Syntheses, characterization, density functional theory calculations, and activity of tridentate SNS zinc pincer complexes based on bis-imidazole or bis-triazole precursors

Miecznikowski, John R.; Lo, Wayne; Lynn, Matthew A.; Jain, Swapan S.; Keilich, Lauren C.; Kloczko, Nathan F.; O’Loughlin, Brianne E.; DiMarzio, Amanda P.; Foley, Kathleen M.; Lisi, George P.; Kwiecien, Daniel J.; Butrick, Elizabeth E.; Powers, Erin; Al-Abbasee, Raed

doi:10.1016/j.ica.2011.12.047

Cited by 25 publications

(19 citation statements)

References 44 publications

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“…Many N,N,S tridentate zinc complexes were explored by paying attention to both structural and spectroscopic behavior. More rarely, S,N,S tridentate pincer ligands with zinc salts [124] were explored, mainly screened for their reactivity and/or catalytic activity rather than for the PL properties. On the other hand, a few significative examples of mixed N,S,O binding sites were recently proposed.…”

Section: Nitrogen Oxygen and Sulfur Binding Sitesmentioning

confidence: 99%

The Role of Zinc(II) Ion in Fluorescence Tuning of Tridentate Pincers: A Review

Diana

Panunzi

2020

Molecules

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Tridentate ligands are simple low-cost pincers, easy to synthetize, and able to guarantee stability to the derived complexes. On the other hand, due to its unique mix of structural and optical properties, zinc(II) ion is an excellent candidate to modulate the emission pattern as desired. The present work is an overview of selected articles about zinc(II) complexes showing a tuned fluorescence response with respect to their tridentate ligands. A classification of the tridentate pincers was carried out according to the binding donor atom groups, specifically nitrogen, oxygen, and sulfur donor atoms, and depending on the structure obtained upon coordination. Fluorescence properties of the ligands and the related complexes were compared and discussed both in solution and in the solid state, keeping an eye on possible applications.

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Section: Nitrogen Oxygen and Sulfur Binding Sitesmentioning

confidence: 99%

The Role of Zinc(II) Ion in Fluorescence Tuning of Tridentate Pincers: A Review

Diana

Panunzi

2020

Molecules

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“…[17][18][19]34,35 Additionally, thione and bisthione ligands have been successfully applied in catalysis. [38][39][40] In this regard, the only metal complexes containing pincer-type ligands containing NHTs are the copper(I), copper(II), and zinc (II) compounds reported by Miecznikowski and coworkers [41][42][43][44][45] and the rhodium(I) and iridium(I) derivatives synthesized by Jia, Huang and Jin. [38][39][40] In this regard, the only metal complexes containing pincer-type ligands containing NHTs are the copper(I), copper(II), and zinc (II) compounds reported by Miecznikowski and coworkers [41][42][43][44][45] and the rhodium(I) and iridium(I) derivatives synthesized by Jia, Huang and Jin.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, photophysical properties, and catalytic activity of an SCS bis(N-heterocyclic thione) (SCS-NHT) Pd pincer complex

et al. 2015

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Treatment of 1,3-bis(3'-butylimidazolyl-1'-yl)benzene diiodide with elemental sulfur in the presence of a base produced a bis(N-heterocyclic thione) (NHT) pincer ligand precursor. Its reaction with PdCl2(CH3CN)2 produced chloro[1,3-bis(3'-butylimidazole-2'-thione-κ-S)benzene-κ-C]palladium(ii), a 6,6-fused ring SCS-NHT palladium pincer complex. This air stable compound is, to our knowledge, the first SCS pincer complex that utilizes N-heterocyclic thione (NHT) donor groups. The molecular structures of the ligand precursor and the palladium complex were determined by X-ray crystallography and computational studies provided insight into the interconversion between its rac and meso conformations. The photophysical properties of the complex were established, and its catalytic activity in Suzuki, Heck, and Sonogashira cross-coupling reactions was evaluated.

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“…Pincer ligand precursors can be tuned electronically by including electron-withdrawing or electrondonating groups, and sterically by including bulky substituents (van Koten & Milstein, 2013; van Koten & Gossage, 2015). Previously, Miecznikowski and co-workers prepared tridentate pincer ligand precursors with sulfur, nitrogen and sulfur donor atoms (Miecznikowski et al, 2011(Miecznikowski et al, , 2012) (Fig. 1).…”

