Practical Synthesis of Vinyl-Substitutedp-Phenylenevinylene Oligomers and Their Triethoxysilyl Derivatives

Abstract

Luminescent semiconducting organic compounds are widely used as active layers in electro-optical devices. Apart from conjugated polymers, monodisperse oligomers also represent attractive materials. The synthesis of stilbenoid oligomers with polymerizable end groups is presented. Oligo(phenylenevinylene)s with terminal vinyl groups 17–19 are prepared in good yields by Horner–Emmons olefinations or by the Heck reaction of the iodo-substituted oligomers 15, 16 with compressed ethene. Triethoxysilyl groups can be linked via rigid 1,2-vinylene units to the chromophores 26–30, either in the direct reaction of 14, 24 with silanes 21, 22 or by cross-metathesis of 17–19 with the vinylsilanes 21, 22 using Grubbs catalyst.