Syntheses, Characterization, and Luminescent Properties of Monoethylzinc Complexes with Anilido–Imine Ligands

The syntheses of three anilido-imine ligands of the general formula ortho-C 6 H 4 (NHAr')(CH=NAr" [Ar' = 7-(2,4-Me 2 )-C 9 H 4 N, Ar" = 2,6-Me 2 C 6 H 3 (2a); Ar' = 7-(2,4-Me 2 )C 9 H 4 N, Ar"= 2,6-Et 2 C 6 H 3 (2b); Ar' = 7-(2,4-Me 2 )C 9 H 4 N, Ar"= 2,6-iPr 2 C 6 H 3 (2c)] and four zinc(II) complexes of the general formula [orho-C 6 H 4 (NHAr')(CH=NAr")]ZnEt [Ar' = 7-(2,4-Me 2 )C 9 H 4 N, Ar"= 2,6-Me 2 C 6 H 3 (3a); Ar' = 7-(2,4-Me 2 )-C 9 H 4 N, Ar"= 2,6-Et 2 C 6 H 3 (3b); Ar' = 7-(2,4-Me 2 )C 9 H 4 N, Ar" = 2,6-iPr 2 C 6 H 3 (3c); Ar" = 2,6-Me 2 C 6 H 3 , Ar" = 2,6-iPr 2 C 6 H 3 (3d)] are described. The complexes were synthesized from the reaction of ZnEt 2 with corresponding ligands 2 by alkane elimination. All compounds were characterized by elemental analysis and 1 H and 13 C NMR spectroscopy. The molecular structures of compounds 2a, 2b, 3b, and 3c were determined by single-crystal X-ray crystallography. The X-ray analysis reveals that complexes 3b and 3c exist in the dimeric form with the N atom in the quinolyl ring coordinating to the other Zn atom to make the Zn atoms four coordinate. Luminescent properties of ligands 2a-2d and complexes 3a-3d in both solution and the solid state were studied.

[1]  Hong Xia,et al.  Boron Complexes with Chelating Anilido-Imine Ligands: Synthesis, Structures and Luminescent Properties , 2007 .

[2]  J. A. Gareth Williams,et al.  Photochemistry and Photophysics of Coordination Compounds: Platinum , 2007 .

[3]  H. Yun,et al.  Bimetallic fluorine-substituted anilido-aldimine zinc complexes for CO2/(cyclohexene oxide) copolymerization. , 2006, Inorganic chemistry.

[4]  Hong Xia,et al.  Synthesis, Structures, and Luminescent Properties of Aluminum Complexes with Chelating Anilido‐Imine Ligands , 2006 .

[5]  Guanghua Li,et al.  Dialkylaluminum Complexes with Chelating Anilido-Imine Ligands: Synthesis, Structures, and Luminescent Properties , 2005 .

[6]  Hoseop Yun,et al.  Bimetallic anilido-aldimine zinc complexes for epoxide/CO2 copolymerization. , 2005, Journal of the American Chemical Society.

[7]  Feng Bao,et al.  Synthesis, Molecular Structure, and Solution-Dependent Behavior of Nickel Complexes Chelating Anilido−Imine Donors and Their Catalytic Activity toward Olefin Polymerization , 2004 .

[8]  P. Chou,et al.  Synthesis of photo-luminescent Zn(II) Schiff base complexes and its derivative containing Pd(II) moiety. , 2004, Dalton transactions.

[9]  Laura A. MacManus-Spencer,et al.  Pyridylpyrrolides as alternatives to cyclometalated phenylpyridine ligands: synthesis and characterization of luminescent zinc and boron pyridylpyrrolide complexes. , 2004, Dalton transactions.

[10]  I. Sazanovich,et al.  Structural control of the excited-state dynamics of bis(dipyrrinato)zinc complexes: self-assembling chromophores for light-harvesting architectures. , 2004, Journal of the American Chemical Society.

[11]  M. Ghedini,et al.  Fine-tuning the luminescent properties of metal-chelating 8-hydroxyquinolines through amido substituents in 5-position , 2004 .

[12]  Shui-Tong Lee,et al.  A bis-salicylaldiminato Schiff base and its zinc complex as new highly fluorescent red dopants for high performance organic electroluminescence devices , 2003 .

[13]  Suning Wang,et al.  Blue luminescent rigid molecular rods bearing N-7-azaindolyl and 2,2'-dipyridylamino and their Zn(II) and Ag(I) complexes. , 2003, Inorganic chemistry.

[14]  Paul G. Hayes,et al.  A New Chelating Anilido-Imine Donor Related to β-Diketiminato Ligands for Stabilization of Organoyttrium Cations , 2003 .

