The synthesis, condensation, and luminescence of stilbenoid oligomers with alkoxysilane end groups

A synthetic route to highly luminescent organic semiconductors with curable alkoxysilyl groups is described. Monodisperse oligo(phenylenevinylene)s are rigidly connected to di- and triethoxysilanes via Heck reactions or via cross-metathesis. Hydrolysis of the silicic esters yields silanols condensing to linear and cyclic oligo-OPV-siloxanes or to three-dimensional networks, thus allowing the transformation of small molecules to fluorescent materials with well-defined chromophores. Transparent films are obtained by casting of soluble cyclosiloxanes and from OPV-silanetriols, the latter can be cured to insoluble networks.