Boron-Nitrogen-Doped Nanographenes: A Synthetic Tale from Borazine Precursors was written by Dosso, Jacopo;Battisti, Tommaso;Ward, Benjamin D.;Demitri, Nicola;Hughes, Colan E.;Williams, P. Andrew;Harris, Kenneth D. M.;Bonifazi, Davide. And the article was included in Chemistry – A European Journal in 2020.Reference of 1890136-54-5 The following contents are mentioned in the article:
In this work, a comprehensive account of the authors’ synthetic efforts to prepare borazino-doped hexabenzocoronenes by using the Friedel-Crafts-type electrophilic aromatic substitution is reported. Hexafluoro-functionalized aryl borazines, bearing an ortho fluoride leaving group on each of the N- and B-aryl rings, was shown to lead to cascade-type electrophilic aromatic substitution events in the stepwise C-C bond formation, giving higher yields of borazinocoronenes than those obtained with borazine precursors bearing fluoride leaving groups at the ortho positions of the B-aryl substituents. By using this pathway, an unprecedented boroxadizine-doped PAH (I) featuring a gulf-type periphery could be isolated, and its structure proven by single-crystal X-ray diffraction anal. Mechanistic studies on the stepwise Friedel-Crafts-type cyclization suggest that the mechanism of the planarization reaction proceeds through extension of the π system. To appraise the doping effect of the boroxadizine unit on the optoelectronic properties of topol.-equivalent mol. graphenes, the all-carbon and pyrylium PAH analogs, all featuring a gulf-type periphery, were also prepared As already shown for the borazino-doped hexabenzocoronene, the replacement of the central benzene ring by its B3N2O congener widens the HOMO-LUMO gap and dramatically enhances the fluorescence quantum yield. This study involved multiple reactions and reactants, such as 2-Bromo-5′-phenyl-1,1′:3′,1”-terphenyl (cas: 1890136-54-5Reference of 1890136-54-5).
2-Bromo-5′-phenyl-1,1′:3′,1”-terphenyl (cas: 1890136-54-5) belongs to organobromine compounds. Organo bromine compounds are versatile compounds and are widely used in diverse fields. Organo bromine derivatives are used in the dye sector, as an indicator in analytical chemistry (Bromothymol blue is a popular indicator). The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.Reference of 1890136-54-5
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary