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Direct Observation ofα-Chloro-p-quinodimethane as the Real Monomer in the Gilch Polymerization Leading to Poly(p-phenylene vinylene)s

Wiesecke, Jens and Rehahn, Matthias (2007):
Direct Observation ofα-Chloro-p-quinodimethane as the Real Monomer in the Gilch Polymerization Leading to Poly(p-phenylene vinylene)s.
In: Macromolecular Rapid Communications, pp. 188-193, 28, (2), ISSN 10221336, [Online-Edition: http://dx.doi.org/10.1002/marc.200600649],
[Article]

Abstract

It is the general consensus that in Gilch polymerizations the 1,4-bis(chloromethylene)benzene starting material first changes into p-quinodimethane intermediates which then act as the real monomers. However, direct observation of these intermediates has not been possible so far. This is because usually the p-quinodimethane auto-initiates its rapid radical polymerization instantaneously, keeping its concentration extremely low throughout the whole process. Here it is shown that, when the reaction is carried out at very low temperatures, the formation of p-quinodimethane still proceeds but chain growth is suppressed. Hence, the concentration of the active monomer reaches a level sufficient for NMR analysis.

Item Type: Article
Erschienen: 2007
Creators: Wiesecke, Jens and Rehahn, Matthias
Title: Direct Observation ofα-Chloro-p-quinodimethane as the Real Monomer in the Gilch Polymerization Leading to Poly(p-phenylene vinylene)s
Language: German
Abstract:

It is the general consensus that in Gilch polymerizations the 1,4-bis(chloromethylene)benzene starting material first changes into p-quinodimethane intermediates which then act as the real monomers. However, direct observation of these intermediates has not been possible so far. This is because usually the p-quinodimethane auto-initiates its rapid radical polymerization instantaneously, keeping its concentration extremely low throughout the whole process. Here it is shown that, when the reaction is carried out at very low temperatures, the formation of p-quinodimethane still proceeds but chain growth is suppressed. Hence, the concentration of the active monomer reaches a level sufficient for NMR analysis.

Journal or Publication Title: Macromolecular Rapid Communications
Volume: 28
Number: 2
Uncontrolled Keywords: conducting polymers; Gilch reaction; light-emitting diodes (LEDs); poly(p-phenylene vinylene)s (PPVs); reaction mechanism
Divisions: DFG-Collaborative Research Centres (incl. Transregio) > Collaborative Research Centres > CRC 595: Electrical fatigue > A - Synthesis > Subproject A5: Synthesis of semiconducting model polymers and their characterization before and after cyclic electrical fatigue
DFG-Collaborative Research Centres (incl. Transregio) > Collaborative Research Centres > CRC 595: Electrical fatigue > A - Synthesis
DFG-Collaborative Research Centres (incl. Transregio) > Collaborative Research Centres > CRC 595: Electrical fatigue
Zentrale Einrichtungen
DFG-Collaborative Research Centres (incl. Transregio) > Collaborative Research Centres
DFG-Collaborative Research Centres (incl. Transregio)
Date Deposited: 04 Aug 2011 12:33
Official URL: http://dx.doi.org/10.1002/marc.200600649
Additional Information:

SFB 595 A5

Identification Number: doi:10.1002/marc.200600649
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