Ethylene Glycol-Based Side Chain Length Engineering in Polythiophenes and its Impact on Organic Electrochemical Transistor Performance

Maximilian Moser, Lisa R. Savagian, Achilleas Savva, Micaela Matta, James F. Ponder, Tania Cecilia Hidalgo, David ohayon, Rawad Hallani, Maryam Reisjalali, Alessandro Troisi, Andrew Wadsworth, John R. Reynolds, Sahika Inal, Iain McCulloch

Research output: Contribution to journalArticlepeer-review

93 Scopus citations

Abstract

Replacing the alkyl side chains on conventional semiconducting polymers with ethylene glycol (EG)-based chains is a successful strategy in the molecular design of mixed conduction materials for bioelectronic devices, including organic electrochemical transistors (OECTs). Such polymers have demonstrated the capability to conduct both ionic and electronic charges and can offer superior performance compared to the most commonly used active material, poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate). While many research efforts have been dedicated to optimizing OECT performance through the engineering of the semiconducting polymers’ conjugated backbones, variation of the EG chain length has been investigated considerably less. In this work, a series of glycolated polythiophenes with pendant EG chains spanning two to six EG repeat units was synthesized and the electrochemical and structural characteristics of the resulting films were characterized by experimental means and molecular dynamics simulations. OECTs were fabricated and tested, and their performance showed a strong correlation to the the EG side chain length, thereby elucidating important structure−property guidelines for the molecular design of future channel materials. Specifically, a careful balance in the EG length must be struck during the design of EG-functionalized conjugated polymers for OECTs. While minimizing the EG side chain length appears to boost both the capacitive and charge carrier transport properties of the polymers, the chosen EG side chain length must be kept sufficiently long to induce solubility for processing, and allow for the necessary ion interactions with the conjugated polymer backbone.
Original languageEnglish (US)
JournalChemistry of Materials
DOIs
StatePublished - Jul 22 2020

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledged KAUST grant number(s): OSR-2015-CRG4-2572, OSR-2018-CARF/CCF-3079
Acknowledgements: We acknowledge generous funding from KAUST for financial support. The research reported in this publication was supported by funding from King Abdullah University of Science and Technology Office of Sponsored Research (OSR) under awards nos. OSR-2018-CARF/CCF-3079, OSR-2015-CRG4-2572, and OSR-4106 CPF2019. We acknowledge EC FP7 Project SC2 (610115), EC H2020 (643791), and EPSRC
Projects EP/G037515/1, EP/M005143/1, and EP/L016702/1. J.R.R. acknowledges funding of this work from the Office of Naval Research (N00014-18-1-2222) and the Air Force Office of Scientific Research (FA9550-18-1-0184). L.R.S. was supported by the National Science Foundation Graduate Research Fellowship under Grant No. DGE-1650044. M.M.acknowledges financial support of the Royal Society in the
form of a Newton International Fellowship (NIF\R1\181379). Use of the Stanford Synchrotron Radiation Lightsource, SLAC National Accelerator Laboratory, is supported by the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences, under Contract No. DE-AC02-76SF00515. S.I. acknowledges funding from KAUST Office of Sponsored Research (OSR) under Award No. OSR-2018-CRG7-3709.

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