One-dimensional organic semiconductor spiral nano-wires with fluorescence response upon organic amine gases, and preparation method and application thereof

An organic semiconductor, fluorescence response technology, applied in organic chemistry, fluorescence/phosphorescence, chemical instruments and methods, etc., can solve the problems of unfavorable amine vapor adsorption and diffusion, lack of porous structure, low fluorescence quantum yield, etc. Effect of Fluorescence Quantum Yield

Active Publication Date: 2014-11-05
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the surface of these one-dimensional organic semiconductor nanowires used for fluorescence sensors lacks nanoscale porous structure, which is not conducive to the adsorption and diffusion of the detected amine vapor on the surface of the nanowires.
In addition, the existing one-dimensional organic nanowires constructed based on peryleneimide derivatives with different end group substitutions all have the characteristics of low fluorescence quantum yield (the gel using peryleneimide as the center overcomes the problem to a certain extent). this feature)

Method used

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  • One-dimensional organic semiconductor spiral nano-wires with fluorescence response upon organic amine gases, and preparation method and application thereof
  • One-dimensional organic semiconductor spiral nano-wires with fluorescence response upon organic amine gases, and preparation method and application thereof
  • One-dimensional organic semiconductor spiral nano-wires with fluorescence response upon organic amine gases, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] One end with the following molecular formula is prepared as 3,5-dimethoxybenzyl, and the other end is a perylene imide derivative monomer containing perylene anhydride substituted by a dodecyl chain (the monomer is the aforementioned R 2 The subscript in the class is number 3).

[0056]

[0057] (1) Mix 50 mg of perylene-3,4,9,10-tetracarboxylic dianhydride and 8 grams of imidazole and heat to 110°C, 120°C or 130°C to dissolve, then slowly inject into the mixture solution relative to perylene -3,4,9,10-tetracarboxylic dianhydride molar excess dodecylamine solution was reacted for about 3 hours to obtain a reaction solution, then added 8 milliliters, 10 milliliters or 15 milliliters of ethanol and 8 milliliters, 10 milliliters or 15 milliliters of concentrated hydrochloric acid (mass concentration is 36%) after stirring overnight; Take out product, wash with water until pH is neutral, dry;

[0058] (2) Take 50 mg, 80 mg or 100 mg of the product obtained after drying ...

Embodiment 2

[0067] One end of the following molecular formula is prepared as 3,5-dimethoxyphenethyl, and the other end is a perylene imide derivative monomer containing perylene anhydride substituted by a dodecyl chain (the monomer is the aforementioned R 3 The subscript in the class is number 3).

[0068]

[0069] (1) Mix 50 mg, 80 mg or 100 mg of perylene-3,4,9,10-tetracarboxylic dianhydride and 8 g of imidazole and heat to 110°C, 120°C or 130°C to dissolve and pour into the mixture Slowly inject dodecylamine solution in excess relative to the molar amount of perylene-3,4,9,10-tetracarboxylic dianhydride to react for about 3 hours to obtain a reaction solution, and then add 8 ml, 10 ml Or 15 milliliters of ethanol and 8 milliliters, 10 milliliters or 15 milliliters of concentrated hydrochloric acid (mass concentration is 36%) after stirring overnight; Take out the product, rinse with water until the pH is neutral, and dry;

[0070] (2) get 80 milligrams of products obtained after st...

Embodiment 3

[0074] Preparation of perylene anhydride containing perylene anhydride with one end of the following molecular formula being 2,4-dimethoxyphenyl, 3-methoxyphenyl or 2-methoxyphenethyl, and the other end being substituted with a dodecyl chain The perylene imide derivative monomers (monomers are the aforementioned R 1 The subscript in the class is number 1, the aforementioned R 1 The subscript in the class is number 5, the aforementioned R 3 The subscript in the class is number 4).

[0075]

[0076] (1) Mix 50 mg of perylene-3,4,9,10-tetracarboxylic dianhydride and 8 grams of imidazole and heat to 130°C to dissolve, then slowly inject into the mixture solution relative to perylene-3,4,9 10-Tetracarboxylic dianhydride molar excess dodecylamine solution was reacted for about 3 hours to obtain a reaction solution, then in the reaction solution, add 10 milliliters of ethanol and 15 milliliters of concentrated hydrochloric acid (mass concentration is 36%) After stirring overnig...

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Abstract

The invention relates to one-dimensional organic semiconductor spiral nano-wires with ultra-sensitive fluorescence response upon organic amine gases, and a preparation method and an application thereof. According to the invention, perylene imide derivatives comprising perylene and with asymmetric amphiphilic substituents on two ends are adopted as construction units; in a mixed liquid of a good solvent and a poor solvent, through pi-pi interactions between perylenes of a plurality of perylene imide derivatives comprising perylene and with asymmetric amphiphilic substituents on two ends, the one-dimensional organic semiconductor spiral nano-wires are obtained through self-assembly. The one-dimensional organic semiconductor spiral nano-wires have two significant advantages of a nano-grade spiral structure and good fluorescence quantum yield (up to 25%), such that the nano-wires are suitable to be used in fluorescence detection of organic amine in air. When a network-structured porous membrane woven by using the one-dimensional organic semiconductor spiral nano-wires contacts trace amine vapour (with a concentration of ppb-ppm level), the fluorescence is quenched.

Description

technical field [0001] The invention belongs to organic semiconductor nanomaterials, in particular to a one-dimensional organic semiconductor helical nanowire with ultrasensitive fluorescence response to organic amine gases, a preparation method thereof, and an application of the one-dimensional organic semiconductor helical nanowire. Background technique [0002] Organic semiconductor nanomaterials have many advantages that inorganic nanomaterials do not have. For example, the structure of organic semiconductor nanomaterials can be adjusted, and they can be prepared by flexible synthesis methods. The manufacturing cost of materials is low, and they are easy to process in large areas. Applied to flexible substrates, etc. Therefore, although organic semiconductor nanomaterials started relatively late compared with inorganic nanomaterials, they have developed rapidly in recent years. Among them, one-dimensional organic semiconductor nanomaterials prepared by π-conjugated orga...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/06C09K11/06G01N21/64
CPCC07D471/06C09K11/06C09K2211/1029G01N21/64
Inventor 车延科张一帆鄂月马小杰籍宏伟赵进才
Owner INST OF CHEM CHINESE ACAD OF SCI
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