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Preparation method and application of Schiff base derivative based on tricarbazole

A technology of trioxacarbazole and its derivatives, which is applied in the field of detection, can solve the problems of complex material preparation and difficult detection of HCl gas, and achieve the effects of simple preparation method, convenient and quick operation, high selectivity and sensitivity

Active Publication Date: 2014-12-24
NANJING UNIV OF POSTS & TELECOMM
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Provides a high-sensitivity, high-stability, and easy-to-preparation method for the preparation of tricarbazole Schiff base derivatives based on HCl gas detection, which solves the current problems of difficult HCl gas detection and complex material preparation

Method used

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  • Preparation method and application of Schiff base derivative based on tricarbazole
  • Preparation method and application of Schiff base derivative based on tricarbazole
  • Preparation method and application of Schiff base derivative based on tricarbazole

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preparation example Construction

[0031] The preparation method includes: reduction of 3-nitrotrioxcarbazole to 3-amino-trioxcarbazole, and then reacting with 2,7-dibromo-9-fluorenone to synthesize compound II, and finally compound II with different fluorescent light The chromophore Ar undergoes Suzuki reaction to prepare compound I. Such Schiff base derivatives have high sensitivity and good stability for HCl gas detection.

[0032]

[0033] Wherein Ar in formula I is one of the following structures:

[0034]

[0035] Among them, R, R 1 , R 2 And R 3 C1-C12 linear or branched alkyl or alkoxy; * is the position of attachment; N is a nitrogen atom; S is a sulfur atom.

[0036] The preparation method of the ternary carbazole Schiff base derivative material includes the following steps:

[0037] Step 1: Preparation of 3-amino-trioxcarbazole: Under nitrogen protection, dissolve 1mmol of 3-nitro-trioxcarbazole and 0.6-1.0mmol of palladium on carbon (Pd / C) catalyst in 5-10mL N,N-dimethylformamide (DMF), slowly add 8-12mmo...

Embodiment 1

[0046]

[0047] Reaction condition 1: Under nitrogen protection, combine 3-nitro-5,10,15-trihexyl-triscarbazole (643.0mg, 1.0mmol) and Pd / C (9.8mg, 0.6mmol) with 5mL of N ,N-Dimethylformamide (DMF) is mixed, and the temperature is controlled at 45℃, slowly adding N 2 H 4 ·H 2 O (0.4mL, 8.0mmol), react for 8h. After the reaction, it was cooled to room temperature, extracted with dichloromethane, then dried with anhydrous magnesium sulfate, filtered, and the solvent was evaporated to separate and purify the solid obtained by column chromatography to obtain a red powder (459 mg) with a yield of 74.8%.

[0048] Reaction condition 2: Under nitrogen protection, combine 3-nitro-5,10,15-trihexyl-triscarbazole (643.0mg, 1.0mmol) and Pd / C (13.0mg, 0.8mmol) with 8mL of DMF Mix and slowly add N under the condition of temperature control 55℃ 2 H 4 ·H 2 O (0.5 mL, 10.0 mmol), react for 10 h. After the reaction, it was cooled to room temperature, extracted with dichloromethane, dried with anhy...

Embodiment 2

[0052]

[0053] Reaction condition 1: Add 3-amino-5,10,15-trihexyl-trioxcarbazole (613.0mg, 1.0mmol) and 2,7-dibromo-9-fluorenone (338.0mg, 1.0mmol) to Add 15 mL of ethanol and 0.15 mL of glacial acetic acid to the two-necked flask, and reflux for 5 hours at 100°C. After the reaction, it was cooled and filtered with suction, washed with a small amount of anhydrous ethanol, dried, and recrystallized with anhydrous ethanol to obtain a dark red solid compound II (643 mg) after drying, with a yield of 69.0%.

[0054] Reaction condition 2: Add 3-amino-5,10,15-trihexyl-triscarbazole (613.0mg, 1.0mmol) and 2,7-dibromo-9-fluorenone (338.0mg, 1.0mmol) to Add 20 mL of ethanol and 0.2 mL of glacial acetic acid to the two-neck flask, and reflux for 6 hours at 110°C. After the reaction, it was cooled and filtered with suction, washed with a small amount of anhydrous ethanol, dried, and recrystallized with anhydrous ethanol to obtain a dark red solid compound II (695 mg) after drying, with a ...

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Abstract

The invention discloses a Schiff base derivative material based on tricarbazole as well as a preparation method and an application method of the Schiff base derivative material. The preparation method comprises the following steps: reducing 3-nitryl tricarbazole into 3-amino-tricarbazole; then, reacting the 3-amino-tricarbazole with 2,7-dibromo-9-fluorenone to synthesize a compound II; and finally, preparing a compound I from the compound II and different fluorophores Ar by virtue of Suzuku reaction. The Schiff base derivative has good detecting performance on an HCl gas, and can be used as a small-molecule fluorescent probe. The compound is simple to prepare, the intermediate cost is low, the reaction process is easy to control; the Schiff base derivative is easy to separate, high in yield and high in purity, and has potential application value in sensors, electroluminescent devices, organic solar cells, organic field effect transistors, and the like. The compounds I and II are as shown in the specification.

Description

Technical field [0001] The invention belongs to the technical field of detection, and specifically relates to a preparation method and application of a Schiff base derivative material based on a tri-carbazole. Background technique [0002] Organic molecules have structural diversity and easy tailoring, and can combine molecular design and organic synthesis to obtain new compounds with certain specific properties. Because organic molecules can be designed and easily functionalized, in recent years, with the development of molecular engineering and organic synthesis, the research of fluorescence sensors has been extensively developed, and many fluorescence sensors with excellent performance have appeared. They are used in the detection of environmental pollutants. Explosives detection and drug searches have played a major role. As an important challenge facing human beings, environmental issues have received more and more attention. Many countries invest a lot of manpower and mate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/14C09K11/06G01N21/64
CPCC07D487/14C09K11/06C09K2211/1011C09K2211/1029G01N21/64G01N21/643G01N2021/6497
Inventor 赖文勇李祥春王芳黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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