5326-53-4

Usage

Uses

Used in Optoelectronic Materials:
4,4''-Azobiphenyl is used as a key component in the development of optoelectronic materials due to its reversible photoisomerization property, which allows for the manipulation of its molecular structure through light exposure. This feature is crucial for creating materials that can interact with light and change their properties accordingly, such as in optical switches and sensors.
Used in Molecular Switches:
As a molecular switch, 4,4''-Azobiphenyl is utilized for its ability to undergo structural changes in response to light, enabling the control of molecular functions and interactions. This application is vital in the development of smart materials and systems that can respond to external stimuli, such as light, and perform specific tasks or functions.
Used in Liquid Crystals and Dyes:
4,4''-Azobiphenyl is used as a building block in the synthesis of liquid crystals and dyes, where its photoisomerization property contributes to the unique optical and electronic characteristics of these materials. This makes it valuable in the production of displays, sensors, and other optoelectronic devices that require tunable optical properties.
Used in Nanotechnology:
In the field of nanotechnology, 4,4''-Azobiphenyl is used as a component in the development of molecular-scale devices and systems. Its ability to change structure upon light exposure makes it a promising candidate for creating nanoscale machines and devices that can perform specific functions or respond to environmental changes at a very small scale.

InChI:InChI=1/C24H18N2/c1-3-7-19(8-4-1)21-11-15-23(16-12-21)25-26-24-17-13-22(14-18-24)20-9-5-2-6-10-20/h1-18H/b26-25+

Upstream product

• 4088-58-8 4,4'-hydrazodibiphenyl 
• 92-93-3 1-phenyl-4-nitrobenzene 
• 1227476-15-4 Azobenzene 
• 71-43-2 benzene 
• 7466-42-4 4-phenylazobenzene 
• 31656-91-4 4-azidobiphenyl 
• 67-56-1 methanol 
• 92-67-1 4-phenylalanine 
• 546-67-8 lead(IV) tetraacetate 
• 7647-01-0 hydrogenchloride 
• 7446-70-0 aluminium trichloride 
• 17082-12-1 trans-azobenzene 
• 7334-12-5 1,2-di([1,1'-biphenyl]-4-yl)diazene oxide 
• 60-29-7 diethyl ether 

Downstream Products

• 92-67-1 4-phenylalanine 
• 92-69-3 4-Phenylphenol 
• 92-96-6 N,N'-bis-biphenyl-4-yl-thiourea 
• 17082-80-3 1.2.4.5-Tetrakis-biphenyl-4-yl-3.3.6.6-tetraphenyl-1.2.4.5-tetraaza-3.6-disila-cyclohexan 

Relevant academic research and scientific papers

Ruthenium porphyrins with axial π-conjugated arylamide and arylimide ligands

A series of ruthenium porphyrins [RuIV(por)(NHY)2] and [RuVI(por)(NY)2] bearing axially coordinated π-conjugated arylamide and arylimide ligands, respectively, have been synthesized. The crystal structures of [RuIV(tmp)(NHY)2] (tmp=5,10,15,20-tetramesitylporphyrinato(2-)) with Y=4-methoxy-biphenyl-4-yl (Ar-Ar-p-OMe), 4-chloro-biphenyl-4-yl (Ar-Ar-p-Cl), and 9,9-dibutyl-fluoren-2-yl (Ar^Ar) show axial Ru-N(arylamide) distances of 1.978(4), 1.971(6), and 1.985(13) A, respectively. [RuIV(tmp)(NH{Ar^Ar})2] is an example of metalloporphyrins that bind an arylamide ligand featuring a co-planar biphenyl unit. The [RuIV(por)(NHY)2] complexes show a quasi-reversible reduction couple or irreversible reduction wave attributed to RuIV→RuIII with Epc from -1.06 to -1.40 V versus Cp2Fe+/0 and an irreversible oxidation wave with Epa from -0.04 to 0.19 V versus Cp 2Fe+/0. Reaction of the [RuIV(por)(NHY) 2] with bromine afforded [RuIV(por)(NHY)Br]. PhI(OAc) 2 oxidation of the [RuIV(por)(NHY)2] gave [RuVI(por)(NY)2]; the latter can be prepared from reaction of [RuII(por)(CO)] with aryl azides N3Y. The crystal structure of [RuVI(tmp)(N{Ar-Ar-p-OMe})2] features Ru-N(arylimide) distances of 1.824(5) and 1.829(5) A. Alkene aziridination and C-H amination catalyzed by [RuII(tmp)(CO)]+π-conjugated aryl azides , or mediated by [RuVI(por)(NY)2] with Y=biphenyl-4-yl (Ar-Ar) and Ar-Ar-p-Cl, gave aziridines and amines in moderate yields. The electronic structure of [RuVI(por)(NY)2] was examined by DFT calculations.

