Abstract
Chrysene and its bisbenzannulated homologue, naphtho[2,3‐c]tetraphene, were synthesized through a PtCl2‐catalyzed cyclization of alkynes, which also furnished corresponding biaryls subsequent to a Glaser coupling reaction of the starting alkynes. The optoelectronic properties of 5,5′‐bichrysenyl and 6,6′‐binaphtho[2,3‐c]tetraphene were compared to their chrysene‐based “monomers”. Oxidative cyclodehydrogenations of bichrysenyl and its higher homologue towards large nanographenes were also investigated.
Highlights
The development of new blue-emitting materials based on polycyclic aromatic hydrocarbons (PAHs) continues to be an important challenge for organic chemistry and material science.[1]
Dibenzochrysenes[6] have attracted interest as they provide blue to blue-green emission with remarkably high external efficiencies up to 2.0 % in OLEDs.[7,8]
Among the different isomers, the synthesis of naphtho[2,3-c]tetraphene is only reported in one article[9] and due to its low solubility it remained poorly investigated
Summary
Changing the torsional angle (DFT, B3LYP/6-311++G**, gas phase, see Supporting Information Figure S15) yields a potential with a minimum at 788, in accordance with the value obtained via X-ray structure analysis. Whereas polyphenylene dendrimers are conventionally employed as precursors to large unsubstituted PAHs, as they planarize under Scholl conditions, we explored a new strategy through cyclodehydrogenation of (soluble) biaryl systems in this work, which could furnish nanographenes with hitherto unexplored edge type combinations These types of sparsely investigated PAHs are of interest for lasing applications[19] and NIR emission.[16] We investigated oxidative Scholl coupling of 11 furnishing 14, but full cyclodehydrogenation of its higher homologue 13 was only observed in trace amounts: Most likely, solubility limits the full conversion of the twofold cyclodehydrogenated intermediate, which will be circumvented by utilizing surface-assisted fusion[20] in the future
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