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; Hu 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

doi:10.1021/acsmaterialslett.1c00478

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^*, Hu 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

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

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 language	English
Pages (from-to)	1503-1512
Number of pages	10
Journal	ACS Materials Letters
Volume	3
Issue number	10
Early online date	16 Sept 2021
DOIs	https://doi.org/10.1021/acsmaterialslett.1c00478
Publication status	Published - 4 Oct 2021

Bibliographical note

Funding Information:
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, OSR-2019-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).

Publisher Copyright:
© 2021 American Chemical Society.

ASJC Scopus subject areas

General Chemical Engineering
Biomedical Engineering
General Materials Science

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10.1021/acsmaterialslett.1c00478

Cite this

Ponder, J. F., Chen, H., Luci, A. M. T., Moro, S., Turano, M., Hobson, A. L., Collier, G. S., Perdigão, L. M. A., Moser, M., Zhang, W., Costantini, G., Reynolds, J. R., & McCulloch, I. (2021). Low-Defect, High Molecular Weight Indacenodithiophene (IDT) Polymers Via a C-H Activation: Evaluation of a Simpler and Greener Approach to Organic Electronic Materials. ACS Materials Letters, 3(10), 1503-1512. https://doi.org/10.1021/acsmaterialslett.1c00478

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

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.",

author = "Ponder, {James F.} and Hu Chen and Luci, {Alexander M.T.} and Stefania Moro and Marco Turano and Hobson, {Archie L.} and Collier, {Graham S.} and Perdig{\~a}o, {Lu{\'i}s M.A.} and Maximilian Moser and Weimin Zhang and Giovanni Costantini and Reynolds, {John R.} and Iain McCulloch",

note = "Funding Information: 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, OSR-2019-CRG8-4086 and OSR-2018-CRG7-3749. The authors acknowledge funding from ERC Synergy Grant SC2 (610115), the European Union{\textquoteright}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{\textquoteright}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). Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

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doi = "10.1021/acsmaterialslett.1c00478",

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Ponder, JF, Chen, H, Luci, AMT, Moro, S, Turano, M, Hobson, AL, Collier, GS, Perdigão, LMA, Moser, M, Zhang, W, Costantini, G, Reynolds, JR & McCulloch, I 2021, 'Low-Defect, High Molecular Weight Indacenodithiophene (IDT) Polymers Via a C-H Activation: Evaluation of a Simpler and Greener Approach to Organic Electronic Materials', ACS Materials Letters, vol. 3, no. 10, pp. 1503-1512. https://doi.org/10.1021/acsmaterialslett.1c00478

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AU - Chen, Hu

AU - Luci, Alexander M.T.

AU - Moro, Stefania

AU - Turano, Marco

AU - Hobson, Archie L.

AU - Collier, Graham S.

AU - Perdigão, Luís M.A.

AU - Moser, Maximilian

AU - Zhang, Weimin

AU - Costantini, Giovanni

AU - Reynolds, John R.

AU - McCulloch, Iain

N1 - Funding Information: 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, OSR-2019-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). Publisher Copyright: © 2021 American Chemical Society.

PY - 2021/10/4

Y1 - 2021/10/4

N2 - 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.

AB - 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.

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

Abstract

Bibliographical note

ASJC Scopus subject areas

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