Synthesis of free and ruthenium coordinated 5,6-diamino-1,10-phenanthroline

Bodige, Swamy; MacDonnell, Frederick M.

doi:10.1016/s0040-4039(97)10223-4

Cited by 150 publications

(109 citation statements)

References 7 publications

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“…2,2'-Bipyridine (bpy) and 1,10-phenanthroline (phen) were obtained from Janssen Chemical Company. 1,10-phenanthroline-5,6-diamine (1), [28] 3,5- Figure 14. EPR spectra of [Ru(bpy) 2 (DPSalHArOC)] 2 + obtained after illumination of the sample in the presence of [Co III (NH 3 ) 5 Cl] 2 + .…”

Section: Methodsmentioning

confidence: 99%

Heteroditopic Ligand Accommodating a Fused Phenanthroline and a Schiff Base Cavity as Molecular Spacer in the Study of Electron and Energy Transfer

Pellegrin

Quaranta

Dorlet

et al. 2005

Chemistry A European J

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The synthesis and characterisation of the heteroditopic ligand N,N'-bis(3,5-di-tert-butylsalicylidene)-5,6-(1,10-phenanthroline)diamine (DPSalH(2)) bearing a phenanthroline and a bis(salicylidene)diimine cavity are reported. This versatile ligand combines two of the most widely used ligands in coordination chemistry. Sequential metallation of the phenanthroline end with Ru(II) and the salophenic cavity with Cu(II) is described. Electrochemical behaviour of the supramolecular complexes [Ru(bpy)(2)(DPSalH(2))](2+) and [Ru(bpy)(2)(DPSalCu)](2+) are analysed in connection with UV/Vis and EPR spectroscopy. The data for the one-electron-reduced species and the singly oxidised species of the binuclear Ru(II)-Cu(II) complex confirmed the formation of metalloradical complexes. Density functional calculations on the free ligand and the copper-only complex indicate in both cases that the HOMOs and LUMOs are developed on the Schiff base cavity with minor contributions on the bipyridine end. These findings support a bichromophoric character for our ruthenium complexes in the ground state, a necessary condition in the design of supramolecular systems for the study of electron transfer. Photophysical studies indicate fast quenching of the triplet excited state in both complexes, which suggests strong intercomponent excited-state interactions. Evidence is presented that this quenching is due to intramolecular electron transfer, at least in the case of [Ru(bpy)(2)(DPSalH(2))](2+), for which a charge-separated state with a remarkable lifetime of about 30 mus was observed.

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Section: Methodsmentioning

confidence: 99%

Heteroditopic Ligand Accommodating a Fused Phenanthroline and a Schiff Base Cavity as Molecular Spacer in the Study of Electron and Energy Transfer

Pellegrin

Quaranta

Dorlet

et al. 2005

Chemistry A European J

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“…The resulting mixture was filtered and the pale yellow precipitate was washed with water, ethanol and ether respectively and dried in a vacuum oven at 80 °C [42]. Yield: 1.80 g (50%), mp 231 °C.…”

Section: Synthesis Of 110-phenanthroline-56-dioxime (Step 2)mentioning

confidence: 99%

“…The solution was left for a night at 4 °C. The resulting well-formed yellowish-brown precipitate was filtered, washed with cold water and dried in vacuum [42]. Yield: 0.77 g (44%), mp > 300 °C.…”

Section: Synthesis Of Dap (Step 3)mentioning

confidence: 99%

A rational synthesis of a novel imidazo[4,5-f][1,10]phenanthroline templated Schiff base: Characterization, photoluminescence and DFT/TD-DFT study

Karslıoğlu¹,

Demir²,

Yilmaz³

et al. 2017

Bull. Chem. Soc. Eth.

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H-NMR, IR, elemental analysis and electrospray ionization mass spectroscopy (ESI-MS) techniques. Solid state emission spectrum of impap showed two distinct strong emission maxima with large Stokes shifts. The ground state gas phase geometry of impap was predicted by DFT calculations. Excited state properties of the molecule were examined through TD-DFT calculations conducted at the optimized geometry. Responsible transitions for the strong fluorescence of impap were assigned to single component charge transfer transitions with large oscillator strengths based on the ground state calculated molecular orbital contributions.

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“…Synthesis of 1,10-phenanthroline-5,6-dione [41] 1: To a dry mixture of 1,10-phenanthroline (2 g, 0.011 mol) and KBr (10 g, 0.084 mol), H 2 SO 4 (40 mL) followed by HNO 3 (20 mL) were added drop-wise at 0 °C. The resulting mixture was heated at 100 °C until the bromine vapors disappeared.…”

Section: Synthesesmentioning

confidence: 99%

Synthesis and evaluation of the europiumIII and zincII complexes as luminescent bioprobes in high content cell-imaging analysis

Sergeeva

Donnier-Maréchal

Vaz

et al. 2011

Journal of Inorganic Biochemistry

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SummaryNovel phenanthroline derivatives and their europium(III) and zinc(II) complexes have been prepared in up to 92 %. In contrast to the stable zinc complexes, the europium compounds exhibit a strong luminescence in THF solution and complete dissociation of the complexes back to free ligands in DMSO. 1 H NMR studies of the Eu(III)-complexes 5 and 6 also confirmed the existence of different states depending on the solvent used. Moreover, it was found that the compound 5 is stable in EtOH-PBS solutions; here a strong signal in the emission spectra corresponding to the europium ion was detected. These metal complexes can be used as fluorescence markers for the diagnosis of esophageal squamous carcinoma (OE21) cells at low concentrations. Cell images were acquired using the compound 5, 7-9 as luminescent markers. The first images were taken already after 20 min incubation time at a very low concentration range (0.7-1.6 µM).Published as: Sergeeva, N. N.; Donnier-Marechal, M.; Vaz, G.; Davies, A. M.; Senge, M. O. (2011): Synthesis and evaluation of the europium III and zinc II complexes as luminescent bioprobes in high content cell-imaging analysis.

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Synthesis of free and ruthenium coordinated 5,6-diamino-1,10-phenanthroline

Cited by 150 publications

References 7 publications

Heteroditopic Ligand Accommodating a Fused Phenanthroline and a Schiff Base Cavity as Molecular Spacer in the Study of Electron and Energy Transfer

Heteroditopic Ligand Accommodating a Fused Phenanthroline and a Schiff Base Cavity as Molecular Spacer in the Study of Electron and Energy Transfer

A rational synthesis of a novel imidazo[4,5-f][1,10]phenanthroline templated Schiff base: Characterization, photoluminescence and DFT/TD-DFT study

Synthesis and evaluation of the europiumIII and zincII complexes as luminescent bioprobes in high content cell-imaging analysis

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