Chromophores, Fluorophores and Robust Ancillary Ligands for Molecular Catalysts: 1,3‐Bis(2‐pyridylimino)isoindolines

Sauer, Désirée C.; Melen, Rebecca L.; Kruck, Matthias; Gade, Lutz H.

doi:10.1002/ejic.201402595

Cited by 27 publications

(33 citation statements)

References 73 publications

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“…[5][6][7]9 The C(4)−N(4) double bond of the uncoordinated pyridyl unit adopts an E configuration with a torsion angle N(1)−C(4)−N(4)−C(14) of −166.8(2)°(1-Cl), −169. 4(2)°(2-Cl), and −174. 7(2)°(3-Cl).…”

Section: ■ Introductionmentioning

confidence: 99%

Iridium Half-Sandwich Complexes with Di- and Tridentate Bis(pyridylimino)isoindolato Ligands: Stoichiometric and Catalytic Reactivity

et al. 2015

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A series of κ 2 -(N,N)-coordinated bis(2-pyridylimino)isoindolato (BPI) complexes [Cp*Ir(BPI)Cl], which possess "three-legged piano-stool" structures, with the iridium atom being coordinated by the Cp* ligand 2 × N and Cl, were prepared via deprotonation of the BPIH ligands with either potassium hydride or LDA and subsequent reaction with [Cp*IrCl 2 ] 2 in THF. Cationic complexes [Cp*Ir(BPI)] + containing κ 3 -(N,N,N)-coordinated BPI ligands were prepared as well as complexes with bidentate-coordinated BPI ligands, where the chloride ligand was substituted by either neutral or anionic ligands. Substitution in the orthoposition of the PBI ligands led to the formation of cycloiridated κ 3 -(N,N,C) species. Upon substitution of the anionic ligand by triphenylphosphine, a product was obtained with a hitherto unobserved κ 2 -(N,N) coordination of oMe-BPI to the metal center via the deprotonated nitrogen atom of the isoindole unit and one of the imine nitrogen atoms of the BPI ligand. A series of (para-cymene) osmium half-sandwich complexes with analogous structures and reactivities to their isoelectronic Cp*Ir(BPI) congeners were also prepared. Finally, it has been demonstrated that both Ir and Os complexes are catalytically active in the transfer hydrogenation of various ketones and imines.

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Section: ■ Introductionmentioning

confidence: 99%

Iridium Half-Sandwich Complexes with Di- and Tridentate Bis(pyridylimino)isoindolato Ligands: Stoichiometric and Catalytic Reactivity

et al. 2015

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“…In the last decade, the syntheses of such BPIs have attracted significant interest, due to their tunable and versatile structure, which makes them suitable building blocks for the construction of more complex molecular architectures. The applications of BPIs span different fields, ranging from materials science to asymmetric catalysis . The synthesis of BPI derivatives is extremely versatile, allowing easy access to a large variety of compounds through the fine‐tuning of the substituents on both the isoindolato backbone and pendant pyridine rings, owing to their modular assembly.…”

Section: Methodsmentioning

confidence: 99%

Joining Chromophores: a Porphyrin‐BPI Fused System

et al. 2018

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A diminoisoindoline‐tetraphenylporphyrin (as Zn complex) unit has been used as building block for the preparation of a tetraphenylporphyrin‐1,3‐bis(2‐pyridylimino)isoindoline conjugate (3). The chelating system of this molecule possesses two different binding centers. The optimization of the synthetic procedure allowed to obtain the ZnTPP‐BPI moiety in very good yields, the structure of which was identified by means of UV/Vis, NMR, mass and X‐ray methods. The Zn‐porphyrin complex was then subject to Zn ion removal from the porphyrin core, allowing the isolation of the corresponding free base derivative. The optical features of the compound are very interesting, as expected from the fusion of two chromophores active in the UV and visible regions of the optical spectrum; this has also been confirmed by testing ZnTPP‐BPI (3) as chemosensor for metal cations detection.

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“…This is then converted into the anticipated product in 70% yield through a copper-catalyzed amination reaction with pyrazole [29]. Bis(2-pyridylimino)isoindole (BPI) ligands were first reported over 60 years ago [30][31][32] and are examples of tridentate pincer ligands which have found applications in catalysis and materials science [33]. The current preferred method of synthesis involves the reaction of commercially available phthalonitrile with 2-aminopyridines in a high boiling alcohol solvent in the presence of CaCl 2 (Scheme 5) [34][35][36][37][38].…”

Section: Ligand Designmentioning

confidence: 99%

New Chemistry with Anionic NNN Pincer Ligands

Melen

Gade

2015

The Privileged Pincer-Metal Platform: Coordination Chemistry &Amp; Applications

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The use of tridentate anionic pincer ligands in organometallic chemistry has gained considerable importance, particularly in the field of homogenous catalysis. This chapter focuses on the recent developments of anionic tridentate NNN pincer ligands from their synthesis to coordination chemistry and their applications in forming stable transition metal complexes for applications in catalytic transformations.

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Chromophores, Fluorophores and Robust Ancillary Ligands for Molecular Catalysts: 1,3‐Bis(2‐pyridylimino)isoindolines

Cited by 27 publications

References 73 publications

Iridium Half-Sandwich Complexes with Di- and Tridentate Bis(pyridylimino)isoindolato Ligands: Stoichiometric and Catalytic Reactivity

Iridium Half-Sandwich Complexes with Di- and Tridentate Bis(pyridylimino)isoindolato Ligands: Stoichiometric and Catalytic Reactivity

Joining Chromophores: a Porphyrin‐BPI Fused System

New Chemistry with Anionic NNN Pincer Ligands

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