Alternate copolymers of head to head coupled dialkylbithiophenes and oligoaniline substituted thiophenes: preparation, electrochemical and spectroelectrochemical properties

Abstract

New processable, electroactive, alternate copolymers consisting of dialkylbithiophene units and oligoanilinethiophene units have been prepared by post-polymerization functionalization of a specially prepared precursor polymer, namely poly [(4,40-dioctyl-2,29:59,20-terthiophene-39-yl)ethyl acetate], carried out via its hydrolysis and consecutive branching aniline dimer or tetramer through the amidation reaction. The precursor polymer is interesting by itself because it gives a very clear spectroelectrochemical response over a very narrow potential range. The proposed method enables the preparation of regiochemically better defined alkylthiopheneoligoanilinethiophene copolymers with higher content of oligoaniline side groups as compared to previously used methods. Cyclic voltammetry investigations combined with UV-vis-NIR, EPR and Raman spectroelectrochemistry show that both the oligoaniline side groups and poly(thienylene) main chain are electrochemically active. Significant differences for the side group electrochemistry are observed in acidified and nonacidified electrolytes making the prepared new copolymer a good candidate for electrochromic applications in diversified electrolytes.

Synthesis of a functionalized polythiophene as an active substrate for a label-free electrochemical genosensor

“…The color of the polymer changed from brown to dark blue with increasing film thickness. Unlike alkyl substituted polythiophene [30], the obtained polymer was not soluble in common organic solvents such as acetonitrile, dichloromethane and propylene carbonate. Fig.…”

“…This problem can be avoided using post-polymerization functionalisation since thiophene monomers with protected carboxyl acid group can be easily electropolymerized. This approach is a widely used method for the preparation of new electroactive organic systems with tunable electronic, electrochemical and spectroscopic properties [29,30]. For example, Li et al synthesized thiophene bearing an activated ester group, N-succinimido thiophene-3-acetate, and obtained its homopolymer [31].…”

Electrochemomechanical properties of aniline/2-methoxyaniline copolymers

“…To overcome that, polymers of derivatives such as 2-methylaniline [24][25][26][27], 2-ethylaniline [28] or 2-methoxyaniline (MOA) [29][30][31][32][33] have been investigated, and also copolymers or composites [34] of aniline (ANI) and other suitable monomers [35][36][37]. A copolymer which is gaining increasing attention is poly(aniline-co-2-methoxyaniline) (PAcoM) [38][39][40][41][42][43].…”

Patterns of adaptation in patients living long term with advanced cancer

“…Considerable effort has been devoted recently toward chemically synthesizing polymers based on oligoanilines, such as graft, alternating, and block‐like polymers. Pron and coworkers21, 22 copolymerized 3‐octylthiophene with thiophene containing tetra‐aniline in the 3‐position to prepare a hybrid copolymer, which exhibits very interesting spectroscopic and electrochemical properties. Both of the oligoaniline side chains and the polymer main chains could be doped consecutively.…”