One-pot procedures for the formation of secondary aryl amines from nitro aryls

Strategies for the one-pot formation of secondary aryl amines from the corresponding nitro aryls by utilizing reductive amination procedures are discussed. The extension of this chemistry where a Suzuki-Miyaura cross-coupling is conducted between a boronic acid and bromonitrobenzene prior to the reductive amination in one-pot is also presented. Georg Thieme Verlag Stuttgart, New York.

Ruthenium nanoparticle-catalyzed, controlled and chemoselective hydrogenation of nitroarenes using ethanol as a hydrogen source

This communication describes a ruthenium nanoparticle-catalyzed reduction of nitroarenes giving azoxyarenes, azoarenes, or anilines in good to excellent yields using ethanol as a hydrogen source. Copyright

Facile synthesis of azo compounds from aromatic nitro compounds using magnesium and triethylammonium formate

Magnesium/triethylammonium formate is a convenient reagent for the reduction of aromatic nitro compounds to corresponding symmetrically substituted azo compounds. Various azo compounds containing additional reducible substituents, including halogen, nitrile, acid, phenol, ester, and methoxy functions, have been synthesized in a single step by the use of this reagent. The conversion is reasonably fast, clean, high yielding, and occurs at room temperature in methanol.

The synthesis of azo compounds from nitro compounds using lead and triethylammonium formate

Aromatic nitro compounds were reduced to the corresponding symmetrically substituted azo compounds using lead as catalyst and triethylammonium formate as hydrogen donor. Various azo compounds containing additional reducible substituents including halogens, nitrile, acid, phenol, ester, methoxy functions, etc, have been synthesized in a single step by the use of this reagent. The conversion is reasonably fast, clean, high yielding and occurs at room temperature in methanol.

Chemical Consequences of Arylnitrenes in the Crystalline Environment

UV photolysis of powdered crystals of several aryl azides at cryogenic temperatures afforded azo compounds predominantly. In the cases of p-(N-methylacetamido)phenyl azide and 2-azidobiphenyl, a CH insertion product or a carbazole was formed, competing with azo formation. These products can be considered to be formed through topotactic processes when the crystal structures are taken into account. The arylnitrenes generated in the azide crystals were monitored by ESR spectroscopy; they turned out to have extremely long half life-times, compared with those in the gas phase or in solution. Such high kinetic stabilities are ascribed to the inert environment around the generated nitrenes. The decay process of arylnitrenes in the initial stage obeyed a pseudo-first order kinetics; activation parameters were evaluated by Arrhenius plots. The activation enthalpies and entropies indicate that the diffusional processes of arylnitrenes may be the vital factors determining the kinetic stability and the product distribution in the crystalline environment.

Chemoselective reductive coupling of nitroarenes with magnesium in methanol via single electron transfer

A chemoselective reductive coupling of nitroarenes using magnesium in methanol has been reported at ambient temperature. While the cyano, formyl, methoxycarbonyl, methyl, methoxy, phenyl, amino, and chloro groups are unaffected, iodo and bromo groups undergo dehalogenation but in a slower reaction than the coupling of nitro group. The coupling is believed to be proceeding via SET from Mg to nitroarenes.

Reduction of Aromatic Nitro Compounds and Thioketones with Sodium Telluride under Aprotic Conditions

Sodium telluride, prepared by heating tellurium and sodium hydride in a 1:2 molar ratio in dry N,N-dimethylformamide, reduces aromatic nitro compounds to azo compounds and thioketones to hydrocarbons under mild conditions.

STUDIES ON THE MECHANISM OF THE OXIDATION OF AROMATIC PRIMARY AMINES WITH LEAD TETRAACETATE

The oxidation of eight substituted anilines with lead tetraacetate gives azo derivatives and products deriving from nucleophilic nuclear attack.A ligand transfer mechanism and a reaction path via aminium radical is suggested for these oxidations.