This talk will present our synthetic, structural, computational and materials studies of a new class of carbon-rich, electron-accepting molecules based on the indenofluorene (IF) skeleton. Access to the fully conjugated, 20 π-electron, formally antiaromatic, pentacyclic ring system is accomplished using a variety of intermediate diones. These molecules in turn can be prepared via a simple three-step process (Suzuki cross-coupling, oxidation, Friedel-Crafts acylation). Optimization of their synthesis now permits access to IF derivatives in multigram quantities. We have shown that thin films or single crystals of several different IF scaffolds can serve as an active layer in organic field effect transistors (OFETs) that exhibit ambipolar behavior. Current studies (Figure 1) are focused on varying the antiaromaticity of the indacene unit by systematic replacement of the outer benzene groups with other aromatic units (diarenoindacenes) as well as on increasing the diradical character of the framework by expansion of the quinoidal core (diindenoarenes).

Diarenoindacenes and diindenoarenes: From quinoidal electron-accepting materials to stable organic diradicals

2019 Spring National Meeting

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