Different Hemi-Salen/Salan Ligand Containing Binuclear Boron-Fluoride Complexes: Synthesis, Spectroscopy, Fluorescence Properties, and Catalysis

ABSTRACT A family of hemi-salen (L1H–L6H) and hemi-salan (L1aH–L2aH) ligands-based N,O-chelated binuclear boron-fluoride [Ln(BF2)2] (n = L1–L6 or L1a–L2a) complexes have been prepared and characterized by a variety of spectroscopic techniques (1H, 13C and 19F NMR, FT-IR, UV-Vis, LC-MS, and fluorescence spectra) and elemental analysis. All of the binuclear boron-fluoride complexes exhibit strong absorption bands due to S0→S1 transitions and strong fluorescence properties were observed at room temperature in the solution. The binuclear boron complexes containing two naphthyl groups are significantly red-shifted in comparison with the other binuclear boron-fluoride complexes. After the structures are characterized, these hemi-salen and salan ligand-based N, O-chelated binuclear boron-fluoride complexes were utilized to the transfer hydrogenation of the different acetophenone derivatives conversion to 1-phenylethanol derivatives as catalysts.

[1]  Y. Liu,et al.  Naphthalene-fused BODIPY with large Stokes shift as saturated-red fluorescent dye for living cell imaging , 2015 .

[2]  P. A. Harris,et al.  Synthesis of novel dehydroacetic acid N-aroylhydrazone-derived boron heterocycles , 2015 .

[3]  Aydın Aktaş,et al.  Erratum to: N-Propylphthalimide-Substituted Silver(I) N-Heterocyclic Carbene Complexes and Ruthenium(II) N-Heterocyclic Carbene Complexes: Synthesis and Transfer Hydrogenation of Ketones , 2015, Catalysis Letters.

[4]  Mo-Yuan Shen,et al.  Step-Economical Syntheses of Functional BODIPY-EDOT π-Conjugated Materials through Direct C-H Arylation. , 2015, Organic letters.

[5]  J. Morgado,et al.  Luminescent Di- and Trinuclear Boron Complexes Based on Aromatic Iminopyrrolyl Spacer Ligands: Synthesis, Characterization, and Application in OLEDs. , 2015, Chemistry.

[6]  J. Rocha,et al.  Synthesis, Post‐Modification and Fluorescence Properties of Boron Diketonate Complexes , 2015 .

[7]  V. Staroverov,et al.  Effect of Extended π Conjugation on the Spectroscopic and Electrochemical Properties of Boron Difluoride Formazanate Complexes. , 2015, The Journal of organic chemistry.

[8]  A. Kilic,et al.  Synthesis, spectroscopic and catalytic properties of some new boron hybrid molecule derivatives by BF2 and BPh2 chelation. , 2015, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[9]  Yongsheng Chen,et al.  Synthesis, crystal structures and photophysical properties of novel boron-containing derivatives of phenalene with bright solid-state luminescence , 2014 .

[10]  A. Kilic,et al.  Fluorine/phenyl chelated boron complexes: Synthesis, fluorescence properties and catalyst for transfer hydrogenation of aromatic ketones , 2014 .

[11]  Aydın Aktaş,et al.  N-Propylphthalimide-Substituted Silver(I) N-Heterocyclic Carbene Complexes and Ruthenium(II) N-Heterocyclic Carbene Complexes: Synthesis and Transfer Hydrogenation of Ketones , 2014, Catalysis Letters.

[12]  M. Xia,et al.  Study on the structure–property relationship in a series of novel BF2 chelates with multicolor fluorescence , 2013 .

[13]  Xi Yang,et al.  Synthesis, characterization and photoluminescence properties of strong fluorescent BF2 complexes bearing (2-quinolin-2-yl)phenol ligands , 2012 .

[14]  E. Taş,et al.  Synthesis of new boron complexes: application to transfer hydrogenation of acetophenone derivatives , 2011 .

[15]  J. W. Faller,et al.  Catalysts for the Asymmetric Transfer Hydrogenation of Ketones Derived from L‐Prolinamide and (p‐CymeneRuCl2)2 or (Cp*RhCl2)2. , 2010 .

[16]  J. Albani Principles and Applications of Fluorescence Spectroscopy , 2007 .

[17]  A. Wakamiya,et al.  Kinetically stabilized dibenzoborole as an electron-accepting building unit. , 2008, Chemical communications.

[18]  T. Ikariya,et al.  Asymmetric transfer hydrogenation of ketones with bifunctional transition metal-based molecular catalysts. , 2007, Accounts of chemical research.

[19]  J. Albani,et al.  Principles and Applications of Fluorescence Spectroscopy , 2007 .

[20]  Yue Wang,et al.  Synthesis and luminescent properties of two Schiff-base boron complexes , 2007 .

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

[22]  Murat Yiğit,et al.  Active ruthenium-(N-heterocyclic carbene) complexes for hydrogenation of ketones , 2006 .

[23]  S. Yaşar,et al.  Ruthenium(II) N-heterocyclic Carbene Complexes in the Transfer Hydrogenation of Ketones , 2005 .

