66-71-7Relevant articles and documents
Novel 1,3-diethyl-2-thiobarbiturates of 2,2′-bipyridine and 1,10-phenanthroline: Synthesis, crystal structure and thermal stability
Golovnev, Nicolay N.,Molokeev, Maxim S.,Sterkhova, Irina V.,Lesnikov, Maxim K.
, p. 488 - 494 (2018)
Co-crystallization of 1,3-diethyl-2-thiobarbituric acid (HDetba) with 2,2′-bipyridine (Bipy) and 1,10-phenanthroline (Phen) results in preparing a salt co-crystal, BipyH(Detba)(HDetba) (1), and the salt, PhenH(Detba)·H2O (2). The compounds are characterized by single–crystal and powder X–ray diffraction and TG-DSC. The nitrogen atoms of BipyH+ adopt a cis conformation and the N–C–C–N torsion angle is ?17.3(1)o. There are six intermolecular hydrogen bonds O–H?O, N–H?O, C–H?O and C–H?S in (1) which form a 2D plane network. One Detba– ion and one HDetba molecule form a pair by means of O–H?O hydrogen bonds. Detba? anions in (2) do not form dimers, they are connected by N–H?O, C–H?S, and C–H?O hydrogen bonds only with PhenH+ cations and water molecules which form a 3D net. Different π?π interactions between the rings are found in (1)?(2).
Deep eutectic solvents used as catalysts for synthesis of 1,10-phenanthroline by improved Skraup reaction
Wu, Mingliang,Bai, Yuansheng,Chen, Xuejun,Wang, Qingyin,Wang, Gongying
, p. 3551 - 3567 (2021)
Abstract: In this study, three different choline chloride-based deep eutectic solvents were synthesized. And it is the first time to synthesize 1,10-phenanthroline through an improved Skraup reaction using deep eutectic solvent as the new catalyst from acrolein and 8-aminoquinoline. The deep eutectic solvents were characterized by Fourier transform infrared (FT-IR), 1H nuclear magnetic resonance (1H NMR), pH/mV meter, and thermogravimetric analysis (TGA). The research results show that the deep eutectic solvent formed by sulfanilic acid and choline chloride has the strongest acidity and highest catalytic active among the three deep eutectic solvents. Besides, the impacts of reaction parameters and molar ratio of raw materials on the reaction were also investigated. Under the optimized reaction conditions, the maximum selectivity and yield of 1,10-phenanthroline were achieved as 84.6 and 75.6%, respectively. The synthesis method, meanwhile, also has simple preparation process and low cheaper catalyst raw. Graphical abstract: [InlineMediaObject not available: see fulltext.] Replacing traditional sulfuric acid and hydrochloric acid with deep eutectic solvents (DESs) as new catalysts provides a more efficient, greener and more economical strategy for the synthesis of 1,10-phenanthroline by a new improved Skraup reaction.
Palladium-(II) and -(IV) complexes as intermediates in catalytic C-C bond-forming reactions
Catellani, Marta,Chiusoli, Gian Paolo
, p. C27 - C30 (1988)
Palladium-(II) and -(IV) species active as catalysts in C-C bond-forming reactions have been stabilized by adding phenanthroline as a ligand.The complexes formed have been characterized by chemical and spectroscopic methods and their formation and subsequent fate have been monitored by 1H NMR spectroscopy.
Electrochemical Study of Reaction of Hyperoxide with Tris(1,10-phenanthroline)iron(II) in Dimethyl Sulfoxide
Umemoto, Kisaburo,Saeki, Toyohumi,Matsuura, Niro,Motegi, Katsue
, p. 746 - 749 (1982)
Reaction of hyperoxide with Fe(phen)32+ in DMSO was studied by polarography, cyclic voltammetry, and spectroscopy.Voltammetric study of oxygen showed that disproportionation of hyperoxide is promoted by Fe(phen)32+.Controlled potenti
INCLUSION COMPOUNDS OF ORGANIC AZOCHROMOPHORES IN THE CAVITIES OF METAL-ORGANIC FRAMEWORKS (Cr,?Al)– MIL-101: SYNTHESIS AND PHOTOCHEMICAL STUDIES
Glebov, E. M.,Kovalenko, K. A.,Orlioglo, B. M.
, p. 152 - 163 (2022/03/09)
Abstract: Inclusion compounds of nitrogen-containing aromatic chromophores 4,4′-bispyridylethylene (bpe) and 4,4′-azopyridine (apy) in the cavities of mesoporous metal-organic frameworks Cr–MIL-101 and Al–MIL-101 are prepared and characterized by elemental analysis and nitrogen adsorption methods with a goal of finding approaches to the design of solid photochromic materials combining the benefits of photochromes in liquid solutions (high quantum yields) and in solid states (increased resistance to photodegradation). Photochemical properties of these compounds are qualitatively studied. Compound apy@Al–MIL-101 exhibits higher photoactivity than polycrystalline apy. Three other inclusion compounds are not photoactive. Possible reasons of the lack of photoactivity in these compounds are discussed. [Figure not available: see fulltext.]
