Category: 1111-67-7

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CuSCN thin films (optimized previously for perovskite photovoltaics) are deposited on glass, F:SnO2 (FTO), Au, glass-like carbon (GC), and reduced graphene oxide (rGO). They exhibit capacitive charging in an electrochemical window from ca. -0.3 to 0.2 V vs Ag/AgCl. Outside this window, CuSCN film is prone to chemical and structural changes. Anodic breakdown (at ca. 0.5 V) causes restructuring into submicrometer particles and denuding of the substrate. The natural p-doping is demonstrated by both the Hall effect and Mott-Schottky plots from electrochemical impedance. The corresponding flatband potentials (in V vs Ag/AgCl) varied with the substrate type as follows: 0.12 V (CuSCN@FTO), 0.08 V (CuSCN@Au), -0.02 V (CuSCN@GC), and 0.00 V (CuSCN@rGO). The acceptor concentrations determined from electrochemical impedance spectroscopy are by orders of magnitude larger than those from electrical conductivity and the Hall effect, the latter being regarded correct. Raman spectra confirm that thiocyanate is the dominating structural motif over the isomeric isothiocyanate. In situ Raman spectroelectrochemistry discloses substrate-specific intensity changes upon electrochemical charging. The blocking function is tested by a newly designed redox probe, Ru(NH3)63+/2+. It not only has the appropriate redox potential for testing of the CuSCN films but also avoids complications of the standard “ferrocyanide test” which is normally used for this purpose. The perovskite solar cells exhibit better solar conversion efficiency, fill factor, and open-circuit voltage for the rGO-containing devices, which is ascribed to a larger driving force for the hole injection from CuSCN into rGO.

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Reference：
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

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Copper(I) thiocyanate (CuSCN) has been drawing much attention in optoelectronics due to its exceptional optical and electrical properties, as well as its processing versatility. The first organic light-emitting diodes (OLEDs) integrated with electro-deposited CuSCN crystalline thin films based on aqueous electrolyte were fabricated. With precisely tuned deposition parameters, the CuSCN thin films with satisfactory surface roughness and sufficient grain density were realized. We found that the driving voltage (voltage at a current density of 100 mA/cm2) and turn-on voltage of OLEDs using CuSCN as the hole injection layer (HIL) can be reduced by 1.41 and 1.79 V, respectively, compared with devices using vacuum-deposited hole injecting transition metal oxide molybdenum trioxide (MoO3). Moreover, the fabricated OLEDs also demonstrated considerably mitigated efficiency roll-off. Optical and energetic analyses were conducted to investigate the characteristics and enhancement mechanisms. Efficient hole-injection, electron blocking, improved charge balance, enhanced optical properties and good compatibility of electro-deposited CuSCN with thermally evaporated organic systems were found to be the primary contributors for the performance improvements of the OLEDs.

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Reference：
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

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A copper-catalyzed C(sp3)-Si cross-coupling of aliphatic C(sp3)-I electrophiles using a Si-B reagent as the silicon pronucleophile is reported. The reaction involves an alkyl radical intermediate that also engages in 5-exo-trig ring closures onto pendant alkenes prior to the terminating C(sp3)-Si bond formation. Several Ueno-Stork-type precursors cyclized with excellent diastereocontrol in good yields. The base-mediated release of the silicon nucleophile and the copper-catalyzed radical process are analyzed by quantum-chemical calculations, leading to a full mechanistic picture.

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Reference：
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

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This study reports the development of copper(I) thiocyanate (CuSCN) hole-transport layers (HTLs) processed from aqueous ammonia as a novel alternative to conventional n-alkyl sulfide solvents. Wide bandgap (3.4?3.9 eV) and ultrathin (3?5 nm) layers of CuSCN are formed when the aqueous CuSCN?ammine complex solution is spin-cast in air and annealed at 100 C. X-ray photoelectron spectroscopy confirms the high compositional purity of the formed CuSCN layers, while the high-resolution valence band spectra agree with first-principles calculations. Study of the hole-transport properties using field-effect transistor measurements reveals that the aqueous-processed CuSCN layers exhibit a fivefold higher hole mobility than films processed from diethyl sulfide solutions with the maximum values approaching 0.1 cm2 V?1 s?1. A further interesting characteristic is the low surface roughness of the resulting CuSCN layers, which in the case of solar cells helps to planarize the indium tin oxide anode. Organic bulk heterojunction and planar organometal halide perovskite solar cells based on aqueous-processed CuSCN HTLs yield power conversion efficiency of 10.7% and 17.5%, respectively. Importantly, aqueous-processed CuSCN-based cells consistently outperform devices based on poly(3,4-ethylenedioxythiophene) polystyrene sulfonate HTLs. This is the first report on CuSCN films and devices processed via an aqueous-based synthetic route that is compatible with high-throughput manufacturing and paves the way for further developments.

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Reference：
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

The prevalence of solvent effects in heterogeneous catalysis in condensed media has motivated developing quantitative kinetic, and theoretical assessments of solvent structures and their interactions with reaction intermediates and transition states. 1111-67-7, Name is Cuprous thiocyanate, belongs to copper-catalyst compound, is a common compound. Reference of 1111-67-7In an article, once mentioned the new application about 1111-67-7.

