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

(2011) MACROMOLECULES. 44(22). p.8716-8726
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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.
Keywords
PALLADIUM-CATALYZED ARYLATION, ANIONIC-POLYMERIZATION MECHANISMS, CONTROLLED GILCH SYNTHESIS, CONJUGATED POLYMERS, P-QUINODIMETHANE, PARA-XYLYLENE, DITHIOCARBAMATE ROUTE, THERMAL ELIMINATION, RADICAL MECHANISM, VAPOR-DEPOSITION

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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.
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.
Chicago author-date
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.
Chicago author-date (all authors)
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.
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.
IEEE
[1]
P. Van Steenberge et al., “Kinetic Monte Carlo modeling of the sulfinyl precursor route for poly(p-phenylene vinylene) synthesis,” MACROMOLECULES, vol. 44, no. 22, pp. 8716–8726, 2011.
@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-Françoise and Adriaensens, Peter J and Lutsen, Laurence and Vanderzande, Dirk JM and Marin, Guy},
  issn         = {0024-9297},
  journal      = {MACROMOLECULES},
  keywords     = {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},
}

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