Structure, physical and photophysical properties of platinum(II) complexes containing 7,8-benzoquinoline and various bis(diphenylphosphine) ligands

DePriest, Jeffrey C.; Zheng, Greg Y.; Woods, Clifton; Rillema, D. Paul; Mikirova, N.A.; Zandler, Melvin E.

doi:10.1016/s0020-1693(97)05688-0

Cited by 44 publications

(65 citation statements)

References 53 publications

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“…[NiCl 2 (dppp)] was purchased from Aldrich and [Pd (1,5- [14] [PtCl 2 (dppp)], [PtCl 2 (dppe)] and [PdCl 2 (dppp)] were obtained by adaptation of published procedures. [15] [Ni(ema)(µ-S,SЈ)Ni(dppp)] (1) and [Ni(ema)(µ-S,SЈ)Ni(dppe)] (2) were prepared as we recently reported. [5] IR spectra were recorded with a Shimadzu FTIR-8000 spectrophotometer and UV/Vis spectra with a Perkin-Elmer Lambda 25.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Structural Characterisation of Group 10 Homo‐ and Hetero‐Dimetallic Sulfur‐Bridged Complexes of the [Ni(ema)(μ‐S,S′)M(diphos)](M = Ni, Pd, Pt) Type

et al. 2005

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The series of group 10 homo‐ and hetero‐dimetallic sulfur‐bridged complexes [Ni(ema)(μ‐S,S′)M(diphos)], [M = nickel, palladium or platinum; diphos = 1,3‐bis(diphenylphosphanyl)propane or 1,2‐bis(diphenylphosphanyl)ethane], have been synthesised. Their properties and the crystal structures of five of the series are described. The dinickel complexes are good structural analogues of the dinickel subunit of the nickel‐containing enzyme acetyl‐CoA synthase. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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Section: Methodsmentioning

confidence: 99%

Synthesis and Structural Characterisation of Group 10 Homo‐ and Hetero‐Dimetallic Sulfur‐Bridged Complexes of the [Ni(ema)(μ‐S,S′)M(diphos)](M = Ni, Pd, Pt) Type

et al. 2005

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“…Starting from [Pt(cod)Cl 2 ] the complex anion [Pt(NAO)Cl 2 ] ) does not form at all either in H 2 O or in methanol (B. Pitteri, personal communication). In conclusion, we belive that the use of cis/trans-[PtCl 2 (SMe 2 ) 2 ] as a precursor for the complexes is superior to the previously reported methods, [7][8][9][10][11][12][13][14]16] in that the synthetic procedures are much simpler and give better yields in the absence of other products, in particular as far as the preparations of the complexes Na It is very likely that the same precursor could be advantageously used for the preparation of many other Pt(II) chelate complexes.…”

Section: Discussionmentioning

confidence: 97%

“…: K 2 [PtCl 4 ] for 2,4,7, and 8 [8][9][10][11], [Pt(PhCN) 2 Cl 2 ] for 3,6 [12,13] and [Pt(cod)Cl 2 ] for 1,5. [7,14]. In the case of the reaction between [PtCl 4 ] 2) and NAN (NAN=1,10-phenanthroline) [8], the formation of the neutral complex [Pt(phen)Cl 2 ] (4) is very slow (weeks), while when the reagent ligand is NAS (NAS=2-[(methylthio)methylpyridine] the pink, very insoluble Magnus type salt [Pt(NAS) 2 ][PtCl 4 ] is first formed [15].…”

Section: Discussionmentioning

confidence: 99%

An Improved Method for the Preparation of Tetra-Coordinate Platinum(II) Chloro-Complexes Containing Bidentate or Terdentate Ligands Starting from cis/trans-[PtCl2(SMe2)2]

Annibale

Bortoluzzi

Marangoni

et al. 2005

Transition Met Chem

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An improved method for the preparation of differently charged chelate Pt(II) chloro-complexes is reported. All the complexes have been obtained rapidly and in high yield, by simply reacting equimolar amounts of cis/transdichlorobis(dimethylsulphide)platinum(II) with the chelate ligand in an appropriate solvent (CH 2 Cl 2 , MeOH or H 2 O). The ligands chosen were: 1,2-bis(diphenylphosphino)ethane (PAP), pyridine-2-carboxylate (NAO ) ), 2-[(methylthio)methyl]pyridine (NAS), 1,10-phenanthroline (NAN), bis(2-pyridylmethyl)sulphide (NASAN), di-(2-picolyl)amine (NANAN), pyridine-2,6-dicarboxylate (OANAO 2) ) and 2,6-bis(methylthiomethyl)pyridine (SANAS).

