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Inducing planarity in redox-active conjugated polymers with solubilizing 3,6-dialkoxy-thieno[3,2-b]thiophenes (DOTTs) for redox and solid-state conductivity applications

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Abstract

In this work, we evaluate a series of dioxythienothiophene (DOTT)-based polymers for their charge transport structure–property relationships for both solid-state and electrochemical applications. The family includes: (i) the homopolymer, (ii) two 3,4-ethylenedioxythiophene (EDOT) co-polymers, (iii) a dimethyl ProDOT (DMP) co-polymer, and (iv) a bulky neopentyl dioxythiophene (NeoDOT) co-polymer. We show that all of the soluble DOTT polymers can be oxidized through chemical or electrochemical processes, through the full depletion of their neutral π–π* absorbance. The DOTT homopolymer and DOTT-NeoDOT co-polymer show high degrees of intermolecular ordering according to GIWAXS measurements, however, this order inhibits both chemical and electrochemical oxidation. DOTT-NeoDOT has the highest onset of electrochemical oxidation at 0.3 V vs. Ag/Ag+. In comparison, DOTT-BiEDOT has lower degrees of intermolecular ordering and the lowest onset of oxidation at −0.5 V vs. Ag/Ag+. Furthermore, this polymer has the highest solid-state conductivity of the family, which approaches 20 S cm−1 after chemical oxidation with the molecular dopant F4TCNQ. This study is the first to report the effects of chemical doping and charge transport on a family of soluble DOTT-based polymers.

Graphical abstract: Inducing planarity in redox-active conjugated polymers with solubilizing 3,6-dialkoxy-thieno[3,2-b]thiophenes (DOTTs) for redox and solid-state conductivity applications

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Supplementary files

Article information


Submitted
21 Feb 2020
Accepted
18 Apr 2020
First published
06 May 2020

J. Mater. Chem. C, 2020, Advance Article
Article type
Paper

Inducing planarity in redox-active conjugated polymers with solubilizing 3,6-dialkoxy-thieno[3,2-b]thiophenes (DOTTs) for redox and solid-state conductivity applications

S. L. Pittelli, S. A. Gregory, J. F. Ponder, S. K. Yee and J. R. Reynolds, J. Mater. Chem. C, 2020, Advance Article , DOI: 10.1039/D0TC00914H

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