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The functionalization of polycyclic aromatic hydrocarbons (PAHs) with arynes has received substantial attention because it offers a way to create π-extended PAHs as well as compounds containing rigid 3D structures.… Click to show full abstract
The functionalization of polycyclic aromatic hydrocarbons (PAHs) with arynes has received substantial attention because it offers a way to create π-extended PAHs as well as compounds containing rigid 3D structures. Herein, we report cycloadditions of benzyne to a π-extended tetracene with a twisted framework. Under kinetic control, this reaction furnished mono- and bisadducts via concerted [4+2] cycloadditions, which was supported by theoretical studies. The bisadduct exhibits blue emission in the solid state on account of the steric protection arising from the two [2.2.2] bicyclic moieties.
Journal Title: Chemistry Letters
Year Published: 2017
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