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“…The 1 H NMR spectra were recorded on a Tesla BS-567 spectrometer (100 MHz) from solutions in benzene-d 6 containing HMDS as internal reference. The IR spectra were obtained on a UR-20 instrument from samples prepared as KBr pellets.…”

Section: Methodsmentioning

confidence: 99%

“…Interest in quinoline derivatives and analogs continuously increases. Some benzoquinolines were found to possess good complexing [6] and fluorescent properties [7].…”

mentioning

confidence: 99%

Synthesis of benzo[f]quinoline derivatives by condensation of N-arylmethylene-2-naphthylamines with acetylcyclohexane and 1-acetylcyclohexene

Грачек

2004

Russ J Gen Chem

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N-Arylmethylene-2-naphthylamines react with acetylcyclohexane and 1-acetylcyclohexene under mild conditions to afford 2-aryl-2-(2-naphthylamino)ethyl cyclohexyl and 1-cyclohexenyl ketones, respectively. Under more severe conditions (110oC), the reaction is accompanied by cyclization with formation of 3-aryl-1-cyclohexyl (or 1-cyclohexenyl)benzo[ f ]quinolines. Proper choice of the amount of catalyst, temperature, and reaction time allows isolation of intermediate 3-aryl-1-cyclohexyl(or 1-cyclohexenyl)-3,4-dihydrobenzo[ f ]quinolines. Quinoline derivatives are structural analogs of alkaloids [1], enzyme inhibitors [2], and antibiotics [3]; therefore, they should exhibit versatile biological activity. In addition, these compounds are good antioxidants [4] and antirads [5] for polymeric materials. Interest in quinoline derivatives and analogs continuously increases. Some benzoquinolines were found to possess good complexing [6] and fluorescent properties [7].A known procedure for the synthesis of benzo[ f ]-quinolines is based on the condensation of Schiff bases derived from 2-naphthylamine with various aliphatic, aromatic, and heterocyclic methyl ketones [8312]. It was found that the formation of benzo[ f ]-quinolines is a multistep process [12]. The reaction of N-arylmethylene-2-naphthylamines with methyl ketones of the cycloaliphatic series has been studied poorly. We previously synthesized benzo[ f ]quinoline derivatives by condensation of N-arylmethylene-2-naphthylamines with acetylcyclohexane and 1-acetylcyclohexene [13,14]. In doing so, either no intermediate products were isolated at all or they were isolated in very small amounts. In the present work we performed condensations of acetylcyclohexane (I) and 1-acetylcyclohexene (II) with Schiff bases IIIa3 IIIh of the 2-naphthylamine series using larger amounts of the initial reactants and tried to isolate and examine intermediate products by varying the reaction conditions.Condensations of Schiff bases with ketones are catalyzed by acids. Proton addition to a Schiff base yields the corresponding cation in which the positive charge is delocalized over the azomethine nitrogen and carbon atoms. Therefore, such cations readily take up even weakly nucleophilic ketones. The reaction mechanism is analogous to the acid-catalyzed aldol addition pattern. The reaction involves the methyl group in methyl ketone, so that the latter acts as CH acid. Amino ketones IVa3IVf and Va3Vg thus formed are the first intermediate products in the synthesis of benzo[ f ]quinolines (see scheme). The double bond in 1-acetylcyclohexene is conjugated with the carbonyl group; as a result, polarization of the C=O bond increases, and protons in the acetyl group become more labile. Therefore, the yields of amino ketones from 1-acetylcyclohexene are greater, and the condensation occurs at a lower temperature, as compared to acetylcyclohexane (Table 1). Amino ketones IVa3IVf and Va3Vg were obtained by heating the reactants in ethanol at 40360oC in the presence of a catalytic amount of hydrochlor...

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Structure, physical and photophysical properties of platinum(II) complexes containing 7,8-benzoquinoline and various bis(diphenylphosphine) ligands

Cited by 44 publications

References 53 publications

Synthesis and Structural Characterisation of Group 10 Homo‐ and Hetero‐Dimetallic Sulfur‐Bridged Complexes of the [Ni(ema)(μ‐S,S′)M(diphos)](M = Ni, Pd, Pt) Type

Synthesis and Structural Characterisation of Group 10 Homo‐ and Hetero‐Dimetallic Sulfur‐Bridged Complexes of the [Ni(ema)(μ‐S,S′)M(diphos)](M = Ni, Pd, Pt) Type

An Improved Method for the Preparation of Tetra-Coordinate Platinum(II) Chloro-Complexes Containing Bidentate or Terdentate Ligands Starting from cis/trans-[PtCl2(SMe2)2]

Synthesis of benzo[f]quinoline derivatives by condensation of N-arylmethylene-2-naphthylamines with acetylcyclohexane and 1-acetylcyclohexene

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