Fluorenofluorenes and structurally related, formally antiaromatic hydrocarbons have potential use as organic semiconductors because of their low HOMO and LUMO energy levels and narrow HOMO-LUMO energy gaps. These electronic properties impart the neutral species with the ability to be oxidized or reduced readily. In addition, these systems strongly absorb visible light, which might permit potential use in photovoltaics. Fluoreno[3,2-b]fluorene ([3,2-b]FF), a new fluorenofluorene regioisomer, was synthesized using a triflate intermediate prepared via a recently reported five step route from naphthalene-2,6-diol. This poster reports our ongoing work toward the assembly of the linear and angular benzo-fused derivatives of [3,2-b]FF from the requisite naphthalene boronate esters, and includes the x-ray structural characterization of one of the angular regioisomers.

Synthesis and characterization of fluoreno[3,2-b]fluorene derivatives

255th National Meeting (2018)

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