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Mechanistic Aspects of Radiation-Induced Oligomerization of 3,4-ethylenedioxythiophene in Ionic Liquids

Mechanistic Aspects of Radiation-Induced Oligomerization of 3,4-ethylenedioxythiophene in Ionic Liquids

Radosław Michalski, Adam Sikora, Jan Adamus, Andrzej Marcinek

J Phys Chem A. 2010 Nov 4;114(43):11552-9.

PMID: 20931950

Abstract:

Thiophene and its disubstituted derivatives, such as 3,4-ethylenedioxythiophene (EDOT), 3,4-dimethoxythiophene (DMT), 3,4-propylenedioxythiophene (PDOT), and 3,4-butylenedioxythiophene (BuDOT) were oxidized in organic solvents and in ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate (BMIM(+)PF₆⁻) at RT and under cryogenic conditions. Their radical cations were spectrally characterized at 77 K. Annealing of the irradiated matrix, which triggers the diffusion processes, led to spontaneous oligomerization. The oxidative coupling between a radical cation and a neutral monomer was identified as the first step of the oligomerization process. The scale of oligomerization could be extended by the addition of chloroform, which acts as a dissociative electron scavenger, whereas the dichloromethylperoxyl radicals formed in the reaction with the dissolved oxygen act as secondary oxidizing agents.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP51792348	3,4-Dimethoxythiophene		51792-34-8	Price

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