title: Synthesis, spectroscopic and catalytic properties of some new boron hybrid molecule derivatives by BF2 and BPh2 chelation.
abstract: A new series of Schiff base ligands (L1-L3) and their corresponding fluorine/phenyl boron hybrid complexes [LnBF2] and [LnBPh2] (n=1, 2 or 3) have been synthesized and well characterized by both analytical and spectroscopic methods. The Schiff base ligands and their corresponding fluorine/phenyl boron hybrid complexes have been characterized by NMR ((1)H, (13)C and (19)F), FT-IR, UV-Vis, LC-MS, and fluorescence spectroscopy as well as melting point and elemental analysis. The fluorescence efficiencies of phenyl chelate complexes are greatly red-shifted compared to those of the fluorine chelate analogs based on the same ligands, presumably due to the large steric hindrance and hard π→π(∗) transition of the diphenyl boron chelation, which can effectively prevent molecular aggregation. The boron hybrid complexes were applied to the transfer hydrogenation of acetophenone derivatives to 1-phenylethanol derivatives in the presence of 2-propanol as the hydrogen source. The catalytic studies showed that boron hybrid complexes are good catalytic precursors for transfer hydrogenation of aromatic ketones in 0.1M iso-PrOH solution. Also, we have found that both steric and electronic factors have a significant impact on the catalytic properties of this class of molecules.
authors.affiliation: Harran University, Chemistry Department, 63190 Sanliurfa, Turkey. Electronic address: kilica63@harran.edu.tr.
authors.forename: Ahmet
authors.initials: A
authors.lastname: Kilic
authors.affiliation: Harran University, Chemistry Department, 63190 Sanliurfa, Turkey.
authors.forename: Ferhat
authors.initials: F
authors.lastname: Alcay
authors.affiliation: Dicle University, Chemistry Department, 21280 Diyarbakır, Turkey.
authors.forename: Murat
authors.initials: M
authors.lastname: Aydemir
authors.affiliation: Harran University, Chemistry Department, 63190 Sanliurfa, Turkey.
authors.forename: Mustafa
authors.initials: M
authors.lastname: Durgun
authors.affiliation: Harran University, Chemistry Department, 63190 Sanliurfa, Turkey.
authors.forename: Armagan
authors.initials: A
authors.lastname: Keles
authors.affiliation: Dicle University, Chemistry Department, 21280 Diyarbakır, Turkey.
authors.forename: Akın
authors.initials: A
authors.lastname: Baysal
mesh_terms: D001555:Benzene Derivatives / Q000138:chemical synthesis / Q000737:chemistry*; D001896:Boron Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D002614:Chelating Agents / Q000138:chemical synthesis / Q000737:chemistry*; D005453:Fluorescence; D017611:Fluorine Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D054879:Halogenation; D006865:Hydrogenation; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D012545:Schiff Bases / Q000138:chemical synthesis / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D001555:Benzene Derivatives; D001896:Boron Compounds; D002614:Chelating Agents; D017611:Fluorine Compounds; D009942:Organometallic Compounds; D012545:Schiff Bases
keywords: Boron hybrid complexes; Fluorescence; Schiff bases; Spectroscopy; Transfer hydrogenation