Synthesis, solid-phase reaction, and patterning of acid-labile 3,4-ethylenedioxythiophene-based conjugated polymers

3,4-Ethylenedioxythiophene (EDOT)-based conjugated polymers bearing tetrahydropyranyl side groups were synthesized. These include poly [(3-(2-(2-tetrahydropyranyloxy)ethyl)thiophene)-(3,4-ethylenedioxythiophene)] (PTHPET-EDOT), and poly [(3-(11-(2-tetrahydropyranyloxy)undecyl)thiophene)-(3,4-ethylenedioxythiophene)I (PTHPUDT-EDOT). PTHPUDT-EDOT exhibits an enhanced stability in its oxidized state and a high optical contrast ratio between its reduced and oxidized states. Despite its rigid-rod nature, PTHPUDT-EDOT undergoes an acid catalytic reaction that leads to the cleavage and complete elimination of the tetrahydropyranyl group. The decrease in solubility of the deprotected polymer allows for the deposition of PTHPUDT-EDOT in a spatially controlled fashion using chemically amplified photolithography and soft lithography.