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

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, 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

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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 (US)
Pages (from-to)	1503-1512
Number of pages	10
Journal	ACS Materials Letters
DOIs	https://doi.org/10.1021/acsmaterialslett.1c00478
State	Published - 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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10.1021/acsmaterialslett.1c00478

https://repository.kaust.edu.sa/bitstream/10754/671297/1/IDT-BT_DHAP_proof.pdf

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Ponder, J. F., Chen, H.-Y., 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, 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 Hung-Yang 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 = "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{\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).",

year = "2021",

month = sep,

day = "16",

doi = "10.1021/acsmaterialslett.1c00478",

language = "English (US)",

pages = "1503--1512",

journal = "ACS Materials Letters",

issn = "2639-4979",

publisher = "American Chemical Society",

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Ponder, JF, Chen, H-Y, 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, pp. 1503-1512. https://doi.org/10.1021/acsmaterialslett.1c00478

TY - JOUR

T1 - Low-Defect, High Molecular Weight Indacenodithiophene (IDT) Polymers Via a C–H Activation: Evaluation of a Simpler and Greener Approach to Organic Electronic Materials

AU - Ponder, James F.

AU - Chen, Hung-Yang

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 - 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).

PY - 2021/9/16

Y1 - 2021/9/16

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.

UR - http://hdl.handle.net/10754/671297

UR - https://pubs.acs.org/doi/10.1021/acsmaterialslett.1c00478

U2 - 10.1021/acsmaterialslett.1c00478

DO - 10.1021/acsmaterialslett.1c00478

M3 - Article

SN - 2639-4979

SP - 1503

EP - 1512

JO - ACS Materials Letters

JF - ACS Materials Letters

ER -

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

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