An efficient access to the novel 5-(aryl)amino-1,2,3-triazole-containing 2,1,3-benzothiadiazole derivatives has been developed. The method is based on 1,3-dipolar azide-nitrile cycloaddition followed ...by Buchwald-Hartwig cross-coupling to afford the corresponding
-aryl and
,
-diaryl substituted 5-amino-1,2,3-triazolyl 2,1,3-benzothiadiazoles under NHC-Pd catalysis. The one-pot diarylative Pd-catalyzed heterocyclization opens the straightforward route to triazole-linked carbazole-benzothiadiazole D-A systems. The optical and electrochemical properties of the compound obtained were investigated to estimate their potential application as emissive layers in OLED devises. The quantum yield of photoluminescence (PLQY) of the synthesized D-A derivatives depends to a large extent on electron-donating strengths of donor (D) component, reaching in some cases the values closed to 100%. Based on the most photoactive derivative and wide bandgap host material mCP, a light-emitting layer of OLED was made. The device showed a maximum brightness of 8000 cd/m
at an applied voltage of 18 V. The maximum current efficiency of the device reaches a value of 3.29 cd/A.
Protective SiO2 coating deposited to iron microparticles is highly demanded both for the chemical and magnetic performance of the latter. Hydrolysis of tetraethoxysilane is the crucial method for ...SiO2 deposition from a solution. The capabilities of this technique have not been thoroughly studied yet. Here, two factors were tested to affect the chemical composition and the thickness of the SiO2 shell. It was found that an increase in the hydrolysis reaction time thickened the SiO2 shell from 100 to 200 nm. Moreover, a decrease in the acidity of the reaction mixture not only thickened the shell but also varied the chemical composition from SiO3.0 to SiO8.6. The thickness and composition of the dielectric layer were studied by scanning electron microscopy and energy-dispersive X-ray analysis. Microwave permeability and permittivity of the SiO2-coated iron particles mixed with a paraffin wax matrix were measured by the coaxial line technique. An increase in thickness of the silica layer decreased the real quasi-static permittivity. The changes observed were shown to agree with the Maxwell Garnett effective medium theory. The new method developed to fine-tune the chemical properties of the protective SiO2 shell may be helpful for new magnetic biosensor designs as it allows for biocompatibility adjustment.
An efficient method of accessing new CF3-containing spiro-indene-proline derivatives has been developed based on a Cp*Rh(III)-catalyzed tandem C-H activation/3+2–annulation reaction of ...5-aryl-2-(trifluoromethyl)-3,4-dihydro-2H-pyrrole-2-carboxylates with alkynes. An important feature of this spiro annulation process is the feasibility of dehydroproline moiety to act as a directing group in the selective activation of the aromatic C-H bond.
A convenient pathway to a new series of α-CF3-substituted α-amino acid derivatives bearing pharmacophore isoquinolone core in their backbone has been developed. The method is based on 4+2-annulation ...of N-(pivaloyloxy) aryl amides with orthogonally protected internal acetylene-containing α-amino carboxylates under Rh(III)-catalysis. The target annulation products can be easily transformed into valuable isoquinoline derivatives via a successive aromatization/cross-coupling operation.
An efficient method for the selective preparation of trifluoromethyl-substituted azepin-2-carboxylates and their phosphorous analogues has been developed via Cu(I)-catalyzed tandem ...amination/cyclization reaction of functionalized allenynes with primary and secondary amines.
Three new benzothiadiazole (BTD)-containing luminophores with different configurations of aryl linkers have been prepared via Pd-catalyzed cross-coupling Suzuki and Buchwald-Hartwig reactions. ...Photophysical and electroluminescent properties of the compounds were investigated to estimate their potential for optoelectronic applications. All synthesized structures have sufficiently high quantum yields in film. The BTD with aryl bridged carbazole unit demonstrated the highest electrons and holes mobility in a series. OLED with light-emitting layer (EML) based on this compound exhibited the highest brightness, as well as current and luminous efficiency. The synthesized compounds are not only luminophores with a high photoluminescence quantum yield, but also active transport centers for charge carriers in EML of OLED devices.
A series of new orthogonally protected α‐CF3‐substituted α‐amino carboxylates, and α‐amino phosphonates decorated with pharmacophore isoquinolone core has been elaborated through the ...Rh(III)‐catalyzed C−H activation/annulation of aryl hydroxamates with propargyl‐containing α‐amino acid derivatives and their phosphorus analogues.
Novel α‐CF3‐containing isoquinolone derivatives have been synthesized throgh the Rh(III)‐catalyzed C−H activation/annulation of aryl hydroxamates with α‐CF3‐α‐propargyl‐α‐amino carboxylates/phosphonates.
An efficient access to the novel 5-(het)arylamino-1,2,3-triazole derivatives has been developed. The method is based on Buchwald-Hartwig cross-coupling reaction of 5-Amino or 5-Halo-1,2,3-triazoles ...with (het)aryl halides and amines, respectively. As result, it was found that palladium complex (THP-Dipp)Pd(cinn)Cl bearing expanded-ring
-heterocyclic carbene ligand is the most active catalyst for the process to afford the target molecules in high yields.
An efficient way to access highly functionalized proline derivatives was developed based on a Cu(I)-catalyzed reaction between CF3-substituted allenynes and tosylazide, which involved a cascade of 3 ...+ 2-cycloaddition/ketenimine and a rearrangement/Alder-ene cyclization to afford the new proline framework with a high diastereoselectivity.
An efficient strategy for the preparation of a novel series of benzothiadiazole‐containing isoquinoline‐bridged D‐A compounds based on Cp*Rh(III)‐catalyzed redox‐neutral annulation of ...N‐(pivaloyloxy)‐benzamides with 4‐ethynyl‐7‐(p‐methoxyphenyl)‐2,1,3‐benzothiadiazole as a key step followed by the installation of donor units, such as diphenylamine, carbazole, and dihydrodibenzoazepine, by aromatization and Suzuki coupling reactions, has been developed. An initial photophysical, electrochemical and DFT investigations of the selected products have been performed.
An efficient access to new benzothiadiazole‐based compounds of donor‐acceptor type has been developed through the Rh(III)‐catalyzed redox‐neutral annulation of (het)aryl amides with 4‐ethynyl‐7‐(p‐methoxyphenyl)‐2,1,3‐benzothiadiazole as a key step followed by the installation of typical donor units. The resulted D‐A systems with extended π‐conjugation are of great interest for designing of optoelectronics with specified properties.
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