The Effect of Alkyl Spacers on the Mixed Ionic-Electronic Conduction Properties of N-Type Polymers

Iuliana P. Maria; Bryan D. Paulsen; Achilleas Savva; David Ohayon; Ruiheng Wu; Rawad Hallani; Aniruddha Basu; weiyuan du; Thomas D. Anthopoulos; Sahika Inal; Jonathan Rivnay; Iain McCulloch; Alexander Giovannitti

doi:10.1002/adfm.202008718

The Effect of Alkyl Spacers on the Mixed Ionic-Electronic Conduction Properties of N-Type Polymers

Iuliana P. Maria, Bryan D. Paulsen, Achilleas Savva, David Ohayon, Ruiheng Wu, Rawad Hallani, Aniruddha Basu, weiyuan du, Thomas D. Anthopoulos, Sahika Inal, Jonathan Rivnay, Iain McCulloch, Alexander Giovannitti

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Abstract

Conjugated polymers with mixed ionic and electronic transport are essential for developing the complexity and function of electrochemical devices. Current n-type materials have a narrow scope and low performance compared with their p-type counterparts, requiring new molecular design strategies. This work presents two naphthalene diimide-bithiophene (NDI-T2) copolymers functionalized with hybrid alkyl-glycol side chains, where the naphthalene diimide unit is segregated from the ethylene glycol (EG) units within the side chain by an alkyl spacer. Introduction of hydrophobic propyl and hexyl spacers is investigated as a strategy to minimize detrimental swelling close to the conjugated backbone and balance the mixed conduction properties of n-type materials in aqueous electrolytes. It is found that both polymers functionalized with alkyl spacers outperform their analogue bearing EG-only side chains in organic electrochemical transistors (OECTs). The presence of the alkyl spacers also leads to remarkable stability in OECTs, with no decrease in the ON current after 2 h of operation. Through this versatile side chain modification, this work provides a greater understanding of the structure-property relationships required for n-type OECT materials operating in aqueous media.

Original language	English (US)
Pages (from-to)	2008718
Journal	Advanced Functional Materials
DOIs	https://doi.org/10.1002/adfm.202008718
State	Published - Jan 20 2021

Bibliographical note

KAUST Repository Item: Exported on 2021-02-04
Acknowledged KAUST grant number(s): OSR-2018-CARF/CCF-3079, OSR-2015- CRG4-2572, OSR-2016-CRG5-3003, OSR-4106 CPF2019
Acknowledgements: The research reported in this publication was supported by funding from King Abdullah University of Science and Technology Office of Sponsored Research (OSlR) under awards no. OSR-2018-CARF/CCF-3079, OSR-2015- CRG4-2572, OSR-2016-CRG5-3003, and OSR-4106 CPF2019. The authors acknowledge EC FP7 Project SC2 (610115), EC H2020 (643791), and EPSRC Projects EP/G037515/1, EP/M005143/1, and EP/L016702/1. A.G. acknowledges funding from the TomKat Center for Sustainable Energy at Stanford University. B.P. and J.R. gratefully acknowledge support from the National Science Foundation grant no. NSF DMR-1751308, and J.R. acknowledges support from the Alfred P. Sloan Foundation. Special thanks to Joseph Strzalka and Qingteng Zhang for beam line assistance. This research used resources of the Advanced Photon Source, a U.S. Department of Energy (DOE) Office of Science User Facility operated for the DOE Office of Science by Argonne National Laboratory under Contract No. DE-AC02-06CH11357.

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@article{6c8beb2254ca47d682855a3c3ae172db,

title = "The Effect of Alkyl Spacers on the Mixed Ionic-Electronic Conduction Properties of N-Type Polymers",

abstract = "Conjugated polymers with mixed ionic and electronic transport are essential for developing the complexity and function of electrochemical devices. Current n-type materials have a narrow scope and low performance compared with their p-type counterparts, requiring new molecular design strategies. This work presents two naphthalene diimide-bithiophene (NDI-T2) copolymers functionalized with hybrid alkyl-glycol side chains, where the naphthalene diimide unit is segregated from the ethylene glycol (EG) units within the side chain by an alkyl spacer. Introduction of hydrophobic propyl and hexyl spacers is investigated as a strategy to minimize detrimental swelling close to the conjugated backbone and balance the mixed conduction properties of n-type materials in aqueous electrolytes. It is found that both polymers functionalized with alkyl spacers outperform their analogue bearing EG-only side chains in organic electrochemical transistors (OECTs). The presence of the alkyl spacers also leads to remarkable stability in OECTs, with no decrease in the ON current after 2 h of operation. Through this versatile side chain modification, this work provides a greater understanding of the structure-property relationships required for n-type OECT materials operating in aqueous media.",

author = "Maria, {Iuliana P.} and Paulsen, {Bryan D.} and Achilleas Savva and David Ohayon and Ruiheng Wu and Rawad Hallani and Aniruddha Basu and weiyuan du and Anthopoulos, {Thomas D.} and Sahika Inal and Jonathan Rivnay and Iain McCulloch and Alexander Giovannitti",

