We have explored a highly efficient benzannulation reaction that transforms carbon-carbon triple bonds into 2,3-disubstituted naphthalene moieties. This transformation offers rapid access to previously unavailable aromatic polymers and fused polycyclic aromatic hydrocarbons. The benzannulation reaction is sufficiently active to functionalize the alkynes of poly(phenylene ethynylene)s, the first such cycloaddition reaction to modify a conjugated polymer backbone. The benzannulated polymers are precursors of structurally precise graphene nanoribbons, which are narrow strips of carbon of interest for their semiconducting electronic structure.  Progress towards this goal will be presented, including characterizing a two-step benzannulation / Scholl oxidation reaction sequence on model compounds to demonstrate the efficiency and lack of rearrangements in these reactions. The products of this two-step sequence are new planar or contorted polycylic aromatic hydrocarbons of interest for optoelectronic devices.

Rational synthesis of carbon nanostructures from the bottom up

246th National Meeting (2013)

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