75519-75-4Relevant articles and documents
Modular Design of Fluorescent Dibenzo- and Naphtho-Fluoranthenes: Structural Rearrangements and Electronic Properties
Mohammad-Pour, Gavin S.,Ly, Richard T.,Fairchild, David C.,Burnstine-Townley, Alex,Vazquez-Molina, Demetrius A.,Trieu, Khang D.,Campiglia, Andres D.,Harper, James K.,Uribe-Romo, Fernando J.
, p. 8036 - 8053 (2018/05/31)
A library of 12 dibenzo- and naphtho-fluoranthene polycyclic aromatic hydrocarbons (PAHs) with MW = 302 (C24H14) was synthesized via a Pd-catalyzed fluoranthene ring-closing reaction. By understanding the various modes by which the palladium migrates during the transformation, structural rearrangements were bypassed, obtaining pure PAHs in high yields. Spectroscopic and electrochemical characterization demonstrated the profound diversity in the electronic structures between isomers. Highlighting the significant differences in emission of visible light, this library of PAHs will enable their standardization for toxicological assessment and potential use as optoelectronic materials.
Probing mechanisms of aryl-aryl bond cleavages under flash vacuum pyrolysis conditions
Jackson, Edward A.,Xue, Xiang,Cho, Hee Yeon,Scott, Lawrence T.
, p. 1279 - 1287 (2014/11/08)
Several biaryls have been subjected to flash vacuum pyrolysis (FVP) at 1100°C and 0.8-0.9hPa. Product compositions are reported for the FVP of 9-phenylanthracene (1), 2-bromobiphenyl (5), biphenyl (8), 1,10- diphenylanthracene (12), 9-(2-naphthyl)anthracene (17), and 9,9′- bianthracenyl (20). The experimental results have been used to evaluate four possible mechanistic pathways for the cleavage of aryl-aryl bonds under these conditions: (1) the 'explosion' of substituted phenyl radicals; (2) hydrogen atom attachment to an ipso-carbon atom of the biaryl followed by C-C bond cleavage; (3) direct homolysis; and (4) loss of a fragment as an aryne. None of these mechanisms by itself successfully accommodates all of the experimental facts. The data suggest that aryl-aryl bond cleavages under FVP conditions involve at least two different mechanistic pathways and that the relative contributions of the competing pathways probably vary from one biaryl to the next.