Carbazole benzaldehyde-p-phenylenediamine bi-schiff base and preparation method thereof

A kind of technology of carbazole benzaldehyde-p-phenylenediamine, carbazole-benzaldehyde-p-phenylenediamine, applied in the field of carbazole benzaldehyde-p-phenylenediamine double Schiff base and preparation thereof

Inactive Publication Date: 2013-02-06
QILU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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  • Carbazole benzaldehyde-p-phenylenediamine bi-schiff base and preparation method thereof
  • Carbazole benzaldehyde-p-phenylenediamine bi-schiff base and preparation method thereof
  • Carbazole benzaldehyde-p-phenylenediamine bi-schiff base and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Weigh 0.54g (0.002mol) of carbazole benzaldehyde and dissolve it in 30ml of methanol, start stirring until the carbazole benzaldehyde is completely dissolved, add 0.1g (0.001mol) of p-phenylenediamine, add 1d formic acid, and control the temperature at 60°C , and reacted for 2 hours to obtain a yellow Schiff base powder. The powder was recrystallized from chloroform to obtain a pure Schiff base, which was dried in vacuo to obtain compound 1 with a yield of 70%.

[0035] P1 (reactants: carbazole benzaldehyde, p-phenylenediamine)

[0036]

[0037] h 1 NMR(400MHz,d-DMSO):δ8.66(s,1H),8.17(t,J=10.0,4H),7.74(d,J=4.0,2H),7.52(d,J=8.0,2H) ,7.45(t,J=8.0,2H),7.39(s,2H),7.32(t,J=8.0,2H);

[0038] Elemental Analysis: C 44 h 30 N 4 : %C85.97(85.98);%H4.92(4.91);9.10(9.11) The measured values ​​are in the brackets;

[0039] MS (ESP) m / z: 614.30 (M).

Embodiment 2

[0041] Weigh 1.08g (0.004mol) of carbazole benzaldehyde and dissolve it in 50ml of ethanol, start stirring until the carbazole benzaldehyde is completely dissolved, add 0.1g (0.001mol) of p-phenylenediamine, add 5d glacial acetic acid, and control the temperature at 75 ℃, reacted for 6 hours, and obtained a yellow Schiff base powder. The powder was recrystallized from chloroform to obtain a pure Schiff base, which was dried in vacuum to obtain compound 1, with a yield of 67%. See Example 1 for the structural characterization data of the compound.

Embodiment 3

[0043] Weigh 2.16g (0.008mol) of carbazole benzaldehyde and dissolve it in 80ml of acetone, start stirring until the carbazole benzaldehyde is completely dissolved, add 0.1g (0.001mol) of p-phenylenediamine, add 8d formic acid, and control the temperature at 50°C , and reacted for 8 hours to obtain a yellow Schiff base powder. The powder was recrystallized from dichloromethane to obtain a pure Schiff base. After vacuum drying, compound 1 was obtained. The yield: 53%. For the structural characterization data of the compound, see Example 1 .

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Abstract

The invention relates to carbazole benzaldehyde-p-phenylenediamine bi-schiff base and a preparation method thereof. Bi-schiff base with a conjugated structure is obtained by the condensation reaction of aldehyde group and primary amine by taking p-phenylenediamine, carbazole and p-fluorobenzaldehyde as raw materials. According to the process, the synthetic cost is low, the yield is high, the reaction condition is moderate, and the product is easy to purify. Therefore the compound has the conjugated and rigid plane structure, so that the strong fluorescence is shown, the fluorescent light of the Cu2+ compound has the strong enhancement action, so that the compound can be used as a Cu2+ fluorescence probe and is applied to the field of fluorescence probes.

Description

Technical field: [0001] The invention relates to a carbazole benzaldehyde p-phenylenediamine bis-Schiff base and a preparation method thereof. The Schiff base has good fluorescence performance and can complex metal ions, and can be used as a metal ion fluorescent probe. Background technique: [0002] Carbazole is an electron-rich aromatic heterocyclic ring with a good electron conjugation plane, so it is the preferred parent nucleus for many fluorescent compounds. In addition, the carbazole ring is easy to undergo structural modification. Therefore, carbazole and its derivatives have been deeply studied and developed as optical materials. [0003] Schiff base refers to a class of compounds containing C=N groups, and there are lone pairs of electrons on the N atom, making Schiff bases an important class of organic ligands. If a Schiff base with fluorescent properties can be developed, since the Schiff base can coordinate with metal ions, the fluorescence properties of the Sc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C09K11/06G01N21/64
Inventor 孟霞卜娟王兴建段洪东
Owner QILU UNIV OF TECH
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