Facile Syntheses of Dioxythiophene-Based
Conjugated Polymers by Direct C–H Arylation
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Abstract
Various substituted dioxythiophenes bearing 3,4-propylenedioxythiophenes
(ProDOT) and 3,4-ethylenedioxythiophene (EDOT) moieties successfully
undergo Pd-catalyzed direct C–H arylation to yield π-conjugated
polymers. The effects of palladium catalysts, phosphine ligands or
additives, and functional groups on this facile polycondensation approach
are investigated. Polymers from alkoxy-substituted ProDOT are synthesized
with reasonable molecular weight (<i>M</i><sub>n</sub> =
6100–9600) and low PDI (1.3–1.9). Four substituted EDOT
with alkoxy or protected functional groups also undergo direct C–H
arylation polycondensation to yield corresponding polymers. The obtained
polydioxythiophenes exhibit UV–vis absorptions ranging from
480 to 590 nm, and these conjugated polymers are electroactive and
reversibly switched between the oxidized and neutral states upon applying
potentials