Section: Chemical Contextmentioning

confidence: 99%

“…The pincer ligand precursors were metallated with zinc(II)chloride in order to prepare zinc(II) model complexes of liver alcohol dehydrogenase (Miecznikowski et al, 2011(Miecznikowski et al, , 2012 (see reaction scheme below). In 2012, Miecznikowski and co-workers reported the preparation of a pincer ligand precursor based on a bis-triazole starting material that could coordinate via sulfur, nitrogen, and sulfur donor atoms or via three nitrogen donor atoms (Miecznikowski et al, 2012). It was reported that the novel ambidentate tridentate pincer ligand precursor was metallated with ZnCl 2 to give a new tridentate NNNbound pincer zinc(II) pincer complex: dichloro(3-N,N,N)- [2,6-bis(3-[N-butyl]triazol-5-thione-1-yl)]pyridinezinc(II), [(NNN)ZnCl 2 ] (Fig.…”

Section: Chemical Contextmentioning

confidence: 99%

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Crystal structure and spectroscopic properties of aquadichlorido{1,1′-[(pyridine-2,6-diyl-κN)bis(methylene)]bis(4-butyl-4,5-dihydro-1H-1,2,4-triazole-5-thione-κN ²)}cobalt(II)

et al. 2020

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The structure of the title compound, [CoCl2(C19H27N7S2)(H2O)], at 173 K has monoclinic (C2/c) symmetry. We report here the synthesis, single-crystal structure, electrospray mass spectrum and NMR spectroscopy of a new six-coordinate cobalt(II) pincer complex. The pincer ligand, in this complex, which is novel, coordinates via three nitrogen atoms (two triazole and one pyridine). The ligand is ambidentate and can coordinate via three nitrogen atoms or two sulfur and one nitrogen atoms. The cobalt(II) metal center has pseudo-octahedral geometry and based on the single-crystal structure, the pincer ligand coordinates in a meridional fashion with the metal and adjacent six-membered ring ligands all in a similar plane and forming two slightly distorted boat configurations. The other two coordinated monodentate ligands are one water molecule and two chloride ions with four cobalt(II) complexes in the unit cell. The asymmetric unit of the complex is comprised of half the pyridine ring and water molecule with the CoII atom at the center of the pincer situated about a twofold axis. The Co—N, Co—O, and Co—Cl bond lengths are consistent with single bonds. In the crystal, the complex forms a three-centre bifurcated weak hydrogen-bonding interaction with a chlorine ion, forming one intermolecular interaction with the pincer group and a water molecule and a second intramolecular interaction with a C—H group within the pincer group. Crystal packing is also highlighted with C 2 2(6)>a<a infinite chains forming along [001] supported by R 2 2(8)>a>a ring motifs, forming a three-dimensional supramolecular network structure. While some stacking of the pyridine rings in the unit cell is observed, there are no relevant π–π interactions in the crystal packing. The 1H and 13C{1H} NMR spectra of the complex are consistent with a plane of symmetry being present. The electrospray mass spectrum, which was collected in positive ion mode, showed the loss of one water molecule and one chloride ligand from the complex. In the future, we plan to screen this cobalt(II) complex for electrocatalysis reactivity.

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Syntheses, characterization, density functional theory calculations, and activity of tridentate SNS zinc pincer complexes based on bis-imidazole or bis-triazole precursors

Cited by 25 publications

References 44 publications

The Role of Zinc(II) Ion in Fluorescence Tuning of Tridentate Pincers: A Review

The Role of Zinc(II) Ion in Fluorescence Tuning of Tridentate Pincers: A Review

Synthesis, characterization, photophysical properties, and catalytic activity of an SCS bis(N-heterocyclic thione) (SCS-NHT) Pd pincer complex

Crystal structure and spectroscopic properties of aquadichlorido{1,1′-[(pyridine-2,6-diyl-κN)bis(methylene)]bis(4-butyl-4,5-dihydro-1H-1,2,4-triazole-5-thione-κN ²)}cobalt(II)

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Syntheses, characterization, density functional theory calculations, and activity of tridentate SNS zinc pincer complexes based on bis-imidazole or bis-triazole precursors

Cited by 25 publications

References 44 publications

The Role of Zinc(II) Ion in Fluorescence Tuning of Tridentate Pincers: A Review

The Role of Zinc(II) Ion in Fluorescence Tuning of Tridentate Pincers: A Review

Synthesis, characterization, photophysical properties, and catalytic activity of an SCS bis(N-heterocyclic thione) (SCS-NHT) Pd pincer complex

Crystal structure and spectroscopic properties of aquadichlorido{1,1′-[(pyridine-2,6-diyl-κN)bis(methylene)]bis(4-butyl-4,5-dihydro-1H-1,2,4-triazole-5-thione-κN 2)}cobalt(II)

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Crystal structure and spectroscopic properties of aquadichlorido{1,1′-[(pyridine-2,6-diyl-κN)bis(methylene)]bis(4-butyl-4,5-dihydro-1H-1,2,4-triazole-5-thione-κN ²)}cobalt(II)