Increased Nuclearity of Salen‐Type Transition Metal Complexes by Incorporation of O‐Alkyloxime Functionality

The effect of incorporation of O-alkyloxime functionality in the salen-type tetradentate ligand was investigated from a viewpoint of complexation behavior with cobalt(II), nickel(II), and zinc(II). The complexation of salamo ligands (H2salamo = 1,2-bis(salicylideneaminooxy)ethane) with zinc(II) and cobalt(II) afforded trinuclear complexes [M3L2(OAc)2] (M = ZnII, CoII; L = salamo, 3-MeOsalamo). The phenoxo groups of the two [ML] units coordinate to the third MII, which results in the trinuclear structure. Upon complexation with nickel(II) acetate, the parent H2salamo gave a trinuclear complex [Ni3(salamo)2(OAc)2(EtOH)2], whereas H2(3-MeOsalamo) produced a mononuclear complex [Ni(3-MeOsalamo)(H2O)2]. The salamo complexes described here are similar to the corresponding complexes with N,N′-disalicylidene-1,4-diaminobutane (H2salbn), indicating that the difference between the –OCH2CH2O– and –(CH2)4– groups has a small influence on the structural features of the complexes. However, this difference affects the complexation process with zinc(II) acetate. The trinuclear complex [Zn3(3-MeOsalamo)2(OAc)2] was formed cooperatively, whereas the imine analog [Zn3(3-MeOsalbn)2(OAc)2] was not.

[1]  Shigehisa Akine,et al.  Dynamic Helicity Control of a Single-helical Oligooxime Complex and Acid–Base-triggered Repeated Helicity Inversion Mediated by Amino Acids , 2014 .

[2]  Shigehisa Akine,et al.  Dynamic helicity control of single-helical oligooxime metal complexes by coordination of chiral carboxylate ions , 2014 .

[3]  Shigehisa Akine,et al.  Stepwise helicity inversions by multisequential metal exchange. , 2013, Journal of the American Chemical Society.

[4]  Shigehisa Akine,et al.  Oligometallic template strategy for synthesis of a macrocyclic dimer-type octaoxime ligand for its cooperative complexation. , 2012, Inorganic chemistry.

[5]  P. A. Vigato,et al.  Acyclic and cyclic compartmental ligands: Recent results and perspectives , 2012 .

[6]  Shigehisa Akine.  Novel ion recognition systems based on cyclic and acyclic oligo(salen)-type ligands , 2012, Journal of Inclusion Phenomena and Macrocyclic Chemistry.

[7]  Shigehisa Akine,et al.  A molecular leverage for helicity control and helix inversion. , 2011, Journal of the American Chemical Society.

[8]  Shigehisa Akine,et al.  Multistep oligometal complexation of the macrocyclic tris(N2O2) hexaoxime ligand. , 2011, Chemistry.

[9]  Takashi Matsumoto,et al.  Spontaneous enrichment of one-handed helices by dissolution of quasiracemic crystals of a tetranuclear single helical complex. , 2011, Chemical communications.

[10]  Takashi Matsumoto,et al.  Synthesis of acyclic tetrakis- and pentakis(N2O2) ligands for single-helical heterometallic complexes with a greater number of winding turns , 2011 .

[11]  Shigehisa Akine,et al.  Dinuclear Complexes of the N2O2 Oxime Chelate Ligand with Zinc(II)–Lanthanide(III) as a Selective Sensitization System for Sm3+ , 2010 .

[12]  Shigehisa Akine,et al.  Synthesis of Ag+-Selective Dipalladium(II) Metallohost Based on O-Alkyloxime Bis(N2SO) Ligands , 2010 .

[13]  Shigehisa Akine,et al.  Modulation of multimetal complexation behavior of tetraoxime ligand by covalent transformation of olefinic functionalities. , 2010, Inorganic chemistry.

[14]  Shigehisa Akine,et al.  Cyclic and acyclic oligo(N2O2) ligands for cooperative multi-metal complexation. , 2009, Dalton transactions.

[15]  Shigehisa Akine,et al.  Multiple folding structures mediated by metal coordination of acyclic multidentate ligand. , 2009, Inorganic chemistry.

[16]  Shigehisa Akine,et al.  Visible and near-infrared luminescence of helical zinc(II)-lanthanide(III) trinuclear complexes having acyclic Bis(N2O2) oxime ligand , 2009 .

[17]  P. A. Vigato,et al.  Advances in acyclic compartmental ligands and related complexes , 2008 .

[18]  Takashi Matsumoto,et al.  Spontaneous formation of a chiral supramolecular superhelix in the crystalline state using a single-stranded tetranuclear metallohelicate. , 2008, Chemical communications.

