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Kinetic Monte Carlo modeling of the sulfinyl precursor route for poly(p-phenylene vinylene) synthesis

Paul Van Steenberge UGent, Joke Vandenbergh, Dagmar D'hooge UGent, Marie-Françoise Reyniers UGent, Peter J Adriaensens, Laurence Lutsen, Dirk JM Vanderzande and Guy Marin UGent (2011) MACROMOLECULES. 44(22). p.8716-8726
abstract
A kinetic Monte Carlo modeling study is presented for precursor polymer formation via the sulfinyl precursor route. The premonomer, 1-(chloromethyl)-4-[(n-octylsulfinyl)methyl]benzene, is subjected to a NatBuO induced 1,6-elimination in sBuOH yielding the actual p-quinodimethane monomer that leads, via a radical polymerization, to the precursor polymer. The kinetic Monte Carlo model is able to predict the experimental trends in yield, mass averaged molar mass and structural defect content. The effect of radical recombination and cyclization is modeled and found to be negligible. The effect of the initial base and premonomer concentration on the polymer properties is investigated. Simulation results indicate a maximum in the polymer yield and chain length for initial [base]/[premonomer] = 1 and that the molecular properties of the precursor polymers can be varied by as much as 50% by an appropriate choice of initial [base]/[premonomer]. The kinetic Monte Carlo model is used to determine reaction conditions to achieve targeted polymer yields, chain lengths and structural defect contents.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
PALLADIUM-CATALYZED ARYLATION, ANIONIC-POLYMERIZATION MECHANISMS, CONTROLLED GILCH SYNTHESIS, CONJUGATED POLYMERS, P-QUINODIMETHANE, PARA-XYLYLENE, DITHIOCARBAMATE ROUTE, THERMAL ELIMINATION, RADICAL MECHANISM, VAPOR-DEPOSITION
journal title
MACROMOLECULES
Macromolecules
volume
44
issue
22
pages
8716 - 8726
Web of Science type
Article
Web of Science id
000296893400003
JCR category
POLYMER SCIENCE
JCR impact factor
5.167 (2011)
JCR rank
5/78 (2011)
JCR quartile
1 (2011)
ISSN
0024-9297
DOI
10.1021/ma201617r
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
1961119
handle
http://hdl.handle.net/1854/LU-1961119
date created
2011-12-06 16:29:44
date last changed
2012-10-29 11:56:44
@article{1961119,
  abstract     = {A kinetic Monte Carlo modeling study is presented for precursor polymer formation via the sulfinyl precursor route. The premonomer, 1-(chloromethyl)-4-[(n-octylsulfinyl)methyl]benzene, is subjected to a NatBuO induced 1,6-elimination in sBuOH yielding the actual p-quinodimethane monomer that leads, via a radical polymerization, to the precursor polymer. The kinetic Monte Carlo model is able to predict the experimental trends in yield, mass averaged molar mass and structural defect content. The effect of radical recombination and cyclization is modeled and found to be negligible. The effect of the initial base and premonomer concentration on the polymer properties is investigated. Simulation results indicate a maximum in the polymer yield and chain length for initial [base]/[premonomer] = 1 and that the molecular properties of the precursor polymers can be varied by as much as 50\% by an appropriate choice of initial [base]/[premonomer]. The kinetic Monte Carlo model is used to determine reaction conditions to achieve targeted polymer yields, chain lengths and structural defect contents.},
  author       = {Van Steenberge, Paul and Vandenbergh, Joke and D'hooge, Dagmar and Reyniers, Marie-Fran\c{c}oise and Adriaensens, Peter J and Lutsen, Laurence and Vanderzande, Dirk JM and Marin, Guy},
  issn         = {0024-9297},
  journal      = {MACROMOLECULES},
  keyword      = {PALLADIUM-CATALYZED ARYLATION,ANIONIC-POLYMERIZATION MECHANISMS,CONTROLLED GILCH SYNTHESIS,CONJUGATED POLYMERS,P-QUINODIMETHANE,PARA-XYLYLENE,DITHIOCARBAMATE ROUTE,THERMAL ELIMINATION,RADICAL MECHANISM,VAPOR-DEPOSITION},
  language     = {eng},
  number       = {22},
  pages        = {8716--8726},
  title        = {Kinetic Monte Carlo modeling of the sulfinyl precursor route for poly(p-phenylene vinylene) synthesis},
  url          = {http://dx.doi.org/10.1021/ma201617r},
  volume       = {44},
  year         = {2011},
}

Chicago
Van Steenberge, Paul, Joke Vandenbergh, Dagmar D’hooge, Marie-Françoise Reyniers, Peter J Adriaensens, Laurence Lutsen, Dirk JM Vanderzande, and Guy Marin. 2011. “Kinetic Monte Carlo Modeling of the Sulfinyl Precursor Route for Poly(p-phenylene Vinylene) Synthesis.” Macromolecules 44 (22): 8716–8726.
APA
Van Steenberge, P., Vandenbergh, J., D’hooge, D., Reyniers, M.-F., Adriaensens, P. J., Lutsen, L., Vanderzande, D. J., et al. (2011). Kinetic Monte Carlo modeling of the sulfinyl precursor route for poly(p-phenylene vinylene) synthesis. MACROMOLECULES, 44(22), 8716–8726.
Vancouver
1.
Van Steenberge P, Vandenbergh J, D’hooge D, Reyniers M-F, Adriaensens PJ, Lutsen L, et al. Kinetic Monte Carlo modeling of the sulfinyl precursor route for poly(p-phenylene vinylene) synthesis. MACROMOLECULES. 2011;44(22):8716–26.
MLA
Van Steenberge, Paul, Joke Vandenbergh, Dagmar D’hooge, et al. “Kinetic Monte Carlo Modeling of the Sulfinyl Precursor Route for Poly(p-phenylene Vinylene) Synthesis.” MACROMOLECULES 44.22 (2011): 8716–8726. Print.