Poly(alkylthiophene) with Pendant Dianiline Groups via Postpolymerization Functionalization:  Preparation, Spectroscopic, and Spectroelectrochemical Characterization

Abstract

Using postpolymerization functionalization, we have prepared a new solution-processable electroactive polymer combining electrochemical properties of poly(thiophene)s and oligoanilines. The elaborated procedure consists of three steps. First, 3-octylthiophene and ethyl 3-thiopheneacetate are copolymerized to give poly(3-octyl-2,5-thienylene-co-3-methylene-ethylcarboxylate-2,5-thienylene)the precursor polymer. The precursor is then hydrolyzed, and in the last step, aniline dimer is attached to it via amidation reaction. UV−vis−NIR and Raman spectroelectrochemical studies combined with cyclic voltammetry show that, as expected, both poly(thienylene) main-chain and dianiline side groups can be oxidatively doped, the latter adopting, upon oxidation, the structure of semiquinone radical cation.

Synthesis and characterization of highly fluorescent polythiophene derivatives containing polystyrene sidearms

“…This demonstrated that the absorption of the macroinitiator depended on the substitutent on thiophene ring and hypsochromically shifted with increasing the fraction of ethyl 2‐bromopropionate. The similar phenomena was also obtained in poly(3‐octyl‐2,5‐thienylene‐ co ‐3‐methylene‐ethylcarboxylate‐2,5‐thienylene) 17. According to the explanation of Buga et al,17 the ester subsituents can lower the polymer backbone planarity and shorten the conjugated length result in blue shift of its λ max .…”

“…The similar phenomena was also obtained in poly(3‐octyl‐2,5‐thienylene‐ co ‐3‐methylene‐ethylcarboxylate‐2,5‐thienylene) 17. According to the explanation of Buga et al,17 the ester subsituents can lower the polymer backbone planarity and shorten the conjugated length result in blue shift of its λ max .…”

Electroactive Polymer with Oligoanilines in the Main Chain: Synthesis, Characterization and Dielectric Properties

“…Recently, the Benicewicz [12] group reported new poly(methacrylamide)s containing oligoaniline side chains synthesized from methacrylamide monomers by free radical polymerization. Zagórska et al [13] prepared a new solution-processable electroactive polymer combining the electrochemical properties of poly(thiophene)s and oligoanilines, using post-polymerization functionalization. Zhu and co-workers [14] prepared a novel polymer with tetraaniline and phenylene sulfide as the repeat units, which displayed good solubility in most common organic solvents, such as THF, DMSO and DMF, and its electrical conductivity could be up to 100 S Á cm À1 upon preliminarily protonic-doping.…”

Synthesis and chemical properties of polyphenols with oligoaniline pendant groups

“…17 Several polymers containing OAN pendant groups have been synthesized by the reaction of polymers featuring reactive sites with reactants containing an OAN group. 17,18 Polymers with OAN pendant groups showed unique optical and electrochemical properties. 18 However, the repeating units of these polymers do not always feature OAN pendant groups, because of incomplete polymer reactions.…”

“…17,18 Polymers with OAN pendant groups showed unique optical and electrochemical properties. 18 However, the repeating units of these polymers do not always feature OAN pendant groups, because of incomplete polymer reactions. HRP-catalyzed polymerization of phenols with OAN groups is a promising method to obtain PPs with OAN pendant groups in every structural unit.…”