[19]  Shigehisa Akine,et al.  Acyclic bis(N2O2 chelate) ligand for trinuclear d-block homo- and heterometal complexes. , 2008, Inorganic chemistry.

[20]  Shigehisa Akine,et al.  Synthesis, stability, and complexation behavior of isolable salen-type N2S2 and N2SO ligands based on thiol and oxime functionalities. , 2008, Inorganic chemistry.

[21]  G. Sheldrick.  A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[22]  Shigehisa Akine,et al.  Oligometallic template strategy for ring-closing olefin metathesis: highly cis- and trans-selective synthesis of a 32-membered macrocyclic tetraoxime. , 2007, Inorganic chemistry.

[23]  Shigehisa Akine,et al.  Core/shell oligometallic template synthesis of macrocyclic hexaoxime. , 2007, Inorganic chemistry.

[24]  A. Forni,et al.  Copper(II) complexes of salen analogues with two differently substituted (push-pull) salicylaldehyde moieties. A study on the modulation of electronic asymmetry and nonlinear optical properties. , 2006, Inorganic chemistry.

[25]  Takashi Matsumoto,et al.  Guest-dependent inversion rate of a tetranuclear single metallohelicate. , 2006, Chemical communications.

[26]  Shigehisa Akine,et al.  Chiral single-stranded metallohelix : metal-mediated folding of linear oligooxime ligand , 2006 .

[27]  Shigehisa Akine,et al.  Helical metallohost-guest complexes via site-selective transmetalation of homotrinuclear complexes. , 2006, Journal of the American Chemical Society.

[28]  H. García,et al.  Chiral salen complexes: an overview to recoverable and reusable homogeneous and heterogeneous catalysts. , 2006, Chemical reviews.

[29]  Shigehisa Akine,et al.  Octanuclear zinc(II) and cobalt(II) clusters produced by cooperative tetrameric assembling of oxime chelate ligands. , 2006, Inorganic chemistry.

[30]  Shigehisa Akine,et al.  Heterometallic Zn2La and ZnLu Complexes Formed by Site-selective Transmetalation of a Dimeric Homotrinuclear Zinc(II) Complex , 2006 .

[31]  O. Atakol,et al.  Synthesis and crystal structure of a homotrinuclear Ni(II) complex , 2005 .

[32]  M. Salavati‐Niasari,et al.  Highly selective thiocyanate membrane electrode based on butane-2,3-dione bis(salicylhydrazonato)zinc(II) complex. , 2005, Talanta.

[33]  Takashi Matsumoto,et al.  Synthesis, structures, and magnetic properties of tri- and dinuclear copper(II)-gadolinium(III) complexes of linear oligooxime ligands. , 2005, Inorganic chemistry.

[34]  Shigehisa Akine,et al.  Novel thiosalamo ligand as a remarkably stable N2S2 salen-type chelate and synthesis of a nickel(II) complex. , 2005, Inorganic chemistry.

[35]  Shigehisa Akine,et al.  Oxime-based salen-type tetradentate ligands with high stability against imine metathesis reaction. , 2005, The Journal of organic chemistry.

[36]  Shigehisa Akine,et al.  Ca2+- and Ba2+-selective receptors based on site-selective transmetalation of multinuclear polyoxime-zinc(II) complexes. , 2005, Journal of the American Chemical Society.

[37]  P. A. Vigato,et al.  The challenge of cyclic and acyclic schiff bases and related derivatives , 2004 .

[38]  Shigehisa Akine,et al.  Cooperative formation of trinuclear zinc(II) complexes via complexation of a tetradentate oxime chelate ligand, salamo, and zinc(II) acetate. , 2004, Inorganic chemistry.

[39]  Y. Elerman,et al.  The Crystal Structures of [N,N’-Bis(3-methoxysalicylidene)-1,3- diaminopropane]nickel(II) and -copper(II) , 2004 .

[40]  S. Mizukami,et al.  First helical zinc(II) complex with a salen ligand. , 2003, Chemical communications.

[41]  Shigehisa Akine,et al.  Novel synthetic approach to trinuclear 3d-4f complexes: specific exchange of the central metal of a trinuclear zinc(II) complex of a tetraoxime ligand with a lanthanide(III) ion. , 2002, Angewandte Chemie.

[42]  J. Reglinski,et al.  Supporting conformational change at metal centres. Part 2: four and five coordinate geometry , 2002 .

[43]  J. Reglinski,et al.  Supporting conformational change at metal centres. Part 1: octahedral systems , 2002 .

