Synthesis of new configurationally stable twisted-acenes that takes advantage of the recently reported “Torque, Lock, and Propagate” approach will be illustrated with efforts to make heli-acenes, <b>1</b> and <b>2</b>. Key benzoquinone homologation and Mallory photocyclization steps will be described in detail. We will also describe computational studies that focus on the comparison of structural features and the electronic character of these heliacenes to pentacene and tetracene. We anticipate that these new twisted acenes will provide promise as chiral organic semiconductors with increased stability towards oxidation, dimerization, and polymerization that decrease the utility of planar acene homologues.

Comparison of structural and electronic character of Heli-acenes and acenes

ACS Fall 2020 Virtual Meeting

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