[15]  M. Vázquez,et al.  Zinc and cadmium complexes with an achiral symmetric helicand. Crystal structure of an enantiomerically pure Λ-Zn(II) monohelicate , 2002 .

[16]  R. S. Schofield,et al.  Electroluminescent zinc(II) bis(8-hydroxyquinoline): structural effects on electronic states and device performance. , 2002, Journal of the American Chemical Society.

[17]  G. Coates,et al.  Single-site beta-diiminate zinc catalysts for the alternating copolymerization of CO2 and epoxides: catalyst synthesis and unprecedented polymerization activity. , 2001, Journal of the American Chemical Society.

[18]  Suning Wang.  Luminescence and Electroluminescence of Al(III), B(III), Be(II) and Zn(II) Complexes with Nitrogen Donors , 2001 .

[19]  V. Yam,et al.  Synthesis, emission, and electrochemical properties of luminescent dinuclear zinc(II) chalcogenolate complexes. Dynamic 1H NMR studies and X-ray crystal structure of [(bpy)Zn2(SC6H4-Cl-p)(mu-SC6H4-Cl-p)(mu-OAc)2]. , 2000, Inorganic chemistry.

[20]  Suning Wang,et al.  Blue-luminescent/electroluminescent Zn(II) compounds of 7-azaindole and N-(2-pyridyl)-7-azaindole: Zn(7-azaindole)2(CH3COO)2, Zn(NPA)(CH3COO)2, and Zn(NPA)((S)-(+)-CH3CH2CH(CH3)COO)2 (NPA = N-(2-pyridyl)-7-azaindole). , 2000, Inorganic chemistry.

[21]  H. Schmider,et al.  Syntheses, structures, and fluxionality of blue luminescent zinc(II) complexes: Zn(2,2',2"-tpa)Cl2, Zn(2,2',2"-tpa)2(O2CCF3)2, and Zn(2,2',3"-tpa)4(O2CCF3)2 (tpa = tripyridylamine). , 2000, Inorganic chemistry.

[22]  W. Wong,et al.  Synthesis, structures and luminescent properties of metal complexes containing 4-[2-(9-anthryl)vinyl]pyridine , 2000 .

[23]  T. Lai,et al.  A Ligand-Stabilized Tetrameric Zinc(II) Cluster with High-Efficiency Emission from Both Singlet and Triplet Excited States for Electroluminescent Devices , 2000 .

[24]  T. Sano,et al.  Design of conjugated molecular materials for optoelectronics , 2000 .

[25]  C. Che,et al.  Blue luminescent zinc(II) complexes with polypyridylamine ligands: crystal structures and luminescence properties , 1999 .

[26]  Yuguang Ma,et al.  A blue electroluminescent molecular device from a tetranucluear zinc(II) compound [Zn4O(AID)6] (AID = 7-azaindolate) , 1998 .

[27]  C. Che,et al.  A blue photoluminescent [Zn(L)(CN)2] (L = 2,2′-dipyridylamine) material with a supramolecular one-dimensional chain structure , 1998 .

[28]  A. Okada,et al.  Novel metal-chelate emitting materials based on polycyclic aromatic ligands for electroluminescent devices , 1998 .

[29]  S. Shaheen,et al.  Substituted aluminum and zinc quinolates with blue-shifted absorbance/luminescence bands: Synthesis and spectroscopic, photoluminescence, and electroluminescence characterization , 1996 .

[30]  T. Katoda,et al.  Characterization of Czochralski Silicon Wafers Grown at a Low Growth Rate by Photoluminescence Spectroscopy , 1996 .

[31]  A. Rheingold,et al.  Monomeric Alkyl and Hydride Derivatives of Zinc Supported by Poly(pyrazoly)hydroborato Ligation: Synthetic, Structural, and Reactivity Studies , 1995 .

[32]  N. Nijegorodov,et al.  The Influence of Planarity and Rigidity on the Absorption and Fluorescence Parameters and Intersystem Crossing Rate Constant in Aromatic Molecules , 1994 .

[33]  C. Che,et al.  A luminescent tetrameric zinc(II) complex containing the 7-azaindolate ligand. Photophysical properties and crystal structure , 1993 .

[34]  T. Ono,et al.  Plasma-Assisted Epitaxial Growth of P-Type ZnSe in Nitrogen-Based Plasma , 1993 .

[35]  D. Rendell.  Fluorescence and Phosphorescence , 1987 .

[36]  W. S. Johnson,et al.  Cyclization Studies in the Benzoquinoline Series , 1944 .

[37]  J. Thomsen.  Die Constitution des Benzols , 1880 .