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2-(nitrogen heterocycle) benzimidazole complex alkyl aluminum compound, and preparation method and application thereof

A technology of benzimidazole and nitrogen heterocycle, applied in the field of organoaluminum compounds and its preparation, to achieve the effects of cheap and easy-to-obtain raw materials, high catalytic activity, and stable properties

Inactive Publication Date: 2010-12-29
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Benzimidazole ligands combined with different heterocyclic skeletons can conveniently construct different coordination models and complex with different metals, and regulate the steric effect and electronic effect of metal complexes, which has aroused great interest of scholars. At present, although there are some reports on metal complexes constructed with benzimidazole as the skeleton (ARKIVOC 2008, 5, 245 and related documents of this special edition, Organometallics 2007, 26, 2439; Organometallics 2007, 26, 2720; Organometallics 2009, 28, 2225 ; J.Organomet.Chem.2008,693,1829; Eur.J.Inorg.Chem.2007,24,3816; Aust.J.Chem.2010,63,109.; Polyhedron, 2010,29,142), but There are no reports of organoaluminum compounds with 2-methyl-6-benzimidazolidine as ligand and 2-methyl-8-benzimidazolinoline as ligand

Method used

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  • 2-(nitrogen heterocycle) benzimidazole complex alkyl aluminum compound, and preparation method and application thereof
  • 2-(nitrogen heterocycle) benzimidazole complex alkyl aluminum compound, and preparation method and application thereof
  • 2-(nitrogen heterocycle) benzimidazole complex alkyl aluminum compound, and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0057] Embodiment 1, compound C1 (Me 2 Preparation of AlL1L1=2-methyl-8-benzimidazole-quinoline)

[0058] The ligand 2-methyl-8-benzimidazole quinoline (0.26g, 1.0mmol) and toluene (15mL) were added to a 100mL schlenk bottle, cooled to -30°C, and 1.0M trimethylaluminum was added with a syringe Toluene solution (1.0 mL, 1.0 mmol) was stirred, and the reaction was stirred at room temperature for 3 hours, and the volatile substances were removed under reduced pressure. Then add 5 mL of toluene to dissolve, add 15 mL of n-hexane, and recrystallize to obtain 0.28 g of compound C1 as a yellow powder, whose structural formula is shown in formula (a), yield: 88.4%.

[0059]

[0060] Characterization data of compound C1: 1 H NMR (CDCl 3 , ppm): δ9.64 (d, 1H, J = 7.35Hz, Quin-H), 8.49 (d, 1H, J = 8.40Hz, Quin-H), 7.94 (d, 1H, J = 7.67Hz, Quin -H), 7.82(m, 2H, Quin-H), 7.69(d, 1H, J=7.41Hz, Ar-H), 7.56(d, 1H, J=8.40Hz, Ar-H), 7.27(m , 2H, Ar-H), 3.23(s, 3H, Quin-CH 3 ), -0.39 (s...

Embodiment 2

[0062] Embodiment 2, compound C2 (Et 2 Preparation of AlL1 L1=2-methyl-8-benzoimidazoquinoline)

[0063] The experimental procedure is the same as that in Example 1. The ligand 2-methyl-8-benzimidazolinoline was reacted with triethylaluminum in equimolar ratios to obtain compound C2, whose structural formula is shown in formula (b). Yield: 0.25 g (72.1%).

[0064]

[0065] Characterization data for compound C2: 1 H NMR (CDCl 3 , ppm): δ9.65 (d, 1H, J = 7.50Hz, Quin-H), 8.51 (d, 1H, J = 8.37Hz, Quin-H), 7.94 (d, 1H, J = 7.79Hz, Quin -H), 7.85(m, 2H, Quin-H), 7.70(d, 1H, J=7.32Hz, Ar-H), 7.58(d, 1H, J=8.39Hz, Ar-H), 7.27(m , 2H, Ar-H), 3.38(s, 3H, Quin-CH 3 ), 0.82(t, 6H, J=8.08Hz, -AlCH 2 C H 3 ), 0.30 (m, 4H, -AlC H 2 CH 3 ). 13 C NMR (CDCl 3C 21 h 22 AlN 3 : C, 73.45; H, 6.46; N, 12.24. Found: C, 73.73; H, 6.16; N, 12.18%.

