The new polymer
poly(thiophene-2,5-diyl-1,2-dimethoxyvinylene) was synthesized by
a
benzoin condensation of thiophene-2,5-dicarboxaldehyde to
poly(2,5-thienylene-1-oxo-2-hydroxyethylene)
(M
w ∼ 1 × 106, pd ∼ 13),
followed by O-alkylation using dimethyl sulfate. A side reaction
of the benzoin
condensation step leading to dimethyl-2,5-thiophenedicarboxylate can be
avoided by using cyclohexanol
as the solvent. The O-alkylation, including the workup, has to be
performed under nitrogen protection
to counteract the degradation of the polymer by air under the influence
of light. A mechanism is proposed
for the oxidative degradation of this
poly(thiophene-2,5-diylvinylene) derivative and other
poly(arylenevinylenes). Conductivity and thermal properties of the new
polymer are given.