Ready access to end-functional polystyrenes via a combination of ARGET ATRP and thiol-ene chemistry

Ozcan Altintas; Thomas Josse; Julien De Winter; Nicholas M. Matsumoto; Pascal Gerbaux; Manfred Wilhelm; Christopher Barner-Kowollik

doi:10.1039/c5py01048a

Ready access to end-functional polystyrenes via a combination of ARGET ATRP and thiol-ene chemistry

Ozcan Altintas, Thomas Josse, Julien De Winter, Nicholas M. Matsumoto, Pascal Gerbaux, Manfred Wilhelm, Christopher Barner-Kowollik

Chemistry (Twin Cities)

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12 Scopus citations

Abstract

We describe a simple and facile method for quantitatively converting bromine end-groups of well-defined polystyrene (PS, M_n,SEC = 4000 Da, D = 1.08) prepared by activators regenerated by electron transfer (ARGET) atom transfer radical polymerization (ATRP) into terminal alkenes by heating at 100 °C in dimethylformamide (DMF) without additional reagents. Subsequently, a facile quantitative post-functionalization of the terminal double bonds to various end functional polymers was performed via light-induced thiol-ene reactions. The quantitative end-group modifications as well as their thermal stability were assessed by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-ToF-MS), nuclear magnetic resonance (¹H NMR) spectroscopy and size-exclusion chromatography (SEC), evidencing the generated functional polystyrenes to be highly stable up to 200 °C for extended periods of time (24 h).

Original language	English (US)
Pages (from-to)	6931-6935
Number of pages	5
Journal	Polymer Chemistry
Volume	6
Issue number	39
DOIs	https://doi.org/10.1039/c5py01048a
State	Published - Oct 21 2015

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10.1039/c5py01048a

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title = "Ready access to end-functional polystyrenes via a combination of ARGET ATRP and thiol-ene chemistry",

abstract = "We describe a simple and facile method for quantitatively converting bromine end-groups of well-defined polystyrene (PS, Mn,SEC = 4000 Da, D = 1.08) prepared by activators regenerated by electron transfer (ARGET) atom transfer radical polymerization (ATRP) into terminal alkenes by heating at 100 °C in dimethylformamide (DMF) without additional reagents. Subsequently, a facile quantitative post-functionalization of the terminal double bonds to various end functional polymers was performed via light-induced thiol-ene reactions. The quantitative end-group modifications as well as their thermal stability were assessed by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-ToF-MS), nuclear magnetic resonance (1H NMR) spectroscopy and size-exclusion chromatography (SEC), evidencing the generated functional polystyrenes to be highly stable up to 200 °C for extended periods of time (24 h).",

author = "Ozcan Altintas and Thomas Josse and {De Winter}, Julien and Matsumoto, {Nicholas M.} and Pascal Gerbaux and Manfred Wilhelm and Christopher Barner-Kowollik",

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T1 - Ready access to end-functional polystyrenes via a combination of ARGET ATRP and thiol-ene chemistry

AU - Altintas, Ozcan

AU - Josse, Thomas

AU - De Winter, Julien

AU - Matsumoto, Nicholas M.

AU - Gerbaux, Pascal

AU - Wilhelm, Manfred

AU - Barner-Kowollik, Christopher

PY - 2015/10/21

Y1 - 2015/10/21

N2 - We describe a simple and facile method for quantitatively converting bromine end-groups of well-defined polystyrene (PS, Mn,SEC = 4000 Da, D = 1.08) prepared by activators regenerated by electron transfer (ARGET) atom transfer radical polymerization (ATRP) into terminal alkenes by heating at 100 °C in dimethylformamide (DMF) without additional reagents. Subsequently, a facile quantitative post-functionalization of the terminal double bonds to various end functional polymers was performed via light-induced thiol-ene reactions. The quantitative end-group modifications as well as their thermal stability were assessed by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-ToF-MS), nuclear magnetic resonance (1H NMR) spectroscopy and size-exclusion chromatography (SEC), evidencing the generated functional polystyrenes to be highly stable up to 200 °C for extended periods of time (24 h).

AB - We describe a simple and facile method for quantitatively converting bromine end-groups of well-defined polystyrene (PS, Mn,SEC = 4000 Da, D = 1.08) prepared by activators regenerated by electron transfer (ARGET) atom transfer radical polymerization (ATRP) into terminal alkenes by heating at 100 °C in dimethylformamide (DMF) without additional reagents. Subsequently, a facile quantitative post-functionalization of the terminal double bonds to various end functional polymers was performed via light-induced thiol-ene reactions. The quantitative end-group modifications as well as their thermal stability were assessed by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-ToF-MS), nuclear magnetic resonance (1H NMR) spectroscopy and size-exclusion chromatography (SEC), evidencing the generated functional polystyrenes to be highly stable up to 200 °C for extended periods of time (24 h).

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DO - 10.1039/c5py01048a

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EP - 6935

JO - Polymer Chemistry

JF - Polymer Chemistry

IS - 39

ER -

Ready access to end-functional polystyrenes via a combination of ARGET ATRP and thiol-ene chemistry

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