88841-77-4Relevant articles and documents
Cage Encapsulated Gold Nanoparticles as Heterogeneous Photocatalyst for Facile and Selective Reduction of Nitroarenes to Azo Compounds
Mondal, Bijnaneswar,Mukherjee, Partha Sarathi
, p. 12592 - 12601 (2018/10/05)
A discrete nanoscopic organic cage (OC1R) has been synthesized from a phenothiazine based trialdehyde treating with chiral 1,2-cyclohexanediamine building block via dynamic imine bond formation followed by reductive amination. The cage compound has been characterized by several spectroscopic methods, which advocate that OC1R has trigonal prismatic shape formed via [2 + 3] self-assembled imine condensation followed by imine reduction. This newly designed cage has aromatic walls and porous interior decorated with two cyclic thioether and three vicinal diamine moieties suitable for binding gold ions to engineer the controlled nucleation and stabilization of ultrafine gold nanoparticles (AuNPs). The functionalized confined pocket of the cage has been used for the controlled synthesis of AuNPs with narrow size distribution via encapsulation of Au(III) ions. Inductively coupled plasma mass spectrometric (ICP-MS) analysis revealed that the composite Au@OC1R has very high (?68 wt %) gold loading. In distinction, reduction of gold salts in absence of the cage yielded structureless agglomerates. The fine-dispersed cage anchored AuNPs (Au@OC1R) have been finally used as potential heterogeneous photocatalyst for very facile and selective conversion of nitroarenes to respective azo compounds at ambient temperature in just 2 h reaction time. Exceptional chemical stability and reusability without any agglomeration of AuNPs even after several cycles of use are the potential features of this material. The composite Au@OC1R represents the first example of organic cage supported gold nanoparticles as photocatalyst.
Reduction of Aromatic Nitro Compounds by Ethylenediamine. A New Selective Reagent for the Synthesis of Symmetric Azo Compounds
Chung, T. F.,Wu, Y. M.,Cheng, C. H.
, p. 1215 - 1217 (2007/10/02)
Ethylenediamine selectively reduces aromatic nitro compounds RC6H4NO2 (R = H, m-CH3, p-CH3, and m-Ph) at 150 deg C to symmetric azo compounds RC6H4N=NC6H4R in good yield but does not reduce their ortho-substituted analogues.The diamine does not react with o- or p-nitroanilines but reduces the meta isomer to 1,3-diaminobenzene and 3,3'-diaminoazobenzene.Its reaction with o- and p-halonitrobenzenes gives substitution products H2NCH2CH2NHC6H4NO2.Nitrosobenzene is reduced to aniline and azobenzene, while α-nitroso-β-naphthol is converted to 1,4-phenanthroline.Among a variety of other amines tested, only 1,3-propylenediamine reduces nitrobenzene to azobenzene.A mechanism for the reaction is proposed.