Extracurricular laboratory:new discovery of (R)-[1,1′-Binaphthalene]-2,2′-diamine

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(Chemical Equation Presented) The synthesis of a new series of Lambda-type, D-Pi-A regioregular oligothiophenes is described. The simultaneous presence of the chiral centers and the Lambda-type structure disfavored the formation of centro-symmetrical dimeric assemblies. Hence, enhanced first hyperpolarizabilities betaHRS were measured in comparison with those of the corresponding monomers.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Simple exploration of (R)-[1,1′-Binaphthalene]-2,2′-diamine

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We demonstrate reversible RGB-color photocontrol of a chiral nematic liquid crystal (N*LC) by using newly synthesized closed- and open-type chiral dopants. The photoswitching elements in the dopants are azobenzene units on axially chiral binaphthyl cores. Owing to cis?trans photoisomerization of the azobenzene units, both closed- and open-type compounds showed higher solubility, larger helical twisting power (HTP), and larger changes in HTP than conventional chiral dopants in host LCs. Thus, even at very low dopant concentrations, we successfully controlled the chirality of the induced helical structure of the N*LCs. Consequently, the N*LCs reflected right- and left-handed circularly polarized light (CPL) under a light stimulus. In the N*LCs with closed-type chiral dopants, the RGB-color reflection was reversibly controlled within several seconds. Interestingly, the open-type chiral dopant reversibly inverted CPL with opposite handedness in the near and short-wave IR regions. These novel materials are expected to realize new applications and perspectives in color information and similar technologies.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Herein, we report the synthesis of C2-symmetric sulfonamides as homogeneous and heterogeneous organocatalysts and their application in the enantioselective conjugate 1,4-Michael addition of carbonylic nucleophiles to beta-nitrostyrene. Organocatalysts hydrogen bond to beta-nitrostyrene and enamine in the transition state, mimicking an enzyme leading to final products in high yields (up to 98%) and good enantioselectivities (up to 96%). In addition, these results were supported by density functional calculations.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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The synthesis of two 2-formylquinolines is reported via the Skraup method followed by SeO2 oxidation. Each aldehyde is condensed with (1R,2R)-diaminocyclohexane and (R)-BINAM, yielding four enantiomerically-pure bis(imine-quinoline) ligands. The neutral ligands are reacted with ZnCl 2 to give complexes with bis(bidentate) coordination of ZnCl 2 units. X-Ray structural characterization of three complexes shows them to have a single-stranded helical motif, with M helicity, except in one case where a 1: 1 mixture of M and P helices is seen. The ligands and complexes are further characterized spectroscopically by solution 1H and 13C NMR, UV-vis and ECD. The Royal Society of Chemistry.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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A highly efficient Cu-catalyzed dual C-S bonds formation reaction, proceeding in alcohol and water under air, is reported, in which inodorous stable Na2S2O3 is used as a sulfurating reagent. This powerful strategy provides a practical and efficient approach to construct thioethers, using readily available aromatic amines and alkyl halides as starting materials. Sensitive and synthetic useful functional groups could be tolerated. Furthermore, pharmaceuticals, glucose, an amino acid, and a chiral ligand are successfully furnished by this late-stage sulfuration strategy.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Chiral Ni(II)-1,1?-binaphthyl-2,2?-diimine complexes were found to be effective Lewis-acid catalysts for an asymmetric 1,3-dipolar cycloaddition reaction of N-benzylideneaniline N-oxide with 3-crotonoyl-2-oxazolidinone. In the presence of molecular sieves (4 A, when the chiral N,N? -bis(2,6-dichlorobenzylidene)-1,1?-binaphthyl-2,2?-diamine (BINIM-DC) and Ni(ClO4)2·6H2O were used to prepare the catalyst, up to 81% ee of the corresponding endo-cycloadduct was obtained with endo- selectivity (87:13, and up to 96:4). The use of N,N?-bis(3-chloro-substituted 2-hydroxybenzylidene) derivatives as ligands under similar conditions showed high exo-selecfivity (up to 95:5) with moderate enantioselectivity. Although almost no diastereoselectivity was observed, endo- and exo-cycloadducts were obtained with promising levels of enantioselectivity (up to > 98%) in the presence of catalysts, which were prepared from chiral BINIM-DC, NiBr2, and AgBF4, AgSbF6, or AgPF6.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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The dilithium diamides [{Li(thf)}2{C20H12(NR)2}] (R = SiMe3 1 or CH2But 2, thf = tetrahydrofuran) were prepared from R,S-2,2?-diamino-1,1?-binaphthyl, C20H12(NH2)2, via C20H12[N(H)SiMe3]2 or C20H12[NHC(O)But]2 and C20H12[N(H)CH2But]2, respectively, and were transformed into SiCl2[C20H12(NR)2] by treatment with SiCl4. The crystal structures of 1 and 2 were determined. They are monomers, having a Li(1)N(1)Li(2)N(2) buckled ring, with Li(1)-N(2) ca. 0.2 A shorter than Li(1)-N(1), the two groups R cis to one another, and N(1)-C(1) eta2 bonded to Li(1). The R and S enantiomers were similarly prepared and their optical stability was demonstrated by their hydrolysis to R- and S-C20H12(NH2)2, respectively. Evidence is provided for the structures of [M{C20H12[N(SiMe3)]2}] (M = Ge or Sn), obtained by conversion of the stannylene into the crystallographically characterised [{Sn[(NSiMe3)2C20H12](mu-O)} 3].

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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A dimeric proline derived diamidobinaphthyl dilithium salt represents the first example of a chiral main group metal based catalyst for asymmetric hydroamination/cyclisation reactions of aminoalkenes. The Royal Society of Chemistry 2006.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

More research is needed about 18741-85-0

The proportionality constant is the rate constant for the particular unimolecular reaction. the reaction rate is directly proportional to the concentration of the reactant. I hope my blog about 18741-85-0 is helpful to your research. Quality Control of: (R)-[1,1′-Binaphthalene]-2,2′-diamine

In homogeneous catalysis, the catalyst is in the same phase as the reactant. The number of collisions between reactants and catalyst is at a maximum.In a patent, 18741-85-0, name is (R)-[1,1′-Binaphthalene]-2,2′-diamine, introducing its new discovery. Quality Control of: (R)-[1,1′-Binaphthalene]-2,2′-diamine

Disclosed are carbenes of the general formula: and including salts thereof, and metal complexes thereof. The carbenes are useful in any reaction where carbenes and carbene-metal complexes are used. The carbenes disclosed herein are particularly useful in asymmetric catalysis.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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A new tunable laser based on a photoresponsive chiral liquid crystal emulsion is reported. Such a laser can be reversibly photo-tuned in a wide spectral range of 112 nm (566-678 nm), and it simultaneously possesses stable emission performance and quasi-continuous tunability. Typically, unlike the conventional liquid crystal laser, the proposed laser can be fabricated by simply coating the material on a single substrate, which will simplify the production process and broaden the application of liquid crystal laser. In addition, the mechanisms of tunability are explored on a molecular scale. The studies reveal that the molecular conformation transition of a photosensitive chiral switch during isomerization leads to changes in not only the molecular geometry and the direction of dipole moment, but also the molecular interactions and the miscibility of the materials. These changes cause the rearrangement of liquid crystals, thus rendering the variation of helical twisted power and achieving tuning on the photonic band-edge of the chiral liquid crystal, consequently forming a photo-tunable laser.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI