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

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

doi:10.1021/ma061901g

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

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

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

19 Scopus citations

Abstract

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 language	English
Pages (from-to)	7854-7858
Number of pages	5
Journal	Macromolecules
Volume	39
Issue number	23
DOIs	https://doi.org/10.1021/ma061901g
State	Published - 14 Nov 2006

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

abstract = "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.",

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year = "2006",

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doi = "10.1021/ma061901g",

language = "English",

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T1 - Anthryl-based poly(phenylene ethynylene)s

T2 - Tuning optical properties with Diels-Alder reactions

AU - Ishow, Eléna

AU - Bouffard, Jean

AU - Kim, Youngmi

AU - Swager, Timothy M.

PY - 2006/11/14

Y1 - 2006/11/14

N2 - 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.

AB - 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.

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JO - Macromolecules

JF - Macromolecules

IS - 23

ER -

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

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