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Preparation method and application of benzimidazole ligands and dinuclear complexes thereof

A technology of binuclear complexes and benzimidazoles, which is applied in the fields of zinc organic compounds, cadmium organic compounds, chemical instruments and methods, etc., can solve the problem of rare research on dinuclear complexes, and achieve high yield, stable structure and thermal stability. Good results

Inactive Publication Date: 2016-01-27
LINGNAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there are many studies on mononuclear complexes using benzimidazoles for coordination, but the research on dinuclear complexes containing benzimidazoles is still relatively rare [XieQ., LiuS.G., LiX.L., WuQ., LuoZ .D., FuX.Y., CaoW.Q., LanG.Q., LiD., ZhengW.J., ChenT.F., Dalton Trans. , 2014 ,43,6973-6976], the study of dinuclear complexes coordinated by benzimidazoles can open up new avenues for the development of new fluorescent materials and the exploration of biologically active drugs

Method used

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  • Preparation method and application of benzimidazole ligands and dinuclear complexes thereof
  • Preparation method and application of benzimidazole ligands and dinuclear complexes thereof
  • Preparation method and application of benzimidazole ligands and dinuclear complexes thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0038] Example 1 Synthesis of benzimidazole ligands (tbb)

[0039] The synthetic reaction formula is as follows:

[0040]

[0041] Mix 1,2,3,4-tetracarboxylic butane (2.34g, 0.01mol) and o-phenylenediamine (4.32g, 0.04mol) in 10ml of phosphoric acid with a purity of 85%, at 180°C Heated for 3 hours to produce a green reaction product, cooled to room temperature, diluted with distilled water, and neutralized with sodium carbonate solution to obtain a white solid, then washed 3 times with distilled water, filtered, DMF recrystallized to obtain white solids 1, 2, 3 , 4-tetra(1H-benzimidazole-2-)butane, the ligand (tbb). Yield: 5.2 g, yield: 58.6%.

[0042]Elemental Analysis C 44 h 62 N 12 o 8 (tbb · 4DMF · 4H 2 O), theoretical calculation: C, 59.58%; H, 7.05%; N, 18.95%; experimental value: C, 59.48%; H, 7.01%; N, 18.93%. Infrared spectral data (KBr, cm -1 ): 3593, 3150, 1644, 1531, 1440, 13861274, 1030, 839, 746.

[0043] 1 HNMR (300MHz, d 6 -DMSO): 2.72(s,1H...

Embodiment 2

[0044] Example 2 Benzimidazole zinc dinuclear complexes (Zn 2 (tbb)Cl 4 )Synthesis

[0045] The synthetic reaction formula is as follows:

[0046] .

[0047] ZnCl 2 (0.272g, 0.02mol) and benzimidazole ligand (0.886g, 0.01mol) were dissolved in 50ml of DMF solvent under heating, the mixture was stirred evenly, and naturally volatilized for 3 days to obtain a white cuboid-shaped complex single crystallization, and obtained 1,2,3,4-tetrakis(1H-benzimidazole-2-)zinc dinuclear complex Zn 2 (tbb)Cl 4 · 4DMF, the benzimidazole zinc dinuclear complex. Yield 0.69g, yield 63.48%.

[0048] Elemental Analysis: C 44 h 54 Cl 4 N 12 o 4 Zn 2 ([Zn 2 (tbb)Cl 4 ] · 4DMF · 3H 2 O), theoretical calculation: C, 48.59%; H, 5.00%; N, 15.45%; experimental value: C, 48.48%; H, 4.91%; N, 15.33%. Infrared spectral data (KBr, cm -1 ): 3479, 2924, 1651, 1454, 1387, 1281, 1105, 1064, 847, 768, 671.

[0049] The single crystal molecular structure obtained in DMF is as figure 1 sh...

Embodiment 3

[0050] Example 3 Benzimidazole cadmium dinuclear complexes (Cd 2 (tbb)Cl 4 )Synthesis

[0051] The synthetic reaction formula is as follows:

[0052] .

[0053] CdCl 2 (0.336g, 0.02mol) and benzimidazole ligand (0.886g, 0.01mol) were dissolved in 50ml of DMF solvent under heating, the mixture was stirred evenly, and naturally volatilized for 3 days to obtain a white cuboid-shaped complex single crystallization, and obtained 1,2,3,4-tetrakis(1H-benzimidazole-2-)cadmium dinuclear complex Cd 2 (tbb)Cl 4 ·4DMF·3H 2 O, namely benzimidazole cadmium dinuclear complexes. Yield 0.82g, yield 67.10%.

[0054] Elemental Analysis C 44 h 49 Cl 4 Cd 2 N 12 o 7 ([Cd 2 (tbb)Cl 4 ] · 4DMF · 3H 2 O), theoretical calculation: C, 43.16%; H, 4.03%; N, 13.73%; experimental value: C, 43.29%; H, 4.01%; N, 13.53%. Infrared spectral data (KBr, cm -1 ): 3518, 3025, 1655, 1537, 1426, 1395, 1324, 1270, 1206, 1086, 1034, 971, 743, 656.

[0055] The single crystal molecular structur...

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Abstract

The invention discloses a new benzimidazole ligand and a preparation method thereof. The benzimidazole ligand has a simple synthesis method, easy post-treatment, high product purity, high yield and low cost, and can be further used in the preparation of Benzimidazole zinc dinuclear complexes and benzimidazole cadmium dinuclear complexes, the resulting dinuclear complexes have a stable structure, good thermal stability, can emit blue fluorescence, and can be applied to the preparation of blue fluorescent materials; in addition, the results of in vitro cell experiments It shows that the benzimidazole zinc dinuclear complex also has antitumor activity, and can be applied to the preparation of new antitumor drugs.

Description

technical field [0001] The invention belongs to the technical field of blue fluorescent materials and the field of antitumor drugs, and specifically relates to a preparation method and application of a benzimidazole ligand and a dinuclear complex thereof. Background technique [0002] In recent years, nitrogen-containing heteroligands and their complexes have become a very active research field, and the luminescent nitrogen-containing heteroligand complexes have been widely used in the fields of chemistry, biology, medicine and material science [XiaoL.,ChenZ .,QuB.,LuoJ.,KongS.;Gong,Q.;KidoJ., Adv. Mater. 2011, 23, 926–952; Lo K.K.W., Louie M.W., Zhang K.Y., Coord. Chem. Rev. 2010, 254, 2603–2622; ZhaoQ., LiF., HuangC., Chem.Soc.Rev. 2010, 39, 3007–3030]. One strategy for designing light-emitting complexes is to combine organic compounds containing atoms capable of coordinating with large π-electron structures with d 10 Metal ions such as zinc and cadmium in the electr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D235/08C07F3/06C07F3/08C09K11/06A61P35/00
CPCC07D235/08C07F3/06C07F3/08C09K11/06C09K2211/1044C09K2211/188
Inventor 刘生桂李国璧潘荣楷苏文义
Owner LINGNAN NORMAL UNIV