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From one-pot stabilisation to in situ functionalisation in nitroxide mediated polymerisation: an efficient extension towards atom transfer radical polymerisation

Lionel Petton UGent, Andrés E Ciolino, Bart Dervaux UGent and Filip Du Prez UGent (2012) POLYMER CHEMISTRY. 3(7). p.1867-1878
abstract
A one-pot controlled method for the nitroxide end-group removal from synthetic polymers prepared by nitroxide mediated polymerisation (NMP) is reported. The strategy relies on the controlled addition of compounds such as thiols, radical initiators and carbon tetrabromide with high chain transfer constants. From a practical point of view, when the desired molar mass and conversion are reached, 1 to 10 equivalents of the transfer agent compared to the nitroxide are added and a few minutes later, after transformation of all chain-ends, the reaction is quenched. The versatility of the procedure was successfully tested with a wide range of monomers (styrene (S), isobornyl acrylate (iBA) or methyl methacrylate (MMA)) and nitroxides (2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) and N-tert-butyl-1-diethylphosphono-2,2-dimethylpropyl nitroxide (SG1)). The removal of the nitroxide end-group proceeds with high fidelity for all the transfer agents studied, while at the same time the thermal stability of the resulting polymer chains increases when thiols are employed. Furthermore, a functional group that allows for chain extension by atom transfer radical polymerisation (ATRP) has been introduced through the direct synthesis of bromine terminated macroinitiators via a chain transfer reaction with carbon tetrabromide.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
STYRENE, BUTYL ACRYLATE, MASS-SPECTROMETRY, METHYL-METHACRYLATE, CHAIN-TRANSFER, KINETICS, POLYMERS, ALKOXYAMINE, POLYSTYRENE, COPOLYMERS
journal title
POLYMER CHEMISTRY
Polym. Chem.
volume
3
issue
7
pages
1867 - 1878
Web of Science type
Article
Web of Science id
000304913800023
JCR category
POLYMER SCIENCE
JCR impact factor
5.231 (2012)
JCR rank
5/82 (2012)
JCR quartile
1 (2012)
ISSN
1759-9954
DOI
10.1039/c2py00444e
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
3065298
handle
http://hdl.handle.net/1854/LU-3065298
date created
2012-12-05 08:49:20
date last changed
2013-08-01 00:30:37
@article{3065298,
  abstract     = {A one-pot controlled method for the nitroxide end-group removal from synthetic polymers prepared by nitroxide mediated polymerisation (NMP) is reported. The strategy relies on the controlled addition of compounds such as thiols, radical initiators and carbon tetrabromide with high chain transfer constants. From a practical point of view, when the desired molar mass and conversion are reached, 1 to 10 equivalents of the transfer agent compared to the nitroxide are added and a few minutes later, after transformation of all chain-ends, the reaction is quenched. The versatility of the procedure was successfully tested with a wide range of monomers (styrene (S), isobornyl acrylate (iBA) or methyl methacrylate (MMA)) and nitroxides (2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) and N-tert-butyl-1-diethylphosphono-2,2-dimethylpropyl nitroxide (SG1)). The removal of the nitroxide end-group proceeds with high fidelity for all the transfer agents studied, while at the same time the thermal stability of the resulting polymer chains increases when thiols are employed. Furthermore, a functional group that allows for chain extension by atom transfer radical polymerisation (ATRP) has been introduced through the direct synthesis of bromine terminated macroinitiators via a chain transfer reaction with carbon tetrabromide.},
  author       = {Petton, Lionel and Ciolino, Andr{\'e}s E and Dervaux, Bart and Du Prez, Filip},
  issn         = {1759-9954},
  journal      = {POLYMER CHEMISTRY},
  keyword      = {STYRENE,BUTYL ACRYLATE,MASS-SPECTROMETRY,METHYL-METHACRYLATE,CHAIN-TRANSFER,KINETICS,POLYMERS,ALKOXYAMINE,POLYSTYRENE,COPOLYMERS},
  language     = {eng},
  number       = {7},
  pages        = {1867--1878},
  title        = {From one-pot stabilisation to in situ functionalisation in nitroxide mediated polymerisation: an efficient extension towards atom transfer radical polymerisation},
  url          = {http://dx.doi.org/10.1039/c2py00444e},
  volume       = {3},
  year         = {2012},
}

Chicago
Petton, Lionel, Andrés E Ciolino, Bart Dervaux, and Filip Du Prez. 2012. “From One-pot Stabilisation to in Situ Functionalisation in Nitroxide Mediated Polymerisation: An Efficient Extension Towards Atom Transfer Radical Polymerisation.” Polymer Chemistry 3 (7): 1867–1878.
APA
Petton, L., Ciolino, A. E., Dervaux, B., & Du Prez, F. (2012). From one-pot stabilisation to in situ functionalisation in nitroxide mediated polymerisation: an efficient extension towards atom transfer radical polymerisation. POLYMER CHEMISTRY, 3(7), 1867–1878.
Vancouver
1.
Petton L, Ciolino AE, Dervaux B, Du Prez F. From one-pot stabilisation to in situ functionalisation in nitroxide mediated polymerisation: an efficient extension towards atom transfer radical polymerisation. POLYMER CHEMISTRY. 2012;3(7):1867–78.
MLA
Petton, Lionel, Andrés E Ciolino, Bart Dervaux, et al. “From One-pot Stabilisation to in Situ Functionalisation in Nitroxide Mediated Polymerisation: An Efficient Extension Towards Atom Transfer Radical Polymerisation.” POLYMER CHEMISTRY 3.7 (2012): 1867–1878. Print.