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Nickel(II) Complexes Bearing 4-Arylimino-1,2,3-trihydroacridines: Synthesis, Characterization, and Ethylene Oligomerization.

Wang S, Du S, Zhang W, Asuha S, Sun WH - ChemistryOpen (2015)

Bottom Line: Nickel(II) complexes have attracted much attention as a new generation of olefin catalysts since the α-diiminonickel complex was discovered as a highly efficient procatalyst for ethylene polymerization.A series of novel 4-arylimino-1,2,3-trihydroacridylnickel(II) dihalide complexes was synthesized in a one-pot reaction of 2,3-dihydroacridine-4-one and different anilines with nickel(II) chloride or nickel(II) bromide 1,2-dimethoxyethane complex.With the activation of trimethylaluminium (TMA), all nickel(II) complexes exhibited good activity for ethylene oligomerization, and oligomer products ranged from butene (C4) to hexadecene (C16).

View Article: PubMed Central - PubMed

Affiliation: Chemistry & Environment Science College, Inner Mongolia Normal University, and Key Laboratory of Physics & Chemistry of Functional Materials, Inner Mongolia 81 Zhaowudalu, Huhhot, 010022, P. R. China ; Key Laboratory of Engineering Plastics and Beijing National Laboratory for Molecular Sciences Institute of Chemistry, Chinese Academy of Science Beijing, 100190, P. R. China.

ABSTRACT
Nickel(II) complexes have attracted much attention as a new generation of olefin catalysts since the α-diiminonickel complex was discovered as a highly efficient procatalyst for ethylene polymerization. A series of novel 4-arylimino-1,2,3-trihydroacridylnickel(II) dihalide complexes was synthesized in a one-pot reaction of 2,3-dihydroacridine-4-one and different anilines with nickel(II) chloride or nickel(II) bromide 1,2-dimethoxyethane complex. The complexes were characterized by infrared spectroscopy and elemental analysis. The molecular structures of the representative complexes 4-(2,6-diisopropylphenylimino)-1,2,3-trihydroacridylnickel(II) dichloride (C3), 4-(2,4,6-trimethylphenylimino)-1,2,3-trihydroacridylnickel dichloride(II) (C4), and 4-(2,4,6-trimethylphenylimino)-1,2,3-trihydroacridylnickel(II) dibromide (C9) were confirmed by single-crystal X-ray crystallography, revealing a distorted tetrahedral geometry around the nickel(II) of C3 and distorted trigonal bipyramidal geometry for C4 and C9. With the activation of trimethylaluminium (TMA), all nickel(II) complexes exhibited good activity for ethylene oligomerization, and oligomer products ranged from butene (C4) to hexadecene (C16).

No MeSH data available.


Synthetic procedure for 4-arylimino-1,2,3-trihydroacridylnickel(II) dihalides. (See Experimental Section for specific reagents, conditions, and yields for the ten complexes.)
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sch02: Synthetic procedure for 4-arylimino-1,2,3-trihydroacridylnickel(II) dihalides. (See Experimental Section for specific reagents, conditions, and yields for the ten complexes.)

Mentions: Firstly, the individual mixtures of the 2,3-dihydroacridine-4-one with anilines in toluene were refluxed for several hours to prepare the corresponding Schiff bases. The products could be observed by thin layer chromatography (TLC); however, the isolation and purification of these compounds always failed due to their easy decomposition. Therefore, the target nickel(II) complexes were synthesized using the one-pot process, in which the mixtures of 2,3-dihydroacridin-4-one and the corresponding anilines together with nickel(II) chloride or nickel(II) bromide–1,2-dimethoxyethane (DME) complex were refluxed in acetic acid (Scheme 2). The complexes were then isolated and characterized by Fourier transform infrared (FTIR) spectroscopy and elemental analysis. Their FTIR spectra showed a strong band in the range of 1600–1630 cm−1 which can be ascribed to the stretching vibration of C=N. All the nickel(II) complexes are stable in both solution and solid state.


