Organoselenium-substituted poly(p-phenylenevinylene)

✍ Scribed by Nicolai Stuhr-Hansen; Edwin H. A. Beckers; Lars Engman; René A. J. Janssen

• Book ID: 102229969
• Publisher: John Wiley and Sons
• Year: 2005
• Tongue: English
• Weight: 105 KB
• Volume: 16
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.20167

✦ Synopsis

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 M~w~ of approximately 300,000 g/mol and with polydispersity M~w~/M~n~ = 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