Low-Defect, High Molecular Weight Indacenodithiophene (IDT) Polymers Via a C–H Activation: Evaluation of a Simpler and Greener Approach to Organic Electronic Materials

James F. Ponder, Hung-Yang Chen, Alexander M. T. Luci, Stefania Moro, Marco Turano, Archie L. Hobson, Graham S. Collier, Luís M. A. Perdigão, Maximilian Moser, Weimin Zhang, Giovanni Costantini, John R. Reynolds, Iain McCulloch

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

The development, optimization, and assessment of new methods for the preparation of conjugated materials is key to the continued progress of organic electronics. Direct C–H activation methods have emerged and developed over the last 10 years to become an invaluable synthetic tool for the preparation of conjugated polymers for both redox-active and solid-state applications. Here, we evaluate direct (hetero)arylation polymerization (DHAP) methods for the synthesis of indaceno[1,2-b:5,6-b′]dithiophene-based polymers. We demonstrate, using a range of techniques, including direct visualization of individual polymer chains via high-resolution scanning tunneling microscopy, that DHAP can produce polymers with a high degree of regularity and purity that subsequently perform in organic thin-film transistors comparably to those made by other cross-coupling polymerizations that require increased synthetic complexity. Ultimately, this work results in an improved atom economy by reducing the number of synthetic steps to access high-performance molecular and polymeric materials.
Original languageEnglish (US)
Pages (from-to)1503-1512
Number of pages10
JournalACS Materials Letters
DOIs
StatePublished - Sep 16 2021

Bibliographical note

KAUST Repository Item: Exported on 2021-09-20
Acknowledged KAUST grant number(s): OSR-2018-CRG/CCF-3079, OSR-2018-CRG7-3749, OSR2019-CRG8-4086
Acknowledgements: JFP would like to thank Abigail A. Advincula for assistance in electrochemical measurements and Dr. Austin L. Jones for assistance in GPC measurements. The authors acknowledge financial support from KAUST, including Office of Sponsored Research (OSR) awards no. OSR-2018-CRG/CCF-3079, OSR2019-CRG8-4086 and OSR-2018-CRG7-3749. The authors acknowledge funding from ERC Synergy Grant SC2 (610115), the European Union’s Horizon 2020 research and innovation program under grant agreement no. 952911, project BOOSTER
and grant agreement no. 862484, project RoLAFLEX, as well as EPSRC Project EP/T026219/1. G.C. acknowledges financial support from the University of Warwick. A.M.T.L. and M.T. gratefully acknowledge financial support from the Engineering and Physical Sciences Research Council (EPSRC) grant EP/L015307/1 for the Molecular Analytical Science Centre for Doctoral Training (MAS-CDT). S.M. acknowledges funding though an EU Chancellor’s Scholarship by the University of Warwick. G.S.C and J.R.R acknowledges funding from the Office of Naval Research (N00014-20-1-2129).

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