Nickel(II) Complexes Bearing 4-Arylimino-1,2,3-trihydroacridines: Synthesis, Characterization, and Ethylene Oligomerization.

Wang S, Du S, Zhang W, Asuha S, Sun WH - ChemistryOpen (2015)

Synthetic procedure for 4-arylimino-1,2,3-trihydroacridylnickel(II) dihalides. (See Experimental Section for specific reagents, conditions, and yields for the ten complexes.)
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4522183&req=5

sch02: Synthetic procedure for 4-arylimino-1,2,3-trihydroacridylnickel(II) dihalides. (See Experimental Section for specific reagents, conditions, and yields for the ten complexes.)
Mentions: Firstly, the individual mixtures of the 2,3-dihydroacridine-4-one with anilines in toluene were refluxed for several hours to prepare the corresponding Schiff bases. The products could be observed by thin layer chromatography (TLC); however, the isolation and purification of these compounds always failed due to their easy decomposition. Therefore, the target nickel(II) complexes were synthesized using the one-pot process, in which the mixtures of 2,3-dihydroacridin-4-one and the corresponding anilines together with nickel(II) chloride or nickel(II) bromide–1,2-dimethoxyethane (DME) complex were refluxed in acetic acid (Scheme 2). The complexes were then isolated and characterized by Fourier transform infrared (FTIR) spectroscopy and elemental analysis. Their FTIR spectra showed a strong band in the range of 1600–1630 cm−1 which can be ascribed to the stretching vibration of C=N. All the nickel(II) complexes are stable in both solution and solid state.

Bottom Line: Nickel(II) complexes have attracted much attention as a new generation of olefin catalysts since the α-diiminonickel complex was discovered as a highly efficient procatalyst for ethylene polymerization.A series of novel 4-arylimino-1,2,3-trihydroacridylnickel(II) dihalide complexes was synthesized in a one-pot reaction of 2,3-dihydroacridine-4-one and different anilines with nickel(II) chloride or nickel(II) bromide 1,2-dimethoxyethane complex.With the activation of trimethylaluminium (TMA), all nickel(II) complexes exhibited good activity for ethylene oligomerization, and oligomer products ranged from butene (C4) to hexadecene (C16).

View Article: PubMed Central - PubMed

Affiliation: Chemistry & Environment Science College, Inner Mongolia Normal University, and Key Laboratory of Physics & Chemistry of Functional Materials, Inner Mongolia 81 Zhaowudalu, Huhhot, 010022, P. R. China ; Key Laboratory of Engineering Plastics and Beijing National Laboratory for Molecular Sciences Institute of Chemistry, Chinese Academy of Science Beijing, 100190, P. R. China.

ABSTRACT
Nickel(II) complexes have attracted much attention as a new generation of olefin catalysts since the α-diiminonickel complex was discovered as a highly efficient procatalyst for ethylene polymerization. A series of novel 4-arylimino-1,2,3-trihydroacridylnickel(II) dihalide complexes was synthesized in a one-pot reaction of 2,3-dihydroacridine-4-one and different anilines with nickel(II) chloride or nickel(II) bromide 1,2-dimethoxyethane complex. The complexes were characterized by infrared spectroscopy and elemental analysis. The molecular structures of the representative complexes 4-(2,6-diisopropylphenylimino)-1,2,3-trihydroacridylnickel(II) dichloride (C3), 4-(2,4,6-trimethylphenylimino)-1,2,3-trihydroacridylnickel dichloride(II) (C4), and 4-(2,4,6-trimethylphenylimino)-1,2,3-trihydroacridylnickel(II) dibromide (C9) were confirmed by single-crystal X-ray crystallography, revealing a distorted tetrahedral geometry around the nickel(II) of C3 and distorted trigonal bipyramidal geometry for C4 and C9. With the activation of trimethylaluminium (TMA), all nickel(II) complexes exhibited good activity for ethylene oligomerization, and oligomer products ranged from butene (C4) to hexadecene (C16).

No MeSH data available.