Cationic tetra-and pentacoordinate complexes of nickel based on POCN-and POCOP-Type pincer ligands: Synthesis, characterization, and ligand exchange studies
Rahimi, Naser,Zargarian, Davit
supporting information, p. 15063 - 15073 (2021/09/04)
Stirring acetonitrile solutions of the charge-neutral pincer complexes (POCN)NiBr (1, POCN = κP,κC,κN-{2-(i-Pr)2PO,6-CH2{c-N(CH2)5}-C6H3) and (POCOP)NiBr (2, POCOP = κP,κC,κP′-2,6-(i-Pr2OP)2C6H3) with AgSbF6 facilitates Br- abstraction to give the corresponding cationic acetonitrile adducts [(POCN)Ni(NCMe)]+, 1a, and [(POCOP)Ni(NCMe)]+, 2a. Treating 1a and 2a with pyridine (py), 2,2′-bipyridine (bipy), phenanthroline (phen), or 4,4′-bipyridine (bipy?) gave the corresponding monocationic adducts [(POCN or POCOP)Ni(ligand)]+ (ligand = py: 1b and 2b; κN,κN′-bipy: 1c and 2c; κN,κN′-phen: 1d and 2d) and the dicationic dinuclear adducts [(POCN or POCOP)2Ni2(μ-bipy?)]2+ (1e and 2e). The new adducts 1a-1d and 2b-2e have been characterized by NMR spectroscopy; complex 1e proved to be insoluble and could not be analyzed by NMR. Single crystal X-ray diffraction studies were used to establish the solid-state structures of 1a-1e, and 2b-2d. UV-vis spectra have also been recorded for the pentacoordinated complexes 1c, 1d, 2c, and 2d. Studying the equilibria that govern the displacement of halides in (pincer)NiX (X = Cl, Br) by the in-coming nucleophiles py, bipy, and phen has allowed us to determine the following order for the relative nucleophilicities of the ligands involved in the halide substitution equilibria: Cl- > Br- > phen > bipy ? py > MeCN. Similar Keq measurements showed that cationic species are better stabilized with the POCN platform compared to POCOP. This implies that POCN is a better net donor of electron density compared to POCOP, such that the relative Lewis acidity (electrophilicity) of the cationic fragments should follow the order [(POCOP)Ni]+ > [(POCN)Ni]+. Cyclic voltammetry measurements on the bipy adducts showed reversible, one-electron oxidation events occurring at a lower value for [(POCN)Ni(bipy)]+, implying a more electron-rich Ni(ii) centre with POCN vs. POCOP. Consistent with these assertions, mixing (POCN)NiBr and [(POCOP)Ni(phen)]+ in acetonitrile gave [(POCN)Ni(phen)]+ and (POCOP)NiBr. Similarly, the Keq value of 0.19 for the equilibrium exchange (POCN)NiCl + (POCOP)NiBr ? (POCN)NiBr + (POCOP)NiCl indicates that the [(POCOP)Ni]+ fragment is better stabilized by Cl-vs. Br-. These exchange reactions do not occur in THF or CH2Cl2, implying that they are driven by the nucleophilic character of the solvent. This journal is
Iron(II)-Catalyzed Aerobic Biomimetic Oxidation of N-Heterocycles
Manna, Srimanta,Kong, Wei-Jun,B?ckvall, Jan-E.
supporting information, p. 13725 - 13729 (2021/09/08)
Herein, an iron(II)-catalyzed biomimetic oxidation of N-heterocycles under aerobic conditions is described. The dehydrogenation process, involving several electron-transfer steps, is inspired by oxidations occurring in the respiratory chain. An environmentally friendly and inexpensive iron catalyst together with a hydroquinone/cobalt Schiff base hybrid catalyst as electron-transfer mediator were used for the substrate-selective dehydrogenation reaction of various N-heterocycles. The method shows a broad substrate scope and delivers important heterocycles in good-to-excellent yields.
An effective non-chromatographic method for the purification of phenanthrolines and related ligands
Ferretti, Francesco,Ragaini, Fabio
, (2020/06/03)
1,10-Phenanthrolines are widely employed as ligands, but their use on a large scale is constrained by their difficult purification, which usually requires lengthy chromatographic separations. Herein, we describe a purification strategy that takes advantage of the high stability and low solubility of phenanthroline complexes to separate them from the by products of their synthesis. The formation of ZnCl2 complexes was employed, from which the free ligand can be recovered by reaction with aqueous NH3 in a biphasic CH2Cl2/H2O system. The same strategy was also successfully employed to purify related quinolino-guanidine ligands, demonstrating that the procedure is of general applicability.
METHOD OF PRODUCING PHENANTHRILINE AND DERIVATIVE THEREOF
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Paragraph 0107-0112, (2020/05/20)
An application of the present invention provides a method of producing ortho-aminoarenecarbaldehyde, ortho-aminoarenecarbaldehyde produced therefrom, and a method for producing phenanthroline and derivatives thereof which can be utilized in the field of OLED and diagnostic reagents using the same. The application comprises: a first step of producing a compound of formula 2 by oxidizing a compound of formula 1 with NaIO_4; and a second step of producing a compound of formula 3 by reducing the compound of formula 2 with nascent hydrogen generated by acid and metal.COPYRIGHT KIPO 2020
Synthesis and Photochemical Properties of Manganese(I) Tricarbonyl Diimine Complexes Bound to Tetrazolato Ligands
Stout, Matthew J.,Stefan, Alessandra,Skelton, Brian W.,Sobolev, Alexandre N.,Massi, Massimiliano,Hochkoeppler, Alejandro,Stagni, Stefano,Simpson, Peter V.
supporting information, p. 292 - 298 (2020/01/25)
Ten manganese(I) tricarbonyl diimine complexes bound to variably functionalised 5-aryl-tetrazolato ligands were prepared, and their photochemical properties were investigated. Upon exposure to light at 365 nm, each complex decomposed to its free diimine and tetrazolato ligands, simultaneously dissociating three CO ligands, as evidenced by changes in the IR spectra of the irradiated complexes over time. The anti-bacterial properties of one of these complexes were tested against Escherichia coli. While the complex displayed no effect on the bacterial growth in the dark, pre-irradiated solutions inhibited bacterial growth. Comparative studies revealed that the antibacterial properties originate from the presence of free 1,10-phenanthroline.