[24]  Z. Dong,et al.  Highly efficient iridium catalyst for asymmetric transfer hydrogenation of aromatic ketones under base-free conditions. , 2005, Organic letters.

[25]  Z. Dong,et al.  Asymmetric transfer hydrogenation of aromatic ketones catalyzed by the iridium hydride complex under ambient conditions , 2004 .

[26]  H. Tønnesen,et al.  Corrected Emission Spectra and Quantum Yields for a Series of Fluorescent Compounds in the Visible Spectral Region , 2004, Journal of Fluorescence.

[27]  G. Clarkson,et al.  A new class of "tethered" ruthenium(II) catalyst for asymmetric transfer hydrogenation reactions. , 2004, Journal of the American Chemical Society.

[28]  J. Bäckvall,et al.  Studies on the mechanism of metal-catalyzed hydrogen transfer from alcohols to ketones. , 2001, Chemistry.

[29]  J. T. F. and,et al.  Catalysts for the Asymmetric Transfer Hydrogenation of Ketones Derived from l-Prolinamide and (p-CymeneRuCl2)2 or (Cp*RhCl2)2 , 2001 .

[30]  H. Wan,et al.  New chiral catalysts for reduction of ketones. , 2000, Chirality.

[31]  E. Kelson,et al.  Synthesis and structure of a ruthenium(II) complex incorporating κN bound 2-pyridonato ligands; a new catalytic system for transfer hydrogenation of ketones , 2000 .

[32]  H. Wan,et al.  New chiral cationic rhodium-aminophosphine complexes for asymmetric transfer hydrogenation of aromatic ketones , 1999 .

[33]  B. Scott,et al.  Asymmetric catalysis in organic synthesis , 1998 .

[34]  T. Ikariya,et al.  trans-[RuCl2 (phosphane)2 (1,2-diamine)] and Chiral trans-[RuCl2 (diphosphane)(1,2-diamine)]: Shelf-Stable Precatalysts for the Rapid, Productive, and Stereoselective Hydrogenation of Ketones. , 1998, Angewandte Chemie.

[35]  Xumu Zhang,et al.  A New Chiral Bis(oxazolinylmethyl)amine Ligand for Ru-Catalyzed Asymmetric Transfer Hydrogenation of Ketones , 1998 .

[36]  D. Atwood,et al.  BIMETALLIC BORATE DERIVATIVES OF THE SALEN LIGANDS , 1997 .

[37]  T. Ikariya,et al.  The Catalyst Precursor, Catalyst, and Intermediate in the RuII‐Promoted Asymmetric Hydrogen Transfer between Alcohols and Ketones , 1997 .

[38]  R. Noyori,et al.  Ruthenium(II)-Catalyzed Asymmetric Transfer Hydrogenation of Ketones Using a Formic Acid−Triethylamine Mixture , 1996 .

[39]  R. Noyori,et al.  A Ruthenium(II) Complex with a C2-Symmetric Diphosphine/Diamine Tetradentate Ligand for Asymmetric Transfer Hydrogenation of Aromatic Ketones† , 1996 .

[40]  T. Ikariya,et al.  Amino alcohol effects on the ruthenium(II)-catalysed asymmetric transfer hydrogenation of ketones in propan-2-ol , 1996 .

[41]  M. Lemaire,et al.  Asymmetric Catalytic Reduction of Carbonyl Compounds Using C2 Symmetric Diamines as Chiral Ligands. , 1995 .

[42]  M. Lemaire,et al.  Asymmetric catalytic reduction of carbonyl compounds using C2 symmetric diamines as chiral ligands , 1995 .

[43]  S. Gladiali,et al.  Asymmetric Hydrogen Transfer Reactions Promoted by Homogeneous Transition Metal Catalysts , 1992 .

[44]  C. Bolm Bis(4,5‐dihydrooxazolyl) Derivatives in Asymmetric Catalysis , 1991 .

[45]  A. Pfaltz,et al.  C2‐Symmetric 4,4′,5,5′‐Tetrahydrobi(oxazoles) and 4,4′,5,5′‐Tetrahydro‐2,2′‐methylenebis[oxazoles] as Chiral Ligands for Enantioselective Catalysis Preliminary Communication , 1991 .

[46]  W. Leitner,et al.  Enantioselective catalytic transfer hydrogenation of α,β-unsaturated carboxylic acids with formates catalyzed by novel ruthenium phosphine complexes☆ , 1991 .

[47]  M. Marchetti,et al.  The asymmetric hydroformylation in the synthesis of pharmaceuticals. , 1991, Chirality.

[48]  R. Noyori,et al.  BINAP: an efficient chiral element for asymmetric catalysis , 1990 .

[49]  S. Ram,et al.  Ammonium Formate in Organic Synthesis: A Versatile Agent in Catalytic Hydrogen Transfer Reductions , 1988 .

[50]  R. Johnstone,et al.  Heterogeneous catalytic transfer hydrogenation and its relation to other methods for reduction of organic compounds , 1985 .

[51]  H. Siegel,et al.  Synthese von Zwischenprodukten durch rhodiumkatalysierte Hydroformylierung , 1980 .

[52]  W. Himmele,et al.  Synthesis of Intermediates by Rhodium‐Catalyzed Hydroformylation , 1980 .