2-acetyl benzimidazolyl glycine-condensate Schiff base rare-earth complex and process for preparing same

A technology of acetylbenzimidazole glycine Schiff base and rare earth complexes, which is applied in the field of rare earth complexes and their preparation, can solve the problems of prolonging the reaction time, failing to reach the yield, serious pollution in the reaction process, etc. The process is simple, the synthesis method is improved, and the effect of excellent luminescence characteristics

Inactive Publication Date: 2008-05-28
NORTHWEST UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] ①The reaction takes a long time and the yield is not high. By reproducing the synthesis steps reported in the literature and prolonging the reaction time, the reported yield cannot reach 63%, but only about 30%.
[0006] ②The reaction process of this synthesis method has serious pollution and is difficult to synthesize in large quantities
[0008] The solubility in the used recrystallization solvent n-hexane is very poor, the recrystallized product in 300ml hot n-hexane is less than 1g, the waste of reagent is very large, and the recrystallization efficiency is very low, far less than 90% of its report Yield, only about 60%

Method used

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  • 2-acetyl benzimidazolyl glycine-condensate Schiff base rare-earth complex and process for preparing same
  • 2-acetyl benzimidazolyl glycine-condensate Schiff base rare-earth complex and process for preparing same
  • 2-acetyl benzimidazolyl glycine-condensate Schiff base rare-earth complex and process for preparing same

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Experimental program
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Effect test

Embodiment 1

[0033] The synthetic method of embodiment 1 precursor 2-acetyl benzimidazole

[0034] Step 1: Synthesis of 2-(1'-hydroxyethyl)benzimidazole:

[0035]

[0036] In a 100ml three-neck flask, dissolve 10g of o-phenylenediamine in 25ml of 4mol / L HCl, stir until completely dissolved, adjust the pH to 2 with HCl, and then add 0.1g of catalyst FeCl 3 ·6H 2 O and 13ml lactic acid, heated to reflux for 4 hours, cooled, slowly added solid Na 2 CO 3 Neutralize the powder and stir vigorously until the pH is close to 7, then add 20% Na 2 CO 3 Adjust until the solution changes from black-red to yellow-green, and a large amount of precipitates are formed, which is left to stand and filtered with suction to obtain the crude product. Recrystallize directly with water, add activated carbon for decolorization, filter while hot, and precipitate 13.5 g of white crystals after cooling, with a yield of 80% and a melting point of 180.4-181.0°C (literature value of 177-179°C).

[0037] Step 2:...

Embodiment 2

[0039] The preparation of embodiment 2 ligand

[0040] Glycine (0.7507g, 0.01mol) and KOH (0.56g, 0.01mol) were dissolved in 25mL of methanol, stirred for about 15 minutes until dissolved, filtered, and 2-acetylbenzo Imidazole (1.602g, 0.01mol) in 20mL of methanol solution, after reflux for 5-14 hours, the color of the solution changed from yellow to dark brown red, part of the methanol was evaporated, cooled, a precipitate formed, suction filtered, washed with methanol and chloroform respectively, Dry it under infrared light, place it in a concentrated sulfuric acid desiccator to obtain a khaki powder.

[0041] 1 H NMR hydrogen spectrum (400MHz, CD 3 OD): δ7.6(q, 2H, a Coupling peak on H-Ar), δ7.3(q, 2H, b Coupling peak on H-Ar), δ5.311 (d, 1H, H-N), δ2.582 (s, 2H, -CH 2 -), δ1.652(s, 3H, CH 3 ).

[0042] Infrared (cm -1 )(KBr) 1643(C=N), 1570(v as COO - ), 1428 (v s COO - )

[0043] Raman (cm -1 ): 1644.76 (C=N), 1566.93 v as COO - ), 1436.76 (v s COO - ), ...

Embodiment 3

[0045] Embodiment 3 rare earth Pr complexes [Pr 2 L 3 (NO 3 ) 3 ·2CH 3 OH] Preparation

[0046] The rare earth nitrate Pr(NO 3 ) 3 ·6H 2 O (0.87g, 2mmol) in 25mL of methanol was slowly added dropwise to 30mL of hot methanol in which Schiff base (KL) ligand (0.79g, 3mmol) was dissolved in a stoichiometric ratio of 2:3 (rare earth ion: Schiff base ligand) In the solution, the reaction solution immediately became cloudy and earthy yellow. After reacting at 50°C for 3 hours, it was cooled and filtered with suction. After the precipitate was washed with hot methanol solution for several times, it was slowly dried in an oven at 50°C and placed in a concentrated sulfuric acid drier. Up to constant weight.

[0047] Infrared (cm -1 )(KBr): 1655(C=N), 1591(v as COO - ), 1437 (v s COO - ), 1384 (NO - 3 ), 1508 (NO - 3 ), 822 (NO - 3 ), 1316 (NO - 3 )

[0048] Raman (cm -1 ): 1639.40 (C=N), 1586.82 (v as COO - ), 1442.92 (v s COO - ), 1485.49 (NO - 3 ), 817.80...

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Abstract

Disclosed is a 2-acetyl benzimidazolyl glycine-condensate Schiff base rare-earth complex, which has the chemical composition of M2L3(NO3)3*2CH3OH, wherein M=La3+, Ce3+, Pr3+, Nd3+, Sm3+, Eu3+, Gd3+, Tb3+, Dy3+, Er3+ or Y3+, L is 2-acetyl benzimidazole condensed glycine Schiff's base. The preparing process consists of mixing rare earth nitrate with 2-acetyl benzimidazole condensed glycine Schiff's base by the mol ratio of 2:3, reacting 3-10 hours at 45-70 deg. C in methanol solvent, finally filtering to obtain the product.

Description

technical field [0001] The invention relates to a class of rare earth complexes and a preparation method thereof, in particular to a 2-acetylbenzimidazole glycine Schiff base rare earth complex and a preparation method thereof. The rare earth complexes can be used as optical functional materials. Background technique [0002] Rare earth amino acid complexes have been one of the hotspots of people's research because of their wide use in agriculture and medicine. Rare earth ions have a similar ionic radius to the life metal element calcium, and the unique fluorescence properties of rare earth ions due to the existence of 4f electrons can be used as probes to reveal Na + 、K + , Ca 2+ Therefore, the depth and breadth of research in this area are increasing day by day. However, due to the Na in the living system + 、K + , Ca 2+ The coordination environment of the plasma is very complicated, and its function is not only reflected by the interaction with amino acids. Therefore...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/00
Inventor 杨一心王党辉赵天成李青翠陈冬梅
Owner NORTHWEST UNIV
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