Ammine[1-(2-hydroxyphenyl)-3,5-diphenylformazanato]nickel(II), [Ni(C19H14N4O)(NH3)], and [1-(2-hydroxyphenyl)-5-phenyl-3-(p-tolyl)formazanato](pyridine)nickel(II), [Ni(C5H5N)(C20H16N4O)]

Meuldijk, J.; RENKEMA, W. E.; Herk, van Am Alex; Stam, C. H.

doi:10.1107/s0108270183009166

Cited by 9 publications

(3 citation statements)

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“…As expected, the ligand bite angles differ considerably at 78.93(9)° and 88.90(9)° for the 5 and 6-membered rings, respectively. Balt and co-workers described the formation of an intermediate en route to copper and nickel complexes with the formazan (2-OHPh)NNC(Ph)NNHPh, which they tentatively identified as isomers with a 5-membered formazanate chelate ring, and a crystal structure was reported for the nickel derivative . Furthermore, large structural diversity in alkali-metal formazanate complexes was recently reported by us that includes 4- and 5-membered chelate rings .…”

Section: Resultsmentioning

confidence: 93%

Formazanate Ligands as Structurally Versatile, Redox-Active Analogues of β-Diketiminates in Zinc Chemistry

et al. 2014

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A range of tetrahedral bis(formazanate)zinc complexes with different steric and electronic properties of the formazanate ligands were synthesized. The solid-state structures for several of these were determined by X-ray crystallography, which showed that complexes with symmetrical, unhindered ligands prefer coordination to the zinc center via the terminal N atoms of the NNCNN ligand backbone. Steric or electronic modifications can override this preference and give rise to solid-state structures in which the formazanate ligand forms a 5-membered chelate by binding to the metal center via an internal N atom. In solution, these compounds show dynamic equilibria that involve both 5- and 6-membered chelates. All compounds are intensely colored, and the effect of the ligand substitution pattern on the UV-vis absorption spectra was evaluated. In addition, their cyclic voltammetry is reported, which shows that all compounds may be electrochemically reduced to radical anionic (L2Zn(-)) and dianionic (L2Zn(2-)) forms. While unhindered NAr substituents lie in the plane of the ligand backbone (Ar = Ph), the introduction of sterically demanding substituents (Ar = Mes) favors a perpendicular orientation in which the NMes group is no longer in conjugation with the backbone, resulting in hypsochromic shifts in the absorption spectra. The redox potentials in the series of L2Zn compounds may be altered in a straightforward manner over a relatively wide range (∼700 mV) via the introduction of electron-donating or -withdrawing substituents on the formazanate framework.

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Section: Resultsmentioning

confidence: 93%

Formazanate Ligands as Structurally Versatile, Redox-Active Analogues of β-Diketiminates in Zinc Chemistry

et al. 2014

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“…Additional functional groups (−OH, carboxyl, or N-heterocyclic , ) on the N-aromatic substituents can increase the denticity of formazan ligands. We recently described the synthesis and characterizization of bis( o -methoxyphenyl) and bis( o -hyroxyphenyl) cyanoformazans and present preliminary explorations of their coordination chemistry here.…”

Section: Resultsmentioning

confidence: 99%

Transition Metal Complexes of 3-Cyano- and 3-Nitroformazans

et al. 2008

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The synthesis and characterization of six transition metal complexes of 3-cyano- and 3-nitroformazans are described. Three different formazans were reacted with nickel(II) to produce complexes with bidentate formazan ligands. Mononuclear NiL2 (L = deprotonated formazan) or binuclear hydroxo-bridged (LNi)2(mu-OH) 2 species were produced depending on the steric bulk on the formazan N-aromatic substituents. 1,5-Bis(2-methoxyphenyl)-3-cyanoformazan acts as a tetradentate monoanionic ligand in a copper(II) complex, whereas the analogous 1,5-bis(2-hydroxyphenyl)-3-cyanoformazan binds as a trianion in a tetradentate manner to Fe(III) and Co(III). Crystal structures-the first examples of metal complexes of cyano- or nitroformazans-as well as the electronic spectra of the complexes are discussed in relation to each other as well as that of the uncoordinated formazans.

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“…Balt and co-workers reported nickel and copper complexes with the (2-OHPh)NNC(Ph)NNHPh formazan derivative, which they tentatively defined as 5-membered formazanate chelate ring isomers. 54–56 In addition, alkali–metal formazanate complexes with four- and five-membered chelate rings have been reported recently by Otten and co-workers. 57 The same group also reported zinc complexes based on formazanates in which the ligand forms a 5-membered ring by bonding to the metal through an internal N atom.…”

Section: Resultsmentioning

confidence: 94%

Design and synthesis of a solution-processed redox-active bis(formazanate) zinc complex for resistive switching applications

Birara,

Saini,

Majumder

et al. 2023

Dalton Trans.

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Ammine[1-(2-hydroxyphenyl)-3,5-diphenylformazanato]nickel(II), [Ni(C19H14N4O)(NH3)], and [1-(2-hydroxyphenyl)-5-phenyl-3-(p-tolyl)formazanato](pyridine)nickel(II), [Ni(C5H5N)(C20H16N4O)]

Cited by 9 publications

References 1 publication

Formazanate Ligands as Structurally Versatile, Redox-Active Analogues of β-Diketiminates in Zinc Chemistry

Formazanate Ligands as Structurally Versatile, Redox-Active Analogues of β-Diketiminates in Zinc Chemistry

Transition Metal Complexes of 3-Cyano- and 3-Nitroformazans

Design and synthesis of a solution-processed redox-active bis(formazanate) zinc complex for resistive switching applications

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