Acridine Variations for Coordination Chemistry

Omolo, Kevin O.; Bacsa, John; Sadighi, Joseph P.

doi:10.1002/ijch.202000006

Israel Journal of Chemistry

2020

DOI: 10.1002/ijch.202000006

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Acridine Variations for Coordination Chemistry

Kevin O. Omolo

John Bacsa

Joseph P. Sadighi

Abstract: This study describes the synthesis of an acridone through the directed lithiation of a diarylamine, and elaboration via the 4,5-dibromoacridone. The bromo substituents are amenable to Suzuki-Miyaura coupling. Conversion to a 9chloro-4,5-dibromoacridine, followed by bromine-lithium ex-change, allows the preparation of a 4,5-bis (phosphino)-9chloroacridine. The 9-chloro moiety undergoes nucleophilic aromatic substitution by methoxide or an aryloxide. Oneelectron reduction of a 9-(aryloxy)-4,5-bis(phosphino)acrid… Show more

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2024

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Cited by 2 publications

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Iron Complexes of 4,5-Bis(diorganophosphinomethyl)acridine Ligands

Roca Jungfer,

Rominger,

Oeser

et al. 2024

Inorg. Chem.

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The search for an iron analog of the established ruthenium-based catalysts containing methylene-extended 4,5bis(diorganophosphinomethyl)acridine ligands, [FeHCl(CO)-(L R )], resulted in the discovery of a bidentate coordination mode of these usually tridentate pincer ligands toward iron. The acridines nitrogen atom does not coordinate to iron, leading to the formation of iron diphos-type complexes with unusually large cis bite angles of up to 124°as well as trans bite angles around 155°. The iron-containing complexeshave been isolated in crystalline form and characterized by spectroscopic methods and mass spectrometry. Their structures were verified unambiguously through X-ray diffraction. The stability of the iron(II) complexes decreased in the order Cy > Ph > i Pr and Cl > Br > I, although all iron(II) complexes were found to be relatively stable enough for short-term handling in air in the solid state. Notably, no iron(0) complex of the phenyl derivative could be isolated. The iron(0) complex [Fe(CO) 3 (κ 2 -L Cy )] was found to be significantly more stable toward hydrolysis and oxygen compared to [Fe(CO) 3 (κ 2 -L iPr )] and can be stored in air for months without significant decomposition in the solid state, while [Fe(CO) 3 (κ 2 -L iPr )] decomposes in air within seconds. The decomposition products [FeI 2 (κ 2 -O 2 L Cy )], [{Fe(CO) 3 (κ 2 -HL R )} 2 ] (R = i Pr, Cy) and [FeCl 2 (CO) 2 (κ 1 -L Cy )(κ 1 -OL Cy )] were identified and characterized crystallographically. The iron(0) complex [Fe(CO) 3 (κ 2 -L Cy )] is oxidized by [Fe(Cp) 2 ](BPh 4 ) to give the paramagnetic, low-spin iron(I) cation [Fe(CO) 3 (κ 2 -L Cy )] + . The electron paramagnetic resonance spectrum of the highly sensitive cation as well as density functional theory calculations suggest a partial delocalization of the unpaired electron over the three carbonyl ligands and the acridines aromatic ring system. The catalytic activity and photophysical properties of the complexes have been preliminarily investigated.

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Iron Complexes of 4,5-Bis(diorganophosphinomethyl)acridine Ligands

Roca Jungfer,

Rominger,

Oeser

et al. 2024

Inorg. Chem.

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Tuning the Coordination Environment of Ru(II) Complexes with a Tailored Acridine Ligand

Awada,

Lanoë,

Philouze

et al. 2024

Molecules

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A novel tridentate ligand featuring an acridine core and pyrazole rings, namely 2,7- di-tert-butyl-4,5-di(pyrazol-1-yl)acridine, L, was designed and used to create two ruthenium(II) complexes: [RuL2](PF6)2 and [Ru(tpy)L](PF6)2. Surprisingly, the ligand adopted different coordination modes in the complexes: facial coordination for the homoleptic complex and meridional coordination for the heteroleptic complex. The electronic absorption and electrochemical properties were evaluated. Although both complexes exhibited favorable electronic properties for luminescence, neither emitted light at room temperature nor at 77 K. This study highlights the complex interplay between ligand design, coordination mode, and luminescence in ruthenium(II) complexes.

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Acridine Variations for Coordination Chemistry

Cited by 2 publications

References 39 publications

Iron Complexes of 4,5-Bis(diorganophosphinomethyl)acridine Ligands

Iron Complexes of 4,5-Bis(diorganophosphinomethyl)acridine Ligands

Tuning the Coordination Environment of Ru(II) Complexes with a Tailored Acridine Ligand

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