Monoanionic Dipyrrin–Pyridine Ligands: Synthesis, Structure and Photophysical Properties

Ducloiset, Clémence; Jouin, Pauline; Paredes, Elisa; Guillot, Régis; Sircoglou, Marie; Orio, Maylis; Leibl, Winfried; Aukauloo, Ally

doi:10.1002/ejic.201500783

Cited by 16 publications

(9 citation statements)

References 43 publications

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“…As mentioned in the Introduction, the Py-BTD ligands are luminescent. Their coordination to metal ions with d 10 configurations such as Zn(II) should provide luminescent complexes with, in principle, an increase of the emission efficiency as a consequence of a more rigid structure [47][48][49][50]. Moreover, emission wavelength could vary because of the different dihedral angles between the pyridine and BTD units, influencing the extension of the π-conjugated system.…”

Section: Photophysical Propertiesmentioning

confidence: 99%

Dimensionality Control in Crystalline Zinc(II) and Silver(I) Complexes with Ditopic Benzothiadiazole-Dipyridine Ligands

et al. 2021

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Three 2,1,3-benzothiadiazole-based ligands decorated with two pyridyl groups, 4,7-di(2-pyridyl)-2,1,3-benzothiadiazol (2-PyBTD), 4,7-di(3-pyridyl)-2,1,3-benzothiadiazol (3-PyBTD) and 4,7-di(4-pyridyl)-2,1,3 benzothiadiazol (4-PyBTD), generate ZnII and AgI complexes with a rich structural variety: [Zn(hfac)2(2-PyBTD)] 1, [Zn2(hfac)4(2-PyBTD)] 2, [Ag(CF3SO3)(2-PyBTD)]23, [Ag(2-PyBTD)]2(SbF6)24, [Ag2(NO3)2(2-PyBTD)(CH3CN)] 5, [Zn(hfac)2(3-PyBTD)] 6, [Zn(hfac)2(4-PyBTD)] 7, [ZnCl2(4-PyBTD)2] 8 and [ZnCl2(4-PyBTD)] 9 (hfac = hexafluoroacetylacetonato). The nature of the resulting complexes (discrete species or coordination polymers) is influenced by the relative position of the pyridyl nitrogen atoms, the nature of the starting metal precursors, as well as by the synthetic conditions. Compounds 1 and 8 are mononuclear and 2, 3 and 4 are binuclear species. Compounds 6, 7 and 9 are 1D coordination polymers, while compound 5 is a 2D coordination polymer, the metal ions being bridged by 2-PyBTD and nitrato ligands. The solid-state architectures are sustained by intermolecular π–π stacking interactions established between the pyridyl group and the benzene ring from the benzothiadiazol moiety. Compounds 1, 2, 7–9 show luminescence in the visible range. Density Functional Theory (DFT) and Time Dependent Density Functional Theory (TD-DFT) calculations have been performed on the ZnII complexes 1 and 2 in order to disclose the nature of the electronic transitions and to have an insight on the modulation of the photophysical properties upon complexation.

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Section: Photophysical Propertiesmentioning

confidence: 99%

Dimensionality Control in Crystalline Zinc(II) and Silver(I) Complexes with Ditopic Benzothiadiazole-Dipyridine Ligands

et al. 2021

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“…The tetradentate chelation of the N 2 O 2 dipyrrin unit employed in this study successfully yielded stable neutral complexes of these Lewis acidic elements in methanol. The study of these new chromophores contributes to the active fields of coordination and photophysical chemistry for a series of dipyrrin‐metal complexes …”

Section: Resultsmentioning

confidence: 99%

Heterodinuclear Group 13 Element Complexes of N₄O₆‐Type Dipyrrin with an Unsymmetrical Twisted Structure

et al. 2018

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Heterodinuclear group 13 element complexes of an N 4 O 6 -type dipyrrin cyclic dimer were synthesized by the stepwise reaction with boron and group 13 elements (Al, Ga, and [a] NMR Spectroscopy: 1 H and 13 C NMR spectra were recorded on a Bruker AVANCE III-400 or 600 spectrometers. Tetramethylsilane was used as an internal standard (δ = 0.00 ppm) for 1 H and 13 C NMR measurements.Single-Crystal X-ray Diffraction: Single-crystal X-ray diffraction measurements were performed using a Bruker APEX II ULTRA with Mo-K α radiation (graphite-monochromated, λ = 0.71073 Å) at 120 K. The collected diffraction images were processed by Bruker APEX2. The initial structure was solved using SHELXS-2013 [49] and refined using SHELXL-2016, [50] which were running on Yadokari-XG crystallographic software. [51] CCDC 1848533 (for [LBGa(CH 3 OH) 2 ]), and 1848537 (for [LBIn(CH 3 OH) 2 ]) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre.Mass Spectroscopy: MALDI-TOF mass data were recorded on an AB SCIEX TOF/TOF 5800 system. UV/Vis and Fluorescence Spectroscopy:UV-Vis spectra were recorded on a JASCO V-660 or V-670 spectrophotometer. Emission spectra were recorded on a JASCO FP-8600 fluorescence spectrophotometer. Absolute fluorescence quantum yields were determined with a Hamamatsu Photonics absolute PL quantum yield measurement system C9920-02. Solvents used for measurements were air-saturated.DFT Calculations: DFT calculations were carried out using the Spartan '16 software (Wavefunction, Inc. Irvine, CA). The geometry optimization of [LBGa(MeOH) 2 ] were performed at the B3LYP/6-31G(d) level. [52] Eur.

