Synthesis of Poly(arylenevinylene)s with Fluorinated Vinylene Units

Poly(arylenevinylene) polymers bearing fluorine atoms in the vinylene units were obtained by a Stille cross-coupling reaction of (E)-(1,2-difluoro-1,2-ethenediyl)bis(tributylstannane) with diiodoaryl derivatives. The introduction of fluorine atoms on the double bond of the stannane leads to polymers with relatively high molecular weights, Furthermore, the presence of fluorinated vinylene units changes the optical properties of the polymers and shifts the emission towards the blue region of the visible spectrum. A fluorinated analogue of MEH-PPV was obtained, and it shows photoluminescence that is considerably blueshifted, also in the solid state, relative to that found for nonfluorinated MEH-PPV and to other PPVs with fluorinated double bonds.