| Abstract: | A new type of conjugated polymer, organoselenium substituted poly(p‐phenyleneviny‐ lene) (PPV), was synthesized from the corresponding alkylselenenyl p‐xylylene dibromide via a Gilch route using potassium tert‐butoxide in THF. The p‐xylylene dibromide precursors were synthesized by reacting lithiated bis(methoxymethyl)benzenes with elemental selenium, followed by alkylation of the generated selenolates. As a final demasking step, the bromomethyl functions were liberated by ether cleavage using boron tribromide. Bis‐alkylselenenyl PPV was obtained with an average molecular weight Mw of approximately 300,000 g/mol and with polydispersity Mw/Mn = 2. Due to low solubility, monoalkylselenenyl PPV was obtained with a considerably lower average molecular weight in the proximity of 16,000 g/mol and with a polydispersity slightly larger than 3. Absorption and fluorescence spectroscopy revealed that the bis‐alkylselenenyl PPV is extensively conjugated. © 2005 Wiley Periodicals, Inc. Heteroatom Chem 16:656–662, 2005; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20167 |
