Two π-conjugated thienoisoindigo-based
organic small molecules
have been designed to be synthetically accessible through sustainable
direct heteroarylation or Sonogashira C–C bond forming cross-coupling
reactions utilizing a heterogeneous palladium catalyst. To access
these materials, one molecule, TII-ThNaph2, contains a
thiophene π-bridge to facilitate direct heteroarylation protocols,
whereas the other, TII-AcNaph2, contains an acetylene π-bridge
required for Sonogashira couplings. The synthetic route to both final
materials was optimized to investigate the reactivity of thienoisoindigo,
which to this point has not been significantly explored in comparison
to other popular organic dyes such as diketopyrrolopyrrole and isoindigo.
Considering the reported interest of thienoisoindigo-based materials
in organic solar cells and field-effect transistors, both final materials
have been characterized for their optical, electrochemical and thermal
properties offering a comparison of the structure–property
relationships that manifest as a result of the two different π-bridging
units.