Anthryl-based poly(phenylene ethynylene)s: Tuning optical properties with Diels-Alder reactions

Eléna Ishow, Jean Bouffard, Youngmi Kim, Timothy M. Swager

Research output: Contribution to journalArticlepeer-review

19 Scopus citations


Soluble anthryl-based conjugated poly(phenylene ethynylene)s (PPEs) have been synthesized using palladium-catalyzed Sonogashira-Hagihara cross-coupling polymerization reactions. Molecular weights up to 3.5 × 10 4 g·mol -1 were obtained, making them suitable for spectroscopic solution characterizations and thin film processing. The selective reactivity of these polymers as multidienes has been successfully demonstrated with strong dienophiles. Diels-Alder reactions proceed cleanly to completion with unhindered dienophiles such as N-alkylated maleimide derivatives. TGA analysis revealed thermal retro-Diels-Alder reactions at modest temperatures around 210°C. Compared with their parent polymers, the cycloadduct polymers exhibited dramatic hypsochromic shifts of their emission and absorption maxima up to 80 nm along with a considerable quantum yield enhancement. These original anthryl-based polymers appear attractive as reactive conjugated materials whose optical properties can easily be tuned with quantitative Diels-Alder reactions.

Original languageEnglish
Pages (from-to)7854-7858
Number of pages5
Issue number23
StatePublished - 14 Nov 2006


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