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One-dimensional organic semiconductor nanotube with fluorescent response to organic amine gas and preparation method and application of one-dimensional organic semiconductor nanotube

A technology of organic semiconductors and nanotubes, applied in the application field of one-dimensional organic semiconductor nanotubes, can solve the problems of lack of porous structure, expensive preparation and processing, low quantum efficiency, etc., achieve large specific surface area, high application value, improve detection out of the limit effect

Active Publication Date: 2015-12-23
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, all these methods have more or less defects: the preparation and processing steps before sample analysis are cumbersome; the preparation and processing before sample analysis are expensive; High training requirements for personnel
However, the one-dimensional organic semiconductor nanowires used for fluorescence sensors are not conducive to the adsorption and diffusion of the detected amine vapor on the surface of the nanowires due to the low quantum efficiency and the lack of nano-scale porous structure on the surface.

Method used

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  • One-dimensional organic semiconductor nanotube with fluorescent response to organic amine gas and preparation method and application of one-dimensional organic semiconductor nanotube
  • One-dimensional organic semiconductor nanotube with fluorescent response to organic amine gas and preparation method and application of one-dimensional organic semiconductor nanotube
  • One-dimensional organic semiconductor nanotube with fluorescent response to organic amine gas and preparation method and application of one-dimensional organic semiconductor nanotube

Examples

Experimental program
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Effect test

Embodiment 1

[0061] (1) Preparation of a peryleneimide derivative monomer having the following molecular formula with a 3-pentyloxyphenethyl group at one end and a dodecyl chain at the other end.

[0062]

[0063] 1.1) 100 mg of perylene-3,4,9,10-tetracarboxylic dianhydride and 10 g of imidazole were mixed and heated to 130°C to dissolve, then injected into 40 mg of dodecylamine for reaction to obtain a reaction solution, Then add 15 milliliters of ethanol and 15 milliliters of concentrated hydrochloric acid to the reaction solution and stir overnight; take out the product, wash it with water until the pH is neutral, and dry it;

[0064] 1.2) Get 100 mg of the product obtained after drying in step 1.1), add 10 grams of imidazole and 300 microliters of 3-isoamyloxyphenethylamine to it, and react at a temperature of 140° C., and then add to the obtained Add 8-15 ml of concentrated hydrochloric acid to the reaction solution, stir overnight, and take out the product to obtain a peryleneimid...

Embodiment 2

[0073] (1) Preparation of peryleneimide derivative monomers having the following molecular formula, one end of which is respectively 3-propoxybenzyl group, and the other end is substituted with a dodecyl chain.

[0074]

[0075] 1.1) 100 mg of perylene-3,4,9,10-tetracarboxylic dianhydride and 10 g of imidazole were mixed and heated to 130°C to dissolve, then injected into 40 mg of dodecylamine for reaction to obtain a reaction solution, Then add 15 milliliters of ethanol and 15 milliliters of concentrated hydrochloric acid to the reaction solution and stir overnight; take out the product, wash it with water until the pH is neutral, and dry it;

[0076] 1.2) Get 100 mg of the product obtained after drying in step 1.1), add 10 grams of imidazole and 300 microliters of 3-isopropoxybenzylamine to it, and react at a temperature of 140 ° C, and then add to the obtained Add 8-15 ml of concentrated hydrochloric acid to the reaction solution, stir overnight, and take out the product...

Embodiment 3

[0081] (1) Prepare a peryleneimide derivative monomer having the following molecular formula with a 3-pentyloxybenzyl group at one end and a dodecyl chain at the other end.

[0082]

[0083] 1.1) 100 mg of perylene-3,4,9,10-tetracarboxylic dianhydride and 10 g of imidazole were mixed and heated to 130°C to dissolve, then injected into 40 mg of dodecylamine for reaction to obtain a reaction solution, Then add 15 milliliters of ethanol and 15 milliliters of concentrated hydrochloric acid to the reaction solution and stir overnight; take out the product, wash it with water until the pH is neutral, and dry it;

[0084] 1.2) Get 100 mg of the product obtained after drying in step 1.1), add 10 grams of imidazole and 300 microliters of 3-isoamyloxybenzylamine to it, and react at a temperature of 140° C. Add 8-15 ml of concentrated hydrochloric acid to the reaction solution, stir overnight, and take out the product to obtain a peryleneimide derivative. NMR data 1 HNMR (400MHz, CD...

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Abstract

The invention relates to a one-dimensional organic semiconductor nanotube and a preparation method thereof. The one-dimensional organic semiconductor nanotube is formed by self-assembling a plurality of perylene bisimide derivatives with asymmetric amphipathic substituent groups at the two ends through the pai-pai interaction between perylene bisimide. The obtained one-dimensional organic semiconductor nanotube has a high fluorescence quantum yield (up to 50%). The organic nanotube suspending in a solution can be smeared to different substrates, such as glass sheets, silicon wafers and tetrafluoroethylene films, through a direct dripping film forming or rotary film forming method. The prepared organic nanotube films are provided with porous net structures, and organic amine molecules can be dispersed in the films. When the naotube is in contact with gas (with the concentration lower than the ppb grade) generated by bad meat and seafood products, the fluorescence intensity can be quenched. The safety condition of meat food can be detected with high sensitivity through the provided fluorescence method.

Description

technical field [0001] The invention belongs to organic semiconductor nanometer materials, in particular to the application of one-dimensional organic semiconductor nanotubes with supersensitive fluorescence response to organic amine gases produced by meat and seafood. Background technique [0002] For health and economic reasons, the monitoring of meat deterioration has been widely concerned and researched. The detector with the function of monitoring meat deterioration can well prevent unnecessary waste of safe meat and consumption of unsafe meat by consumers. Among them, the most significant sign of meat decomposition is the formation of biogenic amines, which are formed by microbial amino acid enzymatic decarboxylation and amination of carbonyls. The most common biogenic amines in food are putrescine (butane-1,4-diamine), cadaverine (pentane-1,5-diamine), methylamine, dimethylamine, and trimethylamine. [0003] So far, analytical methods for detecting meat spoilage mai...

Claims

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Application Information

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IPC IPC(8): C07D471/06C09K11/06G01N21/64
CPCC07D471/06C09K11/06C09K2211/1029G01N21/643
Inventor 车延科胡艳勇赵进才
Owner INST OF CHEM CHINESE ACAD OF SCI
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