Synthesis and Properties of Quinoidal Fluorenofluorenes

Published on 2017-09-13T14:16:06Z (GMT) by
The synthesis and optoelectronic properties of 24 π-electron, formally antiaromatic fluoreno­[3,2-<i>b</i>]­fluorene and fluoreno­[4,3-<i>c</i>]­fluorene (FF), are presented. The solid-state structure of [4,3-<i>c</i>]­FF along with computationally analogous molecules shows that the outer rings are aromatic while the central four rings possess a bond-localized 2,6-naphthoquinodimethane motif. The antiaromaticity and biradical character of the FFs is assessed computationally, the results of which indicate the dominance of the closed-shell ground state for these molecules.

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Barker, Joshua

E.; Frederickson, Conerd K.; Jones, Michael H.; Zakharov, Lev N.; Haley, Michael M. (2017): Synthesis and Properties of Quinoidal Fluorenofluorenes. ACS Publications. Collection.