Synthesis and characterization of water-soluble poly(p-phenylene vinylene) derivatives via the dithiocarbamate precursor route

Two hydrophilic branched oligo(ethylene glycol)-substituted PPV derivatives, poly(2,5-bis(1,3-bis(triethoxymethoxy)propan-2-yloxy)-1,4-phenylene vinylene) (BTEMP-PPV) and poly(2-methoxy-5-(1,3-bis(triethoxymethoxy)propan-2-yloxy)-1,4-phenylene vinylene) (MTEMP-PPV), are presented. Polymerizations have been performed via the dithiocarbamate precursor route, using lithium hexamethyldisilazide (LHMDS) as a base, to obtain high molecular weight precursor polymers. After thermal conversion of the precursor polymers into the fully conjugated systems, the solubility of the polymers has been examined. The polar nonionic side chains of MTEMP-PPV and BTEMP-PPV render the PPV backbone soluble in a variety of solvents, including alcohols and even water, making these polymers suitable candidates to be used in optoelectronic devices that can be processed from environmentally friendly solvent systems.