6 mL of acetic acid aqueous solution with a concentration of 3 mol / L and 1 mL of mesitylene, then degas the reaction system in liquid nitrogen for three times of freezing-vacuum-thawing cycle, seal the reaction mixture in a constant temperature oven and heat to 120 °C And keep warm for 3 days. After the reaction was completed, it was cooled to room temperature, and the resulting mixture was centrifuged to collect the solid, which was then successively washed with N,N-dimethylformamide and tetrahydrofuran, and vacuum-dried at 80°C for 12 hours to obtain an orange powder TFPB-DAPO-COF. The yield was 98%.

Embodiment 2

[0061] Preparation of phenoxazine-based two-dimensional covalent organic framework material TFPT-DAPO-COF:

[0062] Add 20.4mg of 10-methylphenoxazine-2,7-diamine and 23.6mg of 1,3,5-benzenetricarbaldehyde into a 10mL Slack tube, then add 2mL of acetonitrile, dissolve it by ultrasonic, and add 0.6mL of 3mol / L acetic acid aqueous solution. Then the reaction system was degassed in liquid nitrogen by freezing-vacuum-thawing cycle three times. The reaction mixture was sealed in a constant temperature oil bath and heated to 120°C for 3 days. After the reaction was completed, it was cooled to room temperature, and the resulting mixture was centrifuged to collect the solid, which was then successively washed with N, N-dimethylformamide and tetrahydrofuran. Vacuum drying at 80° C. for 12 h gave reddish-brown powder TFPT-DAPO-COF with a yield of 88%.

[0063] Performance Characterization:

[0064] The phenoxazine-based two-dimensional covalent organic framework materials TFPB-DAPO-C...

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Abstract

The invention discloses a phenoxazine-based two-dimensional covalent organic framework material and a preparation method and application thereof. The phenoxazine-based two-dimensional covalent organic framework material has a structure as shown in any one of the following formulas: the phenoxazine-based two-dimensional covalent organic framework material prepared by the invention has high crystallinity and specific surface area, uniform pore size distribution and better thermal stability; meanwhile, the phenoxazine-based two-dimensional covalent organic framework material has fluorescence emission with specific wavelength in an organic solvent, and the fluorescence emission intensity is related to the moisture content in the organic solvent. Therefore, the phenoxazine-based two-dimensional covalent organic framework material prepared by the method can be applied to detection of the moisture content in an organic solvent, and has a good application prospect in the field of functional organic materials.

Description

technical field [0001] The invention belongs to the field of organic functional materials, and specifically relates to a phenoxazine-based two-dimensional covalent organic framework material and its preparation method and application. Background technique [0002] Detection methods in the sensing field include electromagnetic methods, luminescence methods, and colorimetric methods. The luminescence method has the advantages of rapid detection, high selectivity and simple operation, and compared with small molecule probes, nanoprobes are easy to prepare, easy to recover, and have good stability. The current fluorescent probes for detecting humidity and moisture content have shown high sensitivity and lower detection limit, but the stability is still very low, and the difficulty of preparation is still high, making it difficult to achieve large-scale commercial production. [0003] Covalent organic framework (COF) is a highly regular porous material composed of light elements...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G12/06C09K11/06G01N21/64
CPCC08G12/06C09K11/06G01N21/6428C09K2211/1466C09K2211/1475
Inventor 杜亚崔凤敏李震谭晓宇陈江海
Owner NANJING UNIV OF TECH
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