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Carborane-perylene diimide derivative and synthesis method thereof, sensing array based on derivative and preparation method and application of sensor array

A perylene diimide and sensing array technology, which is applied in the field of small molecule fluorescent sensing thin film materials, can solve the problems of complex synthesis methods of fluorescent components, large differences in excitation and emission characteristics, and increasing difficulty in the preparation process, and achieves practical application. High performance, eliminate interference, and ensure the effect of simplicity

Active Publication Date: 2018-02-16
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, for this type of fluorescent sensor array, the synthesis method of fluorescent components is relatively complicated, and the preparation process is relatively cumbersome, which greatly increases the difficulty of the preparation process.
At the same time, since this type of fluorescent sensor array is composed of different fluorescent materials, the excitation and emission characteristics are quite different, which greatly increases the complexity of the instrument developed by this type of fluorescent sensor array.

Method used

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  • Carborane-perylene diimide derivative and synthesis method thereof, sensing array based on derivative and preparation method and application of sensor array
  • Carborane-perylene diimide derivative and synthesis method thereof, sensing array based on derivative and preparation method and application of sensor array
  • Carborane-perylene diimide derivative and synthesis method thereof, sensing array based on derivative and preparation method and application of sensor array

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] Synthesis of carborane-perylene diimide derivatives (in this example, n=9)

[0070] Wherein the raw material selects p-iodoaniline, p-ethynyl aniline, and the alkyl ketone selects 12-tritricone;

[0071] (1) Synthesis of compound 1

[0072] Take by weighing 2.19g p-iodoaniline, 0.58g Pd(PPh 3 ) 4 , 0.095g CuI and 1.17g p-ethynylaniline were placed in a 100mL two-necked bottle. Under nitrogen protection, 10 mL of triethylamine and 40 mL of tetrahydrofuran were sequentially added to the reaction system, heated to 70° C., stirred for 12 hours, cooled to room temperature, and spin-dried. A brown solid was obtained by column chromatography using dichloromethane:petroleum ether (1:1) as the eluent. The resulting solid was dried under vacuum at 50°C. Its reaction equation is as follows:

[0073]

[0074] (2) Synthesis of Compound 2

[0075] Weigh 3.39g of 12-docotriconone and 1.38g of hydroxylamine hydrochloride in a 100mL single-necked bottle, add 10mL of pyridine a...

Embodiment 2

[0091] Synthesis of carborane-perylene diimide derivatives (n=5 in this embodiment)

[0092] Wherein the raw material selects p-iodoaniline, p-ethynyl aniline, and the alkyl ketone selects 8-pentadecanone;

[0093] (1) Synthesis of compound 1

[0094] Take by weighing 2.19g p-iodoaniline, 0.58g Pd(PPh 3 ) 4 , 0.095g CuI and 1.17g p-ethynylaniline were placed in a 100mL two-necked bottle. Under nitrogen protection, 10 mL of triethylamine and 40 mL of tetrahydrofuran were sequentially added to the reaction system, heated to 70° C., stirred for 12 hours, cooled to room temperature, and spin-dried. A brown solid was obtained by column chromatography using dichloromethane:petroleum ether (1:1) as the eluent. The resulting solid was dried under vacuum at 50°C. Its reaction equation is as follows:

[0095]

[0096] (2) Synthesis of compound 2

[0097] Weigh 2.26g of 8-pentadecanone and 1.38g of hydroxylamine hydrochloride in a 100mL single-necked bottle, add 10mL of pyridin...

Embodiment 3

[0112] Synthesis of Carborane-Perylene Diimide Derivatives (n=9 in this example)

[0113] Wherein the raw material selects m-iodoaniline, m-ethynyl aniline, and the alkyl ketone selects 12-tritricone;

[0114] (1) Synthesis of compound 1

[0115] Weigh 2.19g m-iodoaniline, 0.58g Pd(PPh 3 ) 4 , 0.095g CuI and 1.17g m-ethynylaniline were placed in a 100mL two-necked flask. Under nitrogen protection, 10 mL of triethylamine and 40 mL of tetrahydrofuran were sequentially added to the reaction system, heated to 60° C., stirred for 8 hours, cooled to room temperature, and spin-dried. A brown solid was obtained by column chromatography using dichloromethane:petroleum ether (1:1) as the eluent. The resulting solid was dried under vacuum at 40°C. Its reaction equation is as follows:

[0116]

[0117] (2) Synthesis of compound 2

[0118] Weigh 3.39g of 12-docotriconone and 1.38g of hydroxylamine hydrochloride in a 100mL single-necked bottle, add 10mL of pyridine and 22mL of eth...

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Abstract

The invention discloses a carborane-perylene diimide derivative and a synthesis method thereof, a sensing array based on the derivative and a preparation method and an application of the sensor array,and belongs to the technical field of small-molecular fluorescent sensing thin film materials. The carborane-perylene diimide derivative is placed in a solution, is assembled into a fiber structure with relatively large specific surface, and then is transferred to different substrate surfaces, so as to obtain the sensing array composed of a variety of fluorescent thin films; the sensing array canbe sensitive to sense six important drug gases, and drug samples have no need of any treatment; at the same time, through array combination, the interference of common interferents is eliminated thoroughly. The operation is simple, and the reaction conditions are mild. The prepared fluorescent sensing thin film has good stability and long service life, and is an excellent drug gas sensing thin film array. With combination use of the thin film and commercial fluorescent instruments, the drug gases can be sensitively detected. In addition, the drug gas special detection instrument can be developed through the device of the sensing thin film.

Description

technical field [0001] The invention belongs to the technical field of small molecule fluorescent sensing thin film materials, and relates to a carborane-perylene diimide derivative, a synthesis method, a sensing array based on the same, a preparation method and an application. Background technique [0002] After the release of the "2014 China Drug Situation Report", on February 18, 2016, the Chinese government released the "2015 China Drug Situation Report". According to the report, as of the end of 2015, there were 2.345 million registered drug users in my country (excluding the number of relapses, deaths and departures after three years of withdrawal), and the actual number of drug users exceeded 12 million. Among the drug users, 35 years old The following teenagers accounted for more than 62%. Crimes involving drug addicts occur from time to time. Among the criminal cases cracked by public security organs in 2015, cases caused by drug addicts accounted for 14%. It can b...

Claims

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Application Information

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IPC IPC(8): C07F5/05C09K11/06G01N21/64
CPCC07F5/05C09K11/06C09K2211/1007C09K2211/1029C09K2211/1096G01N21/6428
Inventor 房喻刘科
Owner SHAANXI NORMAL UNIV
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