[44]  E. Spodine,et al.  Electrochemical studies of copper(II) complexes with Schiff-base ligands , 2002 .

[45]  M. Mcpartlin,et al.  Synthesis of cobalt(II) complexes of derivatised salicylaldoxime ligands; X-ray crystal structures of DMSO adducts of bis(3-nitro-5-methylsalicylaldoximato)cobalt(II) and bis(3-nitro-5-phenylsalicylaldoximato)cobalt(II) , 2001 .

[46]  Shigehisa Akine,et al.  Synthesis and Characterization of Novel Ligands 1,2-Bis(salicylideneaminooxy)ethanes. , 2001 .

[47]  A. Pombeiro,et al.  Chlorination of Platinum‐Bound Salicylaldoxime. The First Example of a Structurally Characterized Monodentate Salicylaldoxime‐Type Ligand , 2001 .

[48]  P. Lacroix.  Second‐Order Optical Nonlinearities in Coordination Chemistry: The Case of Bis(salicylaldiminato)metal Schiff Base Complexes , 2001 .

[49]  I. Fragalà,et al.  Synthesis and second-order nonlinear optical properties of bis(salicylaldiminato)M(II) metalloorganic materials , 2000 .

[50]  Maria Cristina Burla,et al.  SIR97: a new tool for crystal structure determination and refinement , 1999 .

[51]  P. Viswanathamurthi,et al.  Ruthenium(III) complexes with tetradentate Schiff bases containing triphenylphosphine or triphenylarsine , 1998 .

[52]  N. Hoshino.  Liquid crystal properties of metal–salicylaldimine complexes. , 1998 .

[53]  Y. Yablokov,et al.  Mixed-valence Fe(III)Fe(IV) dimers. Preparation and physical properties of oxidation products of oxo-bridged binuclear iron(III) complexes , 1995 .

[54]  T. Katsuki,et al.  Catalytic asymmetric oxidations using optically active (salen)manganese(III) complexes as catalysts , 1995 .

[55]  P. A. Vigato,et al.  From mononuclear to polynuclear macrocyclic or macroacyclic complexes , 1995 .

[56]  L. Marzilli,et al.  Nuclearity and formulation of SALPN2- complexes formed from M(O2CCH3)2: resolution of longstanding problems by x-ray crystallography , 1991 .

[57]  D. Reinhoudt,et al.  Incorporation of nitrogen-oxygen bonds in metallomacrocycles. Synthesis, x-ray structure, and electrochemistry of heterodinuclear complexes , 1989 .

[58]  A. W. Addison,et al.  Synthesis, structure, and spectroscopic properties of copper(II) compounds containing nitrogen–sulphur donor ligands; the crystal and molecular structure of aqua[1,7-bis(N-methylbenzimidazol-2′-yl)-2,6-dithiaheptane]copper(II) perchlorate , 1984 .

[59]  E. Sinn,et al.  Nickel(II) Complexes of Some Quadridentate Schiff Base Ligands I , 1972 .

[60]  R. Harlow,et al.  The crystal and molecular structure of bis(salicylaldoximato)palladium(II) , 1970 .

[61]  W. Schaefer,et al.  Oxygen-carrying cobalt compounds. I. Bis(salicylaldehyde)ethylenediiminecobalt(II) monochloroformate , 1969 .

[62]  L. Randaccio,et al.  The crystal structure of the form of N,N'‐ethylenebis(salicylaldehydeiminato)cobalt(II) inactive towards oxygenation , 1969 .

[63]  P. C. Jain,et al.  Bond lengths in bis‐salicylaldoximato‐nickel , 1967 .

[64]  G. Batley,et al.  Studies in the stereochemistry of zinc(II). VI. Zinc complexes with quadridentate Schiff bases , 1967 .

[65]  F. H. Moore,et al.  The crystal structure of NN′-disalicylidene-ethylenediaminezinc(II) monohydrate , 1966 .

[66]  E. C. Lingafelter,et al.  The crystal structure of bis(salicylaldoximato)‐copper(II) , 1964 .

[67]  P. Orioli,et al.  The crystal structure of bis(5‐chlorosalicylaldoximato)copper(II) , 1964 .

[68]  C. Guare,et al.  THE CRYSTAL STRUCTURE OF NICKEL SALICYLALDOXIME , 1956 .

[69]  P. Pfeiffer,et al.  Innere Komplexsalze der Aldimin‐ und Azoreihe , 1937 .

[70]  W. Wardlaw,et al.  99. The planar configuration for quadricovalent nickel, palladium, and platinum , 1935 .

[71]  P. Pfeiffer,et al.  Tricyclische orthokondensierte Nebenvalenzringe , 1933 .