76129-19-6

Upstream product

• 76129-22-1 2,5-diphenyliodobenzene 
• 60366-15-6 4-phenyl-2-nitro-1,1′-biphenyl 
• 25176-17-4 2'-amino-p-terphenyl 
• 4085-18-1 4-amino-3-nitrobiphenyl 
• 98905-05-6 2′-chloro-1,1′:4′,1″-terphenyl 
• 71-43-2 benzene 
• 1730-04-7 1,8-diiodonaphthalene 

Relevant academic research and scientific papers

Synthesis of partially and fully fused polyaromatics by annulative chlorophenylene dimerization

Since the discovery by Ullmann and Bielecki in 1901, reductive dimerization (or homocoupling) of aryl halides has been extensively exploited for the generation of a range of biaryl-based functional molecules. In contrast to the single-point connection in these products, edge-sharing fused aromatic systems have not generally been accessible from simple aryl halides via annulation cascades. Here we report a single-step synthesis of fused aromatics with a triphenylene core by the palladium-catalyzed annulative dimerization of structurally and functionally diverse chlorophenylenes through double carbon-hydrogen bond activation. The partially fused polyaromatics can be transformed into fully fused, small graphene nanoribbons, which are otherwise difficult to synthesize. This simple, yet powerful, method allows access to functional p-systems of interest in optoelectronics research.

Preparation and Conformational Properties of Several 1,8-Diarylnaphthalenes

Six new 1,8-diarylnaphthalenes, each having closely held parallel aromatic rings, were synthesized by a Kharash-type Grignard cross-coupling of arylmagnesium iodide and 1,8-diiodonaphthalene in the presence of N,N'-bis(1-methyl-3-oxobutylidene)ethylenediaminatonickel(II) as a catalyst.Among them, 1,8-di(1-naphthyl)naphthalene was obtained as cis and trans rotamers, caused by the restricted rotation at the 1,8-position.Interconversion between the rotamers on heating above their melting points was confirmed by differential scanning calorimetry.The proton magnetic resonance spectral studies of the 1,8-diarylnaphthalenes indicated the presence of a face-to-face arrangement of aromatic rings in the peri-position.Two new 8,8'-diaryl-1,1'-binaphthyls, each having two sets of closely held parallel aromatic rings, were isolated as minor coupling products.Trans-trans conformations were proposed for them on the basis of their thermal behavior.Several nickel(II) complexes were found to be effective catalysts for preparative Grignard cross-coupling reaction involving closely crowded geometry.

Syntheses and Physical Properties of Several Symmetrical Sexiphenyls

Seven sexiphenyls, including three new isomers, 3,4,3',4'-tetraphenylbiphenyl (Id), 2,5,2',5'-tetraphenylbiphenyl (IIId), and 2,2'-di(3-biphenylyl)biphenyl (Vd), were synthesized by Ullmann homo-coupling of iodoterphenyl.The characteristic band of the infrared spectra (675-920 cm-1) and signals of the nuclear magnetic resonance spectra of the sexiphenyls were assigned tentatively and are discussed briefly.Infrared studies indicated that the range 730-770 cm-1, generally accepted as the position of the C-H out-of-plane bending bands of phenyl rings, should be widened slightly to 730-782 cm-1.The ultraviolet spectra commonly displayed an intense E-band in the narrow region of 192-207 nm.The prominent K-band above ca. 260 nm of branched sexiphenyls was taken as indicative of the presence of one or more p-linkages, as in the case of linear compounds.Keywords - polyphenyls; Ullmann reaction; infrared spectra; ultraviolet spectra; NMR spectra; iodoterphenyls