Fluoreno[4,3-c]fluorene: A Closed-Shell, Fully Conjugated Hydrocarbon

Rose, Bradley D.; Vonnegut, Chris L.; Zakharov, Lev N.; Haley, Michael M.

Fluoreno[4,3-c]fluorene: A Closed-Shell, Fully Conjugated Hydrocarbon

2012

Rose, Bradley D. | Vonnegut, Chris L. | Zakharov, Lev N. | Haley, Michael M.

The synthesis and optoelectronic properties of 24 π-electron, formally antiaromatic 4,11-di-t-butyl-1,8-dimesitylfluoreno[4,3-c]fluorene (FF) are presented. The solid-state structure shows that the outer rings are aromatic, while the central four rings possess a bond-localized 2,6-naphthoquinone dimethide motif (in red). The biradical character of FF is assessed experimentally and computationally; the results of which implicate a closed-shell ground state.

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