Embodiment 3

[0066] Embodiment 3, compound C3 ( i Bu 2 Preparation of AlL1 L1=2-methyl-8-benzoimidazoquinoline)

[0067] The experimental procedure is the same as that in Example 1. The ligand 2-methyl-8-benzimidazole quinoline reacts with triisobutylaluminum equimolarly to obtain compound C3, whose structural formula is shown in formula (c). Yield: 0.27 g (68.3%).

[0068]

[0069] Characterization data of compound C3: 1 H NMR (CDCl 3 , ppm): δ9.68 (d, 1H, J = 7.50Hz, Quin-H), 8.53 (d, 1H, J = 8.28Hz, Quin-H), 7.96 (d, 1H, J = 8.89Hz, Quin -H), 7.86(m, 2H, Quin-H), 7.75(d, 1H, J=6.81Hz, Ar-H), 7.59(d, 1H, J=8.54Hz, Ar-H), 7.23-7.30 (m, 2H, Ar-H), 3.30(s, 3H, Quin-CH 3 ), 1.58 (m, 2H, -CH 2 C H (CH 3 ) 2 ), 0.66 (d, 6H, J=6.35Hz, -CH 2 CH(CH 3 ) 2 ), 0.61 (d, 6H, J=6.35Hz, -CH 2 CH(CH 3 ) 2 ), 0.45(m, 2H, -C H 2 CH(CH 3 ) 2 ), 0.33(m, 2H, -C H 2 CH(CH 3 ) 2 ). 13 C NMR (CDCl 3 , ppm): δ162.3, 153.2, 145.9, 144.1, 142.1, 141.3, 134.9, 130.4, 128.6, 128.2, 126.6,...

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Abstract

The invention discloses a 2-(nitrogen heterocycle) benzimidazole complex alkyl aluminum compound, and a preparation method and application thereof. A ligand of the compound is 2-(nitrogen heterocycle) benzimidazole which may be 2-methyl-6-benzimidazole pyridine or 2-methyl-8-benzimidazole quinoline. The preparation method of the invention comprises the following steps of: reacting the 2-(nitrogen heterocycle) benzimidazole ligand with alkyl aluminum in different ratios, and performing concentration and recrystallization to obtain the target compound. The 2-(nitrogen heterocycle) benzimidazolyl-aluminum compound is a high-efficiency lactone ring-opening polymerization catalyst. The 2-(nitrogen heterocycle) benzimidazole complex alkyl aluminum compound has the advantages of readily available materials, simple synthetic route, high product yield, relatively more stable properties, changeful structures of the prepared products, relatively higher catalytic activity and capability of meeting polymerization requirements of different lactones, obtaining poly lactones with high molecular weights and meeting requirements of industrial departments.

Description

technical field [0001] The invention relates to an organoaluminum compound and its preparation method and application, in particular to a 2-(nitrogen-containing heterocycle) benzimidazole complexed alkylaluminum compound and its preparation method and application. Background technique [0002] Polylactone is a kind of aliphatic lactone polymer containing repeating lactone monomer unit structure. It has degradability, biocompatibility and good mechanical processing performance. It is widely used in people's production and life. Polylactone is completely biodegradable under natural environmental conditions and does not cause any pollution to the environment. Its excellent biocompatibility, permeability, low toxicity and its hydrolytic instability make polylactone materials a substitute for non-degradable polymer products, and can be used to make garbage bags, food containers and agricultural covering films. and other purposes, especially in the field of biomedicine has a high...

Claims

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Application Information

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IPC IPC(8): C07F5/06C08G63/08C08G63/84
Inventor 申淼孙文华刘绍峰
Owner INST OF CHEM CHINESE ACAD OF SCI
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