Syntheses and Properties of Hole-Transporting Biindenofluorenes.

Described herein is a straightforward approach to synthesizing three biindenofluorene (BIF) derivatives, composed of antiaromatic indenofluorene units, which are the first non-alternant congeners of known bipentacene. Dimerization of indeno[1,2- b ]fluorene and indeno[2,1- c ]fluorene units by connecting carbons 3 and 3' and carbons 2 and 2', respectively, is shown to influence the highest occupied and lowest unoccupied molecular orbital energy levels of the resulting BIFs, affording band gaps (1.5-1.6 eV) that are smaller than that of a known indenofluorene polymer (2.3 eV). The hole mobilities of BIFs were determined to be ∼10 -2 cm 2 V -1 s -1 .