Reaction of copper(i) thiocyanate with 1,1?-bis(di-tert- butylphosphino) ferrocene (dtbpf) in a 2:1 molar ratio in DCM-MeOH (50:50 V/V) afforded a tetranuclear copper(i) complex [Cu4(mu3-SCN) 4(kappa1-P,P-dtbpf)2] (1) with a cubane-like structure. Complex 1 was shown to be an efficient catalyst in comparison to CuI in the Sonogashira reaction. The coupling products were obtained in high yields by using Pd loadings of 0.2 mol% as well as complex-1 of 0.1 mol%.

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Reference：
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

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The new area of lithio(thiocyanato)cuprates has been developed. Using inexpensive, stable and safe CuSCN for their preparation, these complexes revealed Lipshutz-type dimeric motifs with solvent-dependent point group identities; planar, boat-shaped and chair shaped conformers are seen in the solid state. In solution, both Lipshutz-type and Gilman structures are clearly seen. Since the advent in 2007 of directed ortho cupration, effort has gone into understanding the structure-reactivity effects of amide ligand variation in and alkali metal salt abstraction from Lipshutz-type cuprates such as (TMP)2Cu(CN)Li2(THF) 1 (TMP = 2,2,6,6-tetramethylpiperidide). The replacement of CN- with SCN- is investigated presently as a means of improving the safety of lithium cuprates. The synthesis and solid state structural characterization of reference cuprate (TMP)2Cu(CN)Li2(THP) 8 (THP = tetrahydropyran) precedes that of the thiocyanate series (TMP)2Cu(SCN)Li2(L) (L = OEt29, THF 10, THP 11). For each of 9-11, preformed TMPLi was combined with CuSCN (2 : 1) in the presence of sub-stoichiometric Lewis base (0.5 eq. wrt Li). The avoidance of Lewis basic solvents incurs formation of the unsolvated Gilman cuprate (TMP)2CuLi 12, whilst multidimensional NMR spectroscopy has evidenced the abstraction of LiSCN from 9-11 in hydrocarbon solution and the in situ formation of Gilman reagents. The synthetic utility of 10 is established in the selective deprotometalation of chloropyridine substrates, including effecting transition metal-free homocoupling in 51-69% yield.

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Reference：
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

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The present application is directed to a coating composition comprising a ceramic binder and inorganic copper compound particles. Generally, the inorganic copper compound particles have a median particle size of less than 5 micrometers. In some embodiments, the particles have a median particle size of greater than 1 micrometer. The inorganic copper compound particles may be non-photocatalytic. The coating may also be placed on a structural layer.

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Reference：
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

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Reference：
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

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The versatile coordination behavior of the PNP ligands 1A (2,6-bis[(di-tert-butylphosphino)methyl]pyridine) and 1B (2,6- bis[(diphenylphosphino)methyl]pyridine) to CuI is described, whereby a hemilabile interaction of the pyridine N-donor atom to the copper center resulted in a rare T-shaped complex with 1A, while with 1B also a tetracoordinated species could be isolated. Theoretical calculations support the weak interaction of the pyridine N donor in 1A with the Cu center.

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Reference：
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

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Reaction of copper(I) thiocyanate and triphenylphosphane with the bidentate Schiff base N,N?-bis(trans-2-nitrocinnamaldehyde)ethylenediamine {Nca2en, (1); systematic name (1E,1?E,2E,2?E)-N,N?-(ethane-1,2-diyl)bis[3-(2-nitrophenyl)prop-2-en-1-imine]}, C20H18N4O4, in a 1:1:1 molar ratio in acetonitrile resulted in the formation of the complex {(1E,1?E,2E,2?E)-N,N?-(ethane-1,2-diyl)bis[3-(2-nitrophenyl)prop-2-en-1-imine]-kappa2 N,N?}(thiocyanato-kappaN)(triphenylphosphane-kappaP)copper(I)], [Cu(NCS)(C20H18N4O4)(C18H15P)] or [Cu(NCS)(Nca2en)(PPh3)], (2). The Schiff base and copper(I) complex have been characterized by elemental analyses, IR, electronic and 1H NMR spectroscopy, and X-ray crystallography [from synchrotron data for (1)]. The molecule of (1) lies on a crystallographic inversion centre, with a trans conformation for the ethylenediamine unit, and displays significant twists from coplanarity of its nitro group, aromatic ring, conjugated chain and especially ethylenediamine segments. It acts as a bidentate ligand coordinating via the imine N atoms to the CuI atom in complex (2), in which the ethylenediamine unit necessarily adopts a somewhat flattened gauche conformation, resulting in a rather bowed shape overall for the ligand. The NCS- ligand is coordinated through its N atom. The geometry around the CuI atom is distorted tetrahedral, with a small N-Cu-N bite angle of 81.56(12) and an enlarged opposite angle of 117.29(9) for SCN-Cu-P. Comparisons are made with the analogous Schiff base having no nitro substituents and with metal complexes of both ligands.

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Reference：
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”