ol7b02605_si_001.pdf (1.08 MB)
Synthesis and Properties of Quinoidal Fluorenofluorenes
journal contribution
posted on 2017-09-13, 14:16 authored by Joshua
E. Barker, Conerd K. Frederickson, Michael H. Jones, Lev N. Zakharov, Michael M. HaleyThe synthesis and
optoelectronic properties of 24 π-electron,
formally antiaromatic fluoreno[3,2-b]fluorene and
fluoreno[4,3-c]fluorene (FF), are presented. The
solid-state structure of [4,3-c]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.