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“…For this study, we prepared an iron complex with the DPPy (DipyrrinDiPyridine) ligand we previously designed in our lab (Figure left) . Metalation of the DPPy ligand with Fe(OTf) 2 led to the formation of the iron(II) precursor complex that upon exposure to air yielded {[(DPPy)(EtOH)Fe III ] 2 O}(OTf) 2 , a μ ‐oxo iron(III) dimer abbrieviated as I (OTf) 2 (see the Supporting Information).…”

Section: Figurementioning

confidence: 99%

“…Fort his study,w ep repared an iron complex with the DPPy (DipyrrinDiPyridine) ligand we previously designed in our lab (Figure 1left). [25] Metalation of the DPPy ligand with Fe(OTf) 2 led to the formation of the iron(II) precursor complex that upon exposure to air yielded {[(DPPy)-(EtOH)Fe III ] 2 O}(OTf) 2 ,am-oxo iron(III) dimer abbrieviated as I(OTf) 2 (see the Supporting Information). Theu nderlying reactivity is reminiscent of that of the corresponding iron(II) porphyrin (Por) derivatives where O 2 binding and subsequent OÀObond cleavage leads to the highly oxidized iron(IV)-oxo species that ultimately reacts with the starting iron(II) complex to generate the [(Por)Fe III ] 2 Od erivative.…”

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confidence: 99%

A Reversible Electron Relay to Exclude Sacrificial Electron Donors in the Photocatalytic Oxygen Atom Transfer Reaction with O₂ in Water

Mekmouche

Tron

et al. 2019

Angew Chem Int Ed

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Using light energy and O2 for the direct chemical oxidation of organic substrates is a major challenge. A limitation is the use of sacrificial electron donors to activate O2 by reductive quenching of the photosensitizer, generating undesirable side products. A reversible electron acceptor, methyl viologen, can act as electron shuttle to oxidatively quench the photosensitizer, [Ru(bpy)3]2+, generating the highly oxidized chromophore and the powerful reductant methyl‐viologen radical MV+.. MV+. can then reduce an iron(III) catalyst to the iron(II) form and concomitantly O2 to O2.− in an aqueous medium to generate an active iron(III)‐(hydro)peroxo species. The oxidized photosensitizer is reset to its ground state by oxidizing an alkene substrate to an alkenyl radical cation. Closing the loop, the reaction of the iron reactive intermediate with the substrate or its radical cation leads to the formation of two oxygenated compounds, the diol and the aldehyde following two different pathways.

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Monoanionic Dipyrrin–Pyridine Ligands: Synthesis, Structure and Photophysical Properties

Cited by 16 publications

References 43 publications

Dimensionality Control in Crystalline Zinc(II) and Silver(I) Complexes with Ditopic Benzothiadiazole-Dipyridine Ligands

Dimensionality Control in Crystalline Zinc(II) and Silver(I) Complexes with Ditopic Benzothiadiazole-Dipyridine Ligands

Heterodinuclear Group 13 Element Complexes of N₄O₆‐Type Dipyrrin with an Unsymmetrical Twisted Structure

A Reversible Electron Relay to Exclude Sacrificial Electron Donors in the Photocatalytic Oxygen Atom Transfer Reaction with O₂ in Water

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Monoanionic Dipyrrin–Pyridine Ligands: Synthesis, Structure and Photophysical Properties

Cited by 16 publications

References 43 publications

Dimensionality Control in Crystalline Zinc(II) and Silver(I) Complexes with Ditopic Benzothiadiazole-Dipyridine Ligands

Dimensionality Control in Crystalline Zinc(II) and Silver(I) Complexes with Ditopic Benzothiadiazole-Dipyridine Ligands

Heterodinuclear Group 13 Element Complexes of N4O6‐Type Dipyrrin with an Unsymmetrical Twisted Structure

A Reversible Electron Relay to Exclude Sacrificial Electron Donors in the Photocatalytic Oxygen Atom Transfer Reaction with O2 in Water

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Product

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Heterodinuclear Group 13 Element Complexes of N₄O₆‐Type Dipyrrin with an Unsymmetrical Twisted Structure

A Reversible Electron Relay to Exclude Sacrificial Electron Donors in the Photocatalytic Oxygen Atom Transfer Reaction with O₂ in Water