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2,3,5,6,7,8-hexa-substituted imidazole[1,2-a] pyridine fluorescent material and synthesis method thereof

A technology for fluorescent materials and synthesis methods, which is applied in the fields of luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problems of low product yield, cumbersome steps, and difficult to obtain raw materials, and achieves high yield, simple operation, and steps. short effect

Inactive Publication Date: 2013-10-16
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The purpose of the present invention is to overcome the difficulty of obtaining raw materials for the preparation of multi-substituted imidazo[1,2-a]pyridine compounds in the prior art, complicated steps, low product yield and low purity, which cannot meet the high purity required by the material industry. Defects of the product, providing a 2,3,5,6,7,8-hexa-substituted imidazo[1,2-a]pyridine fluorescent material and its synthesis method

Method used

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  • 2,3,5,6,7,8-hexa-substituted imidazole[1,2-a] pyridine fluorescent material and synthesis method thereof
  • 2,3,5,6,7,8-hexa-substituted imidazole[1,2-a] pyridine fluorescent material and synthesis method thereof
  • 2,3,5,6,7,8-hexa-substituted imidazole[1,2-a] pyridine fluorescent material and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1: Preparation of 2,3,4,5-tetraphenylcyclopentadienone

[0020]

[0021] The following steps are adopted: (1) 2.10 grams of benzil, 2.10 grams of dibenzyl ketone, and 50 milliliters of ethanol are added to a 100 ml three-necked reaction flask, heated to a slight boiling state, and 0.62 grams of KOH dissolved in 10 grams of ethanol is added dropwise. After the dropwise addition, the reaction took 2 hours. (2) The reactant was allowed to stand and cooled to room temperature. Suction filtration, wash the filter cake with 85% ethanol, dry in vacuo, finally obtain 3.26 grams of black powdery solids, the productive rate is 85%. 1 H NMR (400 MHz, CDCl 3 ) δ 7.24 ~7.21 (m, 12H), 7.15 (m, 4H), 6.93 (m, 4H).

Embodiment 2

[0022] Example 2: Preparation of 1,3-diphenyl-2H-cyclopenta[l]phenanthrene-2-one

[0023]

[0024] Steps: (1) Add 2.08 grams of phenanthrenequinone into a 100ml three-necked reaction flask, add 2.10 grams of dibenzyl ketone, add 50 milliliters of ethanol, heat to a slight boiling state, add dropwise 10 milliliters of ethanol dissolved in 0.62 grams of KOH, drop The reaction was completed for 2 hours after the addition (2) The reactant was allowed to stand and cooled to room temperature. Suction filtration, the filter cake was washed with 85% ethanol, and vacuum-dried to finally obtain 3.17 grams of a black solid with a yield of 83%. 1 H NMR (400MHz, CDCl 3 ): δ 7.77 (d, J = 8.4 Hz, 2 H), 7.51 (d, J = 8.4 Hz, 2 H), 7.32~7.42 (m, 10 H), 7.20~7.26 (m, 2 H), 6.87~6.94 (m, 2 H). 13 C NMR (100MHz, CDCl 3 ) δ 199.7, 148.2, 133.5, 132.3, 131.4, 130.0, 129.0, 128.6, 128.5, 128.3, 128.2, 124.4, 123.1.

Embodiment 3

[0025] Example 3: Preparation of 10,11,12,13-tetraphenylphenanthrene[9',10':4,5]imidazo[1,2-a]pyridine

[0026]

[0027] Steps: (1) Add 0.384 g of 2,3,4,5-tetraphenylcyclopentadienone, 0.188 g of 9,10-phenanthrenequinone, 0.307 g of ammonium acetate, and 2 ml of anhydrous acetic acid into a 25 ml sealed tube . After installing the condenser tube, use a balloon to seal the pressure and adjust it, and heat it to 100 under stirring. o c. (2) Reactants at 100 o C for 2 hours, then stop heating, and let stand to cool to room temperature. The reaction solution was poured into 50 ml of deionized water, extracted three times with dichloromethane, dried over anhydrous magnesium sulfate, the magnesium sulfate was removed by suction filtration, and the filtrate was concentrated. (3) The concentrated solution obtained is separated by silica gel column chromatography, gradient elution, and the developing solvent is from n-hexane and dichloromethane with a volume ratio of 1:1 to n-he...

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Abstract

The invention discloses a 2,3,5,6,7,8-hexa-substituted imidazole[1,2-a] pyridine fluorescent material and a synthesis method thereof. The molecular structural formula is shown in the specification. The method comprises the following specific steps: dissolving a cyclopentadienone derivative, a 1,2-dicarbonyl compound and an ammonium salt in an anhydrous solvent, wherein the molar ratio of the cyclopentadienone derivative to the 1,2-dicarbonyl compound to ammonium salt is 1:(0.9-1.1):(4-10); heating to 100-160 DEG C to react for 2-6 hours, performing reduced pressure distillation after the reaction to remove the solvent, and purifying to obtain the solid, namely the fluorescent material 2,3,5,6,7,8-hexa-substituted imidazole[1,2-a] pyridine compound. In the method, the cyclopentadienone derivative and 1,2-dicarbonyl compound are utilized as raw materials and the inorganic ammonium salt is utilized as an ammonia source, thus the source range of the raw materials is wide, the raw materials are easily available, the operations are simple, a one-pot method is adopted for synthesis, the steps are short, the yield is high and the method can be used in mass production easily.

Description

technical field [0001] The invention relates to a 2,3,5,6,7,8-hexa-substituted imidazo[1,2-a]pyridine fluorescent material and a synthesis method thereof. Background technique [0002] The 21st century is the information age, and the information age is inseparable from information display technology. Organic electroluminescent device (OLED), as a new display technology and display method, has made great progress and is on the verge of industrialization. And as its core component, the fluorescent material plays an important role. [0003] At present, the focus of research on fluorescent materials is to develop new fluorescent materials, or improve the preparation methods of original fluorescent materials, shorten the process route, and increase the yield. Compounds with imidazo[1,2-a]pyridine core structure are a class of fluorescent materials with excellent performance. The original synthesis methods, such as EP204 285, EP228 206 and EP308 917, use 2-aminopyridine with...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07D471/04
Inventor 李继超李熙晖吕萍王彦广
Owner ZHEJIANG UNIV
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