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Carbazole benzaldehyde o-phenylenediamine bis-schiff base and preparation method thereof

A technology of carbazole benzaldehyde o-phenylenediamine and carbazole benzaldehyde phenylenediamine, applied in the field of carbazole benzaldehyde o-phenylenediamine bis-Schiff base and its preparation

Inactive Publication Date: 2013-01-30
QILU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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  • Carbazole benzaldehyde o-phenylenediamine bis-schiff base and preparation method thereof
  • Carbazole benzaldehyde o-phenylenediamine bis-schiff base and preparation method thereof
  • Carbazole benzaldehyde o-phenylenediamine bis-schiff base and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Weigh 2.16g (0.008mol) of carbazole benzaldehyde and dissolve it in 30ml of acetone, start stirring until the carbazole benzaldehyde is completely dissolved, add 0.1g (0.001mol) of o-phenylenediamine, add 3d glacial acetic acid, and control the temperature at 56 ℃, reacted for 12 hours, and obtained yellow Schiff base powder, which was recrystallized from ethanol, and dried in vacuum to obtain carbazole benzaldehyde o-phenylenediamine bis-Schiff base, yield: 65%.

[0036] P1 (reactants: carbazole benzaldehyde, o-phenylenediamine)

[0037]

[0038] 1H NMR (d-DMSO) δ: 8.48(d, 4H, J=7.6), 8.28(d, 4H, J=7.6), 7.85(d, 4H, J=8.0), 7.72(s, 2H), 7.59 (d, 2H, J=7.6), 7.50(m, 6H), 7.32(t, 4H, J=7.2), 7.24(t, 4H, J=7.8).

[0039] Elemental Analysis: C 44 h 30 N 4 : %C85.97(85.99);%H4.92(4.89);9.10(9.11) The measured values ​​are in the brackets;

[0040] MS (ESP) m / z: 614.25 (M).

Embodiment 2

[0042] Weigh 1.08g (0.004mol) of carbazole benzaldehyde and dissolve it in 40ml of ethanol, start stirring until the carbazole benzaldehyde is completely dissolved, add 0.1g (0.001mol) of o-phenylenediamine, add 8d formic acid, and control the temperature at 75°C , and reacted for 8 hours to obtain a yellow Schiff base powder. The powder was recrystallized from dichloromethane and dried in vacuo to obtain carbazole benzaldehyde o-phenylenediamine bis-Schiff base. Yield: 70%. For the structural characterization data of the compound, see Example 1.

Embodiment 3

[0044] Weigh 2.16g (0.008mol) of carbazole benzaldehyde and dissolve it in 60ml of methanol, start stirring until the carbazole benzaldehyde is completely dissolved, add 0.3g (0.003mol) of o-phenylenediamine, add 5d formic acid, and control the temperature at 65°C , and reacted for 2 hours to obtain a yellow Schiff base powder. The powder was recrystallized from chloroform and dried in vacuum to obtain carbazole benzaldehyde o-phenylenediamine bis-Schiff base. The yield: 67%. For the structural characterization data of the compound, see the examples 1.

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Abstract

The invention relates to carbazole benzaldehyde o-phenylenediamine bis-schiff base and a preparation method thereof. The bis-schiff base with a conjugated structure is obtained by using o-phenylenediamine, carbazole and p-fluorobenzaldehyde as raw materials through condensation reaction of aldehyde group and primary amine. The method is low in synthesis cost, high in yield and mild in reaction condition; and the bis-schiff base is easy to purify. The bis-schiff base has the conjugated and rigid plane structure and shows strong fluorescence emission property in a solution, and Cu<2+> has a strong enhancing effect on fluorescence of the bis-schiff base, so the bis-schiff base can be used as a Cu<2+> fluorescence probe and is applied in the field of fluorescence probes.

Description

Technical field: [0001] The invention relates to a carbazole benzaldehyde o-phenylenediamine bis-Schiff base and a preparation method thereof. The Schiff base has good fluorescence performance, can complex metal ions, and can be used as a metal ion fluorescent probe. Background technique: [0002] Research on fluorescent materials and their applications in sensors has attracted more and more attention. Due to the characteristics of simple operation and high detection line, fluorescence detection is a widely used tool in analytical chemistry, biochemistry and cell biology. Fluorescent chemical sensors amplify the bonding between metal ions and sensors at the molecular level through fluorescence enhancement or fluorescence quenching. Carbazole derivatives are often used as fluorescent groups in fluorescent chemical sensors due to their high fluorescence quantum yield. [0003] Schiff base refers to a class of compounds containing C=N groups. The lone pair of electrons on the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C09K11/06
Inventor 段洪东卜娟王兴建孟霞
Owner QILU UNIV OF TECH
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