Naphthalene diimide-incorporated helical thienoacene: a helical molecule with high electron mobility, good solubility, and thermally stable solid phase.

A Naphthalene diimide (NDI)-incorporated helical thienoacene was developed. The compound has high electron mobility (1.4 cm2 V-1 s-1) thanks to its two-dimensional π-π interaction assisted by the intermolecular C-HO hydrogen bonding of the NDI moieties. Moreover, its bow-shaped π-skeleton reduces molecular fluctuation and gives the compound a thermally stable solid phase, which enables us to fabricate thermally stable organic devices.

Intra- and intermolecular interaction of anthracene moieties in 7,8-disilabicyclo[3.3.0]octadienyl-bridged bisanthracenes.

Ruthenium-catalyzed dimerization of 9-anthrylarylsilanes afforded air-stable V-shaped bisanthracenes bridged by a 7,8-disilabicyclo[3.3.0]octadiene moiety. The intra- and intermolecular proximity of the anthracene moieties were determined by single-crystal X-ray analysis. Absorption and emission maxima of the disilabicyclo[3.3.0]octadienyl-bridged bisanthracenes in the solution state were observed at longer wavelengths than those of 9-anthryldimethylsilane and bis(9-anthryl)dimethylsilane. The V-shaped bisacenes in the solid state showed excimer emissions with moderate quantum yields.