A series of 3-(p-X-phenyl) thiophene monomers (X= –H, –CH3, –
OCH3, –COOC2H5, –COCH3,–NO2) was electrochemically polymerized
to furnish polymer films that could be reversibly reduced
and oxidized (n- and p-doped). The oxidation potentials of the
monomers and formal potentials of the n- and p-doping processes
of polymers were correlated with resonance and inductive effects
of the substituents on the phenyl ring as well as the semiempirically
calculated heats of formation of the monomer radical cations.
Moreover, the oxidation potentials of the monomers were correlated
with the ionization potentials of the monomers calculated using
density functional theory. The reactivity for coupling reactions
and the major regioselective products of the polymerization reaction
of mono- and oligo-3-phenylthiophenes are inferred from the
calculated lone electron spin densities of the respective radical
cations. The ionization potentials, which correspond to the energies
for generating radical cations during oxidative processes were estimated.
| Identifer | oai:union.ndltd.org:DRESDEN/oai:qucosa:de:qucosa:19114 |
| Date | 21 April 2009 |
| Creators | Alhalasah, Wasim, Holze, Rudolf |
| Publisher | Technische Universität Chemnitz |
| Source Sets | Hochschulschriftenserver (HSSS) der SLUB Dresden |
| Language | English |
| Detected Language | English |
| Type | doc-type:article, info:eu-repo/semantics/article, doc-type:Text |
| Source | Electrochemical Society Transactions. – 2 (23) 45 – 62 (2007); DOI:10.1149/1.2409008 |
| Rights | info:eu-repo/semantics/openAccess |
| Relation | 10.1149/1.2409008, 1938-6737online, 1938-5862print |
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