Synthesis and Characterization of Copper Complexes with the <i>N</i>‐(2,6‐Diisopropylphenyl)‐<i>N′</i>‐acylthiourea Ligands

Wang, Dan; Wu, Su‐Yun; Li, Haipu; Yang, Ying; Roesky, Herbert W.

doi:10.1002/ejic.201601451

Cited by 30 publications

(5 citation statements)

References 61 publications

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“…ese chemical shift changes are attributed to the copper(I) complexes formation, and similar results were found for related three-coordinate copper(I) complexes [33][34][35]. Intramolecular hydrogen-bonding between the coordinated halide ions and NH group was evidenced by X-ray structural analysis for several related complexes [37][38][39].…”

Section: Synthesissupporting

confidence: 74%

“…e reaction between copper(II) salts and, more generally, the versatile acylthiourea compounds leads to a variety of copper(I) complexes, including tetra-and threecoordinate mononuclear complexes, halide-bridged dinuclear complexes, or cluster-type polynuclear complexes, depending on the halide type and reaction conditions [33][34][35][36][37][38][39]. e complexity of the redox reaction between the copper(II) salts and thiourea compounds results from the combination between the versatility of the acylthiourea ligands and the coordination flexibility of the copper(I) ion.…”

Section: Introductionmentioning

confidence: 99%

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Discotic Liquid Crystals Based on Cu(I) Complexes with Benzoylthiourea Derivatives Containing a Perfluoroalkyl Chain

Iliş

Cı̂rcu

2018

Journal of Chemistry

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Mesomorphic three-coordinate copper(I) complexes ([Cu(BTU) 2 X], where X � Cl or Br) based on a new N-benzoylthiourea (BTU) ligand with two decyloxy and one perfluorooctyl groups at its periphery were designed and prepared. e BTU ligand coordinates via the S atom in a neutral monodentate fashion as confirmed by IR and NMR spectroscopy data. e liquid crystalline behavior of these copper(I) complexes was investigated by a combination of polarized optical microscopy (POM), differential scanning calorimetry (DSC), and X-ray diffraction analysis (XRD), while their thermal stability was studied by thermogravimetric analysis (TGA). ese new copper(I) complexes have mesomorphic properties and exhibit a hexagonal columnar mesophase over a large temperature range, more than 100°C.

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Section: Synthesissupporting

confidence: 74%

Section: Introductionmentioning

confidence: 99%

Discotic Liquid Crystals Based on Cu(I) Complexes with Benzoylthiourea Derivatives Containing a Perfluoroalkyl Chain

Iliş

Cı̂rcu

2018

Journal of Chemistry

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“…2.4 Å). Structurally similar Cu (I) complexes have been reported for dimethylthiourea and several acylthiourea derivatives. − These were either prepared from the respective thioureas and CuCl or by reduction of CuCl 2 with an excess of thiourea. Evidently here too, the arenesulfonylthiourea has reduced the copper(II) precursor and binds to the metal as a neutral sulfur donor ligand.…”

Section: Resultssupporting

confidence: 54%

S,O or S,N Coordination? Unraveling the Coordination Modes of Arenesulfonylthiourea Ligands

Beele

Bill

Mohr

2022

Crystal Growth & Design

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Two arenesulfonylthioureas were prepared and reacted with a variety of transition-metal salts, including Ni(OAc) 2 , Co(OAc) 2 , Cu(OAc) 2 , CuCl 2 , AgNO 3 , and Zn(OAc) 2 . In all cases, complexes containing the arenesulfonylthioureas acting as monoanionic [S,N] − chelating ligands were isolated and characterized by X-ray diffraction, NMR spectroscopy, and magnetic measurements. Copper(I) and silver(I) complexes exist as hexanuclear [M 6 L 6 ] clusters, which are luminescent in the solid state and solution.

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“…It is well documented that the complex redox reaction of N -acylthiourea derivatives and copper(II) salts produce mono-, di-, or polynuclear species with halide or S -thioureato-bridges in which the copper(II) ion is reduced to copper(I). The geometry around the copper(I) could be either plan-trigonal for three-coordinate species or tetrahedral for tetra-coordinate species, proving the versatility of these organic compounds and the coordination flexibility of the copper(I) ion [ 60 , 61 , 62 , 63 , 64 , 65 , 66 ]. For example, there is a growing number of reported three-coordinate copper(I) complexes with acylthiourea ligands in which the planar trigonal geometry with a typical butterfly-like structure is stabilized by hydrogen bonding involving the halide ligand, the carbonyl, and the NH groups [ 67 , 68 , 69 , 70 , 71 ].…”

Section: Resultsmentioning

confidence: 99%

Columnar Liquid Crystals of Copper(I) Complexes with Ionic Conductivity and Solid State Emission

et al. 2023

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Two neutral copper(I) halide complexes ([Cu(BTU)2X], X = Cl, Br) were prepared by the reduction of the corresponding copper(II) halides (chloride or bromide) with a benzoylthiourea (BTU, N-(3,4-diheptyloxybenzoyl)-N′-(4-heptadecafluorooctylphenyl)thiourea) ligand in ethanol. The two copper(I) complexes show a very interesting combination of 2D supramolecular structures, liquid crystalline, emission, and 1D ionic conduction properties. Their chemical structure was ascribed based on ESI–MS, elemental analysis, IR, and NMR spectroscopies (1H and 13C), while the mesomorphic behavior was analyzed through a combination of differential scanning calorimetry (DSC), polarizing optical microscopy (POM), and powder X-ray diffraction (XRD). These new copper(I) complexes have mesomorphic properties and exhibit a hexagonal columnar mesophase over a large temperature range, more than 100 K, as evidenced by DSC studies and POM observations. The thermogravimetric analysis (TG) indicated a very good thermal stability of these samples up to the isotropization temperatures and over the whole temperature range of the liquid crystalline phase existence. Both complexes displayed a solid-state emission with quantum yields up to 8% at ambient temperature. The electrical properties of the new metallomesogens were investigated by variable temperature dielectric spectroscopy over the entire temperature range of the liquid crystalline phase. It was found that the liquid crystal phases favoured anhydrous proton conduction provided by the hydrogen-bonding networks formed by the NH…X moieties (X = halide or oxygen) of the benzoylthiourea ligand in the copper(I) complexes. A proton conductivity of 2.97 × 10−7 S·cm−1 was achieved at 430 K for the chloro-complex and 1.37 × 10−6 S·cm−1 at 440K for the related bromo-complex.

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Synthesis and Characterization of Copper Complexes with the N‐(2,6‐Diisopropylphenyl)‐N′‐acylthiourea Ligands

Cited by 30 publications

References 61 publications

Discotic Liquid Crystals Based on Cu(I) Complexes with Benzoylthiourea Derivatives Containing a Perfluoroalkyl Chain

Discotic Liquid Crystals Based on Cu(I) Complexes with Benzoylthiourea Derivatives Containing a Perfluoroalkyl Chain

S,O or S,N Coordination? Unraveling the Coordination Modes of Arenesulfonylthiourea Ligands

Columnar Liquid Crystals of Copper(I) Complexes with Ionic Conductivity and Solid State Emission

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