Tetrathiafulvalene-functionalized triptycenes: synthetic protocols and elucidation of intramolecular Coulomb repulsions in the oxidized species

A large selection of triptycenes functionalized with tetrathiafulvalene (TTF) units as well as triptycenes containing extended TTFs as a part of the triptycene core have been synthesized utilizing new triptycene di- and tetraaldehydes as well as bis-, tetrakis- and hexakis(bromomethyl) derivatives. The largest scaffold contains a total of 12 TTFs around the central triptycene core. From spectroelectrochemical and chemical oxidation studies, we have elucidated the extent to which an increasing number of electrostatic interactions among oxidized TTF units exert an influence on the absorption characteristics.