note = "KAUST Repository Item: Exported on 2021-02-04 Acknowledged KAUST grant number(s): OSR-2018-CARF/CCF-3079, OSR-2015- CRG4-2572, OSR-2016-CRG5-3003, OSR-4106 CPF2019 Acknowledgements: The research reported in this publication was supported by funding from King Abdullah University of Science and Technology Office of Sponsored Research (OSlR) under awards no. OSR-2018-CARF/CCF-3079, OSR-2015- CRG4-2572, OSR-2016-CRG5-3003, and OSR-4106 CPF2019. The authors acknowledge EC FP7 Project SC2 (610115), EC H2020 (643791), and EPSRC Projects EP/G037515/1, EP/M005143/1, and EP/L016702/1. A.G. acknowledges funding from the TomKat Center for Sustainable Energy at Stanford University. B.P. and J.R. gratefully acknowledge support from the National Science Foundation grant no. NSF DMR-1751308, and J.R. acknowledges support from the Alfred P. Sloan Foundation. Special thanks to Joseph Strzalka and Qingteng Zhang for beam line assistance. This research used resources of the Advanced Photon Source, a U.S. Department of Energy (DOE) Office of Science User Facility operated for the DOE Office of Science by Argonne National Laboratory under Contract No. DE-AC02-06CH11357.",

year = "2021",

month = jan,

day = "20",

doi = "10.1002/adfm.202008718",

language = "English (US)",

pages = "2008718",

journal = "Advanced Functional Materials",

issn = "1616-301X",

publisher = "Wiley",

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TY - JOUR

T1 - The Effect of Alkyl Spacers on the Mixed Ionic-Electronic Conduction Properties of N-Type Polymers

AU - Maria, Iuliana P.

AU - Paulsen, Bryan D.

AU - Savva, Achilleas

AU - Ohayon, David

AU - Wu, Ruiheng

AU - Hallani, Rawad

AU - Basu, Aniruddha

AU - du, weiyuan

AU - Anthopoulos, Thomas D.

AU - Inal, Sahika

AU - Rivnay, Jonathan

AU - McCulloch, Iain

AU - Giovannitti, Alexander

N1 - KAUST Repository Item: Exported on 2021-02-04 Acknowledged KAUST grant number(s): OSR-2018-CARF/CCF-3079, OSR-2015- CRG4-2572, OSR-2016-CRG5-3003, OSR-4106 CPF2019 Acknowledgements: The research reported in this publication was supported by funding from King Abdullah University of Science and Technology Office of Sponsored Research (OSlR) under awards no. OSR-2018-CARF/CCF-3079, OSR-2015- CRG4-2572, OSR-2016-CRG5-3003, and OSR-4106 CPF2019. The authors acknowledge EC FP7 Project SC2 (610115), EC H2020 (643791), and EPSRC Projects EP/G037515/1, EP/M005143/1, and EP/L016702/1. A.G. acknowledges funding from the TomKat Center for Sustainable Energy at Stanford University. B.P. and J.R. gratefully acknowledge support from the National Science Foundation grant no. NSF DMR-1751308, and J.R. acknowledges support from the Alfred P. Sloan Foundation. Special thanks to Joseph Strzalka and Qingteng Zhang for beam line assistance. This research used resources of the Advanced Photon Source, a U.S. Department of Energy (DOE) Office of Science User Facility operated for the DOE Office of Science by Argonne National Laboratory under Contract No. DE-AC02-06CH11357.

PY - 2021/1/20

Y1 - 2021/1/20

N2 - Conjugated polymers with mixed ionic and electronic transport are essential for developing the complexity and function of electrochemical devices. Current n-type materials have a narrow scope and low performance compared with their p-type counterparts, requiring new molecular design strategies. This work presents two naphthalene diimide-bithiophene (NDI-T2) copolymers functionalized with hybrid alkyl-glycol side chains, where the naphthalene diimide unit is segregated from the ethylene glycol (EG) units within the side chain by an alkyl spacer. Introduction of hydrophobic propyl and hexyl spacers is investigated as a strategy to minimize detrimental swelling close to the conjugated backbone and balance the mixed conduction properties of n-type materials in aqueous electrolytes. It is found that both polymers functionalized with alkyl spacers outperform their analogue bearing EG-only side chains in organic electrochemical transistors (OECTs). The presence of the alkyl spacers also leads to remarkable stability in OECTs, with no decrease in the ON current after 2 h of operation. Through this versatile side chain modification, this work provides a greater understanding of the structure-property relationships required for n-type OECT materials operating in aqueous media.

AB - Conjugated polymers with mixed ionic and electronic transport are essential for developing the complexity and function of electrochemical devices. Current n-type materials have a narrow scope and low performance compared with their p-type counterparts, requiring new molecular design strategies. This work presents two naphthalene diimide-bithiophene (NDI-T2) copolymers functionalized with hybrid alkyl-glycol side chains, where the naphthalene diimide unit is segregated from the ethylene glycol (EG) units within the side chain by an alkyl spacer. Introduction of hydrophobic propyl and hexyl spacers is investigated as a strategy to minimize detrimental swelling close to the conjugated backbone and balance the mixed conduction properties of n-type materials in aqueous electrolytes. It is found that both polymers functionalized with alkyl spacers outperform their analogue bearing EG-only side chains in organic electrochemical transistors (OECTs). The presence of the alkyl spacers also leads to remarkable stability in OECTs, with no decrease in the ON current after 2 h of operation. Through this versatile side chain modification, this work provides a greater understanding of the structure-property relationships required for n-type OECT materials operating in aqueous media.

UR - http://hdl.handle.net/10754/667200

UR - https://onlinelibrary.wiley.com/doi/10.1002/adfm.202008718

U2 - 10.1002/adfm.202008718

DO - 10.1002/adfm.202008718

M3 - Article

SN - 1616-301X

SP - 2008718

JO - Advanced Functional Materials

JF - Advanced Functional Materials

ER -

The Effect of Alkyl Spacers on the Mixed Ionic-Electronic Conduction Properties of N-Type Polymers

Abstract

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