Synthesis and Properties of Dithiocarbamate-Linked Acenes.

A small set of unsymmetrically substituted acene derivatives containing either aniline or dithiocarbamate moieties was synthesized. A stepwise, one-pot procedure was used to transform appropriate acenequinones to aniline-linked acenes in one step with moderate yields. A heretofore-unreported carbon disulfide activation process involving the formation of a trialkylammonium dithiocarbamate intermediate was found to be essential to convert these acene anilines to acene dithiocarbamates. The effects of the aniline and dithiocarbamate moieties on the photophysical properties of selected acene chromophores were assessed by UV/vis absorption and fluorescence spectroscopies.